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CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level

s er om .c

CHEMISTRY
Paper 1 Multiple Choice

9701/01
May/June 2003 1 hour

Additional Materials:

Data Booklet Multiple Choice Answer Sheet Soft clean eraser Soft pencil (type B or HB is recommended)

READ THESE INSTRUCTIONS FIRST Write in soft pencil. Do not use staples, paper clips, highlighters, glue or correction fluid. Write your name, Centre number and candidate number on the answer sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. Answer all questions. For each question there are four possible answers, A, B, C, and D. Choose the one you consider correct and record your choice in soft pencil on the separate answer sheet. Read the instructions on the Answer Sheet very carefully. Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet.

This document consists of 14 printed pages and 2 blank pages.
SP (KN/KN) S34069/2 ? CIE 2003

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2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct.

1

The use of the Data Booklet is relevant to this question. What is the number of molecules in 500 cm3 of oxygen under room conditions? A B C D 1.25 x 1022 1.34 x 1022 3.0 x 1022 3.0 x 1026

2

In the preparation of soft margarine, glyceryl trieleostearate CH3(CH2)3CH CH3(CH2)3CH CH3(CH2)3CH CHCH CHCH CHCH CHCH CHCH CHCH CH(CH2)7CO2CH2 CH(CH2)7CO2CH CH(CH2)7CO2CH2

is suitably hydrogenated so that, on average, one of its side-chains is converted into the CH3(CH2)4CH=CHCH2CH=CH(CH2)7CO2 residue and two side-chains are converted into the CH3(CH2)7CH=CH(CH2)7CO2 residue. How many moles of hydrogen are required to convert one mole of glyceryl trieleostearate into the soft margarine? A 4 B 5 C 6 D 9

3

Which isotope of an element in the third period of the Periodic Table contains the same number of 32 neutrons as 16 S? A B C D
23 11 Na 24 12 Mg 28 14 Si 31 15 P

4

The successive ionisation energies, in kJ mol–1, of an element X are given below. 870 1800 3000 3600 5800 7000 13 200

What is X? A
33As

B

40Zr

C

52Te

D
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53I

3 5 Which of the following solids has a simple molecular lattice? A B C D magnesium oxide sodium silicon(IV) oxide sulphur

6

Measured values of the pressure, volume and temperature of a known mass of a gaseous compound are to be substituted into the equation pV = nRT in order to calculate the relative molecular mass, Mr, of the compound. Which conditions of pressure and temperature would give the most accurate value of Mr? pressure A B C D high high low low temperature high low high low

7

Gaseous phosphorus pentachloride can be decomposed into gaseous phosphorus trichloride and chlorine by heating. The table below gives the bond energies. bond P-Cl (in both chlorides) Cl-Cl bond energy / kJ mol–1 330 240

What is the enthalpy change in the decomposition of PCl5 to PCl3 and Cl2? A –420 kJ mol–1 B –90 kJ mol–1 C +90 kJ mol–1 D +420 kJ mol–1

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4 8 When ammonia is converted into nitric acid on a commercial scale, the following reactions can occur. In which reaction does the greatest change in oxidation number of the nitrogen occur? reaction A B C D 4NH3 + 5O2 → 4NO + 6H2O 3NO2 + H2O → 2HNO3 + NO 2NO + O2 → 2NO2 4NH3 + 6NO → 5N2 + 6H2O

9

At the age of 17, in a woodshed in Ohio, Charles Martin Hall discovered the commercial process for the production of aluminium metal by the electrolysis of a mixture of bauxite, Al2O3, and cryolite, Na3AlF6. What is the main purpose of the cryolite? A Al2O3 is covalent, and AlF 6 discharged at the cathode.
3–

ions interact with it to produce Al 3+ ions which can be

B C D

Cryolite is a base, forming NaAlO2 with bauxite, enabling aluminium to be discharged at the anode. Cryolite reduces the melting point of the bauxite. Cryolite minimises the release of O2– ions at the graphite anodes, which are otherwise burnt away to CO.

10 When 0.20 mol of hydrogen gas and 0.15 mol of iodine gas are heated at 723 K until equilibrium is established, the equilibrium mixture is found to contain 0.26 mol of hydrogen iodide. The equation for the reaction is as follows. H2(g) + I2(g) 2HI(g)

What is the correct expression for the equilibrium constant Kc? A B C D 2 x 0.26 ––––––––– 0.20 x 0.15 (2 x 0.26)2 ––––––––– 0.20 x 0.15 (0.26)2 ––––––––– 0.07 x 0.02 (0.26)2 ––––––––– 0.13 x 0.13

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5 11 Why is ethanoic acid a stronger acid in liquid ammonia than in aqueous solution? A B C D Ammonia is a stronger base than water. Ammonium ethanoate is completely ionised in aqueous solution. Ammonium ethanoate is strongly acidic in aqueous solution. Liquid ammonia is a more polar solvent than water.

12 It is often said that the rate of a typical reaction is roughly doubled by raising the temperature by 10 °C. What explains this observation? A B C D Raising the temperature by 10 °C doubles the average energy of each molecule. Raising the temperature by 10 °C doubles the average velocity of the molecules. Raising the temperature by 10 °C doubles the number of molecular collisions in a given time. Raising the temperature by 10 °C doubles the number of molecules having more than a certain minimum energy.

13 A mixture of the oxides of two elements of the third period is dissolved in water. The solution is approximately neutral. What could be the constituents of the mixture? A B C D Al2O3 and MgO Na2O and MgO Na2O and P4O10 SO3 and P4O10

14 Aluminium chloride catalyses certain reactions by forming carbocations (carbonium ions) with chloroalkanes as shown. RCl + AlCl3 → R+ + AlCl – 4 Which property makes this reaction possible? A B C D AlCl3 is a covalent molecule. AlCl3 exists as the dimer Al2Cl6 in the vapour. The aluminium atom in AlCl 3 has an incomplete octet of electrons. The chlorine atom in RCl has a vacant p orbital.

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6 15 What are the products of the thermal decomposition of magnesium nitrate? A B C D magnesium nitride and oxygen magnesium oxide and nitrogen magnesium oxide, nitrogen and oxygen magnesium oxide, nitrogen dioxide and oxygen

16 Chlorine compounds show oxidation states ranging from –1 to +7. What are the reagent(s) and conditions necessary for the oxidation of elemental chlorine into a compound containing chlorine in the +5 oxidation state? A B C D AgNO3(aq) followed by NH3(aq) at room temperature concentrated H2SO4 at room temperature cold dilute NaOH(aq) hot concentrated NaOH(aq)

17 Which gaseous hydride most readily decomposes into its elements on contact with a hot glass rod? A B C D ammonia hydrogen chloride hydrogen iodide steam

18 Which reagent, when mixed and heated with ammonium sulphate, liberates ammonia? A B C D aqueous bromine dilute hydrochloric acid limewater acidified potassium dichromate(VI)

19 Which pollutant is formed in the internal combustion engine and, if not removed by the catalytic converter, may become involved in the formation of acid rain? A C B C8H18 C CO D NO

20 How many structural and cis-trans isomers are there for dichloropropene, C3H4Cl2? A 3 B 5 C 6 D 7

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7 21 The isomers, citric acid and isocitric acid, are intermediates in the Krebs cycle of the oxidation of glucose in living cells. CH2CO2H C(OH)CO2H CH2CO2H citric acid How many chiral centres does each acid possess? citric acid A B C D 0 0 1 1 isocitric acid 1 2 1 2 CH2CO2H CHCO2H CH(OH)CO2H isocitric acid

22 The compound hex-3-en-1-ol, P, has a strong ‘leafy’ smell of newly cut grass and is used in perfumery. CH3CH2CH=CHCH2CH2OH P What is produced when P is treated with an excess of hot concentrated acidic KMnO4? A B C D CH3CH2CH(OH)CH(OH)CH2CH2OH CH3CH2CH=CHCH2CO2H CH3CH2CHO and OCHCH2CH2OH CH3CH2CO2H and HO2CCH2CO2H

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8 23 The complete combustion of alkanes to produce carbon dioxide and water is an important exothermic reaction. Which line on the graph shows the relationship between the number of carbon atoms in the alkane and the number of moles of oxygen gas needed for complete combustion of the alkane? A B

number of moles of oxygen gas

C

D 1 number of carbon atoms in alkane

24 Cyclohexa-1,4–diene is treated with a solution of bromine in tetrachloromethane.

cyclohexa-1,4-diene Which product is formed? A Br Br Br Br B

Br Br C Br

Br

Br

D Br Br

Br
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Br

Br

9 25 Which reaction is not an electrophilic addition? A B C D CH2=CH2 + HI ?→ CH3CH2I CH3CH=CH2 + Br2 ?→ CH3CHBrCH2Br
2 4 CH3CH=CH2 + H2O ???→ CH3CH(OH)CH3

conc H SO

CH3CHO + HCN ?→ CH3CH(OH)CN

26 The reaction scheme outlines the production of one of the monomers of nylon 66 from compound X. KCN reduction H2N(CH2)6NH2 compound X NCCH2CH2CH2CH2CN in ethanol Which compound could be X? A B C D BrCH2CH2CH2CH2Br CH2=CHCH=CH2 HOCH2CH2CH2CH2OH HO2CCH2CH2CH2CH2CO2H

27 Chlorofluoroalkanes, commonly known as CFCs, undergo homolytic fission by ultraviolet irradiation in the stratosphere. Which radical could result from this irradiation of CHFClCF2Cl ? A B C D CHFCl CFCl

·

· · CHFCF2Cl · CFCl CF Cl
2

CHCl CF2Cl

28 In its reaction with sodium, 1 mol of a compound X gives 1 mol of H2(g). Which compound might X be? A B C D CH3CH2CH2CH2OH (CH3)3COH CH3CH2CH2CO2H CH3CH(OH)CO2H

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10 29 In a preparation of ethene, ethanol is added a drop at a time to a heated reagent Y. To purify the ethene it is bubbled through a solution Z and then collected. What could reagent Y and solution Z be? reagent Y A B C D acidified K2Cr2O7 concentrated H2SO4 concentrated H2SO4 ethanolic NaOH solution Z dilute NaOH dilute H2SO4 dilute NaOH concentrated H2SO4

30 The product of the reaction between propanone and hydrogen cyanide is hydrolysed under acidic conditions. What is the formula of the final product? A B C D CH3CH(OH)CO2H CH3CH2CH2CO2H (CH3)2CHCONH2 (CH3)2C(OH)CO2H

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11 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct

No other combination of statements is used as a correct response.

31 Silicon tetrachloride, SiCl4, is a liquid of low boiling point. In the presence of water it decomposes to form silicon(IV) oxide and hydrogen chloride. What types of bonding occur in SiCl4(I)? 1 2 3 co–ordinate bonding covalent bonding van der Waals forces

32 Long-chain alkanes are converted on an industrial scale into alkylsulphates for use as detergents, e.g. sodium lauryl sulphate. O CH3(CH2)10CH2O S O sodium lauryl sulphate What deductions about the properties of this substance can be made from this structure? 1 2 3 Part of the structure is polar and is water–attracting. The alkyl chain is soluble in oil droplets. All the C-C-C bond angles are tetrahedral. ONa

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12 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct

No other combination of statements is used as a correct response. 33 The conversion of graphite into diamond is an endothermic reaction (?H = +3 kJ mol–1). C(graphite) → C(diamond) Which statements are correct? 1 2 3 The enthalpy change of atomisation of diamond is smaller than that of graphite. The bond energy of the C–C bonds in graphite is greater than that in diamond. The enthalpy change of combustion of diamond is greater than that of graphite.

34 Which of the following statements are correct for the sequence of compounds below considered from left to right? NaF 1 2 3 MgO Al N SiC

The electronegativity difference between the elements in each compound increases. The formula-units of these compounds are isoelectronic (have the same number of electrons). The bonding becomes increasingly covalent.

35 Which statements are reasons why sulphur dioxide is used as a food preservative? 1 2 3 It is a reducing agent and therefore an anti-oxidant. It prevents alcohols forming sour-tasting acids. It does not smell and therefore can be used in more than trace quantities.

36 Why is the addition of concentrated sulphuric acid to solid potassium iodide unsuitable for the preparation of hydrogen iodide? 1 2 3 Hydrogen iodide is not displaced by sulphuric acid. Iodide ions are oxidised to iodine. The product is contaminated by sulphur compounds.

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13 37 What will always be a characteristic of a compound containing a single carbon atom with four different groups bonded to it? 1 2 3 It will have an optical isomer. It will have a chiral centre. It will have a structural isomer.

38 Chloroethane can be formed from bromoethane in two steps. step X C2H5Br C2H5OH step Y C2H5Cl

Which statements about these steps are correct? 1 2 3 Step X involves a nucleophilic substitution. Hot aqueous sodium hydroxide is the reagent in step X. Hot aqueous sodium chloride is the reagent in step Y.

39 When the apparatus below was used with compound Z, a brick-red precipitate formed in the righthand tube. air to pump

Fehling's reagent compound Z in acidified potassium dichromate(VI)

heat Which compound could be Z? 1 CH3CH(OH)CH3 2 CH3CH2CH2OH 3 CH3OH

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14 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct

No other combination of statements is used as a correct response.

40 Mevalonic acid is an intermediate in the biosynthesis of cholesterol, and is shown below. OH HO2CCH2CCH2CH2OH CH3 Which properties does mevalonic acid have? 1 2 3 It has only one chiral carbon atom. It can be esterified both by ethanoic acid and by ethanol, in the presence of H+ ions. It contains both primary and secondary alcohol groups.

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UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level CHEMISTRY Paper 1 Multiple Choice May/June 2004 1 hour
Additional Materials: Multiple Choice Answer Sheet Soft clean eraser Soft pencil (type B or HB is recommended) Data Booklet

9701/01

w w w e tr .X m ap eP s er om .c

READ THESE INSTRUCTIONS FIRST Write in soft pencil. Do not use staples, paper clips, highlighters, glue or correction fluid. Write your name, Centre number and candidate number on the answer sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. Answer all questions. For each question there are four possible answers A, B, C, and D. Choose the one you consider correct and record your choice in soft pencil on the separate answer sheet. Read the instructions on the answer sheet very carefully. Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet.

This document consists of 13 printed pages and 3 blank pages.
IB04 06_9701_01/3RP ? UCLES 2004

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2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct. 1 Which of these samples of gas contains the same number of atoms as 1g of hydrogen (Mr : H2, 2)? A B C D 2 22 g of carbon dioxide (Mr : CO2, 44) 8 g of methane (Mr : CH4, 16) 20 g of neon (Mr : Ne, 20) 8 g of ozone (Mr : O3, 48)

Self-igniting flares contain Mg3P2. With water this produces diphosphane, P2H4, which is spontaneously flammable in air. Which equation that includes the formation of diphosphane is balanced? A B C D Mg3P2 + 6H2O ? 3Mg(OH)2 + P2H4 Mg3P2 + 6H2O ? 3Mg(OH)2 + P2H4 + H2 2Mg3P2 + 12H2O ? 6Mg(OH)2 + P2H4 + 2PH3 2Mg3P2 + 12H2O ? 6Mg(OH)2 + 3P2H4

3

Use of the Data Booklet is relevant to this question. Most modern cars are fitted with airbags. These work by decomposing sodium azide to liberate nitrogen gas, which inflates the bag. 2NaN3 ? 3N2 + 2Na A typical driver’s airbag contains 50 g of sodium azide. Calculate the volume of nitrogen this will produce at room temperature. A 9.2 dm3 B 13.9 dm3 C 27.7 dm3 D 72.0 dm3

4

What is the order of increasing energy of the listed orbitals in the atom of titanium? A B C D 3s 3p 3d 4s 3s 3p 4s 3d 3s 4s 3p 3d 4s 3s 3p 3d

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3 5 Which of the following particles would, on losing an electron, have a half-filled set of p orbitals? A 6 C– B N C N– D O
+

Magnesium oxide is used to line industrial furnaces because it has a very high melting point. Which type of bond needs to be broken for magnesium oxide to melt? A B C D co-ordinate covalent ionic metallic

7

Which solid exhibits more than one kind of chemical bonding? A B C D brass copper diamond ice

8

The standard enthalpy changes of formation of iron(II) oxide, FeO(s), and aluminium oxide, Al2O3(s), are –266 kJ mol–1 and –1676 kJ mol–1 respectively. What is the enthalpy change under standard conditions for the following reaction? 3FeO(s) + 2Al (s) ? 3Fe(s) + Al 2O3(s) A + 878 kJ B – 878 kJ C –1942 kJ D –2474 kJ

9

Which substance, in 1 mol dm–3 aqueous solution, would have the same hydrogen ion concentration as 1 mol dm-3 of hydrochloric acid? A B C D ethanoic acid nitric acid sodium hydroxide sulphuric acid

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4 10 When vanadium(II) compounds are dissolved in water, the following equilibrium is established. V 2+ + H2O V 3+ + 1 H 2 + OH–
2

What would alter the composition of the equilibrium mixture in favour of the V 2+ ions? A B C D adding an acid adding a reagent that selectively precipitates V3+ ions allowing the hydrogen to escape as it forms making the solution more alkaline

11 In an industrial process, two gases X and Y react together to form a single gaseous product Z. X (g) + Y (g) Z (g)

The percentage yield of product Z varies according to the pressure and the temperature as shown in the graphs. 100 90 80 70 equilibrium % of Z 60 50 40 30 20 10 0 25 100 200 300 400 pressure / atm 773 K 673 K 373 K 473 K 573 K

Which statement about this equilibrium reaction is correct? A B C D Decreasing the temperature decreases the value of the equilibrium constant. Decreasing the temperature increases the rate of this reaction. Increasing the pressure increases the value of the equilibrium constant. The reaction is exothermic in the forward direction.

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5 12 Four reactions of the type shown are studied at the same temperature. X (g) + Y (g) ? Z (g) Which is the correct reaction pathway diagram for the reaction that would proceed most rapidly and with good yield?
A B

energy

energy

reactant C

product

reactant D

product

energy

energy

reactant

product

reactant

product

13 Which of these equations represents the reaction of sulphur dioxide with an excess of aqueous sodium hydroxide? A B C D SO2 + NaOH ? NaHSO3 SO2 + 2NaOH ? Na2SO3 + H2O SO2 + 2NaOH ? Na2SO4 + H2O SO2 + 2NaOH ? Na2SO4 + H2

14 Which ion is most polarising? A B C D Al 3+ Ba2+ Mg2+ Na+

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6 15 Which element has the same oxidation number in all of its known compounds? A B C D beryllium chlorine nitrogen sulphur

16 Due to their similar ionic radii, the reactions of lithium and magnesium and their corresponding compounds are very similar. Which statement concerning the reactions of lithium and its compounds is correct? A B C D Lithium carbonate decomposes on heating at a relatively low temperature, forming lithium oxide and carbon dioxide. Lithium nitrate decomposes on heating, forming lithium nitrite and oxygen. Lithium only burns slowly in oxygen. Lithium reacts violently with cold water, liberating hydrogen.

17 Which statement is most likely to be true for astatine, which is below iodine in Group VII of the Periodic Table? A B C D Astatine and aqueous potassium chloride react to form aqueous potassium astatide and chlorine. Potassium astatide and hot dilute sulphuric acid react to form white fumes of only hydrogen astatide. Silver astatide reacts with dilute aqueous ammonia in excess to form a solution of a soluble complex. Sodium astatide and hot concentrated sulphuric acid react to form astatine.

18 Use of the Data Booklet is relevant to this question. In the commercial electrolysis of brine, the products are chlorine, hydrogen and sodium hydroxide. What is the maximum yield of each of these products when 58.5 kg of sodium chloride are electrolysed as brine? yield of chlorine / kg A B C D 35.5 35.5 71 71 yield of hydrogen / kg 1 2 1 2 yield of sodium hydroxide / kg 40 40 40 80

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7 19 Nitrogen dioxide and sulphur dioxide have some properties in common. Which property is shown by one of these compounds, but not by the other? A B C D forms ‘acid-rain’ is a reducing agent is insoluble in water is used as a food-preservative

20 Which molecule is planar? A B C D NF3 C2Cl 4 C3H6 C3H8

21 Which of these always applies to a nucleophile? A B C D It attacks a double bond. It has a lone pair of electrons. It is a single atom. It is negatively charged.

22 Compound P displays cis-trans isomerism and gives a red-brown precipitate with Fehling’s solution. What is P?
A H C H C CH3 CH3 CH2CHO H C C H B COCH3

C H C H C CHO H CH3 CH3 C

D H C CHO

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8 23 Which compound could not be obtained from cracking a sample of nonane, CH3(CH2)7CH3? A B C D CH3CH=CHCH=CHCH2CH2CH2CH3 CH3CH2CH2CH2CH3 CH3CH2CH2CH2CH2CH=CH2 (CH3CH2CH2)3CH

24 In which way are ethene and propane similar? CH2=CH2 ethene A B C D CH3CH2CH3 propane

They are both obtained by the dehydration of alcohols. They are both neutral to an indicator solution. They can both be hydrogenated using a suitable catalyst. They can both undergo polymerisation under suitable conditions.

25 Which reaction in the catalytic converter does not remove hazardous and polluting gases from the exhaust fumes of a motor car?

gases going out

gases going in: carbon monoxide, hydrocarbons and oxides of nitrogen

surfaces coated with platinum and rhodium catalyst

These equations are qualitative and unbalanced. [HC = unburnt hydrocarbons; NOx = oxides of nitrogen] A B C D HC + NOx ? H2O + CO + N2 CO + NOx ? CO2 + N2 HC + NOx ? H2O + CO2 + N2 CO + O2 ? CO2

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9 26 A possible mechanism of the hydrolysis of 2-chloro-2-methylpropane is shown.
CH3 CH3 C CH3 Cl slow CH3 CH3 C+ + Cl CH3
_

CH3 CH3 C+ + CH3 OH
_

CH3 fast CH3 C CH3 OH

Which diagram represents the reaction profile for this mechanism?
A B C D

energy

energy

energy

reaction path

reaction path

reaction path

energy
reaction path

27 Ethene reacts with aqueous bromine to give two products, CH2BrCH2Br and CH2BrCH2OH. Which statement is correct for these products? A B C D Both products are obtained in this reaction by electrophilic substitution. Both products are obtained in this reaction by nucleophilic addition. Both products can be hydrolysed to form the same diol. Both products can form hydrogen bonds with water.

