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Chemistry MCQ Book

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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.

Use of the Data Booklet may be appropriate for some questions.

1 Which contains the largest number of hydrogen atoms?

A 0.10 mol of pentane


B 0.20 mol of but-2-ene
C 1.00 mol of hydrogen molecules

D 6.02  1023 hydrogen atoms

2 In which pair of species do both species have only one unpaired p electron?

A Ar+ and C– B B and Ti+ C F and Ga D Se– and Si–

3 Phosphorus forms two chlorides. Phosphorus(III) chloride, PCl 3, is a covalent liquid.

Phosphorus(V) chloride is an ionic solid. One of the ions present is [PCl 4]+.

What is the shape of the PCl 3 molecule and the [PCl 4]+ ion?

PCl 3 [PCl 4]+

A pyramidal square planar


B pyramidal tetrahedral
C tetrahedral square planar
D trigonal planar tetrahedral

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3

4 is the standard enthalpy of formation of methane.

is the standard enthalpy of combustion of carbon.

is the standard enthalpy of combustion of hydrogen.

CH4(g) + 2O2(g) CO2(g) + 2H2O(l)

Which expression is equivalent to ?

A – +
B – 2 –
C – +
D + 2 –

5 The diagram shows the Boltzmann distribution for the same gas at two different temperatures, T1
and T2.

T1

T2
y

0
0 x

What is plotted on the y-axis and which line represents the higher temperature?

plotted on y-axis higher temperature

A number of molecules T1
B number of molecules T2
C molecular energy T1
D molecular energy T2

6 What is the minimum mass of oxygen required to ensure the complete combustion of 12 dm3 of
propane measured under room conditions?

A 60 g B 80 g C 120 g D 160 g

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7 Why is the first ionisation energy of oxygen less than that of nitrogen?

A The nitrogen atom has its outer electron in a different subshell.


B The nuclear charge on the oxygen atom is greater than that on the nitrogen atom.
C The oxygen atom has a pair of electrons in one p orbital that repel one another.
D There is more shielding in an oxygen atom.

8 Which gas would behave most like an ideal gas under room conditions?

A helium
B nitrogen
C ammonia
D krypton

9 When hydrogen iodide is reacted with concentrated sulfuric acid, several reactions occur,
including:

8HI + H2SO4  H2S + 4H2O + 4I2

Which row gives the change in oxidation number of iodine and of sulfur in this reaction?

change in oxidation change in oxidation


number of iodine number of sulfur

A –1 +6
B –1 +8
C +1 –6
D +1 –8

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5

10 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 to cool the incoming gas mixture to avoid overheating the catalyst


B to cool the reaction products and separate the NH3 from unused N2 and H2
C to warm the incoming gas mixture and shift the equilibrium to give more NH3
D to warm the incoming gas mixture and speed up the reaction

11 Which statement about catalysts is correct?

A They change the reaction pathway by increasing the activation energy.


B They increase the rate of reaction by lowering the enthalpy change of the reaction.
C They increase the number of particles that have sufficient energy to react.
D Heterogeneous catalysts are in the same state as the reactant.

12 Element X is in Period 3. Element X forms a solid oxide Y.

Y reacts with hot concentrated hydrochloric acid. Y reacts with hot aqueous sodium hydroxide to
form a compound in which X is part of an anion.

How many p electrons does one atom of X have in its outer shell?

A 0 B 1 C 2 D 3

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13 The gaseous products of heating a mixture of Ca(OH)2 and NH4Cl are passed through solid CaO.
A single gaseous product, W, is collected.

A sample of W reacts with Cl 2(g) to produce two gases, X and Y.

X is an element. Y is acidic.

Y reacts with W to produce Z.

What are X and Z?

X Z

A N2 CaCl 2
B N2 NH4Cl
C O2 CaCl 2
D O2 NH4Cl

14 Q is a mixture of a Group 2 oxide and a Group 2 sulfate. Q contains equal amounts of the two
compounds.

Q is shaken with water and the resulting mixture filtered; a solid residue is obtained. There is no
reaction when the solid residue is shaken with HCl (aq). Shaking the filtrate with H2SO4(aq)
produces a white precipitate.

What could be Q?

A BaO + BaSO4
B BaO + MgSO4
C MgO + BaSO4
D MgO + MgSO4

15 Which substance will not be a product of the thermal decomposition of hydrated


magnesium nitrate?

A dinitrogen monoxide
B magnesium oxide
C oxygen
D steam

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16 A 5 cm3 sample of 0.05 mol dm–3 sodium chloride is mixed with a 5 cm3 sample of 0.05 mol dm–3
potassium iodide. 10 cm3 of acidified 0.05 mol dm–3 silver nitrate is then added, followed by
concentrated ammonia solution.

What is seen after the addition of an excess of concentrated ammonia solution?

A a cream precipitate
B a white precipitate
C a yellow precipitate
D no precipitate

17 The volatility of the Group 17 elements, chlorine, bromine and iodine, decreases down the group.

What is responsible for this trend?

A bond length in the halogen molecule


B bond strength in the halogen molecule
C electronegativity of the halogen atom
D number of electrons in the halogen atom

18 Acid rain is a dilute solution of sulfuric acid.

Which pollutant also contributes to the formation of acid rain?

A carbon monoxide
B carbon dioxide
C nitrogen dioxide
D hydrocarbons

19 R is an oxide of Period 3 element T. 5.00 g of R contains 2.50 g of T.

What is T?

A magnesium
B aluminium
C silicon
D sulfur

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20 Bromoethane reacts with cyanide ions, producing propanenitrile.

Which statement about the SN2 mechanism of this reaction is correct?

A The lone pair of electrons on C of CN– attacks the carbon atom of the C–Br bond.
B The lone pair of electrons on C of CN– attacks the carbocation formed when the C–Br bond
breaks.
C The lone pair of electrons on N of CN– attacks the carbon atom of the C–Br bond.
D The lone pair of electrons on N of CN– attacks the carbocation formed when the C–Br bond
breaks.

21 Which compound would produce two different carboxylic acids when treated with hot,
concentrated, acidified manganate(VII) ions?

A B C D

22 Which compound could show both cis-trans isomerism and optical isomerism?

A B C D
Cl Cl O Br Cl
H H H
Br Br Br C C Br Br
C C C

C C Br C C Br C C Cl C C I

Br H I H Cl H Br H

23 Limonene is a hydrocarbon found in the rind of citrus fruits.

limonene

What is the molecular formula of limonene?

A C10H12 B C10H14 C C10H16 D C10H18

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24 The compound cetyl palmitate, C15H31CO2C16H33, is a waxy solid.

Cetyl palmitate is heated under reflux with an excess of aqueous sodium hydroxide.

Which products will be formed?

A C15H31ONa and C16H33CO2Na


B C15H31CO2Na and C16H33ONa
C C15H31OH and C16H33CO2Na
D C15H31CO2Na and C16H33OH

25 When an organic compound is oxidised, any oxygen atom gained by the organic molecule is
considered to be from a water molecule also producing 2H+ + 2e–. Any hydrogen atom lost may
be considered to be lost as H+ + e–.

These changes can be represented by the following two equations.

H2O  [O] + 2H+ + 2e–

[H]  H+ + e–

Compound X is oxidised by heating under reflux with hot, acidified potassium dichromate(VI) for
one hour. The half-equation for the reduction reaction is shown.

Cr2O72– + 14H+ + 6e–  2Cr3+ + 7H2O

Under these conditions, one mole of potassium dichromate(VI) oxidises three moles of X.

What could X be?

A propanal
B propan-1-ol
C propan-1,2-diol
D propan-1,3-diol

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26 Compound X has the empirical formula C2H4O. Its infra-red spectrum is shown.

100

transmittance / %
50

0
4000 3000 2000 1500 1000 500
–1
wavenumber / cm

What could be the skeletal formula of compound X?

A B C D
OH O
O O
O O
O
H OH

27 How many moles of hydrogen, H2, are evolved when an excess of sodium metal is added to
one mole of citric acid?

citric acid

CO2H

HO C CH2CO2H

CH2CO2H

A 0.5 B 1.5 C 2 D 4

28 Which statement is correct for the reaction of carbonyl compounds with HCN?

A The reaction is catalysed by concentrated H2SO4.


B Pentan-2-one and HCN react to give a chiral product.
C The reaction is a condensation reaction.
D The reaction is nucleophilic substitution.

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11

29 The table describes four reactions of propene.

Which row is correct?

name of main
reagent used
organic product

A aqueous bromine 2-bromopropane


B cold acidified aqueous potassium manganate(VII) propane-1,3-diol
C hydrogen chloride 2-chloropropane
D steam propan-1-ol

30 Butanoic acid is prepared from 1-bromopropane.

This synthesis requires a sequence of two reactions.

Which compound is prepared in the first stage of the synthesis?

A 1-aminopropane
B propan-1-ol
C butanal
D butanenitrile

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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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

Use of the Data Booklet may be appropriate for some questions.

31 Ethanol combines with ethanoic acid to form ethyl ethanoate according to the following reaction.

C2H5OH(I) + CH3CO2H(I) CH3CO2C2H5(I) + H2O(I) ∆H o = –6 kJ mol–1

9.2 g ethanol, 12 g ethanoic acid and 8.8 g ethyl ethanoate are mixed and allowed to stand at
298 K, until equilibrium is reached.
(Mr: C2H5OH, 46; CH3CO2H, 60; CH3CO2C2H5, 88)

The resulting equilibrium mixture is found to contain 4.8 g ethanoic acid.

The experiment is repeated at 323 K.

Which statements are correct?

1 There are 0.22 moles of ethyl ethanoate in the mixture at equilibrium at 298 K.
2 The equilibrium mixture at 323 K will contain more than 4.8 g of ethanoic acid.
3 If a small amount of water is added at the start of either experiment the value of Kc would not
be affected.

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32 The diagram shows an incomplete energy profile diagram for a reaction.

products

enthalpy

reactants

progress of reaction

Which reactions could this diagram refer to?

1 CaCO3(s)  CaO(s) + CO2(g)

2 H2(g)  2H(g)

3 Cl –(aq)  Cl –(g) + aq

33 A gaseous hydrocarbon has a density of 2.42 g dm–3 under room conditions.

What could be the skeletal formula of this hydrocarbon?

34 Which molecules contain at least one bond angle of 120?

1 C2H4
2 PF5
3 NCl 3

35 Which statements are correct going across Period 3 from sodium to chlorine?

1 The charge on the nucleus increases, pulling the electrons closer to it.
2 The radius of the most common ion of each element decreases.
3 The shielding caused by inner electrons decreases, so the outer electrons are pulled closer
to the nucleus.

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14

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

36 Which statements are correct?

1 Magnesium carbonate decomposes at a lower temperature than calcium carbonate.


2 Calcium hydroxide is more soluble in water than magnesium hydroxide.
3 Calcium is a stronger reducing agent than magnesium.

37 Which statements are correct?

1 1,1-difluoroethane is less reactive than 1,1-dichloroethane.


2 1,1-difluoroethane is polar.
3 The C–F bond is stronger than the C–Cl bond.

38 Which pairs of compounds may be distinguished by testing with alkaline aqueous iodine?

1 butanal and butanone


2 pentan-2-one and pentan-3-ol
3 propanone and propan-2-ol

39 Which reactions have a coloured organic product?

1 ethanal + 2,4-dinitrophenylhydrazine reagent

2 ethanol + acidified potassium dichromate(VI)

3 ethene + cold dilute acidified potassium manganate(VII)

40 Propanoic acid is reacted with an excess of lithium aluminium hydride. The organic product of this
reaction is reacted with ethanoic acid in the presence of concentrated sulfuric acid, forming
product X.

What are major commercial uses of X?