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10 28 Compound X · · has the molecular formula C10H14O; is unreactive towards mild oxidising agents.

What is the structure of the compound formed by dehydration of X?
A CH2 CH2 CH CH2 CH2 B CH CH CH3

C CH3 CH CH CH2

D CH3 C CH CH3

29 For which pair of compounds can the members be distinguished by means of Tollens’ test (the + use of a solution containing Ag(NH3) 2 )? A B C D CH3CHO and CH3COCH3 CH3COCH3 and C2H5COCH3 CH3COCH3 and CH3CO2CH3 CH3CO2H and CH3CO2CH3

30 Compound X changes the colour of acidified sodium dichromate(VI) from orange to green. 1 mol of X reacts with 2 mol of HCN(g). What could X be? A B C D CH3COCH2COCH3 CH3CH2CH2CHO H2C=CHCH2CHO OHCCH2CH2CHO

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11 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct

No other combination of statements is used as a correct response. 31 The isotope cobalt-60 ( 60 27 Co ) is used to destroy cancer cells in the human body. Which statements about an atom of cobalt-60 are correct? 1 2 3 It contains 33 neutrons. Its nucleus has a relative charge of 27+. It has a different number of neutrons from the atoms of other isotopes of cobalt.

32 The conversion of graphite has only a small positive value of DH. C (graphite) ? C (diamond) DH = +2.1 kJ mol –1

However, the production of synthetic diamonds using this reaction is very difficult. Which statements help to explain this? 1 2 3 The activation energy of the reaction is large. An equilibrium exists between diamond and graphite. Only exothermic reactions can be made to occur readily.

33 Which statements about the properties of a catalyst are correct? 1 2 3 A catalyst increases the average kinetic energy of the reacting particles. A catalyst increases the rate of the reverse reaction. A catalyst has no effect on the enthalpy change DH of the reaction.
o

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12 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct

No other combination of statements is used as a correct response. 34 Which pairs of compounds contain one that is giant ionic and one that is simple molecular? 1 Al 2O3 and Al 2Cl 6 2 SiO2 and SiCl 4 3 P4O10 and PCl 3 35 When coal is burnt, gaseous oxides of carbon and sulphur are formed which pollute the atmosphere. One method of preventing such pollution involves adding calcium carbonate to the burning coal. The temperature of the process causes the decomposition of the calcium carbonate into calcium oxide. Which reactions will be important in helping to reduce atmospheric pollution? 1 2 3 Calcium oxide reacts with sulphur dioxide to form calcium sulphite. Calcium oxide reacts with sulphur dioxide and more air to form calcium sulphate. Calcium oxide reacts with carbon monoxide to form calcium carbonate.

36 When a hot glass rod is placed in a gas jar of hydrogen iodide, there is an immediate reaction as the hydrogen iodide decomposes. Which statements about this reaction are correct? 1 2 3 Hydrogen iodide is purple coloured. The hot rod provides the activation energy. One of the products is a solid.

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13 37 Acrolein is produced in photochemical smog. It has a strong smell, irritates eyes and mucous membranes and is carcinogenic.
H C C H H acrolein C O H

What can be deduced from this structure? 1 2 3 All bond angles are approximately 120 o. It will undergo electrophilic addition reactions. It will undergo nucleophilic addition reactions.

38 What can be produced when an aqueous solution of butan-1-ol is heated with dilute acidified potassium manganate(VII)? 1 2 3 butanal butanoic acid butanone

39 Which carbonyl compounds could be easily oxidised to carboxylic acids that are readily soluble in cold water?
1 CH3CH2CHO 2 3 CHO CO

40 Which properties of poly(alkenes) and of pvc can cause their disposal to be difficult? 1 2 3 Poly(alkenes) are highly flammable. Poly(alkenes) are non–biodegradable. pvc produces harmful combustion products.

? UCLES 2004

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UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level CHEMISTRY Paper 1 Multiple Choice May/June 2005 1 hour
Additional Materials: Multiple Choice Answer Sheet Soft clean eraser Soft pencil (type B or HB is recommended) Data Booklet

9701/01

w w w e tr .X m ap eP s er om .c

READ THESE INSTRUCTIONS FIRST Write in soft pencil. Do not use staples, paper clips, highlighters, glue or correction fluid. Write your name, Centre number and candidate number on the answer sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. Answer all questions. For each question there are four possible answers A, B, C and D. Choose the one you consider correct and record your choice in soft pencil on the separate answer sheet. Read the instructions on the answer sheet very carefully. Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet. You may use a calculator.

This document consists of 15 printed pages and 1 blank page.
IB05 06_9701_01/3RP ? UCLES 2005

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2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct. 1 A pure hydrocarbon is used in bottled gas for cooking and heating. When 10 cm3 of the hydrocarbon is burned in 70 cm3 of oxygen (an excess), the final gaseous mixture contains 30 cm3 of carbon dioxide and 20 cm3 of unreacted oxygen. All gaseous volumes were measured under identical conditions. What is the formula of the hydrocarbon? A C2H6 B C3H6 C C3H8 D C4H10

2

On collision, airbags in cars inflate rapidly due to the production of nitrogen. The nitrogen is formed according to the following equations. 2NaN3 → 2Na + 3N2 10Na + 2KNO3 → K2O + 5Na2O + N2 How many moles of nitrogen gas are produced from 1 mol of sodium azide, NaN3? A 1.5 B 1.6 C 3.2 D 4.0

3

The first six ionisation energies of four elements, A to D, are given. Which element is most likely to be in Group IV of the Periodic Table? ionisation energy / kJ mol?1 A B C D

1st 494 736 1090 1400

2nd 4560 1450 2350 2860

3rd 6940 7740 4610 4590

4th 9540 10500 6220 7480

5th 13400 13600 37800 9400

6th 16600 18000 47000 53200

4

In which species are the numbers of electrons and neutrons equal? A
9 4 Be

B

19 9F

C

23 + 11 Na

D

18 2– 8O

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3 5 The diagram shows the variation of the boiling points of the hydrogen halides.

b.p.

HF

HCl

HBr

HI

What explains the higher boiling point of hydrogen fluoride? A B C D The bond energy of HF molecules is greater than in other hydrogen halides. The effect of nuclear shielding is much reduced in fluorine which polarises the HF molecule. The electronegativity of fluorine is much higher than for other elements in the group. There is hydrogen bonding between HF molecules.

6

Three substances, R, S, T, have physical properties as shown. electrical conductivity substance R S T mp / oC 801 2852 3550 bp / oC of solid 1413 3600 4827 poor poor good of liquid good good not known

What could be the identities of R, S and T ? R A B C D NaF NaBr NaCl NaBr S KCl BaO MgO CaO T Cu SiO2 C [graphite] C [diamond]

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4 7 Iodine trichloride, ICl3, is made by reacting iodine with chlorine. I2(s) + Cl2(g) → 2ICl(s) ; ?H o = +14 kJ mol–1 ICl(s) + Cl2(g) → ICl3(s) ; ?H o = –88 kJ mol–1 By using the data above, what is the enthalpy change of the formation for solid iodine trichloride? A B C D –60 kJ mol–1 –74 kJ mol–1 –81 kJ mol–1 –162 kJ mol–1

8

In the extraction of aluminium by electrolysis, why is it necessary to dissolve aluminium oxide in molten cryolite? A B C D to reduce the very high melting point of the electrolyte cryolite provides the ions needed to carry the current cryolite reacts with the aluminium oxide to form ions molten aluminium oxide alone would not conduct electricity

9

A cheap carbon monoxide detector for a gas heater consists of a patch containing palladium chloride crystals. When carbon monoxide is present, the crystals turn from orange to black as the following reaction takes place. CO(g) + PdCl2(s) + H2O(l) → CO2(g) + Pd(s) + 2HCl(aq) orange black Which is the element whose oxidation number decreases in this reaction? A B C D carbon chlorine hydrogen palladium

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5 10 The dissociation of dinitrogen tetraoxide into nitrogen dioxide is represented by the equation below. N2O4(g) 2NO2(g); ?H o = +57 kJ mol –1

If the temperature of an equilibrium mixture of the gases is increased at constant pressure, will the volume of the mixture increase or decrease and why? A B C D The volume will increase, but only because of a shift of equilibrium towards the right. The volume will increase, both because of a shift of equilibrium towards the right and also because of thermal expansion. The volume will stay the same, because any thermal expansion could be exactly counteracted by a shift of equilibrium towards the left. The volume will decrease, because a shift of equilibrium towards the left would more than counteract any thermal expansion.

11 The reaction represented by the following equation was carried out. HCO2CH3(aq) + NaOH(aq) → HCO2Na(aq) + CH3OH(aq) Which graph best shows the relationship between [CH3OH(aq)] and t, the time from mixing of the reactants?

A [CH3OH(aq)] [CH3OH(aq)]

B

0 0 C [CH3OH(aq)]

t

0 0 D [CH3OH(aq)]

t

0 0

t

0 0

t

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6 12 The following species contain the same number of electrons. In which order do their radii increase? smallest radius A B C D Ar Ca2+ Ca2+ K+ K+ Ar K+ Ar largest radius Ca2+ K+ Ar Ca2+

13 Use of the Data Booklet is relevant to this question. Which element is likely to have an electronegativity similar to that of aluminium? A B C D barium beryllium magnesium strontium

14 Use of the Data Booklet is relevant to this question. Which is true for calcium or its compounds compared with the corresponding statements for magnesium? A B C D Calcium has a smaller atomic radius. Calcium oxide reacts less vigorously with water. Calcium reacts more vigorously with water. The sum of the first two ionisation energies of calcium is greater.

15 Concentrated sulphuric acid is added to separate solid samples of sodium chloride, sodium bromide or sodium iodide. With which sample(s) does sulphuric acid act as an oxidising agent? A B C D sodium chloride only sodium chloride and sodium bromide sodium bromide and sodium iodide sodium iodide only

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7 16 Which graph correctly describes a trend found in the halogen group?

A bond length in X2 Cl2 Br2 I2 strength of van der Waals' forces Cl2

B

Br2

I2

C boiling point of X2 Cl2 Br2 I2 bond energy of HX

D

H-Cl H-Br H-I

17 Limestone, CaCO3, has been used as a building material for thousands of years, and was used on the Pyramids in Egypt. In the past hundred years many limestone buildings have begun to suffer damage. What is the cause of this damage? A B C D hydrocarbon emissions from motor vehicles increased temperature due to global warming increased ultraviolet radiation as the ozone layer is destroyed sulphur dioxide from fossil fuels forming ‘acid rain’

18 In an historically famous experiment W?hler heated “inorganic” ammonium cyanate in the absence of air. The only product of the reaction was “organic” urea, CO(NH2)2. No other products were formed in the reaction. What is the formula of the cyanate ion present in ammonium cyanate? A CNO– B CNO2– C CO– D NO–

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8 19 Bromomethane, CH3Br, is used as a fumigant to destroy insect pests in grain that is to be stored. It can be made by reacting methanol with hydrogen bromide. CH3OH + HBr → CH3Br + H2O What type of reaction is this? A B C D condensation electrophilic substitution free radical substitution nucleophilic substitution

20 Prop-2-en-1-ol (allyl alcohol) has the following structure.
H H C H H C C OH H

Which reagent would react with prop-2-en-1-ol to form a product that could exist as optical isomers? A B C D bromine hydrogen and nickel phosphorus pentachloride sodium

21 Under the Montreal Protocol the use of chlorofluorocarbons is to be phased out. Fluorocarbons are often used to replace them. One chlorofluorocarbon which was widely used as a solvent is CCl2FCCl F2 and large stocks of it remain. One process to use up these stocks is to convert it into the fluorocarbon CH2FCF3 by the following route.

step 1 CCl2FCCl F2
What type of reaction is step 1? A B C D elimination free radical substitution isomerisation nucleophilic substitution

step 2 CCl3CF3 CCl2FCF3

step 3 CH2FCF3

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9 22 When bromine reacts with propene in an organic solvent at room temperature, what is the mechanism by which the bromine attacks the propene? A B C D electrophilic addition electrophilic substitution nucleophilic addition nucleophilic substitution

23 Dichlorodifluoromethane, CCl2F2, has been used in aerosol propellants and as a refrigerant. Which statement helps to explain why dichlorodifluoromethane is chemically inert? A B C D The carbon-fluorine bond energy is large. The carbon-fluorine bond has a low polarity. Fluorine is highly electronegative. Fluorine compounds are non-flammable.

24 Under identical conditions, even though it proceeds by the same mechanism, reaction 1 is faster than reaction 2. reaction 1 reaction 2 CH3CHBrCH3 + NaCN → CH3CH(CN)CH3 + NaBr CH3CHBrCH3 + NaI → CH3CHICH3 + NaBr

What factor will explain this result? A B C D The C The C I bond is a stronger bond than the C N bond is a stronger bond than the C Br bond. I bond.

The cyanide ion is a stronger nucleophile than the iodide ion. The cyanide ion is a weaker nucleophile than the iodide ion.

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10 25 Ethyl ethanoate is a very important solvent in industry. Currently, researchers are investigating ways of producing the ester from cheap, low grade ethanol by the following process.
step 1 CH3CH2OH CH3CHO step 2 CH3CH2OCHCH3 OH step 3 CH3CH2OCOCH3

What types of reaction are steps 1 and 3? step 1 A B C D elimination elimination oxidation oxidation step 3 esterification isomerisation esterification oxidation

26 Malic acid occurs in apples.
OH H C CO2H malic acid CH2CO2H

Which substance will react with all three –OH groups present in the malic acid molecule? A B C D ethanol in the presence of concentrated sulphuric acid potassium hydroxide sodium sodium carbonate

27 Which compound reacts with its own oxidation product (an oxidation which involves no loss of carbon) to give a sweet-smelling liquid? A B C D propanal propanoic acid propanone propan–1–ol

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11 28 Which reagent could be used to distinguish between CH3CH(OH)CH2CHO and CH3COCH2CH2OH ? A B C D acidified potassium dichromate(VI) dilute sulphuric acid 2,4–dinitrophenylhydrazine Fehling’s reagent

29 Ibuprofen is an anti-inflammatory drug.
(CH3)2CHCH2 ibuprofen CH(CH3)CO2H

What reaction would lead to its formation?
CH3 A (CH3)2CHCH2 C CH2 B (CH3)2CHCH2 CH(CH3)CHO + warm acidified K2Cr2O7 + hot concentrated KMnO4

C

(CH3)2CHCH2

CH(CH3)COCH3

+ warm H2SO4(aq)

D

CH2=C(CH3)CH2

CCOCH3 CH2

+ H2 / Pt catalyst

30 In many countries plastic waste is collected separately and sorted. Some of this is incinerated to provide heat for power stations. Why is pvc, polyvinylchloride, removed from any waste that is to be incinerated? A B C D It can be melted down and re-used. Its combustion products are harmful. It destroys the ozone layer. It does not burn easily.

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12 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct

No other combination of statements is used as a correct response. 31 Which of the following molecules and ions have a regular trigonal planar shape? 1 2 3 Al Cl3 CH3 PH3
+

32 A quantity of solid Y was placed in a previously evacuated vessel and the apparatus was then held at a series of different temperatures. At each temperature, the mass of Y in the vapour state was calculated from pressure measurements. The results are shown below.
mass of vapour m

T

temperature

What can be deduced from the diagram? 1 2 3 The mass of Y used in the experiment was m. The pressure of the vapour was constant for all temperatures above temperature T. Liquid appeared at temperature T.

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13 33 Which of the enthalpy changes of the following reactions can only be obtained by application of Hess’ Law? 1 2 3 The hydration of anhydrous copper sulphate to form crystals of CuSO4.5H2O. The formation of methane from its elements. The combustion of glucose, C6H12O6.

34 The stoichiometry of a catalysed reaction is shown by the equation below. P (g) + Q (g) R (g) + S (g)

Two experiments were carried out in which the production of R was measured against time. The results are shown in the diagram below.

experiment 1 amount of R experiment 2

0 0 time

Which changes in the conditions from experiment 1 to experiment 2 might explain the results shown? 1 2 3 Less of P was used. A different catalyst was used. Product S was continuously removed from the reaction vessel.

35 Use of the Data Booklet is relevant to this question. Which properties would be expected from radium, 88Ra, or its compounds? 1 2 3 Radium carbonate decomposes only at a very high temperature. Radium hydroxide is very insoluble. Radium does not react with cold water.

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14 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct

No other combination of statements is used as a correct response. 36 The number of moles of chlorine that react with 1 mol of X is twice the number of moles of chlorine that react with 1 mol of Y. Which of these pairs could be X and Y? X 1 2 3 Mg(s) H2 cold NaOH(aq) Y Na(s) KBr(aq) hot NaOH(aq)

37 Which statements are true about the Haber process for the manufacture of ammonia? 1 2 3 At higher temperatures, the yield goes down but the rate of production of ammonia is faster. At higher pressures, the yield goes down but the rate of production of ammonia is faster. In the presence of a catalyst, the yield goes down but the rate of production of ammonia is faster.

38 Which compounds can be obtained from ethene in a single reaction?
1 2 3 CH3CH3 ( CH2CH2 )
n

HOCH2CH2OH

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15 39 The steroid shown is an intermediate compound obtained during the synthesis of Formestane which is used in the treatment of breast cancer.
CH3 O CH3

HO OH

Which statements about this compound are correct? 1 2 3 It reacts with hydrogen cyanide in a nucleophilic addition reaction. It can be oxidised by warm acidified potassium dichromate(VI) to a carboxylic acid. It will react with Fehling’s solution.

40 A sun protection cream contains the following ester as its active ingredient.
CH2CH2 CH2CH2CH2CH3

CH3O

CH CHCO2CH2CH

What are the products of its partial or total hydrolysis by aqueous sodium hydroxide?
1 CH3CH2CH2CH2CH(CH2CH3)CH2OH CH3O CH3O - Na+ CH CHCO2
+ CO2 Na

2

3

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16 BLANK PAGE

Every reasonable effort has been made to trace all copyright holders where the publishers (i.e. UCLES) are aware that third-party material has been reproduced. The publishers would be pleased to hear from anyone whose rights they have unwittingly infringed. University of Cambridge International Examinations is part of the University of Cambridge Local Examinations Syndicate (UCLES), which is itself a department of the University of Cambridge.

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UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level CHEMISTRY Paper 1 Multiple Choice May/June 2006 1 hour
Additional Materials: Multiple Choice Answer Sheet Soft clean eraser Soft pencil (type B or HB is recommended) Data Booklet

9701/01

w w w e tr .X m ap eP s er om .c

READ THESE INSTRUCTIONS FIRST Write in soft pencil. Do not use staples, paper clips, highlighters, glue or correction fluid. Write your name, Centre number and candidate number on the Answer Sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. Answer all questions. For each question there are four possible answers A, B, C and D. Choose the one you consider correct and record your choice in soft pencil on the separate Answer Sheet. Read the instructions on the Answer Sheet very carefully. Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet.

This document consists of 14 printed pages and 2 blank pages.
IB06 06_9701_01/3RP ? UCLES 2006

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2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct. 1 N2O4 is a poisonous gas. It can be disposed of safely by reaction with sodium hydroxide. N2O4(g) + 2NaOH(aq) → NaNO3(aq) + NaNO2(aq) + H2O(l) What is the minimum volume of 0.5 mol dm–3 NaOH(aq) needed to dispose of 0.02 mol of N2O4? A 2 8 cm3 B 12.5 cm3 C 40 cm3 D 80 cm3

A sample of chlorine containing isotopes of mass numbers 35 and 37 was analysed in a mass-spectrometer.
+ were recorded? How many peaks corresponding to Cl 2

A 3

2

B

3

C

4

D

5

Gallium nitride, GaN, could revolutionise the design of electric light bulbs because only a small length used as a filament gives excellent light at low cost. Gallium nitride is an ionic compound containing the Ga3+ ion. What is the electron arrangement of the nitrogen ion in gallium nitride? A B C D 1s2 2s2 1s2 2s2 2p3 1s2 2s2 2p4 1s2 2s2 2p6
201 81

4

A radioactive isotope of thallium, attack. Which statement about A B C D
201 81

Tl, is used to assess damage in heart muscles after a heart

Tl is correct?

This isotope has a nucleon number of 120. The number of electrons in one atom of this isotope is 81. The number of neutrons in one atom of this isotope is 201.
201 82 X

is an isotope of

201 81

Tl.

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3 5 In which process are hydrogen bonds broken? A B C D 6 H2(l) → H2(g) NH3(l) → NH3(g) 2HI(g) → H2(g) + I2(g) CH4(g) → C(g) + 4H(g)

Which of the following least resembles an ideal gas? A B C D ammonia helium hydrogen trichloromethane represent

7

The diagram shows part of the lattice structures of solids X and Y. [In X, particles of different elements.]

X

Y

What are the types of bonding present in X and Y? X A B C D covalent ionic ionic metallic Y metallic covalent metallic ionic

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4 8 In the conversion of compound X into compound Z, it was found that the reaction proceeded by way of compound Y, which could be isolated. The following steps were involved. X → Y ; ?H, positive Y → Z ; ?H, negative Which reaction profile fits these data?
A B Y C D

energy

energy

energy

energy

Y X progress of reaction

Y Z X progress of reaction

X Y progress of reaction Z

X Z progress of reaction

Z

9

The nickel-cadmium rechargeable battery is based upon the following overall reaction. Cd + 2NiOOH + 4H2O → Cd(OH)2 + 2Ni(OH)2.H2O What is the oxidation number of nickel at the beginning and at the end of the reaction? beginning A B C D +1.5 +2 +3 +3 end +2 +3 +2 +4

10 At a total pressure of 1.0 atm, dinitrogen tetraoxide is 50 % dissociated at a temperature of 60 oC, according to the following equation. N2O4 2NO2

What is the value of the equilibrium constant, Kp, for this reaction at 60 oC? A
1

/3 atm

B

2

/3 atm

C

4

/3 atm

D

2 atm

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5 11 Swimming pool water can be kept free of harmful bacteria by adding aqueous sodium chlorate(I), NaOCl. This reacts with water to produce HOCl molecules which kill bacteria. OCl –(aq) + H2O OH–(aq) + HOCl (aq)

In bright sunshine, the OCl – ion is broken down by ultra-violet light. OCl –(aq) + uv light → Cl –(aq) + ?O2(g) Which method would maintain the highest concentration of HOCl (aq)? A B C D acidify the pool water add a solution of chloride ions add a solution of hydroxide ions bubble air through the water

12 Which solid-line curve most accurately represents the distribution of molecular speeds in a gas at 500 K if the dotted-line curve represents the corresponding distribution for the same gas at 300 K?

A fraction of molecules fraction of molecules

B

speed

speed

C fraction of molecules fraction of molecules

D

speed

speed

13 In which pair is the radius of the second atom greater than that of the first atom? A Na, Mg B Sr, Ca C P, N D Cl, Br

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6 14 The oxide and chloride of an element X are separately mixed with water. The two resulting solutions have the same effect on litmus. What is element X? A B C D sodium magnesium aluminium phosphorus

15 Aluminium chloride sublimes at 178 oC. Which structure best represents the species in the vapour at this temperature?
A Cl Al Cl Cl Cl Al Cl Cl Cl Cl Al Cl B Cl Al Cl Cl C Al + 3Cl D Al 3+(Cl –)3

16 Use of the Data Booklet is relevant to this question. What mass of solid residue can be obtained from the thermal decomposition of 4.10 g of anhydrous calcium nitrate? A 0.70 g B 1.00 g C 1.40 g D 2.25 g

17 What happens when chlorine is bubbled through aqueous potassium iodide? A B C D Chlorine is oxidised to chloride ions. Hydrochloric acid is formed. Iodide ions are oxidised to iodine. Potassium iodide is reduced to iodine.

18 The emissions from a power station contain about 14 tonnes of SO2 per hour from the oxidation of FeS2 contained in the coal. What is the most practical way of preventing the SO2 from being released into the atmosphere? A B C D Cool the gases and the SO2 will liquefy and can be removed. Dissolve the ionic FeS2 in hexane. Pass the emissions through a bed of calcium oxide. Pass the gases through concentrated sulphuric acid to dissolve the SO2.

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7 19 The gaseous oxides of nitrogen have positive enthalpy changes of formation. Which factor is likely to make the most significant contribution to these enthalpy changes? A B C D the high bond energy of the nitrogen molecule, N2 the high electron affinity of nitrogen atoms the high electron affinity of oxygen atoms the similarity of the electronegativities of oxygen and nitrogen

20 A new industrial preparation of ethyl ethanoate has been developed using cheap sources of ethanol.
Cu catalyst CH3CH2OH – H2 CH3CHO Cu catalyst + CH3CH2OH CH3CH(OH)OCH2CH3 Cu catalyst – H2 CH3CO2CH2CH3

Which process is involved at some stage in this reaction sequence? A B C D disproportionation electrophilic addition nucleophilic addition reduction

21 Warfarin is used as a rat poison.
O O C C CH CH2 C O CH3

C OH warfarin

How many chiral centres are present in the warfarin molecule? A 0 B 1 C 2 D 3

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8 22 The structures below show isomers of C6H12.

1 CH3 C H C C 2H 5 H CH3 CH3 C

2 C2H 5 C CH3 C 2H 5 C CH3

3 H C CH3 H C 2H 5 C

4 CH3 C CH3

In which pair are the members cis-trans isomers of each other? A 1 and 2 B 1 and 3 C 1 and 4 D 2 and 4

23 Use of the Data Booklet is relevant to this question. In which reaction is the relative molecular mass of the organic product the largest? A B C D bromoethane + aqueous sodium hydroxide bromoethane + alcoholic sodium hydroxide ethane + bromine ethanol + phosphorus pentachloride

24 Light initiates the following reaction. alkane + chlorine → chloroalkane + hydrogen chloride What happens to chlorine in this photochemical reaction? A B C D heterolytic fission to give an electrophile homolytic fission to give an electrophile heterolytic fission to give a free radical homolytic fission to give a free radical

25 High-energy irradiation in the stratosphere produces radicals from chlorofluoroalkanes, commonly known as CFCs. Which radical could result from this irradiation of CHFClCF2Cl?
A B C D CHFClCFCl CHClCF2Cl CHFCF2Cl CFClCF2Cl

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9 26 Which reagent could detect the presence of alcohol in a petrol consisting mainly of a mixture of alkanes and alkenes? A B C D Na Br2 (in CCl4) KMnO4(aq) 2,4-dinitrophenylhydrazine

27 Which alcohol may be oxidised to a product which reacts with 2,4-dinitrophenylhydrazine reagent but not with Fehling’s reagent? A B C D butan-1-ol butan-2-ol 2-methylpropan-1-ol 2-methylpropan-2-ol

28 The first stage in the synthesis of antipyrine, a drug used in reducing fever, is the reaction between compound P and phenylhydrazine.
CH3COCH2CO2CH2CH3 P + NHNH2 phenylhydrazine Q

What is the product Q of this first stage?

A

CH3COCH2CONH

B

NHCH2CO2CH2CH3

C

CH3COCH2CO

NHNH2

D

NHN CH3CCH2CO2CH2CH3

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10 29 Aldehydes and ketones are carbonyl compounds. Which of them react both with NaBH4 and with Tollens’ reagent? A B C D both aldehydes and ketones aldehydes only ketones only neither aldehydes nor ketones

30 Which compound is a product of the hydrolysis of CH3CO2C3H7 by boiling aqueous sodium hydroxide? A CH3OH B C3H7OH C C3H7CO2H D
? C3H7CO 2 Na +

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11 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct

No other combination of statements is used as a correct response. 31 The Group IV elements carbon, silicon and germanium all exist in a diamond structure. The bond lengths in these structures are given below. element X bond length X–X / nm C 0.154 Si 0.234 Ge 0.244

Why does the bond length increase down the group? 1 2 3 Orbital overlap decreases down the group. Atomic radius increases down the group. Nuclear charge increases down the group.

32 Sodium ions can be formed from sodium atoms. Na(s) → Na+(g) Which quantities are required to calculate the enthalpy change of formation of gaseous sodium ions? 1 2 3 enthalpy change of atomisation of sodium first ionisation energy of sodium enthalpy change of formation of sodium

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12 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct

No other combination of statements is used as a correct response. 33 Hydrazine, N2H4, is widely used as a rocket fuel because it reacts with oxygen as shown, producing ‘environmentally friendly’ gases. N2H4(l) + O2(g) → N2(g) + 2H2O(g) ?H = –534 kJ mol–1

Despite its use as a rocket fuel, hydrazine does not spontaneously burn in oxygen. Why does hydrazine not burn spontaneously? 1 The activation energy is too high. 2 The N≡N bond is very strong. 3 Hydrazine is a liquid. 34 Compound X ? does not conduct electricity when in a liquid state, ? when added to water produces a solution that readily conducts electricity. What could X be? 1 MgCl2 2 SiCl4 3 PCl3

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13 35 Hydroxyapatite, a basic calcium phosphate, Ca(OH)2.3Ca3(PO4)2, is the mineral found in bone. In older people, calcium ions can be lost from the hydroxyapatite, weakening the bone structure. In such cases, strontium salts are administered to strengthen the bone. The strontium ions replace the lost calcium ions in the hydroxyapatite. Which statements are correct? 1 2 3 Strontium ions are nearly the same size as calcium ions and so may easily replace them in the hydroxyapatite. Strontium hydroxide is less soluble than calcium hydroxide and so will precipitate better in the bone structure. There is ionic, covalent and metallic bonding in hydroxyapatite which gives it strength.

36 Ammonia and chlorine react in the gas phase. 8NH3 + 3Cl2 → N2 + 6NH4Cl Which statements are correct? 1 2 3 Ammonia behaves as a reducing agent. Ammonia behaves as a base. The oxidation number of the hydrogen changes.

37 In which pairs are the members stereoisomers of each other?

1

CH3 C Br H Cl Br C H H Cl Br C

CH3 C Br H CH3 C H

2

CH3 C H

3

CH3 C H C

Br Cl

CH3 C Br C

H Cl

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14 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct

No other combination of statements is used as a correct response. 38 Deuterium, D, is the 2 1H isotope of hydrogen. DBr has the same chemical properties as HBr. Which compounds could be made by the reaction of DBr with another compound in a single reaction?

Br D 1

2

CHBr2CHDBr OD

3

CH3CH Br

39 How can the rate of reaction between ethanal and aqueous hydrogen cyanide be increased? 1 2 3 by irradiation with ultraviolet light by a rise in temperature by the addition of a small quantity of aqueous sodium cyanide

40 Which statements about lactic acid, CH3CH(OH)CO2H, are correct? 1 2 3 Lactic acid forms optical isomers. Two hydrogen atoms per lactic acid molecule can be involved in hydrogen bonding. Lactic acid would form an aldehyde when oxidised by acidified potassium dichromate(VI).

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UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level

w w w e tr .X
9701/01
May/June 2007 1 hour Additional Materials: Multiple Choice Answer Sheet Soft clean eraser Soft pencil (type B or HB is recommended) Data Booklet

m ap eP s er om .c

CHEMISTRY Paper 1 Multiple Choice

*1603311060*

READ THESE INSTRUCTIONS FIRST Write in soft pencil. Do not use staples, paper clips, highlighters, glue or correction fluid. Write your name, Centre number and candidate number on the Answer Sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. Answer all questions. For each question there are four possible answers A, B, C and D. Choose the one you consider correct and record your choice in soft pencil on the separate Answer Sheet. Read the instructions on the Answer Sheet very carefully. Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet.

This document consists of 14 printed pages and 2 blank pages.
IB07 06_9701_01/3RP ? UCLES 2007

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2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct. 1 The isotopic composition of an element is indicated below.

5 4 relative 3 abundance 2 1 0 9 10 11 12 mass number
What is the relative atomic mass of the element? A 2 10.2 B 10.5 C 10.8 D 11.0

Use of the Data Booklet is relevant to this question. Oxides of nitrogen are pollutant gases which are emitted from car exhausts. In urban traffic, when a car travels one kilometre, it releases 0.23 g of an oxide of nitrogen NxOy, which occupies 120 cm3. What are the values of x and y? (Assume 1 mol of gas molecules occupies 24.0 dm3.) A B C D x = 1, y = 1 x = 1, y = 2 x = 2, y = 1 x = 2, y = 4

3

John Dalton’s atomic theory, published in 1808, contained four predictions about atoms. Which of his predictions is still considered to be correct? A B C D Atoms are very small in size. No atom can be split into simpler parts. All the atoms of a particular element have the same mass. All the atoms of one element are different in mass from all the atoms of other elements.

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3 4 The diagrams show the possible paths of subatomic particles moving in an electric field in a vacuum.
+ electrons neutrons + protons +


1 2


3



Which diagrams are correct? A B C D 5 1 and 2 only 1 and 3 only 2 and 3 only 1, 2 and 3

The CN– ion is widely used in the synthesis of organic compounds. What is the pattern of electron pairs in this ion? bonding pairs of electrons A B C D 2 2 3 3 lone pairs on carbon atom 1 2 1 1 lone pairs on nitrogen atom 1 1 1 2

6

Plastic bottles for ‘fizzy drinks’ are made from a polymer with the following structure.
H C C H H
n

X

The ability of the polymer to prevent escape of carbon dioxide through the wall of the bottle depends on the ability of the group X to form hydrogen bonds with the carbon dioxide in the drink. Which group X best prevents loss of carbon dioxide? A Cl B CN C CO2CH3 D OH

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4 7 An exothermic chemical reaction proceeds by two stages.
stage 1 reactants intermediate stage 2 products

The activation energy of stage 1 is 50 kJ mol–1. The overall enthalpy change of reaction is –100 kJ mol–1. Which diagram represents the reaction pathway for this reaction?

A 100 75 50 25 0 -25 reactants -50 -75 -100 products progress of reaction
8

B 100 75 50 25 0 -25 reactants -50 products -75 -100 progress of reaction

C 100 75 50 25 0 -25 reactants -50 -75 products -100 progress of reaction

D 100 75 50 25 0 -25 reactants -50 products -75 -100 progress of reaction

Skiers trapped by snowstorms use heat packs to keep warm. The heat may be generated by the reaction below. 4Fe(s) + 3O2(g) → 2Fe2O3(s) ; ?HO = –1648 kJ

What is the standard enthalpy change of formation of iron(III) oxide? A B C D 9 0 kJ mol–1 –824 kJ mol–1 –1648 kJ mol–1 –3296 kJ mol–1

Two equilibria are shown below. reaction I reaction II 2X2(g) + Y2(g) X2Y(g) 2X2Y(g)

1 X2(g) + 2 Y 2(g)

The numerical value of Kc for reaction I is 2. Under the same conditions, what is the numerical value of Kc for reaction II? A

1 2

B

1 2

C

1 4

D

–2

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5 10 The Boltzmann distribution shows the number of molecules having a particular kinetic energy at constant temperature.

number of gas molecules having a given energy L M

0

N 0 kinetic energy Ea

If the temperature is decreased by 10 °C, what happens to the size of the areas labelled L, M and N? L A B C D decreases decreases increases increases M decreases increases decreases decreases N decreases decreases decreases increases

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6 11 In the diagram, curve X was obtained by observing the decomposition of 100 cm3 of 1.0 mol dm–3 hydrogen peroxide, catalysed by manganese(IV) oxide.
Y X

volume of oxygen formed

0

0

time

Which alteration to the original experimental conditions would produce curve Y? A B C D adding water adding some 0.1 mol dm–3 hydrogen peroxide using less manganese(IV) oxide lowering the temperature

12 Which chlorine compound has bonding that can be described as ionic with some covalent character? A NaCl B MgCl2 C AlCl3 D SiCl4

13 Al Cl3 reacts with LiAl H4 and (CH3)3N to give (CH3)3NAl H3. Which statement about (CH3)3NAl H3 is correct? A B C D It contains hydrogen bonding. It is dimeric. The Al atom has an incomplete octet of electrons. The bonds around the Al atom are tetrahedrally arranged.

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7 14 Slaked lime, Ca(OH)2, may be made from limestone, CaCO3. On heating in a lime kiln at 1000 °C, limestone decomposes as follows. reaction 1 CaCO3(s) → CaO(s) + CO2(g)

Water is then reacted with calcium oxide, CaO, as follows. reaction 2 CaO(s) + H2O(l) → Ca(OH)2(s)

What are the enthalpy changes of these reactions? reaction 1 A B C D endothermic endothermic exothermic exothermic reaction 2 endothermic exothermic endothermic exothermic

15 In the treatment of domestic water supplies, chlorine is added to the water to form chloric(I) acid, HClO. Cl2(aq) + H2O(I) → H+(aq) + Cl –(aq) + HClO(aq) This reacts further to give the chlorate(I) ion. HClO(aq) + H2O(I) → H3O+(aq) + ClO–(aq) Both HClO and ClO– kill bacteria by oxidation. What is the change in oxidation number of chlorine in forming the chlorate(I) ion from the aqueous chlorine? A –1 B 0 C +1 D +2

16 The standard enthalpy changes of formation of HCl and HI are –92 kJ mol–1 and +26 kJ mol–1 respectively. Which statement is most important in explaining this difference? A B C D Chlorine is more electronegative than iodine. The activation energy for the H2 / Cl2 reaction is much less than that for the H2 / I2 reaction. The bond energy of HI is smaller than the bond energy of HCl. The bond energy of I2 is smaller than the bond energy of Cl2.

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8 17 Methyl mercaptan, CH3SH, is one of the substances responsible for bad breath and is often used to impart a smell to natural gas in a pipeline. What will be formed when CH3SH is burned in an excess of air? A B C D CO CO CO2 CO2 CO2 H2O H2O H2O H2S SO3 SO2 SO3

18 A solid nitrate fertiliser reacts with an alkali to produce a gas which turns damp pH paper blue. What is the empirical formula of this fertiliser? A NO3 B NHO3 C NH2O D N2H4O3

19 Glucose, C6H12O6, is a product of photosynthesis. It has the following structure.

H H HO H H H

C C C C C C H

O OH H OH OH OH

How many chiral centres does the molecule have? A 1 B 2 C 4 D 6

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9 20 Under the Montreal Protocol, the manufacture of chlorofluorocarbons has been phased out, and they are being replaced by fluorocarbons. One chlorofluorocarbon which was widely used as a solvent is CCl2FCCl F2. Large stocks of it remain. One process to use up these stocks is to convert it into the fluorocarbon CH2FCF3 by the following route.
CCl2FCCl F2 step 1 CCl3CF3 step 2 CCl2FCF3 step 3 CH2FCF3

What type of reaction is step 2? A B C D electrophilic substitution free radical reduction isomerisation nucleophilic substitution

21 Which reagent could be used to convert CH3CO2CH3 into ClCH2CO2CH3? A B C D concentrated hydrochloric acid at 100 °C phosphorus pentachloride at room temperature sulphur dichloride oxide (thionyl chloride, SOCl2) at 50 °C chlorine in bright sunlight at 100 °C

22 In which reaction is a carbocation (carbonium ion) an intermediate?
A B C D CH2=CH2 + Br2 CH3CH2Br + NaOH CH3CH3 + Cl2 CH3CHO + HCN CH2BrCH2Br CH3CH2OH + NaBr CH3CH2Cl + HCl CN– CH3CH(OH)CN

23 The compound 1,2-dichloroethene, C2H2Cl 2, has been used as an industrial solvent for a number of compounds including fats, camphor and caffeine. Which statement about this compound is incorrect? A B C D The compound can be catalytically hydrogenated. The compound is a planar molecule. The compound shows cis-trans isomerism. The compound shows optical isomerism.

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10 24 Which term describes the action of NaOH(aq) on a bromoalkane? A B C D acid-base reaction electrophilic substitution elimination of HBr nucleophilic substitution

25 X and Y are the reagents required to convert 1-bromopropane into butanoic acid.
H H C H H C H H C H Br X H H C H H C H H C H CN Y H H C H H C H H C H C OH O

What are the correct identities of X and Y? X A B C D NH3 KCN in C2H5OH KCN in C2H5OH HCN Y HCl(aq) NaOH(aq) HCl(aq) NaOH(aq)

26 An alcohol with molecular formula CnH2n+1OH has a chiral carbon atom but does not react with + MnO ? 4/ H . What is the least number of carbon atoms such an alcohol could possess? A 5 B 6 C 7 D 8

27 Which reagent gives the same visible result with propanal and with propan-2-ol? A B C D 2,4-dinitrophenylhydrazine reagent acidified potassium dichromate(VI) sodium Tollens’ reagent

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11 28 Compound X will decolourise a warm acidified solution of manganate(VII) ions and forms orange crystals on reaction with 2,4-dinitrophenylhydrazine. What is X? A B C D CH3CH=CHCH2OH CH3COCH2CH3 CH3CH2CH2CHO CH3CH(OH)CH2CO2H

29 Which compound would undergo nucleophilic addition? A B C D ethene, C2H4 bromoethane, C2H5Br ethanal, CH3CHO ethane, C2H6

30 Which formula represents the organic compound formed by the reaction of propanoic acid with methanol in the presence of concentrated sulphuric acid as a catalyst? A B C D CH3CH2COCH3 CH3CH2CO2CH3 CH3CO2CH2CH3 CH3CH2CH2CO2CH3

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12 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct

No other combination of statements is used as a correct response. 31 Use of the Data Booklet is relevant to this question. The technetium–99 isotope (99Tc) is radioactive and has been found in lobsters and seaweed adjacent to nuclear fuel reprocessing plants. Which statements are correct about an atom of 99Tc? 1 2 3 It has 13 more neutrons than protons. It has 43 protons. It has 99 nucleons.

32 Which of the following solids contain more than one type of chemical bond? 1 2 3 brass (an alloy of copper and zinc) graphite ice

33 Many crude oils contain sulphur as H2S. During refining, by the Claus process, the H2S is converted into solid sulphur, which is then removed. reaction I reaction II 2H2S(g) + 3O2(g) → 2H2O(l) + 2SO2(g) 2H2S(g) + SO2(g) → 2H2O(l) + 3S(s)

Which statements about the Claus process are correct? 1 2 3 H2S is oxidised in reaction I. SO2 oxidises H2S in reaction II. SO2 behaves as a catalyst.

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13 34 Two bulbs R and S, connected by a mercury manometer, are held in a thermostat, as shown. The volume of R is twice that of S. R contains gas, X, at the same pressure as the nitrogen in S.

R

S nitrogen thermostat manometer mercury

X

When the temperature is increased, which gases in bulb R would cause the mercury level in the right-hand limb of the manometer to rise? 1 2 3 an equilibrium mixture N2F4(g) an equilibrium mixture CH3NC(g) nitrogen 2NF2(g); ?H positive CH3CN(g); ?H negative

35 Which statements concerning the third period elements (sodium to argon) and their compounds are correct? 1 2 3 The elements become more electronegative from sodium to chlorine. Aluminium oxide is the only oxide which is insoluble in water. The maximum oxidation state is shown by silicon.

36 Use of the Data Booklet is relevant to this question. The element astatine lies below iodine in Group VII of the Periodic Table. What will be the properties of astatine? 1 2 3 It forms diatomic molecules which dissociate more readily than chlorine molecules. It reacts explosively with hydrogen. It is a good reducing agent.