1 fuel
2 solvent
3 flavouring

© UCLES 2021 9701/11/M/J/21


9701/11 Cambridge International AS & A Level – Mark Scheme May/June 2021
PUBLISHED

Question Answer Marks

1 C 1

2 C 1

3 B 1

4 D 1

5 B 1

6 B 1

7 C 1

8 A 1

9 D 1

10 D 1

11 C 1

12 B 1

13 B 1

14 A 1

15 A 1

16 C 1

17 D 1

18 C 1

19 D 1

20 A 1

21 B 1

22 B 1

23 C 1

24 D 1

25 A 1

26 A 1

27 C 1

28 B 1

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9701/11 Cambridge International AS & A Level – Mark Scheme May/June 2021
PUBLISHED

Question Answer Marks

29 C 1

30 D 1

31 A 1

32 A 1

33 D 1

34 B 1

35 D 1

36 A 1

37 A 1

38 B 1

39 D 1

40 C 1

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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.

Use of the Data Booklet may be appropriate for some questions.

1 Which statement about the Avogadro constant is correct?

A It is the mass of one mole of any element.

B It is the mass of 6.02  1023 atoms of any element.


C It is the number of atoms in one mole of neon.
D It is the number of atoms in 12 g of any element.

2 Which equation represents the first ionisation energy of iodine?

A 1
2
I2(g) + e–  I–(g)

B I(g) + e–  I–(g)

C 1
2
I2(g)  I+(g) + e–

D I(g)  I+(g) + e–

3 The structures represent three compounds, each with four carbon atoms per molecule.

X Y Z

O O O

OH O O–Na+

Which row is correct?

lowest highest
boiling point boiling point

A X Y Z
B Y X Z
C Z X Y
D Z Y X

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4 The structural formula of alliin is shown.

alliin
H H O NH2
y z
xC C CH2 S CH2 C H

H CO2H

What are the approximate bond angles x, y and z in a molecule of alliin?

x y z

A 90 90 109


B 120 109 90
C 120 120 109
D 180 109 109

5 Flask Q contains 5 dm3 of helium at 12 kPa pressure. Flask R contains 10 dm3 of neon at 6 kPa
pressure.

If the flasks are connected at constant temperature, what is the final pressure?

A 8 kPa B 9 kPa C 10 kPa D 11 kPa

6 Sodium chloride, water and air represent three states of matter – solid, liquid and gas.

Which row is correct?

sodium chloride water air


A particles held can easily be can easily be
in rigid structure compressed compressed
B particles stationary particles move cannot easily be
compressed
C particles stationary particles stationary particles move
D resistant to cannot easily be can easily be
change of shape compressed compressed

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7 The reaction pathway diagram for the catalysed reaction and the uncatalysed reaction between
N2 and H2 is shown.

N2(g) + 3H2(g) 2NH3(g)

Which letter represents the activation energy for the first step in the decomposition of NH3 in the
presence of a catalyst?

A C
B
energy
N2(g) + 3H2(g)
D

2NH3(g)

reaction pathway

8 Nitrogen and oxygen can react together to form nitrogen monoxide, NO.

N2 + O2  2NO H = +180 kJ mol–1

What is the bond energy of the bond between the atoms in NO?

A 630 kJ mol–1 B 810 kJ mol–1 C 1260 kJ mol–1 D 1620 kJ mol–1

9 The equation for a redox reaction is shown.

SnCl 2(aq) + 2HgCl 2(aq)  SnCl 4(aq) + Hg2Cl 2(s)

Which species is being oxidised in this reaction?

A Sn2+ B Cl – C Hg+ D Hg2+

10 3.60 moles of hydrogen gas and 2.00 moles of iodine vapour are placed in a reaction vessel
which is then sealed and maintained at a constant temperature.

The equation for the reaction is shown.

H2 + I2 2HI

At equilibrium, 3.20 moles of hydrogen remain. All reactants and products are gaseous.

What is the value of Kp under these conditions?

A 0.0313 B 0.125 C 0.156 D 8.00

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11 Two chemicals, X and Y, react together in solution to give product Z.

The rate of formation of product Z at the start of the reaction was measured in five experiments,
1–5, using various concentrations of X and Y. The results are shown.

experiment starting concentration starting concentration rate of formation of Z


number of X / mol dm–3 of Y / mol dm–3 at the start / mol dm–3 s–1

1 0.10 0.10 0.0001


2 0.10 0.20 0.0004
3 0.10 0.40 0.0016
4 0.20 0.10 0.0001
5 0.40 0.10 0.0001

Which statement is correct?

A The rate of the reaction is directly proportional to the concentration of reagent X.


B The rate of the reaction is directly proportional to the concentration of reagent Y.
C The rate of the reaction is not affected by the concentration of reagent X.
D The rate of the reaction is not affected by the concentration of reagent Y.

12 A sample of SiCl 4 is added to cold water.

Which statement describes the mixture formed at the end of the reaction?

A acidic solution with no precipitate


B acidic solution with white precipitate
C neutral solution with no precipitate
D neutral solution with white precipitate

13 L and M are elements in Period 3 of the Periodic Table.

● The oxide of L is a solid at room temperature. This oxide has a giant structure.
● The chloride of L does not react with water.
● Argon is the only element in Period 3 with a lower melting point than M.

Which formula represents a compound of elements L and M?

A Al 2S3 B MgS C NaCl D PCl 5

14 A farmer requires a solid compound to raise the pH of the soil in a field from 5.5 to above 6.0.

Which compound could the farmer use?

A (NH4)2SO4 B NH4NO3 C Ca(OH)2 D Ca(NO3)2

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15 Z is an anhydrous compound of a Group 2 element. When it is heated, Z undergoes thermal


decomposition to produce two different gases. Z has relatively low thermal stability compared to
other Group 2 compounds containing the same anion as Z.

What is compound Z?