37 Nitrogen and oxygen react in a hot car engine to form nitrogen monoxide which is a serious pollutant in our cities and in the countryside. However, nitrogen and oxygen do not react at room temperature. Which statements help to explain why nitrogen and oxygen do not react at room temperature? 1 2 3 The reaction is endothermic. A high activation energy is required. Nitrogen has a high bond energy.
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14 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct

No other combination of statements is used as a correct response. 38 What types of reaction are undergone by 2-bromopropane? 1 2 3 elimination free radical substitution nucleophilic substitution

39 Menthol, from oil of mint, is used in soaps and perfumes.
CH3 CH CH2 CH2 CH CH CH3 CH3 menthol CH2 CH(OH)

Which statements about menthol are correct? 1 2 3 There is a total of two chiral centres present in the menthol molecule. On reaction with concentrated sulphuric acid, menthol produces a mixture of two alkenes. A solution of acidified potassium dichromate(VI), on warming with menthol, changes colour from orange to green.

40 Fats and grease that build up on pans used in cooking are esters. Pans which are dirty from fats or grease may be cleaned by heating them with a reagent that will react with the ester group. What may be used to clean such pans by this reaction? 1 2 3 vinegar - aqueous ethanoic acid, CH3CO2H alcohol - ethanol, C2H5OH baking powder - sodium hydrogencarbonate, NaHCO3

? UCLES 2007

9701/01/M/J/07

UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level

w w w e tr .X
9701/01
May/June 2008 1 hour Additional Materials: Multiple Choice Answer Sheet Soft Clean Eraser Soft pencil (type B or HB is recommended) Data Booklet

m ap eP s er om .c

CHEMISTRY Paper 1 Multiple Choice

*7255044678*

READ THESE INSTRUCTIONS FIRST Write in soft pencil. Do not use staples, paper clips, highlighters, glue or correction fluid. Write your name, Centre number and candidate number on the Answer Sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. Answer all questions. For each question there are four possible answers A, B, C and D. Choose the one you consider correct and record your choice in soft pencil on the separate Answer Sheet. Read the instructions on the Answer Sheet very carefully. Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet.

This document consists of 16 printed pages.
IB08 06_9701_01/2RP ? UCLES 2008

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2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct. 1 In the Basic Oxygen steel-making process the P4O10 impurity is removed by reacting it with calcium oxide. The only product of this reaction is the salt calcium phosphate, Ca3(PO4)2. In this reaction, how many moles of calcium oxide react with one mole of P4O10? A 2 1 B 1.5 C 3 D 6

Use of the Data Booklet is relevant to this question. A typical solid fertiliser for use with household plants and shrubs contains the elements N, P, and K in the ratio of 15 g : 30 g :15 g per 100 g of fertiliser. The recommended usage of fertiliser is 14 g of fertiliser per 5 dm3 of water. What is the concentration of nitrogen atoms in this solution? A B C D 3 0.03 mol dm–3 0.05 mol dm–3 0.42 mol dm–3 0.75 mol dm–3
32 15 P

Skin cancer can be treated using a radioactive isotope of phosphorus, containing the phosphide ion area.
32 15 3?

. A compound

P , wrapped in a plastic sheet, is strapped to the affected

What is the composition of the phosphide ion, protons A B C D 15 15 17 32 neutrons 17 17 15 17 electrons 18 32 17 15

32 15

P3 ? ?

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3 4 When barium metal burns in oxygen, the ionic compound barium peroxide, BaO2, is formed. Which dot-and-cross diagram represents the electronic structure of the peroxide anion in BaO2?
key A B C D electron from first oxygen atom electron from second oxygen atom electron from barium atom

5

In this question, the methyl group, CH3, is represented by Me. Trimethylamine, Me3N, reacts with boron trifluoride, BF3, to form a compound of formula Me3N.BF3. How may this reaction be written in terms of the shapes of the reactants and products?

Me Me Me A Me N Me + F B F F F N B F Me Me Me B Me N Me + F B F F F N B F Me Me Me C Me N Me + F B F F F N B F Me Me Me D Me N Me + F B F F B F F F N Me F Me Me F Me F

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4 6 The density of ice is 1.00 g cm–3. What is the volume of steam produced when 1.00 cm3 of ice is heated to 323 °C (596 K) at a pressure of one atmosphere (101 kPa)? [1 mol of a gas occupies 24.0 dm3 at 25 °C (298 K) and one atmosphere.] A 7 0.267 dm3 B 1.33 dm3 C 2.67 dm3 D 48.0 dm3

Which pair of elements have bonds of the same type between their atoms in the solid state? A B C D aluminium and phosphorus chlorine and argon magnesium and silicon sulphur and chlorine

8

Which diagram correctly describes the behaviour of a fixed mass of an ideal gas? (T is measured in K.)
A constant T p pV B constant T pV C constant T V D constant p

0 0

V

0 0

p

0 0

V

0 0

T

9

For which equation does the enthalpy change correspond to the enthalpy change of atomisation of iodine? A B C D ? I2(s) → I(s) ? I2(s) → I(g) I2(g) → 2I(g) I2(s) → 2I(g)

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5 10 Titanium occurs naturally as the mineral rutile, TiO2. One possible method of extraction of titanium is to reduce the rutile by heating with carbon. TiO2(s) + 2C(s) → Ti(s) + 2CO(g) The standard enthalpy changes of formation of TiO2(s) and CO(g) are –940 kJ mol–1 and –110 kJ mol–1 respectively. What is the standard enthalpy change of this reaction? A B C D –830 kJ mol–1 –720 kJ mol–1 +720 kJ mol–1 +830 kJ mol–1

11 For the reaction W(aq) + 2X(aq) 2Y(aq) + 3Z(aq)

what are the correct units for the equilibrium constant Kc? A mol dm–3 B mol2 dm–6 C mol–1 dm3 D mol–2 dm6

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6 12 The molecular energy distribution curve represents the variation in energy of the molecules of a gas at room temperature.

proportion of molecules

0 0 energy

Which curve applies for the same gas at a lower temperature?

A

B

proportion of molecules

proportion of molecules

0 0 energy C

0 0 energy D

proportion of molecules

proportion of molecules

0 0 energy

0 0 energy

13 In an experiment, 0.1 g samples of Na2O, MgO, P4O10 and SO2 are added to separate 100 cm3 volumes of water. For which oxide is the resulting mixture most alkaline? A Na2O B MgO C P4O10 D SO2

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7 14 Which element is expected to show the greatest tendency to form some covalent compounds? A B C D aluminium calcium magnesium sodium

15 Use of the Data Booklet is relevant to this question. The combustion of fossil fuels is a major source of increasing atmospheric carbon dioxide, with a consequential rise in global warming. Another significant contribution to carbon dioxide levels comes from the thermal decomposition of limestone, in the manufacture of cement and of lime for agricultural purposes. Cement works roast 1000 million tonnes of limestone per year and a further 200 million tonnes is roasted in kilns to make lime. What is the total annual mass output of carbon dioxide (in million tonnes) from these two processes? A 440 B 527 C 660 D 880

16 Properties of chlorine, iodine and their compounds are compared. Property Q for chlorine is smaller than for iodine. What is property Q? A B C D oxidising ability of the element solubility of the silver halide in NH3(aq) strength of van der Waals’ forces between the molecules of the element thermal stability of the hydrogen halide

17 Which reagent, when mixed and heated with ammonium sulphate, liberates ammonia? A B C D aqueous bromine dilute hydrochloric acid limewater acidified potassium dichromate(VI)

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8 18 The diagram represents the Haber process for the manufacture of ammonia from nitrogen and hydrogen.

heat exchanger N2 + H2 catalytic converter condenser

NH3
What is the purpose of the heat exchanger? A B C D to cool the incoming gas mixture to avoid overheating the catalyst to cool the reaction products and separate the NH3 from unused N2 and H2 to warm the incoming gas mixture and shift the equilibrium to give more NH3 to warm the incoming gas mixture and speed up the reaction

19 Total elimination of the pollutant sulphur dioxide, SO2, is difficult, both for economic and technical reasons. Its emission can be reduced in furnace chimneys using desulphurisation plants, where the gases are scrubbed (washed) with calcium hydroxide to remove the SO2. What is the main product formed initially? A CaO B Ca(OH)2 C CaSO3 D CaSO4

20 Which pair of reaction types is illustrated by the reaction sequence below?
CH3CH=CHCH3 HI in CH3CO2H CH3CH2CHICH3 NaOH(aq) CH3CH2CH(OH)CH3

A B C D

electrophilic addition and electrophilic substitution electrophilic addition and nucleophilic substitution nucleophilic addition and electrophilic substitution nucleophilic addition and nucleophilic substitution

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9 21 Trichloroethene is widely used as a dry-cleaning agent.

H C Cl C

Cl

Cl

With which of the following does trichloroethene react to give a chiral product? A Br2 B HCl C NaCN(aq) D NaOH(aq)

22 Chloroethene, CH2=CHCl, is the monomer of PVC. What are the C?C?C bond angles along the polymeric chain in PVC? A B C D They are all 109.5°. Half are 109.5° and half are 120°. They are all 120°. They are all 180°.

23 Which hydrocarbon would not be collected in the inverted tube by heating pentane, CH3(CH2)3CH3, in the apparatus shown? pentane on mineral fibre aluminium oxide hydrocarbons

very strong heat

water A B C D CH4 CH3CH3 CH3CH2CH=CH2 CH3(CH2)8CH3

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10 24 Mevalonic acid, 3,5-dihydroxy-3-methylpentanoic acid, is involved in cholesterol formation in the body. It is an oil that occurs as a mixture of the two interchanging molecules shown in the diagram.
HO C CH2 CH2 CH2OH CO2H CH3 I II HO C CH2 CH2 O CH3 CH2 C O

What names are used to describe the pair of interchanging reactions I and II? A B C D condensation and addition dehydrogenation and hydrogenation esterification and hydrolysis neutralisation and acidification

25 Halogenoalkanes are important molecules in organic synthetic reactions. In particular they undergo a range of nucleophilic reactions. Which reaction proceeds only by an SN1 mechanism? A B C D CH3CH2Br + NH3 CH3CH2CH2I + OH– CH3CHBrCH3 + NH3 (CH3)3CI + OH–

26 An alcohol of molecular formula C4H10O2 contains two OH groups and has an unbranched carbon atom chain.
+ On reaction with an excess of hot MnO? 4 / H this alcohol is converted into a compound of molecular formula C4H6O4.

To which two carbon atoms in the chain of the alcohol are the two OH groups attached? A B C D 1st and 2nd 1st and 3rd 1st and 4th 2nd and 3rd

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11 27 Compound X ? ? has the molecular formula C10H14O; is unreactive towards mild oxidising agents.

What is the structure of the compound formed by dehydration of X?

A CH2 CH2 CH CH2 CH2

B CH CH CH3

C CH3 CH CH CH2

D CH3 C CH CH3

28 Ethanal, CH3CHO, can be reduced using an aqueous methanolic solution of NaBH4 as the reducing agent. This is a nucleophilic addition reaction. What could be the first step of this mechanism? A B C D attack of an H+ ion at the carbon atom of the carbonyl group attack of an H+ ion at the oxygen atom of the carbonyl group attack of an H– ion at the carbon atom of the carbonyl group attack of an H– ion at the oxygen atom of the carbonyl group

29 Which compound is both chiral and acidic?
A H C C H CO2H CO2H B CH3 OH C CH2Br HCO2CH CH3 D CH(OH)CO2H CH2CO2H

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12 30 Compound X, C6H12O, is oxidised by acidified sodium dichromate(VI) to compound Y. Compound Y reacts with ethanol in the presence of a little concentrated sulphuric acid to give liquid Z. What is the formula of Z? A B C D CH3(CH2)2CH=CHCO2H CH3(CH2)4CH2COCH2CH3 CH3(CH2)4CO2CH2CH3 CH3CH2CO2(CH2)4CH3

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13 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct

No other combination of statements is used as a correct response. 31 For complete combustion, 1 mol of an organic compound X was found to require 2.5 mol of molecular oxygen. Which compounds could be X? 1 2 3 C2H5OH C2H2 CH3CHO

32 Catalysts are used in many reversible reactions in the chemical industry. Vanadium(V) oxide is used in this way in the Contact process for the formation of SO3. 2SO2(g) + O2(g) 2SO3(g)

What effect does vanadium(V) oxide have on this equilibrium? 1 2 3 It speeds up the forward reaction. It increases the value of Kp. It increases the value of Ea for the reverse reaction.

33 Which statements about the properties of a catalyst are correct? 1 2 3 A catalyst increases the average kinetic energy of the reacting particles. A catalyst increases the rate of the reverse reaction. A catalyst has no effect on the enthalpy change of the reaction.

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14 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct

No other combination of statements is used as a correct response. 34 Water is added to anhydrous aluminium chloride to make a 0.1 mol dm-3 solution. Which observations are correct? 1 2 3 The reaction is endothermic. The solution is acidic. The solution contains the ion [Al(H2O)6]3+.

35 The electronic structure of the outer shell of the element radium is 7s2. Which statements will be correct for radium within its group? 1 2 3 The element will decompose water, liberating hydrogen. The element will show an oxidation number of +2 in all its compounds. Radium has the highest first ionisation energy.

36 When the yellow liquid NCl3 is stirred into aqueous sodium hydroxide, the reaction that occurs can be represented by the following equation. 2NCl3(l) + 6NaOH(aq) → N2(g) + 3NaCl (aq) + 3NaOCl (aq) + 3H2O(l) What will be the result of this reaction? 1 2 3 The nitrogen is oxidised. A bleaching solution remains after the reaction. The final solution gives a precipitate with acidified silver nitrate.

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15 37 Aspirin is a widely-available pain-killer, whose properties have been known for centuries. The structure of aspirin is shown.
OH C O

O C CH3 O

Which functional groups are present in aspirin? 1 2 3 alcohol carboxylic acid ester

38 The structure of monosodium glutamate, a flavour enhancer, is shown.
Na+ O– C O CH2 CH2 CH NH2 CO2H

It may be prepared starting from the following compound.
Cl CH2 CH2 CH NH2 CO2H

Which set of reagents and reaction conditions could be used to prepare monosodium glutamate? 1 2 3 Heat under reflux with ethanolic KCN followed by hydrolysis with NaOH(aq).
? Na+ . Heat with sodium methanoate, HCO2

Heat under reflux with NaOH(aq).

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16 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct

No other combination of statements is used as a correct response. 39 The compound cholesterol has the following structure.
CH3 CH CH2 CH2 CH HO CH2 CH3 CH C C CH CH3 CH C CH CH2 CH2 CH2 CH2 CH2 CH CH3 CH3

Which statements are correct? 1 2 3 Cholesterol reacts with a mixture of ethanoic acid and concentrated sulphuric acid. Cholesterol reacts with bromine to form a compound which has two new chiral centres. Cholesterol is oxidised by acidified sodium dichromate(VI) to form an aldehyde.

40 Ferulic acid is an antioxidant that occurs widely in plants.
HO CH3O ferulic acid CH=CHCO2H

Which reagents can react with the –CH=CHCO2H part of the molecule? 1 2 3 NaOH(aq) acidified KMnO4 HBr

Permission to reproduce items where third-party owned material protected by copyright is included has been sought and cleared where possible. Every reasonable effort has been made by the publisher (UCLES) to trace copyright holders, but if any items requiring clearance have unwittingly been included, the publisher will be pleased to make amends at the earliest possible opportunity. University of Cambridge International Examinations is part of the Cambridge Assessment Group. Cambridge Assessment is the brand name of University of Cambridge Local Examinations Syndicate (UCLES), which is itself a department of the University of Cambridge.

? UCLES 2008

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w w w e tr .X m ap eP
UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level 9701/01
May/June 2009 1 hour Additional Materials: Multiple Choice Answer Sheet Soft clean eraser Soft pencil (type B or HB is recommended) Data Booklet

s er om .c

CHEMISTRY Paper 1 Multiple Choice

*5448023915*

READ THESE INSTRUCTIONS FIRST Write in soft pencil. Do not use staples, paper clips, highlighters, glue or correction fluid. Write your name, Centre number and candidate number on the Answer Sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. Answer all questions. For each question there are four possible answers A, B, C and D. Choose the one you consider correct and record your choice in soft pencil on the separate Answer Sheet. Read the instructions on the Answer Sheet very carefully. Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet.

This document consists of 15 printed pages and 1 blank page.
IB09 06_9701_01/5RP ? UCLES 2009

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2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct.

1

Use of the Data Booklet is relevant to this question. In leaded petrol there is an additive composed of lead, carbon and hydrogen only. This compound contains 29.7 % carbon and 6.19 % hydrogen by mass. What is the value of x in the empirical formula PbC8HX? A 5 B 6 C 16 D 20

2

A household bleach contains sodium chlorate(I), NaClO, as its active ingredient. The concentration of NaClO in the bleach can be determined by reacting a known amount with aqueous hydrogen peroxide, H2O2. NaClO(aq) + H2O2(aq) → NaCl(aq) + O2(g) + H2O(l) When 25.0 cm3 of bleach is treated with an excess of aqueous H2O2, 0.0350 mol of oxygen gas is given off. What is the concentration of NaClO in the bleach? A B C D 8.75 × 10–4 mol dm–3 0.700 mol dm–3 0.875 mol dm–3 1.40 mol dm–3

3

The first seven ionisation energies of an element between lithium and neon in the Periodic Table are as follows. 1310 3390 5320 7450 11 000 13 300 71 000 kJ mol–1

What is the outer electronic configuration of the element? A 2s2 B 2s22p1 C 2s22p4 D 2s22p6

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3 4 Use of the Data Booklet is relevant to this question. Which graph represents the number of unpaired p orbital electrons for atoms with proton numbers 13 to 18?

A

B

number of unpaired electrons

number of unpaired electrons

0 13 14 15 16 17 proton number 18

0 13 14 15 16 17 proton number 18

C

D

number of unpaired electrons

number of unpaired electrons

0 13 14 15 16 17 proton number 18

0 13 14 15 16 17 proton number 18

5

Which statement explains why the boiling point of methane is higher than that of neon? [Ar: H, 1; C, 12; Ne, 20] A B C D A molecule of methane has a greater mass than a molecule of neon. Molecules of methane form hydrogen bonds, but those of neon do not. Molecules of methane have stronger intermolecular forces than those of neon. The molecule of methane is polar, but that of neon is not.

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4 6 In which reaction does the carbon-containing product have a smaller bond angle than the organic reactant? A B C D 7 bromoethane refluxed with ethanolic sodium hydroxide complete combustion of methane in air methane and an excess of chlorine under ultraviolet light polymerisation of ethene

A crystal of iodine produces a purple vapour when gently heated. Which pair of statements correctly describes this process? type of bond broken A B C D covalent covalent induced dipole-dipole permanent dipole-dipole formula of purple species I I2 I2 I2

8

Hydrogen peroxide slowly decomposes into water and oxygen. The enthalpy change of reaction can be calculated using standard enthalpies of formation. (hydrogen peroxide(l)) = –187.8 kJ mol–1 (water(l)) = –285.8 kJ mol–1

Using a Hess cycle, what is the enthalpy change of reaction for this decomposition? 2H2O2(l) → 2H2O(l) + O2(g) A B C D +98 kJ mol–1 ?98 kJ mol–1 ?196 kJ mol–1 ?947.2 kJ mol–1

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5 9 When copper is extracted from its ores, the metal is not pure enough for electrical uses. The impure copper, which contains small amounts of silver and gold, is purified by electrolysis. During this process a ‘sludge’ forms beneath the anode which is found to contain silver and traces of gold. Why is silver found in this sludge? A B C D Silver is less electropositive than copper. Silver is more dense than copper and falls off the cathode. Silver reacts with the electrolyte to form an insoluble chloride salt. Silver reacts with the electrolyte to form an insoluble sulfate salt.

10 The diagram shows the Maxwell-Boltzmann energy distribution curve for molecules of a mixture of two gases at a given temperature. For a reaction to occur the molecules must collide together with sufficient energy.

number of molecules

0 0 energy

Ea2

Ea1

Ea is the activation energy for the reaction between the gases. Of the two values shown, one is for a catalysed reaction, the other for an uncatalysed one. Which pair of statements is correct when a catalyst is used? A B C D Ea1 Ea1 Ea1 Ea1 catalysed reaction fewer effective collisions uncatalysed reaction fewer effective collisions catalysed reaction more effective collisions uncatalysed reaction more effective collisions Ea2 Ea2 Ea2 Ea2 uncatalysed reaction more effective collisions catalysed reaction more effective collisions uncatalysed reaction fewer effective collisions catalysed reaction fewer effective collisions

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6 11 In some fireworks there is a reaction between powdered aluminium and powdered barium nitrate in which heat is evolved and an unreactive gas is produced. What is the equation for this reaction? A B C D 2Al + Ba(NO3)2 → Al2O3 + BaO + 2NO 4Al + 4Ba(NO3)2 → 2Al2O3 + 4Ba(NO2)2 + O2 10Al + 3Ba(NO3)2 → 5Al2O3 + 3BaO + 3N2 10Al + 18Ba(NO3)2 → 10Al(NO3)3 + 18BaO + 3N2

12 Which group of particles is in order of increasing size? A B C D N N3– Na+ Na+ O O2– Mg2+ Ne F F– Al 3+ F–

2? ? ? , HCO 3 , Cl ? and NO 3 13 River water in a chalky agricultural area may contain Ca2+, Mg2+, CO 3 ions. In a waterworks, such water is treated by adding a calculated quantity of calcium hydroxide.

What will be precipitated following the addition of calcium hydroxide? A B C D CaCl2 CaCO3 Ca(NO3) 2 Mg(NO3)2

14 Over half a million tonnes of bromine are manufactured annually and are mainly used for making other compounds. One important use is for agricultural chemicals. What is another important use for bromine? A B C D antiseptic agents bleaches for textiles and the paper industry flame-retardants and fire extinguishers water purification

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7 15 In black and white photographic film, light converts silver chloride into metallic silver. After the film has been developed, the unreacted silver chloride is removed by reaction with sodium thiosulfate to produce a ‘fixed’ negative. AgCl + 2Na2S2O3 → 4Na+ + Cl – + [Ag(S2O3)2]3– What is the function of the thiosulfate ion? A B C D to make the silver ions soluble to oxidise the silver ions to oxidise the silver metal to reduce the silver ions

16 Which statement is most likely to be true for astatine, which is below iodine in Group VII of the Periodic Table? A B C D Astatine and aqueous potassium chloride react to form aqueous potassium astatide and chlorine. Potassium astatide and hot dilute sulfuric acid react to form white fumes of only hydrogen astatide. Silver astatide reacts with dilute aqueous ammonia in excess to form a solution of a soluble complex. Sodium astatide and hot concentrated sulfuric acid react to form astatine.

17 Deposits of ammonium compounds have been discovered in areas of high atmospheric pollution. They are believed to arise from the following reaction. SO3 + H2O + 2NH3 → (NH4)2SO4 What does not occur in this reaction? A B C D acid / base neutralisation dative bond formation ionic bond formation oxidation / reduction

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8 18 Mohr’s salt is a pale green crystalline solid which is soluble in water. It is a ‘double sulfate’ which contains two cations, one of which is Fe2+. The identity of the second cation was determined by heating solid Mohr’s salt with solid sodium hydroxide and a colourless gas was evolved. The gas readily dissolved in water giving an alkaline solution. A grey-green solid residue was also formed which was insoluble in water. What are the identities of the gas and the solid residue? gas A B C D H2 NH3 NH3 SO2 residue FeSO4 Na2SO4 Fe(OH)2 Fe(OH)2

19 In recent years a number of athletes have been banned from sports because of their illegal use of synthetic testosterone, a naturally occurring hormone in the body.
CH3 CH3 OH

O testosterone

How many chiral centres are present in a testosterone molecule? A 1 B 2 C 3 D 6

20 The compound known as ‘gamma-linolenic acid’ is found in significant amounts in the seeds of the Evening Primrose plant. There is evidence that the compound may help patients with diabetes. CH3(CH2)4CH=CHCH2CH=CHCH2CH=CH(CH2)4CO2H gamma-linolenic acid How many cis-trans isomers does gamma-linolenic acid have? A 3 B 6 C 8 D 12

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9 21 What always applies to a nucleophile? A B C D It attacks a double bond. It has a lone pair of electrons. It is a single atom. It is negatively charged.

22 Trichloroethanoic acid, CCl3CO2H, is used in cosmetic surgery to perform a ‘chemical peel’ to remove dead skin. Trichloroethanoic acid can be made by reacting chlorine with ethanoic acid. What is the mechanism of this reaction? A B C D electrophilic addition electrophilic substitution free radical addition free radical substitution

23 Polymerisation of chloroethene gives PVC. How does the carbon-carbon bond in PVC compare with that in chloroethene? A B C D longer and stronger longer and weaker shorter and stronger shorter and weaker

24 In the hydrolysis of bromoethane by aqueous sodium hydroxide, what is the nature of the attacking group and of the leaving group? attacking group A B C D electrophile electrophile nucleophile nucleophile leaving group electrophile nucleophile electrophile nucleophile

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10 25 Which reaction would not give propene as one product? A B C D adding an excess of concentrated sulfuric acid to propan-1-ol adding warm aqueous sodium hydroxide to 2-bromopropane adding warm ethanolic sodium hydroxide to 1-bromopropane passing propan-2-ol vapour over heated aluminium oxide

26 Glycol, used in anti-freeze, has the formula HOCH2CH2OH. It can be oxidised to give a number of products. What is the molecular formula of an oxidation product of glycol that will not react with sodium? A C2H2O2 B C2H2O3 C C2H2O4 D C2H4O2

27 Which ester is formed when the alcohol CH3CH2OH is reacted with CH3CH2CH2CO2H? A B C D ethyl propanoate ethyl butanoate propyl ethanoate butyl ethanoate

28 Carvone gives the characteristic flavour to caraway and spearmint.
O CH3 H3C C CH2 carvone

Prolonged heating of carvone with hot concentrated acidified potassium manganate(VII) produces carbon dioxide and a compound X. X contains nine carbon atoms and reacts with 2,4-dinitrophenylhydrazine reagent. What is the maximum number of molecules of 2,4-dinitrophenylhydrazine that will react with one molecule of X? A 1 B 2 C 3 D 4

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11 29 2-Methylbuta-1,3-diene, CH2=C(CH3)–CH=CH2, is used as a monomer in the manufacture of synthetic rubbers. Which compound would not produce this monomer on treatment with concentrated sulfuric acid at 170 °C? A B C D (CH3)2C(OH)CH(OH)CH3 HOCH2CH(CH3)CH2CH2OH HOCH2CH(CH3)CH(OH)CH3 HOCH2C(CH3)(OH)CH2CH3

30 A compound Y has the following properties. ? It is a liquid at room temperature and atmospheric pressure. ? It does not mix completely with water. ? It does not decolourise acidified potassium manganate(VII). What could Y be? A B C D ethane ethanoic acid ethanol ethyl ethanoate

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12 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct

No other combination of statements is used as a correct response.
12

31 On a scale in which the mass of a sample of chlorine is 72.

C atom is 12 the relative molecular mass of a particular

Which properties of the atoms in this sample are always the same? 1 2 3 radius nucleon number isotopic mass

32 An ideal gas obeys the gas laws under all conditions of temperature and pressure. Which of the following are true for an ideal gas? 1 2 3 The molecules have negligible volume. There are no forces of attraction between molecules. The molecules have an average kinetic energy which is proportional to its absolute temperature.

33 For which reactions does the value of ?Ho represent both a standard enthalpy change of combustion and a standard enthalpy change of formation? 1 2 3 C(s) + O2(g) → CO2(g) 2C(s) + O2(g) → 2CO(g) CO(g) +
1 2

O2(g) → CO2(g)

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13 34 The following reaction takes place using liquid ammonia as a solvent.
? + ? ? Na+ NH2 + NH+ + 2NH3 4 Cl → Na Cl

Which statements best explain why this reaction should be classified as a Br?nsted-Lowry acidbase reaction? 1 2 3 The ammonium ion acts as a proton donor.

Na+ Cl ? is a salt.
Ammonia is always basic.

35 The rock dolomite is a double carbonate of magnesium and calcium, CaCO3.MgCO3. When heated strongly, a product called calcined dolomite is formed which is used to line some furnaces for the production of metals. Why is calcined dolomite used for this purpose? 1 2 3 It is a refractory material. It will absorb acidic impurities in metallurgical processes. It will reduce metallic oxides to metals.

36 Which properties in the sequence hydrogen chloride, hydrogen bromide and hydrogen iodide steadily increase? 1 2 3 thermal stability bond length ease of oxidation

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14 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct

No other combination of statements is used as a correct response.

37 A fraction of distilled crude oil contains molecules with between 15 and 19 carbon atoms. This fraction is cracked by strong heating. Why is this done? 1 2 3 To produce alkenes. To produce smaller molecules which are in higher demand. To insert oxygen atoms into the hydrocarbons.

38 Geraniol is one of several compounds produced by the scent glands of honey bees to help them mark nectar-bearing flowers and locate the entrances to their hives.
OH

geraniol

Which reactions will geraniol undergo? 1 2 3 reaction with hot concentrated acidic KMnO4 to give propanone addition of halogens reaction with aqueous NaHCO3 to give CO2

39 How can the rate of reaction between ethanal and aqueous hydrogen cyanide be increased? 1 2 3 by irradiation with ultraviolet light by a rise in temperature by the addition of a small quantity of aqueous sodium cyanide

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15 40 A sun protection cream contains the following ester as its active ingredient.

CH2CH3 CH3O CH CHCO2CH2CH CH2CH2CH2CH3
What are the products of its partial or total hydrolysis by aqueous sodium hydroxide?
1 CH3CH2CH2CH2CH(CH2CH3)CH2OH CH3O CH3O CH
+ CHCO– 2 Na

2

3

– Na+ CO2

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w w w e tr .X m ap eP
UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level 9701/11
May/June 2010 1 hour Additional Materials: Multiple Choice Answer Sheet Soft clean eraser Soft pencil (type B or HB is recommended) Data Booklet

s er om .c

CHEMISTRY Paper 1 Multiple Choice

*9264472640*

READ THESE INSTRUCTIONS FIRST Write in soft pencil. Do not use staples, paper clips, highlighters, glue or correction fluid. Write your name, Centre number and candidate number on the Answer Sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. Answer all questions. For each question there are four possible answers A, B, C and D. Choose the one you consider correct and record your choice in soft pencil on the separate Answer Sheet. Read the instructions on the Answer Sheet very carefully. Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet.

This document consists of 14 printed pages and 2 blank pages.
IB10 06_9701_11/4RP ? UCLES 2010

[Turn over

2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct. 1 Use of the Data Booklet is relevant to this question. What could be the proton number of an element that has three unpaired electrons in each of its atoms? A 2 5 B 13 C 15 D 21

Use of the Data Booklet is relevant to this question. The elements radon (Rn), francium (Fr) and radium (Ra) have consecutive proton numbers in the Periodic Table. What is the order of their first ionisation energies? least endothermic A B C D Fr Fr Ra Rn Ra Rn Fr Ra most endothermic Rn Ra Rn Fr

3

Which gas closely approaches ideal behaviour at room temperature and pressure? A B C D ammonia carbon dioxide helium oxygen

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3 4 Some bond energy values are listed below. bond C–H C–Cl Cl–Cl Br–Br bond energy / kJ mol–1 410 340 244 193

These bond energy values relate to the following four reactions. P Q R S Br2 → 2Br 2Cl → Cl2 CH3 + Cl → CH3Cl CH4 → CH3 + H

What is the order of enthalpy changes of these reactions from most negative to most positive? A B C D 5 P→Q→R→S Q→R→S→P R→Q→P→S S→P→Q→R

Given the following enthalpy changes, I2(g) + 3Cl2(g) → 2ICl3(s) I2(s) → I2(g) ?Ho = –214 kJ mol–1 ?Ho = +38 kJ mol–1

What is the standard enthalpy change of formation of iodine trichloride, ICl3(s)? A B C D 6 +176 kJ mol–1 –88 kJ mol–1 –176 kJ mol–1 –214 kJ mol–1

Ammonium nitrate, NH4NO3, can decompose explosively when heated. NH4NO3 → N2O + 2H2O What are the changes in the oxidation numbers of the two nitrogen atoms in NH4NO3 when this reaction proceeds? A –2, –4 B +2, +6 C +4, –6 D +4, –4

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4 7 The Haber process for the manufacture of ammonia is represented by the following equation. N2(g) + 3H2(g) 2NH3(g) ?H = –92 kJ mol–1

Which statement is correct about this reaction when the temperature is increased? A B C D 8 Both forward and backward rates increase. The backward rate only increases. The forward rate only increases. There is no effect on the backward or forward rate.

Use of the Data Booklet is relevant to this question. 2.920 g of a Group II metal, X, reacts with an excess of chlorine to form 5.287 g of a compound with formula XCl2. What is metal X? A B C D barium calcium magnesium strontium

9

Which mass of gas would occupy a volume of 3 dm3 at 25 °C and 1 atmosphere pressure? [1 mol of gas occupies 24 dm3 at 25 °C and 1 atmosphere pressure.] A B C D 3.2 g O2 gas 5.6 g N2 gas 8.0 g SO2 gas 11.0 g CO2 gas

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5 10 The table gives the concentrations and pH values of the aqueous solutions of two compounds, X and Y. Either compound could be an acid or a base. X concentration pH Student P concluded that X is a strong acid. Student Q concluded that the extent of dissociation is lower in X(aq) than in Y(aq). Which of the students are correct? A B C D both P and Q neither P nor Q P only Q only 2 mol dm–3 6 Y 2 mol dm–3 9

11 Swimming pool water can be kept free of harmful bacteria by adding aqueous sodium chlorate(I), NaOCl. This reacts with water to produce HOCl molecules which kill bacteria. OCl –(aq) + H2O OH–(aq) + HOCl (aq)

In bright sunshine, the OCl – ion is broken down by ultra-violet light. OCl –(aq) + uv light → Cl –(aq) + ?O2(g) Which method would maintain the highest concentration of HOCl (aq)? A B C D acidify the pool water add a solution of chloride ions add a solution of hydroxide ions bubble air through the water

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6 12 Na2S2O3 reacts with dilute HCl to give a pale yellow precipitate. If 1 cm3 of 0.1 mol dm–3 HCl is added to 10 cm3 of 0.02 mol dm–3 Na2S2O3 the precipitate forms slowly. If the experiment is repeated with 1 cm3 of 0.1 mol dm–3 HCl and 10 cm3 of 0.05 mol dm–3 Na2S2O3 the precipitate forms more quickly. Why is this? A B C D The activation energy of the reaction is lower when 0.05 mol dm–3 Na2S2O3 is used. The reaction proceeds by a different pathway when 0.05 mol dm–3 Na2S2O3 is used. The collisions between reactant particles are more violent when 0.05 mol dm–3 Na2S2O3 is used. The reactant particles collide more frequently when 0.05 mol dm–3 Na2S2O3 is used.

13 How does concentrated sulfuric acid behave when it reacts with sodium chloride? A B C D as an acid only as an acid and oxidising agent as an oxidising agent only as a reducing agent only

14 X is a salt of one of the halogens chlorine, bromine, iodine, or astatine (proton number 85). The reaction scheme shows a series of reactions using a solution of X as the starting reagent.
X HNO3(aq) AgNO3(aq) a precipitate an excess of dilute NH3(aq) a colourless solution an excess of HNO3(aq) a precipitate

What could X be? A B C D sodium chloride sodium bromide potassium iodide potassium astatide

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7 15 The percentage of ammonia obtainable, if equilibrium were established during the Haber process, is plotted against the operating pressure for two temperatures, 400 °C and 500 °C. Which diagram correctly represents the two graphs?

A 40 % NH3 at 20 equilibrium 400 °C 500 °C 40 % NH3 at 20 equilibrium

B 500 °C 400 °C

0 0 10 20 pressure / 103 kPa

0 0 10 20 pressure / 103 kPa

C 40 % NH3 at 20 equilibrium 500 °C 0 0 10 20 pressure / 103 kPa 400 °C 40 % NH3 at 20 equilibrium

D 500 °C

400 °C 0 0 10 20 pressure / 103 kPa

16 Consecutive elements X, Y, Z are in the third period of the Periodic Table. Element Y has the highest first ionisation energy and the lowest melting point. What could be the identities of X, Y and Z? A B C D aluminium, silicon, phosphorus magnesium, aluminium, silicon silicon, phosphorus, sulfur sodium, magnesium, aluminium

17 Which property of Group II elements (beryllium to barium) decreases with increasing atomic number? A B C D reactivity with water second ionisation energy solubility of hydroxides stability of the carbonates

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8 18 Which element of the third period requires the least number of moles of oxygen for the complete combustion of 1 mol of the element? A B C D aluminium magnesium phosphorus sodium

19 Two properties of non-metallic elements and their atoms are as follows. property 1 property 2 has an oxide that can form a strong acid in water has no paired 3p electrons

Which properties do phosphorus and sulfur have? phosphorus A B C D 1 and 2 1 only 1 and 2 2 only sulfur 1 only 1 and 2 1 and 2 1 only

20 When gaseous chemicals are transported by road or by rail they are classified as follows. flammable non-flammable poisonous

Which commonly transported gas is non-flammable? A B C D butane hydrogen oxygen propene

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9 21 When heated with chlorine, the hydrocarbon 2,2-dimethylbutane undergoes free radical substitution. In a propagation step the free radical X? is formed.
CH3 CH3CH2 C CH3 CH3 + Cl ● → X● + HCl

How many different forms of X? are possible? A 1 B 2 with C the 3 two D isomeric 4 alcohols, (CH3)3CCH2OH and

22 What will react differently (CH3)2CHCH2CH2OH? A B C D

acidified aqueous potassium manganate(VII) concentrated sulfuric acid phosphorus pentachloride sodium

23 Which reagent will give similar results with both butanone and butanal? A B C D acidified aqueous potassium dichromate(VI) an alkaline solution containing complexed Cu2+ ions (Fehling’s solution) an aqueous solution containing [Ag(NH3)2]+ (Tollens’ reagent) 2,4-dinitrophenylhydrazine reagent

24 What is formed when propanone is refluxed with a solution of NaBH4? A B C D propanal propan-1-ol propan-2-ol propane

25 Which compound is a product of the hydrolysis of CH3CO2C3H7 by boiling aqueous sodium hydroxide? A CH3OH B C3H7OH C C3H7CO2H D
? C3H7CO 2 Na +

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10 26 In many countries plastic waste is collected separately and sorted. Some of this is incinerated to provide heat for power stations. Why is pvc, polyvinylchloride, removed from any waste that is to be incinerated? A B C D It destroys the ozone layer. It does not burn easily. It is easily biodegradable. Its combustion products are harmful.

27 Polymerisation of 1,1-dichloroethene produces a dense, high melting point substance that does not allow gases to pass through. It is used as cling wrapping. Which sequence appears in a short length of the polymer chain?
A B C D [ CH2CCl2CH2CCl2CH2CCl2 ] [ CHClCHClCHClCHClCHClCHCl ] [ CCl2CCl2CCl2CCl2CCl2CCl2 ] [ CH2CCl2CHClCHClCH2CCl2 ]

28 When an isomer Y of molecular formula C4H9Br undergoes hydrolysis in aqueous alkali to form an alcohol C4H9OH, the rate of reaction is found to be unaffected by changes in the concentration of OH– ions present. Which is the most likely molecular structure of Y? A B C D CH3CH2CH2CH2Br CH3CH2CHBrCH3 (CH3)2CHCH2Br (CH3)3CBr

29 Which isomer of C4H10O forms three alkenes on dehydration? A B C D butan-1-ol butan-2-ol 2-methylpropan-1-ol 2-methylpropan-2-ol

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11 30 Which compound exhibits both cis-trans and optical isomerism? A B C D CH3CH=CHCH2CH3 CH3CHBrCH=CH2 CH3CBr=CBrCH3 CH3CH2CHBrCH=CHBr

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12 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct

No other combination of statements is used as a correct response. 31 Which diagrams represent part of a giant molecular structure?
1 =C 2 =C 3 = Na = Cl

32 Which reactions are redox reactions? 1 2 3 CaBr2 + 2H2SO4 → CaSO4 + Br2 + SO2 + 2H2O CaBr2 + 2H3PO4 → Ca(H2PO4)2 + 2HBr CaBr2 + 2AgNO3 → Ca(NO3)2 + 2AgBr

33 Sodium hydrogensulfide, NaSH, is used to remove hair from animal hides. Which statements about the SH– ion are correct? 1 2 3 It contains 18 electrons. Three lone pairs of electrons surround the sulfur atom. Sulfur has an oxidation state of +2.

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13 34 When organic refuse decomposes in water carboxylic acids are formed. The water becomes acidic and aquatic life is destroyed. Which additives are suitable to remove this acid pollution? 1 2 3 calcium carbonate calcium hydroxide potassium nitrate

35 In a car engine, non-metallic element X forms a pollutant oxide Y. Further oxidation of Y to Z occurs in the atmosphere. In this further oxidation, 1 mol of Y reacts with ? mol of gaseous oxygen. What can X be? 1 2 3 carbon nitrogen sulfur

36 Sulfur dioxide and sulfites are used in food preservation. Why are they used for this purpose? 1 2 3 They are reducing agents so retard the oxidation of food. They inhibit the growth of aerobic bacteria. They react with NO2(g) converting it to NO(g).

37 Propanoic acid occurs naturally as a result of the bacterial fermentation of milk, and is partly responsible for the flavour of Swiss cheese.
O OH propanoic acid

Which starting materials could be used to synthesise propanoic acid? 1 2 3 CH3CH2CH2OH CH3CH2CN CH3CH2CHO

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14 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct

No other combination of statements is used as a correct response. 38 Which structural formulae represent 2,2-dimethylpentane? 1 2 3 (CH3)2CHCH2CH(CH3)2 (CH3)3CCH2CH2CH3 CH3CH2CH2C(CH3)3

39 Which reactions are examples of nucleophilic substitution? 1 2 3 CH3CH2Br + OH– → CH3CH2OH + Br–

H+ → CH3OH + HI CH3I + H2O ???
CH3CH2CH2Cl + NH3 → CH3CH2CH2NH2 + HCl

40 The diagram shows some laboratory apparatus.

water

heat

Which preparations could this apparatus be used for? 1 2 3 bromoethane, from ethanol, sodium bromide and concentrated sulfuric acid ethanal, from ethanol, sodium dichromate(VI) and sulfuric acid 1,2-dibromoethane, from bromine and ethene

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w w w e tr .X m ap eP
UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level 9701/11
May/June 2011 1 hour Additional Materials: Multiple Choice Answer Sheet Soft clean eraser Soft pencil (type B or HB is recommended) Data Booklet

s er om .c

CHEMISTRY Paper 1 Multiple Choice

*5818048303*

READ THESE INSTRUCTIONS FIRST Write in soft pencil. Do not use staples, paper clips, highlighters, glue or correction fluid. Write your name, Centre number and candidate number on the Answer Sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. Answer all questions. For each question there are four possible answers A, B, C and D. Choose the one you consider correct and record your choice in soft pencil on the separate Answer Sheet. Read the instructions on the Answer Sheet very carefully. Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet.

This document consists of 15 printed pages and 1 blank page.
IB11 06_9701_11/4RP ? UCLES 2011

[Turn over

2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct. 1

Which equation represents the second ionisation energy of an element X? A B C D X(g) → X2+(g) + 2e– X+(g) → X2+(g) + e– X(g) + 2e– → X2–(g) X–(g) + e– → X2–(g)

2

In flooded soils, like those used for rice cultivation, the oxygen content is low. In such soils, anaerobic bacteria cause the loss of nitrogen from the soil as shown in the following sequence. In which step is the change in oxidation number (oxidation state) of nitrogen different to the changes in the other steps?
A NO3–(aq) NO2–(aq) B NO(g) C N2O(g) D N2(g)

3

In the extraction of aluminium by the electrolysis of molten aluminium oxide, why is cryolite added to the aluminium oxide? A B C D to ensure the aluminium is not oxidised to ensure the anode is not oxidised to lower the melting point of the aluminium oxide to prevent corrosion of the cathode

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3 4 Different Boltzmann distributions are shown in the diagrams.
diagram 1 P number of molecules Q number of molecules diagram 2 X Y

0 0

molecular speed

0 0

molecular speed

In diagram 1, one curve P or Q corresponds to a temperature higher than that of the other curve. In diagram 2, one line X or Y corresponds to the activation energy for a catalysed reaction and the other line corresponds to the activation energy of the same reaction when uncatalysed. Which combination gives the correct curve and line? higher temperature A B C D 5 P P Q Q presence of catalyst X Y X Y

Which factor helps to explain why the first ionisation energies of the Group I elements decrease from lithium to sodium to potassium to rubidium? A B C D The nuclear charge of the elements increases. The outer electron is in an ‘s’ subshell. The repulsion between spin-paired electrons increases. The shielding effect of the inner shells increases.