A barium carbonate
B barium nitrate
C magnesium carbonate
D magnesium nitrate

16 Which row gives mixtures that both result in the oxidation of a halide ion?

mixture 1 mixture 2

A AgNO3(aq) and NaCl (aq) concentrated H2SO4(aq) and HI(aq)


B Br2(aq) and NaCl (aq) concentrated H2SO4(aq) and HCl (aq)
C Cl 2(aq) and NaBr(aq) CH3CHBrCH3(l) + NaOH (ethanolic)
D Br2(aq) and NaI(aq) concentrated H2SO4(aq) and NaBr(s)

17 Chlorine gas is widely used to treat contaminated water.

When chlorine is added to water, which chemical species present is responsible for killing
bacteria?

A Cl O2– B Cl – C HCl D Cl O–

18 What is an environmental consequence of the uncontrolled use of nitrate fertilisers?

A acid rain
B low oxygen levels in streams
C ozone depletion
D the greenhouse effect

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19 Ammonia gas, NH3, and hydrogen sulfide gas, H2S, react together to form the salt ammonium
sulfide, (NH4)2S. Ammonium sulfide dissolves in water to produce an orange alkaline solution.

(NH4)2S(aq) NH3(aq) + NH4SH(aq)

The addition of NaOH(aq) to this solution produces a gas, X.


The addition of HCl (aq) to a separate portion of this solution produces a gas, Y.

X and Y could represent different gases or identical gases.

What are the identities of X and Y?

X Y

A H2S H2S
B H2S NH3
C NH3 H2S
D NH3 NH3

20 Compound P is treated with an excess of hydrogen gas in the presence of a nickel catalyst. The
product Q is fully saturated.

compound P

What is the number of chiral carbon atoms in the product Q?

A 4 B 5 C 6 D 7

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21 Hexadeca-10,12-dien-1-ol is produced by silk moths from hexadecanoic acid in a three-step


enzymic process.

hexadecanoic acid
O

OH

step 1
O

OH

step 2
O

OH

step 3

OH

Which row contains correct descriptions of the three steps?

step 1 step 2 step 3

A elimination elimination dehydration


B elimination reduction reduction
C oxidation elimination oxidation
D oxidation oxidation reduction

22 Compound X can be converted into compound Y in a single step.

compound Y

OH
X

O O

What could be the identity of X?

A B C D

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23 Methane and bromine react by free radical substitution.

P and Q are involved in the reaction mechanism.

P and Q:

● are both involved in propagation steps as reactants


● are both involved in termination steps as reactants.

What could be P and Q?

A Br and H B Br and CH3 C Br and C2H6 D CH3 and CH3Br

24 A few drops of 2-bromopropane were placed in a test-tube. An equal volume of aqueous


silver nitrate was added. A precipitate was formed.

The experiment was repeated with 2-iodopropane.

Which row is correct?

colour of precipitate from


faster rate of reaction
2-bromopropane + AgNO3(aq)

A cream 2-bromopropane + AgNO3(aq)


B yellow 2-bromopropane + AgNO3(aq)
C cream 2-iodopropane + AgNO3(aq)
D yellow 2-iodopropane + AgNO3(aq)

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25 Sodium methoxide, Na+CH3O–, reacts with 2-chloro-2-methylpropane in a nucleophilic


substitution reaction. The nucleophile is the CH3O– ion.

Which row is correct?

intermediate or
product
transition state

A (CH3)3C+ (CH3)3COCH3
B (CH3)3C+ (CH3)3CCH2OH

H 3C CH3

C H3CO C Cl HOCH2C(CH3)3

CH3


H 3C CH3

D H3CO C Cl H3COC(CH3)3

CH3

26 Alcohol X reacts with concentrated sulfuric acid to produce a mixture of products.

Two of the products are structural isomers of each other.

What could be X?

A hexan-2-ol
B pentan-1-ol
C pentan-3-ol
D propan-2-ol

27 Which reaction will form a strong organic base?

A ethanol and acidified sodium dichromate


B ethanol and hot aluminium oxide
C ethanol and sodium
D ethanol and hydrogen chloride

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28 Which reaction mechanism for the formation of C2H5CH(OH)(CN) is correct?

H+
O– OH
G–
O H H
A G+
C C
N C–
H
N N

H+
O– OH
G–
O H H
B G+
C C
N C–
H
N N

H+
O– OH
G+
O H H
C G–
C C
N C–
H
N N

H+
O– OH
G–
O H H
D G+
C C
N C–
H
N N

29 The synthesis shown may be used for the production of propan-1-ol.

step 1 step 2
compound X OH
N

Which row gives the correct reagents for steps 1 and 2?

step 1 step 2

A HCl (aq) H2 + Ni
B HCl (aq) LiAl H4
C NaOH(aq) H2 + Ni
D NaOH(aq) NaBH4

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30 The molecular formula of Z is C4H8O.

The infra-red spectrum of Z is shown.

100

transmittance / %
50

0
4000 3000 2000 1500 1000 500
wavenumber / cm–1

What could be Z?

A B C D

OH O
O
OH OH

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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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

Use of the Data Booklet may be appropriate for some questions.

31 In which ions are the number of electrons equal to the number of neutrons?
19 
1 9F

2 31
15 P

23 
3 11Na

32 Compound X is a straight chain hydrocarbon with an Mr of 84.

What can be determined about X?

1 empirical formula
2 molecular formula
3 whether X contains a C=C bond or not

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14

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

33 When a sample of ammonium chloride is warmed it decomposes into ammonia and hydrogen
chloride gas.

NH4Cl (s)  NH3(g) + HCl (g) reaction 1

cold surface solid ammonium


chloride (reformed)

solid
ammonium chloride

heat

When the mixture of hot ammonia and hydrogen chloride gases hit a cold surface, a white solid of
ammonium chloride reforms.

Which statements are correct?

1 Reaction 1 is in dynamic equilibrium.


2 Reaction 1 is reversible.
3 Reaction 1 is an endothermic reaction.

34 Hydrogen chloride gas is formed by the reaction shown.

H2(g) + Cl 2(g)  2HCl (g)

What will change the average kinetic energy of the reacting gas particles?