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4 6 In the diagram, curve X was obtained by observing the decomposition of 100 cm3 of 1.0 mol dm–3 hydrogen peroxide, catalysed by manganese(IV) oxide.
Y X

volume of oxygen formed

0

0

time

Which alteration to the original experimental conditions would produce curve Y? A B C D 7 adding some 0.1 mol dm–3 hydrogen peroxide adding water lowering the temperature using less manganese(IV) oxide

In the last century the Haber process was sometimes run at pressures of 1000 atm and higher. Now it is commonly run at pressures below 100 atm. What is the reason for this change? A B C D An iron catalyst is used. Maintaining the higher pressures is more expensive. The equilibrium yield of ammonia is increased at lower pressures. The rate of the reaction is increased at lower pressures.

8

The equation below represents the combination of gaseous atoms of non-metal X and of hydrogen to form gaseous X2H6 molecules. 2X(g) + 6H(g) → X2H6(g) ?H = –2775 kJ mol–1

The bond energy of an X–H bond is 395 kJ mol–1. What is the bond energy of an X–X bond? A B C D – 405.0 kJ mol–1 – 202.5 kJ mol–1 +202.5 kJ mol–1 +405.0 kJ mol–1
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5 9 50 cm3 of 2.50 mol dm–3 hydrochloric acid was placed in a polystyrene beaker of negligible heat capacity. Its temperature was recorded and then 50 cm3 of 2.50 mol dm–3 NaOH at the same temperature was quickly added, with stirring. The temperature rose by 17 °C. The resulting solution may be considered to have a specific heat capacity of 4.2 J g–1 K–1. What is an approximate value for the molar enthalpy change of neutralisation of hydrochloric acid and sodium hydroxide from this experiment? A B C D

?(50 x 4.2 x 17) 1 J mol ? (0.050 x 2.5) ?(50 x 4.2 x 17) 1 J mol ? (0.10 x 2.5) ?(100 x 4.2 x 17) 1 J mol ? (0.050 x 2.5)
?(100 x 4.2 x 17) 1 J mol ? (50 x 2.5)

10 Three substances, R, S and T, have physical properties as shown. substance mp / oC bp / oC electrical conductivity of solid What could be the identities of R, S and T ? R A B C D MgO MgO NaCl NaCl S NaCl NaCl MgO MgO T C [graphite] SiO2 C [graphite] SiO2 R 801 1413 poor S 2852 3600 poor T 3550 4827 good

11 In which change would only van der Waals’ forces have to be overcome? A B C D evaporation of ethanol melting of ice melting of solid carbon dioxide solidification of butane C2H5OH(l) → C2H5OH(g) H2O(s) → H2O(l) CO2(s) → CO2(l) C4H10(l) → C4H10(s)

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6 12 Hydrazine, N2H4, is widely used as a rocket fuel because it reacts with oxygen as shown, producing ‘environmentally friendly’ gases. N2H4(l) + O2(g) → N2(g) + 2H2O(g) ?H = –534 kJ mol–1

Despite its use as a rocket fuel, hydrazine does not burn spontaneously in oxygen. Which statement explains why hydrazine does not burn spontaneously? A B C D Hydrazine is a liquid. The activation energy is too high. The N N bond is very strong. The reaction is exothermic.

13 0.02 mol of aluminium is burned in oxygen and the product is reacted with 2.00 mol dm–3 hydrochloric acid. What minimum volume of acid will be required for complete reaction? A 15 cm3 B 20 cm3 C 30 cm3 D 60 cm3

14 Steam is passed over heated magnesium to give compound X and hydrogen. What is not a property of compound X? A B C D It has an Mr of 40.3. It is basic. It is a white solid. It is very soluble in water.

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7 15 X, Y and Z represent different halogens. The table shows the results of nine experiments in which aqueous solutions of X2, Y2 and Z2 were separately added to separate aqueous solutions containing X –, Y – and Z – ions. X –(aq) X2(aq) Y2(aq) Z2(aq) no reaction X2 formed X2 formed Y –(aq) no reaction no reaction no reaction Z –(aq) no reaction Z2 formed no reaction

Which row in the following table contains the ions X –, Y – and Z – in order of their decreasing strength as reducing agents? strongest A B C D X– X– Y– Z– Y– Z– Z– X– weakest Z– Y– X– Y–

16 A student observed the reactions when sodium chloride and sodium iodide were each reacted separately with concentrated sulfuric acid and with concentrated phosphoric acid. The observations are recorded in the table. sodium chloride conc. H2SO4 conc. H3PO4 colourless acidic gas formed colourless acidic gas formed sodium iodide purple vapour formed colourless acidic gas formed

Which deduction can be made from these observations? A B C D Concentrated phosphoric acid is a stronger oxidising agent than concentrated sulfuric acid. Concentrated phosphoric acid is a stronger oxidising agent than iodine. Concentrated sulfuric acid is a stronger oxidising agent than chlorine. Concentrated sulfuric acid is a stronger oxidising agent than iodine.

17 Ammonium nitrate, NH4NO3, is manufactured in large quantities for use in fertiliser. Which statement about ammonium nitrate fertiliser is not correct? A B C D It can cause environmental problems. It consists of 35 % nitrogen by mass. It is insoluble in water. Nitric acid is used in its manufacture.

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8 18 Nitrogen monoxide, NO, is a primary pollutant produced by petrol engines and is found in their exhaust gases. Which reaction occurs in a catalytic converter and decreases the emission of nitrogen monoxide? A B C D NO(g) + CO(g) → NO2(g) + C(s) NO(g) + CO2(g) → NO2(g) + CO(g) 2NO(g) + 2CO(g) → N2(g) + 2CO2(g) 2NO(g) + CO2(g) → 2NO2(g) + C(s)

19 In the reaction pathway below, an alkane is converted into a carboxylic acid through several stages.
C10H22 stage 1 C2H 4 stage 2 catalytic hydration C2H5OH stage 3 CH3CO2H

Which processes occur at stage 1 and at stage 3? stage 1 A B C D condensation cracking cracking dehydration stage 3 combustion dehydration oxidation combustion

20 Acrylic acid is produced from propene, a gaseous product of oil refineries.
O x y OH acrylic acid

Which statement about acrylic acid is not correct? A B C D Both bond angles x and y are approximately 120°. It decolourises aqueous bromine. It gives an orange precipitate with 2,4-dinitrophenylhydrazine reagent. It reacts with an alcohol to give an ester.

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9 21 Butanedioic acid occurs in amber, algae, lichens, sugar cane and beets. It may be synthesised in two steps from 1,2-dibromoethane.
step 1 BrCH2CH2Br X step 2 HO2CCH2CH2CO2H

Which reagents could be used for this synthesis? step 1 A B C D HCN(g) HCO2Na(aq) KCN(aq / alcoholic) NaOH(aq) step 2 HCl (aq) HCl (aq) H2SO4(aq) K2Cr2O7 / H2SO4(aq)

22 The formula CH3 can represent an anion, a cation or a free radical. Species with the molecular formula CH3 can act as an electrophile, a free radical or a nucleophile depending on the number of outer shell electrons on the central carbon atom. How many outer shell electrons must be present for CH3 to act in these different ways? CH3 as an electrophile A B C D 6 6 7 8 CH3 as a free radical 7 8 6 7 CH3 as a nucleophile 8 7 8 6

23 Pentanol, C5H11OH, has four structural isomers that are primary alcohols. How many of these primary alcohols contain a chiral carbon atom? A 0 B 1 C 2 D 3

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10 24 The diagram shows the structure of the naturally-occurring molecule cholesterol.

H 3C CH3 CH3 H H

H HO

H

cholesterol
Student X claimed that the seventeen carbon atoms in the four rings all lie in the same plane. Student Y claimed that this molecule displays cis-trans isomerism at the C=C double bond. Which of the students are correct? A B C D both X and Y neither X nor Y X only Y only

25 Which isomer of C6H13OH gives the greatest number of different alkenes when it is dehydrated?
A CH3 CH3 CH CH CH3 C CH3 CH3 CH2 C OH CH2 CH3 CH3 CH3 C CH3 CH2 CH2OH D CH2OH CH3 CH2 CH2 CH OH CH2 CH3 B

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11 26 Compound X changes the colour of warm acidified sodium dichromate(VI) from orange to green. 1 mol of X reacts with 2 mol of HCN in the presence of KCN. What could X be? A B C D CH3CH2CH2CHO CH3COCH2COCH3 H2C=CHCH2CHO OHCCH2CH2CHO

27 Which formula represents an ester which will form sodium ethanoate on hydrolysis with aqueous sodium hydroxide?
A O H 3C CH2 C O CH2 CH3 H3C CH2 B O C O CH3

C O H C O CH2 CH3 H 3C O C O

D

CH2

CH2

CH3

28 A compound Y is treated with warm acidified potassium dichromate(VI). The resulting organic product gives an orange precipitate with 2,4-dinitrophenylhydrazine reagent but does not give a silver mirror with Tollens’ reagent. What is Y? A B C D butan-1-ol butan-2-ol butanal 2-methylpropan-2-ol

29 Aldehydes and ketones are carbonyl compounds. Which of them react with NaBH4 and react with Fehling’s reagent? A B C D both aldehydes and ketones aldehydes only ketones only neither aldehydes nor ketones

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12 30 The functional group in a primary alcohol is –CH2OH. Which reagent reacts with a primary alcohol, under suitable conditions, to give an organic product with the same number of oxygen atoms as the alcohol? A Al 2O3 B CH3CO2H C HBr D Na

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13 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct

No other combination of statements is used as a correct response.

31 Which statements are correct in terms of the Br?nsted-Lowry theory of acids and bases? 1 2 3 Water can act as either an acid or a base. Sulfuric acid, H2SO4, does not behave as an acid when dissolved in ethanol, C2H5OH. The ammonium ion acts as a base when dissolved in liquid ammonia.

32 Which are features of the structure of metallic copper? 1 2 3 a lattice of ions delocalised electrons ionic bonds

33 Use of the Data Booklet is relevant to this question. Zinc reacts with hydrochloric acid according to the following equation. Zn + 2HCl → ZnCl 2 + H2 Which statements are correct? [All volumes are measured at room conditions.] 1 2 3 A 3.27 g sample of zinc reacts with an excess of hydrochloric acid to give 0.050 mol of zinc chloride. A 6.54 g sample of zinc reacts completely with exactly 100 cm3 of 1.00 mol dm–3 hydrochloric acid. A 13.08 g sample of zinc reacts with an excess of hydrochloric acid to give 9.60 dm3 of hydrogen.

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14 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct

No other combination of statements is used as a correct response.

34 Which statements are correct? 1 2 3 Aluminium chloride dissolves in water to give an acidic solution. Magnesium chloride dissolves in water to give a slightly acidic solution. Sodium chloride dissolves in water to give an alkaline solution.

35 Which oxides react with water to give a solution of pH 10 or higher? 1 2 3 CaO Na2O SrO

36 Use of the Data Booklet is relevant to this question. The element astatine lies below iodine in Group VII of the Periodic Table. What will be the properties of astatine? 1 2 3 It forms diatomic molecules which dissociate more readily than chlorine molecules. It reacts explosively with hydrogen. It can oxidise iodide to iodine.

37 Which descriptions of the ammonium ion are correct? 1 2 3 It contains ten electrons. It has a bond angle of 109.5°. It has only three bonding pairs of electrons.

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15 38 Which alkenes, on reaction with steam at 600 K and 6 x 106 Pa pressure in the presence of a phosphoric acid catalyst, could produce an alcohol containing a chiral carbon atom? 1 2 3 (CH3)2C=CH2 CH3CH=CHCH3 CH3CH2CH=CH2

39 Bromoethane undergoes all of the conversions shown. Which conversions are examples of nucleophilic substitution? 1 2 3 C2H5Br → C2H5CN C2H5Br → C2H5OH C2H5Br → C2H5NH2

40 Sorbitol is an artificial sweetener used to sweeten chocolate which is suitable for diabetics.
OH H H HO H H H C C C C C C OH sorbitol H OH H OH OH H

Which functional groups can be produced when this molecule is subjected to oxidation under suitable conditions? 1 2 3 aldehyde carboxylic acid ketone

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16 BLANK PAGE

Permission to reproduce items where third-party owned material protected by copyright is included has been sought and cleared where possible. Every reasonable effort has been made by the publisher (UCLES) to trace copyright holders, but if any items requiring clearance have unwittingly been included, the publisher will be pleased to make amends at the earliest possible opportunity. University of Cambridge International Examinations is part of the Cambridge Assessment Group. Cambridge Assessment is the brand name of University of Cambridge Local Examinations Syndicate (UCLES), which is itself a department of the University of Cambridge.

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w w w e tr .X m ap eP
UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Level 9701/12
May/June 2011 1 hour Additional Materials: Multiple Choice Answer Sheet Soft clean eraser Soft pencil (type B or HB is recommended) Data Booklet

s er om .c

CHEMISTRY Paper 1 Multiple Choice

*4625341912*

READ THESE INSTRUCTIONS FIRST Write in soft pencil. Do not use staples, paper clips, highlighters, glue or correction fluid. Write your name, Centre number and candidate number on the Answer Sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. Answer all questions. For each question there are four possible answers A, B, C and D. Choose the one you consider correct and record your choice in soft pencil on the separate Answer Sheet. Read the instructions on the Answer Sheet very carefully. Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet.

This document consists of 14 printed pages and 2 blank pages.
IB11 06_9701_12/2RP ? UCLES 2011

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2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct.

1

Helium, He, is the second element in the Periodic Table. Tritium is the isotope of hydrogen 3H. What is the same in an atom of 4He and an atom of 3H? A B C D the number of electrons the number of neutrons the number of protons the relative atomic mass

2

Which diagram correctly shows the bonding in the ammonium ion, NH4+? key N electron H electron H H N H H A + H H N H H B +

C H H N H H + H H N H

D + H

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3 3 Aluminium is the most abundant metal in the Earth’s crust. The extraction of aluminium is carried out by the electrolysis of aluminium oxide dissolved in molten cryolite. Which material is used for each of the electrodes in this electrolysis? anode A B C D aluminium carbon carbon steel cathode carbon carbon steel aluminium

4

The esterification reaction ethanol + ethanoic acid ethyl ethanoate + water

is an equilibrium. The forward reaction is exothermic. How can the value of the equilibrium constant KC be increased? A B C D by adding a little concentrated sulfuric acid as a catalyst by increasing the initial concentration of ethanol by lowering the temperature by raising the temperature

5

Ammonia is manufactured on a large scale by the Haber process. In a particular plant, conditions of 400 °C and 250 atm in the presence of an iron catalyst are used. N2(g) + 3H2(g) 2NH3(g) ?Ho = –92 kJ mol–1

What could contribute most to increasing the equilibrium yield of ammonia? A B C D adding more catalyst increasing the pressure to 400 atm increasing the temperature to 1000 °C using air rather than nitrogen

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4 6 The Boltzmann distribution for a gas at constant temperature is shown below.
Y Z X n = number of gas molecules having a given kinetic energy

0 0 kinetic energy

If the temperature of the gas is reduced by 10 °C the graph changes shape. What happens to the values of n for the points marked X, Y and Z? X A B C D higher higher lower lower Y lower lower higher lower Z higher lower lower lower

7

Titanium occurs naturally as the mineral rutile, TiO2. One possible method of extraction of titanium is to reduce the rutile by heating with carbon. TiO2(s) + 2C(s) → Ti(s) + 2CO(g) The standard enthalpy changes of formation of TiO2(s) and CO(g) are –940 kJ mol–1 and –110 kJ mol–1 respectively. What is the standard enthalpy change of this reaction? A B C D –830 kJ mol–1 –720 kJ mol–1 +720 kJ mol–1 +830 kJ mol–1

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5 8 Which reaction has an enthalpy change equal to the standard enthalpy change of formation of propane? A B C D 3C(g) + 4H2(g) → C3H8(g) 3C(g) + 8H(g) → C3H8(g) 3C(s) + 4H2(g) → C3H8(g) 3C(s) + 4H2(g) → C3H8(l)

9

In the conversion of compound X into compound Z, it was found that the reaction proceeded by way of compound Y, which could be isolated. The following steps were involved. X → Y ; ?H, positive Y → Z ; ?H, negative Which reaction profile fits these data?
A B Y C D

energy

energy

energy

energy

Y X progress of reaction

Y Z X progress of reaction

X Y progress of reaction Z

X Z progress of reaction

Z

10 Tanzanite is used as a gemstone for jewellery. It is a hydrated calcium aluminium silicate mineral with a chemical formula Ca2Al xSiyO12(OH).6?H2O. Tanzanite has Mr of 571.5. Its chemical composition is 14.04 % calcium, 14.17 % aluminium, 14.75 % silicon, 54.59 % oxygen and 2.45 % hydrogen. (Ar values: H = 1.0, O = 16.0, Al = 27.0, Si = 28.1, Ca = 40.1) What are the values of x and y? x A B C D 1 2 3 6 y 1 3 3 1

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6 11 0.144 g of an aluminium compound X react with an excess of water, to produce a gas. This gas burns completely in O2 to form H2O and 72 cm3 of CO2 only. The volume of CO2 was measured at room temperature and pressure. What could be the formula of X? [C = 12.0, Al = 27.0; 1 mole of any gas occupies 24 dm3 at room temperature and pressure] A Al 2C3 B Al 3C4 C Al 4C3 D Al 5C3

12 Use of the Data Booklet is relevant to this question. Which element is likely to have an electronegativity similar to that of aluminium? A B C D barium beryllium magnesium strontium

13 In 1999, researchers working in the USA believed that they had made a new element and that it had the following electronic configuration. [Rn] 5f146d107s27p6 In which Group of the Periodic Table would you expect to find this element? A II B IV C VI D 0

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7 14 The highest oxides of the elements sodium to chlorine are separately added to water. Which diagram best represents the pH of the resulting mixtures?

A

B

pH

pH

Na2O Al 2O3 P4O10 Cl 2O7 MgO SO3 SiO2

Na2O Al 2O3 P4O10 Cl 2O7 MgO SO3 SiO2

C

D

pH

pH

Na2O Al 2O3 P4O10 Cl 2O7 MgO SO3 SiO2

Na2O Al 2O3 P4O10 Cl 2O7 MgO SO3 SiO2

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8 15 The diagram shows the first ionisation energies of 11 consecutive elements.

first ionisation energy / kJ mol–1 X atomic number
Which type of elements are labelled X and Y ? A B C D Group I metals Group II metals halogens noble gases

Y

16 Why does aluminium oxide dissolve in sodium hydroxide solution? A B C D Aluminium oxide can behave as a base. Aluminium oxide can behave as an acid. Aluminium oxide has a giant structure. The bonding in aluminium oxide is ionic.

17 Concentrated sulfuric acid can behave both as a strong acid and as an oxidising agent. With which compound does concentrated sulfuric acid react in this way? A B C D ethanol magnesium carbonate propanenitrile sodium bromide

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9 18 In the Contact process, what is the nature of the gaseous product and what is the identity of the catalyst? nature of gaseous product A B C D acidic acidic basic basic catalyst Fe V2O5 Fe V2O5

19 Which compound contains two different elements with identical oxidation states? A HCl O B Mg(OH)2 C Na2SO4 D NH4Cl

20 Which reagent gives the same visible result with propanal and with propan-2-ol? A B C D 2,4-dinitrophenylhydrazine reagent acidified potassium dichromate(VI) sodium Tollens’ reagent

21 Which halogenoalkane will undergo an SN1 reaction and produce a yellow precipitate when AgNO3(aq) is added to it? A B C D 1-chlorobutane 1-iodobutane 2-chloro-2-methylpropane 2-iodo-2-methylpropane

22 Which reaction will give 2-chloropropane in the best yield? A B C D propane gas with chlorine gas in the presence of ultraviolet light propan-2-ol with dilute NaCl (aq) propan-2-ol with SOCl 2 propene with dilute HCl (aq)

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10 23 The products obtained by cracking an alkane, X, are methane, ethene and propene. The mole fraction of ethene in the products is 0.5. What is the identity of X? A C6H14 B C8H18 C C9H20 D C11H24

24 Which compound does not show cis-trans isomerism? A B C D 2-methylpent-2-ene 3-methylpent-2-ene 3,4-dimethylhex-3-ene pent-2-ene

25 Which formulae show propanone and propanal as different compounds? A B C D empirical, molecular, structural and displayed formulae molecular, structural and displayed formulae only structural and displayed formulae only displayed formulae only

26 How many isomers with the formula C5H10 have structures that involve π bonding? A 3 B 4 C 5 D 6

27 1,1-dichloropropane reacts with aqueous sodium hydroxide in a series of steps to give propanal.
CH3CH2CHCl 2 NaOH(aq) CH3CH2CHO

Which term describes the first step of this reaction? A B C D electrophilic addition elimination nucleophilic substitution oxidation

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11 28 The ester CH3CH2CH2CO2CH3 is responsible for the aroma of apples. When this ester is hydrolysed by acid in the stomach, what is the empirical formula of the organic acid produced? A CH2O B CH4O C C2H4O D C3H6O2

29 This question should be answered by considering the reactions of KMnO4 with different functional groups under the stated conditions. The diagram shows the structure of the naturally-occurring molecule cholesterol.