1 increasing the temperature and increasing the concentration of hydrogen


2 cooling the reaction mixture and adding a catalyst
3 adding a catalyst and increasing the concentration of chlorine

© UCLES 2021 9701/12/M/J/21


15

35 Which oxides will cause a change in pH when added to water?

1 CaO
2 Al 2O3
3 SiO2

36 Which reaction routes can be used to make a pure sample of barium sulfate?

heat dilute dilute filter, wash


1 Ba product product product
in O2 HCl H2SO4 and dry

strong solid an excess dilute filter, wash


2 Ba(NO3)2 product product
heat in air product of water H2SO4 and dry

dilute dilute filter, wash


3 Ba(OH)2 product product
HNO3 H2SO4 and dry

37 Cortisone is a synthetic hormone.

cortisone

O OH

HO OH
H

H H
O

Which classes of alcohol does this molecule contain?

1 primary alcohol
2 secondary alcohol
3 tertiary alcohol

38 Which changes are commonly involved in the formation of an addition polymer?

1 the formation of a -bond

2 the breaking of a -bond


3 the change in hybridisation of the orbitals of a carbon atom from sp2 to sp3

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16

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

39 Which alcohols can be oxidised to form an organic compound which will give coloured
precipitates with both 2,4-dinitrophenylhydrazine reagent and alkaline aqueous iodine?

OH
1

OH O

3 OH

40 Which mixtures form a carboxylic acid as one of the products?

1
O + H2SO4(aq) o

O–

2
O + H2SO4(aq) o

O
3 + H2SO4(aq) o

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.

To avoid the issue of disclosure of answer-related information to candidates, all copyright acknowledgements are reproduced online in the Cambridge
Assessment International Education Copyright Acknowledgements Booklet. This is produced for each series of examinations and is freely available to download
at www.cambridgeinternational.org after the live examination series.

Cambridge Assessment International Education is part of the Cambridge Assessment Group. Cambridge Assessment is the brand name of the University of
Cambridge Local Examinations Syndicate (UCLES), which itself is a department of the University of Cambridge.

© UCLES 2021 9701/12/M/J/21


9701/12 Cambridge International AS & A Level – Mark Scheme May/June 2021
PUBLISHED

Question Answer Marks

1 C 1

2 D 1

3 B 1

4 C 1

5 A 1

6 D 1

7 D 1

8 A 1

9 A 1

10 B 1

11 C 1

12 B 1

13 C 1

14 C 1

15 D 1

16 D 1

17 D 1

18 B 1

19 C 1

20 B 1

21 D 1

22 A 1

23 B 1

24 C 1

25 A 1

26 A 1

27 C 1

28 D 1

© UCLES 2021 Page 2 of 3


9701/12 Cambridge International AS & A Level – Mark Scheme May/June 2021
PUBLISHED

Question Answer Marks

29 B 1

30 D 1

31 B 1

32 A 1

33 C 1

34 B 1

35 D 1

36 A 1

37 A 1

38 A 1

39 C 1

40 B 1

© UCLES 2021 Page 3 of 3


2

Section A

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

Use of the Data Booklet may be appropriate for some questions.

1 Compound X is an organic compound that contains 30.6% carbon, 3.8% hydrogen, 20.4%
oxygen and 45.2% chlorine by mass.

What is the empirical formula of X?

A C2H3OCl B C2H4OCl C C3H4OCl D C4H3O2Cl 2

2 A sample of propane, C3H8, with a mass of 9.61 g is completely combusted in an excess of


oxygen under room conditions.

Which volume of carbon dioxide gas is produced?

A 4.89 dm3 B 5.24 dm3 C 14.7 dm3 D 15.7 dm3

3 Which atom has the same number of electrons as an ammonium ion?

A Mg B Na C Ne D O

4 Ethanal reacts with hydroxylamine, NH2OH, to form the molecule shown.

H H
y z

H C C N O H
x
H

What is the order of increasing bond angle in this structure from smallest to largest?

A z, x, y B y, z, x C x, z, y D z, y, x

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3

5 Descriptions of the bonding in three substances are given.

substance 1 strong covalent bonds between atoms, permanent dipole-dipole


attractions between molecules
substance 2 strong covalent bonds between atoms, weak forces between molecules
substance 3 strong covalent bonds between atoms, hydrogen bonding between
molecules

Which compounds could be substances 1, 2 and 3?

substance 1 substance 2 substance 3

A CH3OH Al 2Cl 6 CH2Cl 2


B Al 2Cl 6 CH2Cl 2 CH4
C CH2Cl 2 CH4 CH3OH
D CH4 CH3OH H2O

6 Which type of bonding is never found in elements?

A covalent
B ionic
C metallic
D van der Waals’ forces

7 Using the information in the table, what is the enthalpy change, q, for the reaction described?

Cs+(g) + Br –(g)  CsBr(s) ∆H = q kJ mol–1

standard value
enthalpy change / kJ mol–1

H sol
o
CsBr(s) +25.9
H hyd
o
Cs+(g) –276
H hyd
o
Br –(g) –335

A –636.9 B –585.1 C +585.1 D +636.9

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4

8 Which enthalpy change is indicated by X in the enthalpy cycle shown?

C(s) + 2H2(g) + 2O2(g)

CH4(g) CO2(g) + X

CH4(g)
CH4(g) + 2O2(g) CO2(g) + 2H2O(l)

A – 4  the enthalpy of combustion of hydrogen

B + 4  the enthalpy of combustion of hydrogen

C – 2  the enthalpy of formation of water

D + 2  the enthalpy of formation of water

9 Copper dissolves in dilute nitric acid producing a blue solution of Cu(NO3)2, water and
nitrogen(II) oxide as the only products.

How many moles of acid react with three moles of copper in the balanced equation?

A 2 B 4 C 6 D 8

10 Nitrogen reacts with hydrogen to produce ammonia.

N2(g) + 3H2(g) 2NH3(g)

A mixture of 2.00 mol of nitrogen, 6.00 mol of hydrogen and 2.40 mol of ammonia is allowed to
reach equilibrium in a sealed vessel of volume 1 dm3. It is found that 2.32 mol of nitrogen were
present in the equilibrium mixture.