H 3C CH3 CH3 H H

H HO

H

cholesterol
Cholesterol is separately treated with ● ● cold, dilute acidified KMnO4, hot, concentrated acidified KMnO4.

What is the change in the number of chiral carbon atoms in the molecule during each reaction? cold, dilute acidified KMnO4 A B C D +1 +1 +2 +2 hot, concentrated acidified KMnO4 0 –1 0 –1

30 Which reaction would not give ethanoic acid as a product? A B C D heating ethanenitrile under reflux with dilute sodium hydroxide heating ethanenitrile under reflux with dilute sulfuric acid heating ethanal under reflux with acidified sodium dichromate(VI) heating ethanol under reflux with acidified sodium dichromate(VI)

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12 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct

No other combination of statements is used as a correct response. 31 Solid calcium carbonate is added to 100 cm3 of dilute hydrochloric acid and the rate of the reaction is measured. 100 cm3 of distilled water is then added to a second 100 cm3 portion of the acid, and the experiment repeated under the same conditions. Why does the addition of water decrease the rate of the reaction? 1 2 3 Adding water reduces the frequency of collisions between reactant molecules. Adding water reduces the proportion of effective collisions between reactant molecules. Adding water reduces the proportion of reactant molecules possessing the activation energy.

32 When a sample of a gas is compressed at constant temperature from 1500 kPa to 6000 kPa, its volume changes from 76.0 cm3 to 20.5 cm3. Which statements are possible explanations for this behaviour? 1 2 3 The gas behaves non-ideally. The gas partially liquefies. Gas is adsorbed on to the vessel walls.

33 Which equations apply to an ideal gas? [p = pressure, V = volume, M = molar mass, ρ = density, c = concentration, R = gas constant, T = temperature] 1 p=

ρRT
M

2

pV = MRT

3

pV = cRT

M

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13 34 What is involved when a hydrogen bond is formed between two molecules? 1 2 3 a hydrogen atom bonded to an atom less electronegative than itself a lone pair of electrons an electrostatic attraction between opposite charges

35 When the yellow liquid NCl 3 is stirred into aqueous sodium hydroxide, the reaction that occurs can be represented by the following equation. 2NCl 3(l) + 6NaOH(aq) → N2(g) + 3NaCl (aq) + 3NaOCl (aq) + 3H2O(l) What will be the result of this reaction? 1 2 3 The nitrogen undergoes a redox reaction. A bleaching solution remains after the reaction. The final solution gives a precipitate with acidified silver nitrate.

36 In a car engine pollutant oxide Y, which contains non-metallic element X, is formed. Further oxidation of Y to Z occurs in the atmosphere. In this further oxidation, 1 mol of Y reacts with 0.5 mol of gaseous oxygen. X could be either nitrogen or sulfur. Which statements about X, Y and Z can be correct? 1 2 3 The oxidation number of X increases by two from Y to Z. Y may have an unpaired electron in its molecule. Y is a polar molecule.

37 Which compounds can be obtained from ethene in a single reaction?
1 2 3 CH3CH3 ( CH2CH2 )n HOCH2CH2OH

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14 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct

No other combination of statements is used as a correct response.

38 Which compounds when heated under reflux with an excess of hot acidified potassium dichromate(VI), give a product with a chiral centre?

CH3 1 CH3CH2CCH2OH H CH3 2 CH3CH2CCH2OH CO2H CH3 3 CH3COCCH(OH)CH3 CO2CH3

39 In the reaction between an aldehyde and HCN, catalysed by NaCN, which statements about the reaction mechanism are correct? 1 2 3 A new carbon-carbon bond is formed. In the intermediate, the oxygen carries a negative charge. The last stage involves the formation of a hydrogen-oxygen bond.

40 An organic compound, X, will react with an excess of calcium metal to produce a salt with the empirical formula CaC4H6O4. What could be the identity of X? 1 2 3 ethanoic acid butanedioic acid methylpropanedioic acid

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w w w e tr .X m ap eP
UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level 9701/13
May/June 2011 1 hour Additional Materials: Multiple Choice Answer Sheet Soft clean eraser Soft pencil (type B or HB is recommended) Data Booklet

s er om .c

CHEMISTRY Paper 1 Multiple Choice

*4298646254*

READ THESE INSTRUCTIONS FIRST Write in soft pencil. Do not use staples, paper clips, highlighters, glue or correction fluid. Write your name, Centre number and candidate number on the Answer Sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. Answer all questions. For each question there are four possible answers A, B, C and D. Choose the one you consider correct and record your choice in soft pencil on the separate Answer Sheet. Read the instructions on the Answer Sheet very carefully. Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet.

This document consists of 14 printed pages and 2 blank pages.
IB11 06_9701_13/FP ? UCLES 2011

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2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct. 1 Which equation represents the second ionisation energy of an element X? A B C D 2 X(g) → X2+(g) + 2e– X+(g) → X2+(g) + e– X(g) + 2e– → X2–(g) X–(g) + e– → X2–(g)

Which factor helps to explain why the first ionisation energies of the Group I elements decrease from lithium to sodium to potassium to rubidium? A B C D The nuclear charge of the elements increases. The outer electron is in an ‘s’ subshell. The repulsion between spin-paired electrons increases. The shielding effect of the inner shells increases.

3

In the extraction of aluminium by the electrolysis of molten aluminium oxide, why is cryolite added to the aluminium oxide? A B C D to ensure the aluminium is not oxidised to ensure the anode is not oxidised to lower the melting point of the aluminium oxide to prevent corrosion of the cathode

4

In flooded soils, like those used for rice cultivation, the oxygen content is low. In such soils, anaerobic bacteria cause the loss of nitrogen from the soil as shown in the following sequence. In which step is the change in oxidation number (oxidation state) of nitrogen different to the changes in the other steps?
A NO3–(aq) NO2–(aq) B NO(g) C N2O(g) D N2(g)

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3 5 In the last century the Haber process was sometimes run at pressures of 1000 atm and higher. Now it is commonly run at pressures below 100 atm. What is the reason for this change? A B C D 6 An iron catalyst is used. Maintaining the higher pressures is more expensive. The equilibrium yield of ammonia is increased at lower pressures. The rate of the reaction is increased at lower pressures.

In the diagram, curve X was obtained by observing the decomposition of 100 cm3 of 1.0 mol dm–3 hydrogen peroxide, catalysed by manganese(IV) oxide.
Y X

volume of oxygen formed

0

0

time

Which alteration to the original experimental conditions would produce curve Y? A B C D adding some 0.1 mol dm–3 hydrogen peroxide adding water lowering the temperature using less manganese(IV) oxide

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4 7 Different Boltzmann distributions are shown in the diagrams.
diagram 1 P number of molecules Q number of molecules diagram 2 X Y

0 0

molecular speed

0 0

molecular speed

In diagram 1, one curve P or Q corresponds to a temperature higher than that of the other curve. In diagram 2, one line X or Y corresponds to the activation energy for a catalysed reaction and the other line corresponds to the activation energy of the same reaction when uncatalysed. Which combination gives the correct curve and line? higher temperature A B C D 8 P P Q Q presence of catalyst X Y X Y

50 cm3 of 2.50 mol dm–3 hydrochloric acid was placed in a polystyrene beaker of negligible heat capacity. Its temperature was recorded and then 50 cm3 of 2.50 mol dm–3 NaOH at the same temperature was quickly added, with stirring. The temperature rose by 17 °C. The resulting solution may be considered to have a specific heat capacity of 4.2 J g–1 K–1. What is an approximate value for the molar enthalpy change of neutralisation of hydrochloric acid and sodium hydroxide from this experiment? A B C D

?(50 x 4.2 x 17) 1 J mol ? (0.050 x 2.5) ?(50 x 4.2 x 17) 1 J mol ? (0.10 x 2.5) ?(100 x 4.2 x 17) 1 J mol ? (0.050 x 2.5) ?(100 x 4.2 x 17) 1 J mol ? (50 x 2.5)

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5 9 The equation below represents the combination of gaseous atoms of non-metal X and of hydrogen to form gaseous X2H6 molecules. 2X(g) + 6H(g) → X2H6(g) ?H = –2775 kJ mol–1

The bond energy of an X–H bond is 395 kJ mol–1. What is the bond energy of an X–X bond? A B C D – 405.0 kJ mol–1 – 202.5 kJ mol–1 +202.5 kJ mol–1 +405.0 kJ mol–1

10 In which change would only van der Waals’ forces have to be overcome? A B C D evaporation of ethanol melting of ice melting of solid carbon dioxide solidification of butane C2H5OH(l) → C2H5OH(g) H2O(s) → H2O(l) CO2(s) → CO2(l) C4H10(l) → C4H10(s)

11 Hydrazine, N2H4, is widely used as a rocket fuel because it reacts with oxygen as shown, producing ‘environmentally friendly’ gases. N2H4(l) + O2(g) → N2(g) + 2H2O(g) ?H = –534 kJ mol–1

Despite its use as a rocket fuel, hydrazine does not burn spontaneously in oxygen. Which statement explains why hydrazine does not burn spontaneously? A B C D Hydrazine is a liquid. The activation energy is too high. The N N bond is very strong. The reaction is exothermic.

12 0.02 mol of aluminium is burned in oxygen and the product is reacted with 2.00 mol dm–3 hydrochloric acid. What minimum volume of acid will be required for complete reaction? A 15 cm3 B 20 cm3 C 30 cm3 D 60 cm3

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6 13 Three substances, R, S and T, have physical properties as shown. substance mp / oC bp / oC electrical conductivity of solid What could be the identities of R, S and T ? R A B C D MgO MgO NaCl NaCl S NaCl NaCl MgO MgO T C [graphite] SiO2 C [graphite] SiO2 R 801 1413 poor S 2852 3600 poor T 3550 4827 good

14 Steam is passed over heated magnesium to give compound X and hydrogen. What is not a property of compound X? A B C D It has an Mr of 40.3. It is basic. It is a white solid. It is very soluble in water.

15 Nitrogen monoxide, NO, is a primary pollutant produced by petrol engines and is found in their exhaust gases. Which reaction occurs in a catalytic converter and decreases the emission of nitrogen monoxide? A B C D NO(g) + CO(g) → NO2(g) + C(s) NO(g) + CO2(g) → NO2(g) + CO(g) 2NO(g) + 2CO(g) → N2(g) + 2CO2(g) 2NO(g) + CO2(g) → 2NO2(g) + C(s)

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7 16 X, Y and Z represent different halogens. The table shows the results of nine experiments in which aqueous solutions of X2, Y2 and Z2 were separately added to separate aqueous solutions containing X –, Y – and Z – ions. X –(aq) X2(aq) Y2(aq) Z2(aq) no reaction X2 formed X2 formed Y –(aq) no reaction no reaction no reaction Z –(aq) no reaction Z2 formed no reaction

Which row in the following table contains the ions X –, Y – and Z – in order of their decreasing strength as reducing agents? strongest A B C D X– X– Y– Z– Y– Z– Z– X– weakest Z– Y– X– Y–

17 A student observed the reactions when sodium chloride and sodium iodide were each reacted separately with concentrated sulfuric acid and with concentrated phosphoric acid. The observations are recorded in the table. sodium chloride conc. H2SO4 conc. H3PO4 colourless acidic gas formed colourless acidic gas formed sodium iodide purple vapour formed colourless acidic gas formed

Which deduction can be made from these observations? A B C D Concentrated phosphoric acid is a stronger oxidising agent than concentrated sulfuric acid. Concentrated phosphoric acid is a stronger oxidising agent than iodine. Concentrated sulfuric acid is a stronger oxidising agent than chlorine. Concentrated sulfuric acid is a stronger oxidising agent than iodine.

18 Ammonium nitrate, NH4NO3, is manufactured in large quantities for use in fertiliser. Which statement about ammonium nitrate fertiliser is not correct? A B C D It can cause environmental problems. It consists of 35 % nitrogen by mass. It is insoluble in water. Nitric acid is used in its manufacture.

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8 19 Butanedioic acid occurs in amber, algae, lichens, sugar cane and beets. It may be synthesised in two steps from 1,2-dibromoethane.
step 1 BrCH2CH2Br X step 2 HO2CCH2CH2CO2H

Which reagents could be used for this synthesis? step 1 A B C D HCN(g) HCO2Na(aq) KCN(aq / alcoholic) NaOH(aq) step 2 HCl (aq) HCl (aq) H2SO4(aq) K2Cr2O7 / H2SO4(aq)

20 The formula CH3 can represent an anion, a cation or a free radical. Species with the molecular formula CH3 can act as an electrophile, a free radical or a nucleophile depending on the number of outer shell electrons on the central carbon atom. How many outer shell electrons must be present for CH3 to act in these different ways? CH3 as an electrophile A B C D 6 6 7 8 CH3 as a free radical 7 8 6 7 CH3 as a nucleophile 8 7 8 6

21 Acrylic acid is produced from propene, a gaseous product of oil refineries.
O x y OH acrylic acid

Which statement about acrylic acid is not correct? A B C D Both bond angles x and y are approximately 120°. It decolourises aqueous bromine. It gives an orange precipitate with 2,4-dinitrophenylhydrazine reagent. It reacts with an alcohol to give an ester.

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9 22 In the reaction pathway below, an alkane is converted into a carboxylic acid through several stages.
C10H22 stage 1 C2H 4 stage 2 catalytic hydration C2H5OH stage 3 CH3CO2H

Which processes occur at stage 1 and at stage 3? stage 1 A B C D condensation cracking cracking dehydration stage 3 combustion dehydration oxidation combustion

23 A compound Y is treated with warm acidified potassium dichromate(VI). The resulting organic product gives an orange precipitate with 2,4-dinitrophenylhydrazine reagent but does not give a silver mirror with Tollens’ reagent. What is Y? A B C D butan-1-ol butan-2-ol butanal 2-methylpropan-2-ol

24 Compound X changes the colour of warm acidified sodium dichromate(VI) from orange to green. 1 mol of X reacts with 2 mol of HCN in the presence of KCN. What could X be? A B C D CH3CH2CH2CHO CH3COCH2COCH3 H2C=CHCH2CHO OHCCH2CH2CHO

25 Pentanol, C5H11OH, has four structural isomers that are primary alcohols. How many of these primary alcohols contain a chiral carbon atom? A 0 B 1 C 2 D 3

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10 26 Which isomer of C6H13OH gives the greatest number of different alkenes when it is dehydrated?
A CH3 CH3 CH CH CH3 C CH3 CH3 CH2 C OH CH2 CH3 CH3 CH3 C CH3 CH2 CH2OH D CH2OH CH3 CH2 CH2 CH OH CH2 CH3 B

27 The diagram shows the structure of the naturally-occurring molecule cholesterol.

H 3C CH3 CH3 H H

H HO

H

cholesterol
Student X claimed that the seventeen carbon atoms in the four rings all lie in the same plane. Student Y claimed that this molecule displays cis-trans isomerism at the C=C double bond. Which of the students are correct? A B C D both X and Y neither X nor Y X only Y only

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11 28 Which formula represents an ester which will form sodium ethanoate on hydrolysis with aqueous sodium hydroxide?
A O H 3C CH2 C O CH2 CH3 H3C CH2 B O C O CH3

C O H C O CH2 CH3 H 3C O C O

D

CH2

CH2

CH3

29 The functional group in a primary alcohol is –CH2OH. Which reagent reacts with a primary alcohol, under suitable conditions, to give an organic product with the same number of oxygen atoms as the alcohol? A Al 2O3 B CH3CO2H C HBr D Na

30 Aldehydes and ketones are carbonyl compounds. Which of them react with NaBH4 and react with Fehling’s reagent? A B C D both aldehydes and ketones aldehydes only ketones only neither aldehydes nor ketones

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12 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct

No other combination of statements is used as a correct response. 31 Which are features of the structure of metallic copper? 1 2 3 a lattice of ions delocalised electrons ionic bonds

32 Use of the Data Booklet is relevant to this question. Zinc reacts with hydrochloric acid according to the following equation. Zn + 2HCl → ZnCl 2 + H2 Which statements are correct? [All volumes are measured at room conditions.] 1 2 3 A 3.27 g sample of zinc reacts with an excess of hydrochloric acid to give 0.050 mol of zinc chloride. A 6.54 g sample of zinc reacts completely with exactly 100 cm3 of 1.00 mol dm–3 hydrochloric acid. A 13.08 g sample of zinc reacts with an excess of hydrochloric acid to give 9.60 dm3 of hydrogen.

33 Which statements are correct in terms of the Br?nsted-Lowry theory of acids and bases? 1 2 3 Water can act as either an acid or a base. Sulfuric acid, H2SO4, does not behave as an acid when dissolved in ethanol, C2H5OH. The ammonium ion acts as a base when dissolved in liquid ammonia.

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13 34 Which descriptions of the ammonium ion are correct? 1 2 3 It contains ten electrons. It has a bond angle of 109.5°. It has only three bonding pairs of electrons.

35 Use of the Data Booklet is relevant to this question. The element astatine lies below iodine in Group VII of the Periodic Table. What will be the properties of astatine? 1 2 3 It forms diatomic molecules which dissociate more readily than chlorine molecules. It reacts explosively with hydrogen. It can oxidise iodide to iodine.

36 Which statements are correct? 1 2 3 Aluminium chloride dissolves in water to give an acidic solution. Magnesium chloride dissolves in water to give a slightly acidic solution. Sodium chloride dissolves in water to give an alkaline solution.

37 Which alkenes, on reaction with steam at 600 K and 6 x 106 Pa pressure in the presence of a phosphoric acid catalyst, could produce an alcohol containing a chiral carbon atom? 1 2 3 (CH3)2C=CH2 CH3CH=CHCH3 CH3CH2CH=CH2

38 Which oxides react with water to give a solution of pH 10 or higher? 1 2 3 CaO Na2O SrO

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14 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct

No other combination of statements is used as a correct response. 39 Sorbitol is an artificial sweetener used to sweeten chocolate which is suitable for diabetics.
OH H H HO H H H C C C C C C OH sorbitol H OH H OH OH H

Which functional groups can be produced when this molecule is subjected to oxidation under suitable conditions? 1 2 3 aldehyde carboxylic acid ketone

40 Bromoethane undergoes all of the conversions shown. Which conversions are examples of nucleophilic substitution? 1 2 3 C2H5Br → C2H5CN C2H5Br → C2H5OH C2H5Br → C2H5NH2

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w w w e tr .X m ap eP
UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level 9701/11
May/June 2012 1 hour Additional Materials: Multiple Choice Answer Sheet Soft clean eraser Soft pencil (type B or HB is recommended) Data Booklet

s er om .c

CHEMISTRY Paper 1 Multiple Choice

*6083199800*

READ THESE INSTRUCTIONS FIRST Write in soft pencil. Do not use staples, paper clips, highlighters, glue or correction fluid. Write your name, Centre number and candidate number on the Answer Sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. Answer all questions. For each question there are four possible answers A, B, C and D. Choose the one you consider correct and record your choice in soft pencil on the separate Answer Sheet. Read the instructions on the Answer Sheet very carefully. Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet.

This document consists of 14 printed pages and 2 blank pages.
IB12 06_9701_11/3RP ? UCLES 2012

[Turn over

2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct. 1 In which species does the underlined atom have an incomplete outer shell? A 2 BF3 B CH3– C F2O D H3O+

Ammonia is manufactured by the Haber Process, in an exothermic reaction. Assuming that the amount of catalyst remains constant, which change will not bring about an increase in the rate of the forward reaction? A B C D decreasing the size of the catalyst pieces increasing the pressure increasing the temperature removing the ammonia as it is formed

3

The equation for a reaction is shown. H2(g) +
1 2

O2(g) → H2O(l) ; ?H = x kJ mol–1

Which pair of descriptions is fully correct for this reaction? type(s) of enthalpy change A B C D 4 formation only formation only combustion, formation combustion, formation value of x positive negative positive negative

The value of the second ionisation energy of calcium is 1150 kJ mol–1. Which equation correctly represents this statement? A B C D Ca(g) → Ca2+(g) + 2e? ; Ca+(g) → Ca2+(g) + e? ; Ca+(g) ?→ Ca2+(g) + e? ; Ca(g) → Ca2+(g) + 2e? ; ?H o = +1150 kJ mol–1 ?H o = +1150 kJ mol–1 ?H o = –1150 kJ mol–1 ?H o = –1150 kJ mol–1

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3 5 Two conversions are outlined below. NH4+ → NH3 C2H4 → C2H6 What similar feature do these two conversions have? A B C D 6 a lone pair of electrons in the product change in oxidation state of an element decrease in bond angle of the species involved disappearance of a π bond

Use of the Data Booklet is relevant to this question. The gas laws can be summarised in the ideal gas equation. pV = nRT 0.56 g of ethene gas is contained in a vessel at a pressure of 102 kPa and a temperature of 30 °C. What is the volume of the vessel? A 49 cm3 B 494 cm3 C 48 900 cm3 D 494 000 cm3

7

Propanone has the molecular formula C3H6O. The enthalpy change of combustion of hydrogen is –286 kJ mol–1. The enthalpy change of combustion of carbon is –394 kJ mol–1. The enthalpy change of combustion of propanone is –1786 kJ mol–1. Using this information, what is the enthalpy change of formation of propanone? A B C D –1106 kJ mol–1 –540 kJ mol–1 –254 kJ mol–1 +1106 kJ mol–1

8

Under which set of conditions is a gas most likely to behave ideally? temperature A B C D high high low low pressure high low high low

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4 9 Two moles of compound P were placed in a vessel. The compound P was partly decomposed by heating. A dynamic equilibrium between chemicals P, Q and R was established. At equilibrium, x mol of R were present and the total number of moles present was (2 + x). What is the equation for this equilibrium? A B C D P 2P 2P 2P 2Q + R 2Q + R Q+R Q + 2R

10 The oxide of titanium, TiO2, is used as a ‘whitener’ in toothpaste. It is obtained from the ore iron(II) titanate, FeTiO3. What is the change, if any, in the oxidation number (oxidation state) of titanium in the reaction FeTiO3 → TiO2? A B C D It is oxidised from +3 to +4. It is reduced from +3 to +2. It is reduced from +6 to +4. There is no change in the oxidation number.