Which expression will give the value of Kc?

(1.76 )2
A
(2.32)(6.96)3

(1.76)2
B
(2.32)(6.32)3

(2.08 )2
C
(2.32)(6.32)3

(2.40)2
D
(2.32)(6.00)3

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5

11 Nitric acid is produced by oxidising ammonia. The first step is to react ammonia with oxygen in
the presence of a catalyst to form nitrogen monoxide.

4NH3(g) + 5O2(g) 4NO(g) + 6H2O(g) H = –1636 kJ mol–1

Which set of conditions will produce the greatest yield of nitrogen monoxide at equilibrium?

temperature pressure

A high high
B high low
C low high
D low low

12 The height of the peak of the curve in a Boltzmann distribution represents the number of
molecules that have the most probable energy.

A sample of gas has its temperature decreased without changing the number of molecules
present.

Which statement correctly describes a feature of the Boltzmann distribution for the gas when the
temperature decreases?

A The value of the most probable energy would stay the same.
B The number of molecules with the most probable energy would increase.
C The area under the molecular energy distribution curve would decrease.
D The number of molecules at the very high energy end of the distribution would stay the
same.

13 Ammonia exists as simple covalent molecules, NH3. Ammonia can react with suitable reagents to
form products containing ammonium ions, NH4+. Ammonia can also react with suitable reagents
to form products containing amide ions, NH2–.

Which of these nitrogen-containing species are present in an aqueous solution of ammonia?

A ammonia molecules and amide ions


B ammonia molecules and ammonium ions
C ammonia molecules only
D ammonium ions only

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6

14 Which problem can result if too much NH4NO3 is applied to crops by farmers?

A Not all the NH4NO3 is used by plants and the excess makes the soil alkaline.
B Rain washes some of the NH4NO3 into rivers where it forms a precipitate.
C Some of the NH4NO3 dissolves in groundwater which may eventually be used for drinking.
D Ammonia is produced; this lowers the pH of the soil.

15 When descending Group 17 from chlorine to iodine, which statement is correct?

A The hydrides become less thermally stable as they become weaker reducing agents.
B The hydrides become more thermally stable as the reactivity of the elements decreases.
C The volatility of the elements decreases as the van der Waals’ forces increase.
D The volatility of the elements increases as the size of the molecules increases.

16 A powder is known to be either a single sodium halide or a mixture of two sodium halides.
A sample of the powder was dissolved in water.

Aqueous silver nitrate was added, and a pale yellow precipitate was formed. When concentrated
aqueous ammonia was then added, this precipitate partly dissolved leaving a darker yellow
precipitate.

What could the powder be?

A sodium bromide only


B sodium iodide only
C a mixture of sodium chloride and sodium bromide
D a mixture of sodium chloride and sodium iodide

17 Which statement is correct?

A Doctors can use the very insoluble MgSO4 to investigate the digestive system.
B Farmers can lower the pH of soil by spreading CaCO3 on it.
C Students can test a solution for SO42– ions by using Ba(NO3)2(aq) followed by HNO3(aq).
D The insoluble hydroxide, Ba(OH)2, can be safely used to lower the acidity of the stomach.

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7

18 A solid, X, was placed in an excess of the liquid Y.

A colourless gas was given off and a white precipitate was seen. The precipitate was not X.

What could be the identities of X and Y?

X Y

A BaCO3 H2O
B Ca dilute H2SO4
C Mg dilute H2SO4
D SrCO3 dilute HCl

19 Two oxides of Period 3 elements are added separately to water. Both react to form colourless
solutions. One solution is alkaline, the other is acidic.

What could be the two oxides?

A Al 2O3 and SiO2


B Al 2O3 and P4O10
C Na2O and P4O10
D Na2O and SiO2

20 Which compound shows stereoisomerism?

A 2-methylbut-2-ene
B 2-chloropropan-1-ol
C difluorochlorobromomethane
D pent-1-ene

21 Two carbon-containing products result from the reaction of alkene Z with a hot, concentrated,
acidified solution of potassium manganate(VII).

One product forms an orange precipitate with 2,4-dinitrophenylhydrazine reagent. The other
product is a gas which gives a white precipitate with aqueous calcium hydroxide.

Which alkene could be alkene Z?

A but-2-ene
B 2-methylpropene
C 2-methylbut-2-ene
D propene

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8

22 What is the correct mechanism for the addition of hydrogen bromide to ethene?

H H H H H H

A C C H C C+ H C C Br

H
H H Br H H H
Br G
+

HG

H H H H H H

B C C H C C+ H C C Br

Br
H H H H H H
HG
+

Br G

H H H H H H

C C C H C C+ H C C Br

H
H H Br H H H
Br G
+

HG

H H H H H H

D C C H C C+ H C C Br
Br–
H H H H H H
HG
+

Br G

23 Halogenoalkanes react with nucleophiles such as OH–.

Which pair of halogenoalkanes both react via an SN1 mechanism?

A B
Br Cl
and and
Cl
Br

C D
Br
and and
Br Cl Br

© UCLES 2021 9701/13/M/J/21


9

24 A mixture of ethanol and methanol is burned in oxygen to produce 35 cm3 of CO2 and 55 cm3 of
H2O.

Complete combustion occurs and the volumes of both products are measured at 101 kPa and
120 C.

What is the molar ratio, ethanol : methanol, in the mixture?

A 1:3 B 2:3 C 3:2 D 3:1

25 Two reactions are shown. Only one product is identified in each reaction.

ethanol + acidified Cr2O72–  ethanal

ethanol + sodium  sodium ethoxide

Which statement about these reactions is correct?

A The formations of both ethanal and sodium ethoxide are redox reactions.
B The formations of both ethanal and sodium ethoxide result in colour changes.
C The formation of ethanal is catalysed by potassium dichromate.
D The formation of sodium ethoxide is a dehydration reaction.

26 The skeletal formulae of three compounds are shown.

R S T

OH O

O O O

Which compounds will give a positive test with 2,4-dinitrophenylhydrazine reagent?