11 The diagram shows a cell for the manufacture of aluminium.
graphite anodes

mixture of Al 2O3 and molten cryolite graphite lining acting as cathode molten aluminium

Which statement is incorrect? A B C D Aluminium ions are oxidised in this process. Aluminium is liberated at the cathode by the reaction Al 3+ + 3e– → Al . The cryolite acts as a solvent. The graphite anode burns away.

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5 12 Aluminium chloride catalyses certain reactions by forming carbocations with chloroalkanes as shown. RCl + Al Cl 3 → R+ + Al Cl 4– Which property makes this reaction possible? A B C D Al Cl 3 exists as the dimer Al 2Cl 6 in the vapour. Al Cl 3 is a covalent molecule. The aluminium atom in Al Cl 3 has an incomplete octet of electrons. The chlorine atom in RCl has a vacant p orbital.

13 Use of the Data Booklet is relevant to this question. When a mineral was heated in a Bunsen flame to constant mass, a colourless gas that turned lime water milky was evolved. The remaining solid was cooled and then added to aqueous hydrochloric acid. Vigorous effervescence was seen. What was the mineral? A B C D aragonite, CaCO3 artinite, MgCO3.Mg(OH)2.3H2O barytocalcite, BaCO3.CaCO3 dolomite, CaCO3.MgCO3

14 Use of the Data Booklet is relevant to this question. The reaction between aluminium powder and anhydrous barium nitrate is used as the propellant in some fireworks. The metal oxides and nitrogen are the only products. Which volume of nitrogen, measured under room conditions, is produced when 0.783 g of anhydrous barium nitrate reacts with an excess of aluminium? A 46.8 cm3 B 72.0 cm3 C 93.6 cm3 D 144 cm3

15 The oxides BaO, CaO, MgO and SrO all produce alkaline solutions when added to water. Which oxide produces the saturated solution with the highest pH? A BaO(aq) B CaO(aq) C MgO(aq) D SrO(aq)

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6 16 In the treatment of domestic water supplies, chlorine is added to the water to form HCl O. Cl 2(aq) + H2O(I) → H+(aq) + Cl –(aq) + HCl O(aq) The HCl O reacts further to give Cl O– ions. HCl O(aq) + H2O(I) → H3O+(aq) + Cl O–(aq) Both HCl O and Cl O– kill bacteria by oxidation. What is the overall change in oxidation number of chlorine when forming the Cl O– ion from the aqueous chlorine? A –1 B 0 C +1 D +2

17 What trend is observed on descending Group VII? A B C D The colours of the elements become lighter. The elements become more volatile. The hydrides of the elements become more thermally stable. The reactions of the elements with hydrogen become less vigorous.

18 The following two experiments are carried out with anhydrous potassium chloride and observations X and Y are made at the end of each experiment. Concentrated sulfuric acid is added to the potassium chloride and the fumes produced are bubbled into aqueous potassium iodide solution - observation X. The potassium chloride is dissolved in aqueous ammonia and this is then added to aqueous silver nitrate - observation Y. What are the observations X and Y? X A B C D brown solution brown solution colourless solution colourless solution Y colourless solution white precipitate colourless solution white precipitate

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7 19 Carbon monoxide, CO, nitrogen monoxide, NO, and sulfur dioxide, SO2, may all be present in the exhaust fumes from a car engine. Which reaction concerning these compounds occurs in the atmosphere? A B C D CO is spontaneously oxidised to CO2 NO2 is reduced to NO by CO NO2 is reduced to NO by SO2 SO2 is oxidised to SO3 by CO2

20 Fumaric acid can be converted into oxaloacetic acid by a two-step process involving the intermediate Q.
step 1 HO2CCH=CHCO2H fumaric acid Q step 2 HO2CCOCH2CO2H oxaloacetic acid

Each of these steps can be achieved in the laboratory by a single reagent. What could be the intermediate Q and the reagent for step 2? Q A B C D HO2CCHBrCH2CO2H HO2CCHBrCH(OH)CO2H HO2CCH(OH)CH2CO2H HO2CCH(OH)CH2CO2H reagent for step 2 warm acidified KMnO4 warm NaOH(aq) Fehling’s solution warm acidified K2Cr2O7

21 An organic compound J reacts with sodium to produce an organic ion with a charge of –3. J reacts with NaOH(aq) to produce an organic ion with a charge of –1. What could be the structural formula of J? A B C D HO2CCH(OH)CH2CO2H HO2CCH(OH)CH2CHO HOCH2CH(OH)CH2CO2H HOCH2COCH2CHO

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8 22 Use of the Data Booklet is relevant to this question. A sample of ethyl propanoate is hydrolysed by heating under reflux with aqueous sodium hydroxide. The two organic products of the hydrolysis are separated, purified and weighed. Out of the total mass of products obtained, what is the percentage by mass of each product? A B C D 32.4 % and 67.6 % 38.3 % and 61.7 % 42.3 % and 57.7 % 50.0 % and 50.0 %

23 Compound C is used in textile and leather processing.
O C O CH2 C O

compound C

H2C

O

Which starting material(s), on gentle heating with a few drops of concentrated sulfuric acid, generates compound C? A B C D CH3COOH only HOCH2COOH only CH3COOCH2COOH only CH3COOH mixed with HOCH2COOH

24 How many isomeric esters have the molecular formula C4H8O2? A 2 B 3 C 4 D 5

25 Which compound, on reaction with hydrogen cyanide, produces a compound with a chiral centre? A B C D CH3CHO CH3CH2COCH2CH3 CH3CO2CH3 HCHO

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9 26 CH3COCH2CH2OH W CH3COCH2CHO X CH3CH(OH)CH2CH3 Y CH3CH2CH2CHO Z

Which of these compounds can be oxidised by acidified dichromate(VI) solution and also gives a positive response to Tollens’ reagent? A B C D W and X only W and Y only X and Z only Y and Z only

27 The presence of halogen in an organic compound may be detected by warming the organic compound with aqueous silver nitrate. Which compound would produce a precipitate quickest?
A Cl B F C Cl D F

Cl Cl

Cl F

Br F

F I

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10 28 A reaction pathway diagram is shown.

energy

reaction pathway

Which reaction does not have such a profile?
A B C CH3CHO + HCN NaCN CH3CH(OH)CN

C2H5Br + NaOH → C2H5OH + NaBr (CH3)3CBr + NaOH → (CH3)3 COH + NaBr Br

D

+ Br2

Br

29 The depletion of the ozone layer in the upper atmosphere reduces the Earth’s natural protection from harmful ultraviolet radiation. Which compound would cause the most depletion of the ozone layer? A CCl 3F B CF4 C CHCl F2 D CH2F2

30 Which statement does not correctly describe the polymer PVC? A B C D Combustion of PVC waste produces a highly acidic gas. PVC molecules are saturated. The empirical formula of PVC is the same as the empirical formula of its monomer. The repeat unit of PVC is –(CHCl CHCl )–.

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11 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct

No other combination of statements is used as a correct response. 31 The gas laws can be summarised in the ideal gas equation. pV = nRT where each symbol has its usual meaning. Which statements are correct? 1 2 3 One mole of an ideal gas occupies the same volume under the same conditions of temperature and pressure. The density of an ideal gas at constant pressure is inversely proportional to the temperature, T. The volume of a given mass of an ideal gas is doubled if its temperature is raised from 25 °C to 50 °C at constant pressure.

32 Use of the Data Booklet is relevant to this question. In which pairs do both species have the same number of unpaired p electrons? 1 2 3 O and Cl + F+ and Ga– P and Ne+

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12 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct

No other combination of statements is used as a correct response. 33 Nitrogen and phosphorus are both in Group V of the Periodic Table. Phosphorus forms a chloride with the formula PCl 5. Why is it not possible for nitrogen to form NCl 5? 1 2 3 Nitrogen’s outer shell can only contain eight electrons. Nitrogen cannot have oxidation state +5. Nitrogen is almost inert.

34 Ammonia and chlorine react in the gas phase. 8NH3 + 3Cl 2 → N2 + 6NH4Cl Which statements are correct? 1 2 3 Ammonia behaves as a reducing agent. Ammonia behaves as a base. The oxidation number of the hydrogen changes

35 Which statements are correct for all three halogens, chlorine, bromine and iodine? 1 2 3 They all form hydrides that are strong acids in aqueous solution. They all react with aqueous sodium hydroxide to form oxo-anions. They all require one more electron to fill the p orbitals of their outer shells.

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13 36 In the manufacture of sulfuric acid the reaction 2SO2(g) + O2(g) 2SO3(g) usually takes place at 400 °C and 1 atm pressure. In one industrial plant, it is decided to change the pressure to 20 atm. What will be the consequences of this change? 1 2 3 increased running costs an increased percentage of sulfur trioxide in the equilibrium mixture the rate of the backward reaction increases

37 What is always involved in a carbon-carbon π bond? 1 2 3 a shared pair of electrons a sideways overlap of p orbitals delocalised electrons

38 A number of alcohols with the formula C4H10O are separately oxidised. Using 70 g of the alcohols a 62 % yield of organic product is achieved. What mass of product could be obtained? 1 2 3 42.2 g of butanone 51.6 g of butanoic acid 51.6 g of 2-methyl propanoic acid

39 The compound cis-hex-3-enal is responsible for the characteristic smell of cut grass. The human nose is particularly sensitive to this compound, being able to detect 0.25 parts per billion in air.

O cis-hex-3-enal

Which reagents will react with cis-hex-3-enal? 1 2 3 sodium sodium borohydride Fehling’s reagent

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14 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct

No other combination of statements is used as a correct response. 40 How can a good yield of ethylamine be made using bromoethane as starting material? 1 2 3 by heating bromoethane with an excess of ammonia gas in a sealed tube by adding dilute aqueous ammonia to bromoethane at room temperature by heating bromoethane under reflux with aqueous ammonium chloride

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w w w e tr .X m ap eP
UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level 9701/12
May/June 2012 1 hour Additional Materials: Multiple Choice Answer Sheet Soft clean eraser Soft pencil (type B or HB is recommended) Data Booklet

s er om .c

CHEMISTRY Paper 1 Multiple Choice

*7046687152*

READ THESE INSTRUCTIONS FIRST Write in soft pencil. Do not use staples, paper clips, highlighters, glue or correction fluid. Write your name, Centre number and candidate number on the Answer Sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. Answer all questions. For each question there are four possible answers A, B, C and D. Choose the one you consider correct and record your choice in soft pencil on the separate Answer Sheet. Read the instructions on the Answer Sheet very carefully. Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet.

This document consists of 14 printed pages and 2 blank pages.
IB12 06_9701_12/3RP ? UCLES 2012

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2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct. 1 The molecular energy distribution curve represents the variation in energy of the molecules of a gas at room temperature.

proportion of molecules

0 0 energy

Which curve applies for the same gas at a lower temperature?

A

B

proportion of molecules

proportion of molecules

0 0 energy C

0 0 energy D

proportion of molecules

proportion of molecules

0 0 energy

0 0 energy

2

In which species are the numbers of protons, neutrons and electrons all different? A
11 5B

B

19 ? 9F

C

+ 23 11Na

D

24 2+ 12 Mg

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3 3 What is the most likely shape of a molecule of hydrazine, N2H4?
A H 90° N H N H H N H H 90° N H H B H H N C 120° N H H H H N D 107° N H H

4

In which species does the underlined atom have an incomplete outer shell? A Al 2Cl 6 B CH3+ C Cl 2O D H2Cl C?

5

Which solid contains more than one kind of bonding? A B C D iodine silicon dioxide sodium chloride zinc

6

Use of the Data Booklet is relevant to this question. The gas laws can be summarised in the ideal gas equation. pV = nRT 0.96 g of oxygen gas is contained in a glass vessel of volume 7000 cm3 at a temperature of 30 °C. What is the pressure in the vessel? A 1.1 kPa B 2.1 kPa C 10.8 kPa D 21.6 kPa

7

Two moles of compound P were placed in a vessel. The vessel was heated and compound P was partly decomposed to produce Q and R. A dynamic equilibrium between chemicals P, Q and R was established. At equilibrium x moles of R were present and the total number of moles present was (2 + x ). 2 What is the equation for this equilibrium reaction? A B C D P 2P 2P 2P 2Q + R 2Q + R Q+R Q + 2R

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4 8 The value of the third ionisation energy of aluminium is 2740 kJ mol–1. Which correctly represents this statement? A B C D 9 Al (g) → Al 3+(g) + 3e– Al 2+(g) → Al 3+(g) + e– Al (g) → Al 3+(g) + 3e– Al 2+(g) → Al 3+(g) + e– ?Ho = –2740 kJ mol–1 ?Ho = –2740 kJ mol–1 ?Ho = +2740 kJ mol–1 ?Ho = +2740 kJ mol–1

Methanol is manufactured by reacting carbon dioxide and hydrogen. CO2(g) + 3H2(g) CH3OH(g) + H2O(g) ?H = –49 kJ mol–1

What would increase the equilibrium yield of methanol in this process? A B C D adding a catalyst adding an excess of steam increasing the pressure increasing the temperature

10 Which molecule has the largest overall dipole?
A H C H C CH3 CH3 O C CH3 B CH3 O C Cl Cl C Cl H 3C C C CH3 D Cl

11 In which substance does nitrogen exhibit the highest oxidation state? A NO B N2O C N2O4 D NaNO2

12 Red lead oxide, Pb3O4, is used in metal priming paints. It can be made by heating PbO in air. 6PbO(s) + O2(g) → 2Pb3O4(s) Which two values are needed to calculate the enthalpy change for this reaction? A B C D enthalpy change of atomisation of O2 and enthalpy change of formation of Pb3O4 enthalpy change of formation of O2 and enthalpy change of formation of Pb3O4 enthalpy change of formation of PbO and enthalpy change of atomisation of O2 enthalpy change of formation of PbO and enthalpy change of formation of Pb3O4

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5 13 Which gas is present in the exhaust fumes of a car engine in a much greater amount than any other gas? A B C D carbon dioxide carbon monoxide nitrogen water vapour

14 Slaked lime, Ca(OH)2, may be made from limestone, CaCO3. On heating in a lime kiln at 1000 °C, limestone decomposes as follows. reaction 1 CaCO3(s) → CaO(s) + CO2(g)

Water is then reacted with calcium oxide, CaO, as follows. reaction 2 CaO(s) + H2O(l) → Ca(OH)2(s)

What are the enthalpy changes of these reactions? reaction 1 A B C D endothermic endothermic exothermic exothermic reaction 2 endothermic exothermic endothermic exothermic

15 The period 4 elements gallium (Ga), germanium (Ge), arsenic (As) and selenium (Se) are the elements below aluminium, silicon, phosphorus and sulfur in the Periodic Table, a portion of which is shown below. period 3 elements period 4 elements Al Ga Si Ge P As S Se

The properties of each period 4 element resemble those of the period 3 element directly above it. Which period 4 elements form oxides that dissolve in water to give an acid solution? A As and Se B Ga and Ge C Ga and Se D Se only

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6 16 Chlorine shows oxidation states ranging from –1 to +7 in its compounds. What are the reagent(s) and conditions necessary for the oxidation of elemental chlorine into a compound containing chlorine in the +5 oxidation state? A B C D AgNO3(aq) followed by NH3(aq) at room temperature concentrated H2SO4 at room temperature cold dilute NaOH(aq) hot concentrated NaOH(aq)

17 What can be seen when a piece of magnesium ribbon is placed in cold water? A B C D A vigorous effervescence occurs. Bubbles of gas form slowly on the magnesium. The magnesium floats on the surface of the water and reacts quickly. The magnesium glows and a white solid is produced.

18 Use of the Data Booklet is relevant to this question. Sodium and sulfur react together to form sodium sulfide, Na2S. How do the atomic radius and ionic radius of sodium compare with those of sulfur? atomic radius A B C D sodium > sulfur sodium > sulfur sodium < sulfur sodium < sulfur ionic radius sodium > sulfur sodium < sulfur sodium > sulfur sodium < sulfur

19 Which substance does not produce a poisonous gas, when burnt in a limited amount of air? A B C D hydrogen methane propene sulfur

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7 20 Use of the Data Booklet is relevant to this question. A sample of propyl ethanoate is hydrolysed by heating under reflux with aqueous sodium hydroxide. The two organic products of the hydrolysis are separated, purified and weighed. Out of the total mass of products obtained, what is the percentage by mass of each product? A B C D 32.4 % and 67.6 % 38.3 % and 61.7 % 42.3 % and 57.7 % 50.0 % and 50.0 %

21 Which diagram gives the skeletal formula of 2-chloropentan-3-ol?
A Cl Cl B OH Cl C Cl D OH

OH

OH

22 When 1-bromopropane is treated in succession with two reagents, X and Y, it produces propanoic acid. What are reagents X and Y? X A B C D NaOH(aq) NaOH(aq) KCN in ethanol KCN in ethanol Y H+ / Cr2O72–(aq) CO2 HCl (aq) NaOH(aq)

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8 23 Isomers X and Y both react with HBr.
H3C C H 3C X C Br H 3C Y Br Br C C CH3 Br

A mixture of X and Y is reacted with HBr. Which three structures represent three different possible products of this reaction? A B C D (CH3)2CHCBr3 (CH3)2CHCBr3 (CH3)2CBrCBr3 (CH3)2CBrCHBr2 (CH3)2CBrCHBr2 (CH3)2CBrCHBr2 (CH3)2CHCBr3 CHBr2CBr(CH3)CH3 CH3CHBrCHBrCH3 CH3CBr2CHBrCH3 CH3CBr2CHBrCH3 CH3CHBrCBr2CH3

24 Oct-1-ene, CH3(CH2)5CH=CH2, is subjected to thermal cracking. Which combination of compounds W, X, Y and Z can be obtained? CH2=CH2 W A B C D W, X, Y and Z W, X and Y only W, X and Z only W and X only CH3CH=CH2 X CH3CH2CH3 Y CH2=CHCH=CH2 Z

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9 25 When phenacyl chloride, C6H5COCH2Cl, is reacted with aqueous NaOH, the substitution reaction follows an SN2 mechanism. Which structure represents a species formed during the reaction?

A H C 6H 5 C O C+ H C 6H 5

B OH H
δ+ δ–

C O–

C H

Cl

C H C C C 6H 5 H – Cl O
δ–

D H HO C C C 6H 5
δ–

δ–

H

– Cl O
δ–

HO

26 Complete combustion of compound X gives carbon dioxide and water only. A sample of X is mixed with aqueous potassium(V) dichromate and boiled under reflux for one hour. The mixture is then distilled and the only organic substance present is collected. The organic substance collected reacts with sodium to give hydrogen, but does not react with 2,4-dinitrophenylhydrazine reagent and does not react with ethanol in the presence of concentrated sulfuric acid to give an ester. What can be deduced from this information? A B C D X is a carboxylic acid. X is a ketone. X is an alcohol. X is an alkane.

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10 27 A compound Y has the following properties. ? It is a liquid at room temperature and atmospheric pressure. ? It does not mix completely with water. ? It does not give steamy fumes with PCl5. What could Y be? A B C D ethane ethanoic acid ethanol ethyl ethanoate

28 Coniine is the major constituent of the poison ‘oil of hemlock’.

N H coniine

CH2CH2CH3

Coniine can be synthesised by reacting ammonia with a dibromo compound, X. NH3 + C8H16Br2 → coniine + 2HBr X What is the name of compound X? A B C D 1,1-dibromo-2-propylcyclopentane 1,2-dibromo-2-propylcyclopentane 1,4-dibromooctane 1,5-dibromooctane

29 A common industrial solvent is a mixture of propanone, CH3COCH3, and pentyl ethanoate CH3CO2(CH2)4CH3. Which reagent would have no reaction with this industrial solvent? A B C D HCl (aq) HCN(aq) with a little KCN Na(s) NaBH4

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11 30 An organic compound will decolorise dilute acidified aqueous potassium manganate(VII) on warming, but will not decolorise bromine water. What could the organic compound be? A B C D butane ethanol ethene ethanoic acid

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12 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct

No other combination of statements is used as a correct response. 31 Which of the following molecules and ions have a regular trigonal planar shape? 1 2 3 BF3 CH3+ Al Cl 3

32 Ammonia and chlorine react in the gas phase. 8NH3 + 3Cl 2 → N2 + 6NH4Cl Which statements are correct? 1 2 3 Each nitrogen atom is oxidised. Each chlorine atom is reduced. Ammonia behaves as a base.

33 Concentrated sulfuric acid behaves as a strong acid when it reacts with water. H2SO4(l) + aq → H+(aq) + HSO4–(aq) The HSO4– ion formed behaves as a weak acid. HSO4–(aq) H+(aq) + SO42–(aq)

Which statements are true for 1.0 mol dm–3 sulfuric acid? 1 2 3 [H+(aq)] is high [SO42–(aq)] is high [HSO4–(aq)] = [SO42–(aq)]

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13 34 Silver chloride dissolves in aqueous ammonia. What happens in this process? 1 2 3 A co-ordinate bond is formed. The oxidation number of nitrogen is unchanged. Ammonia acts as a Br?nsted-Lowry base.

35 Compared with the HCl molecule, the bond ……X…… of the HBr molecule is ……Y…… Which pairs of words correctly complete the above sentence? X 1 2 3 energy polarity length Y less less greater

36 Which statements are true about the Haber process for the manufacture of ammonia? 1 2 3 At higher temperatures, the yield goes down but the rate of production of ammonia is faster. At higher pressures, the yield goes down but the rate of production of ammonia is faster. In the presence of a catalyst, the yield goes down but the rate of production of ammonia is faster.

37 Which compounds can be obtained from propene in a single reaction? 1 CH2OHCHOHCH3 2 ( CH2CH(CH3) ) n

3 CH2BrCH2CH2Br 38 What are the same for a pair of optical isomers? 1 2 3 their empirical formula their functional groups their structural formula

39 Which statements about the photochemical chlorination of ethane are correct? 1 2 3 Hydrogen gas is one of the products. A propagation step in the mechanism is C2H6 + Cl ? → C2H5? + HCl. The

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