A R only B R and S only C S and T only D R, S and T

© UCLES 2021 9701/13/M/J/21 [Turn over


10

27 The diagram shows the structure of a compound formed by the reaction of HCN with a carbonyl
compound, X.

C 4H 9

H 3C C CN

OH

What is the mechanism of this reaction and what is the functional group in X?

mechanism of reaction functional group in X

A electrophilic addition aldehyde


B electrophilic addition ketone
C nucleophilic addition aldehyde
D nucleophilic addition ketone

28 Compound Y is treated with a single reagent under suitable conditions. 2-methylbutanoic acid is
produced.

What could compound Y be?

A pentan-2-one
B 2-methylbutan-2-ol
C 2-methylbutanenitrile
D methylpropanenitrile

29 Two reactions are shown.

LiAl H4
(CH3)2CHCO2H alcohol P

hydrolysis
CH3CO2CH(CH3)2 alcohol Q + acid R

To which classes of alcohol do P and Q belong?

P Q

A primary primary
B primary secondary
C secondary primary
D secondary secondary

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11

30 The infra-red spectrum of molecule Z is shown.

100

transmittance / %
50

0
4000 3000 2000 1500 1000 500
wavenumber / cm–1

What could be the identity of Z?

A B
HO OH
O O
HO O O O

C D

O O
O O O O

© UCLES 2021 9701/13/M/J/21 [Turn over


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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

Use of the Data Booklet may be appropriate for some questions.

31 Which statements about first ionisation energies are correct?

1 They are always endothermic.


2 They decrease down Group 2.
3 They decrease across Period 3.

32 The equation shows the decomposition of three moles of an ion containing chromium in an acid
solution.

3CrO43–(aq) + 8H+(aq)  2CrO42–(aq) + Cr3+(aq) + 4H2O(l)

Which statements are correct?

1 One mole of CrO43– is reduced.


2 Two moles of CrO43– are oxidised.
3 Three moles of electrons are transferred.

33 Disaccharides are hydrolysed in slightly acidic solutions. This reaction is very slow.

A biological catalyst is added to a slightly acidic mixture of three disaccharides, sucrose, maltose
and lactose. The hydrolysis reaction remains slow for sucrose and maltose but is now much
faster for lactose.

Which statements about the catalyst are correct?

1 The catalyst increases the activation energy of all three hydrolysis reactions.
2 The catalyst shows specificity.
3 The hydrolysis of lactose using a catalyst has a different mechanism to the hydrolysis of
lactose without a catalyst.

© UCLES 2021 9701/13/M/J/21


13

34 Element X is a solid under room conditions. It occurs as a contaminant of fossil fuels.

Its oxide, Y, is formed when fossil fuels are burned.

In the atmosphere, Y can be further oxidised to Z.

Which statements about X, Y and Z are correct?

1 Atoms of X have paired p electrons.


2 The atmospheric oxidation of Y to Z is a catalysed reaction.
3 With water, Z forms a strong acid.

35 Which reagents produce a solution of sodium chlorate(V)?

1 chlorine and hot concentrated sodium hydroxide solution


2 chlorine and cold dilute sodium hydroxide solution
3 chlorine dissolved in water at room temperature

36 Which statements help to explain the increase in melting point from sodium to aluminium?

1 The charge on the metal ion increases.


2 There are more delocalised electrons per metal ion.
3 The radius of the metal ion decreases.

37 The diagram shows a molecule of a compound used as a flame retardant.

Br
Br

Br

Br Br
Br

Which statements about this structure are correct?

1 Each brominated C atom is chiral.


2 The molecular formula is C12H20Br6.

3 The C–C–C bond angles are all 120.

© UCLES 2021 9701/13/M/J/21 [Turn over


14

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

38 Bromoethane reacts with NaOH in different ways depending on the solvent used.

Which rows about these reactions are correct?

solvent used organic product

1 water ethan-1,2-diol
2 ethanol ethene
3 water ethanol

39 Three compounds, X, Y and Z, are shown.

X Y Z
C2H5COCH3 C2H5CHO CH3CO2H

Which statements about X, Y and Z are correct?

1 X reacts with alkaline aqueous iodine.


2 Y reacts with Tollens’ reagent.
3 Z does not react with alkaline aqueous iodine.

40 5-hydroxypentanoic acid is readily converted into the cyclic compound L.

Which statements about this reaction are correct?

1 Acidified sodium dichromate(VI) is used as a reagent.


2 A water molecule is produced in the reaction.
3 The reaction can be catalysed by concentrated H2SO4.

© UCLES 2021 9701/13/M/J/21


9701/13 Cambridge International AS & A Level – Mark Scheme May/June 2021
PUBLISHED

Question Answer Marks

1 A 1

2 D 1

3 C 1

4 A 1

5 C 1

6 B 1

7 A 1

8 D 1

9 D 1

10 A 1

11 D 1

12 B 1

13 B 1

14 C 1

15 C 1

16 D 1

17 C 1

18 B 1

19 C 1

20 B 1

21 B 1

22 B 1

23 A 1

24 D 1

25 A 1

26 A 1

27 D 1

28 C 1

© UCLES 2021 Page 2 of 3


9701/13 Cambridge International AS & A Level – Mark Scheme May/June 2021
PUBLISHED

Question Answer Marks

29 B 1

30 D 1

31 B 1

32 B 1

33 C 1

34 A 1

35 D 1

36 A 1

37 D 1

38 C 1

39 A 1

40 C 1

© UCLES 2021 Page 3 of 3


2

Section A

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

Use of the Data Booklet may be appropriate for some questions.

1 Ethene can be oxidised to form epoxyethane, C2H4O.

C2H4(g) + 1
O (g)
2 2
C2H4O(g) ∆H o = –107 kJ mol–1

Which set of conditions gives the greatest yield of epoxyethane at equilibrium?

temperature
pressure
/ °C

A high 100
B high 200
C low 100
D low 200

2 Cobalt can form the positive ion Co(NH3)4Cl 2+.

What is the oxidation number of cobalt in this ion?

A +1 B +2 C +3 D +6

3 When considering one molecule of ethene, which row describes both the hybridisation of the
atomic orbitals in the carbon atoms and the overall bonding?

hybridisation bonding

A sp2 4 σ bonds 1 π bond


B sp2 5 σ bonds 1 π bond
C sp3 4 σ bonds 1 π bond
D sp3 5 σ bonds 1 π bond

4 10 cm3 of ethane is burned in 45 cm3 of oxygen at a pressure of 101 kPa and a temperature of
200 °C. Complete combustion takes place.

What is the total volume of gas present when the reaction is complete, measured under the same
conditions?

A 30 cm3 B 50 cm3 C 55 cm3 D 60 cm3

© UCLES 2020 9701/11/M/J/20


3

5 Two reactions are shown.

H2(g) → 2H(g)

CO(g) + 1
O (g)
2 2
→ CO2(g)

If molar amounts are used, how can the two energy changes associated with these reactions be
described?

A enthalpy of atomisation and enthalpy of combustion


B enthalpy of atomisation and enthalpy of formation
C bond energy and enthalpy of combustion
D bond energy and enthalpy of formation

6 The diagram shows the Boltzmann energy distribution curves for molecules of a sample of a gas
at two different temperatures.

Which letter on the axes represents the most probable energy for molecules of the same sample
of gas at the lower temperature?

C D

7 What are the units of Kp for the reaction shown?

H2O(g) + C(s) H2(g) + CO(g)

A Pa–1 B Pa C Pa2 D no units

© UCLES 2020 9701/11/M/J/20 [Turn over


4

8 In this question you should use changes in oxidation numbers to balance a chemical equation.

Acidified potassium dichromate(VI) solution can oxidise a solution of V2+ ions. The equation for
this reaction is shown.

a Cr2O72– + b V2+ + c H+ → d Cr3+ + e VO3– + f H2O

What is the ratio a : b in the correctly balanced equation?

A 1:1 B 1:2 C 2:1 D 4:1

9 A sample of argon gas has a mass of 0.20 g, at a pressure of 100 000 Pa and a temperature of
12 °C.

Which volume does the gas occupy?

A 1.2 × 10–4 cm3


B 5.0 cm3
C 59 cm3
D 119 cm3

10 In which pair does each species have the same number of unpaired electrons?

A Al and Cu2+
B Ca and Cr3+
C Ca and Ni2+
D Fe3+ and O2–

11 A sample of solid ammonium chloride decomposes on heating.

solid ammonium chloride → ammonia gas + hydrogen chloride gas

A total of 2.4 × 1021 molecules of gas is formed.

How many hydrogen atoms are present in the gaseous products?

A 1.2 × 1021 B 2.4 × 1021 C 4.8 × 1021 D 9.6 × 1021

© UCLES 2020 9701/11/M/J/20


5

12 A white powder is a mixture of sodium chloride and sodium iodide. It is dissolved in water in a
test-tube. An excess of aqueous silver nitrate is added to the test-tube. A precipitate, X, is
observed.

An excess of concentrated ammonia is then added to the test-tube containing X. After the
test-tube has been shaken, a precipitate, Y, is observed.

Which statement about X or Y is correct?

A X is a pure white colour.


B X is pure silver iodide.
C Y is pure silver chloride.
D Y is yellow.

13 6.90 g of an ammonium salt is heated with an excess of aqueous sodium hydroxide. The volume
of ammonia produced, measured under room conditions, is 2.51 dm3.

Which ammonium salt is used?

A ammonium carbonate (Mr = 96.0)


B ammonium chloride (Mr = 53.5)
C ammonium nitrate (Mr = 80.0)
D ammonium sulfate (Mr = 132.1)

14 An excess of MgO is shaken with water. The resulting mixture is filtered into test-tube P.

An excess of BaO is shaken with water. The resulting mixture is filtered into test-tube Q.

Which oxide reacts more readily with water and which filtrate has the lower pH?

oxide reacts more test-tube with


readily with water filtrate of lower pH

A BaO P
B BaO Q
C MgO P
D MgO Q

© UCLES 2020 9701/11/M/J/20 [Turn over


6

15 Element Z has a giant structure.

The chloride of Z reacts with water to give a solution with a pH less than 5.

Which pair shows two elements which could be Z?

A aluminium, magnesium
B aluminium, silicon
C phosphorus, magnesium
D phosphorus, silicon

16 Sodium, aluminium and silicon are three elements in Period 3. Each element forms an oxide.

Which row has three correct properties of these oxides?

sodium oxide aluminium oxide silicon dioxide

A basic basic amphoteric


B giant ionic giant ionic simple molecular
C high melting point low melting point high melting point
D reacts with water no reaction with water no reaction with water

17 0.25 g of anhydrous magnesium nitrate is heated strongly until it completely decomposes.

What is the total volume of gas produced, measured under room conditions?

A 40 cm3 B 81 cm3 C 101 cm3 D 202 cm3

18 Astatine, At, is below iodine in Group 17 of the Periodic Table.

Which statement is most likely to be correct?

A AgAt(s) reacts with an excess of dilute aqueous ammonia to form a solution of a soluble
complex.
B Astatine and KCl (aq) react to form KAt(aq) and chlorine.
C KAt(aq) and dilute sulfuric acid react to form HAt(g).
D NaAt(s) and concentrated sulfuric acid react to form astatine.

© UCLES 2020 9701/11/M/J/20


7

19 What is the order of increasing melting point of the three chlorides shown?

CCl 4 MgCl 2 PCl 5

lowest highest
melting point melting point

A CCl 4 PCl 5 MgCl 2


B MgCl 2 CCl 4 PCl 5
C MgCl 2 PCl 5 CCl 4
D PCl 5 CCl 4 MgCl 2

20 The skeletal formula of compound X is shown.

Which row is correct?

observation on
molecular
addition of X to
formula of X
Fehling’s reagent

A C7H14O no change
B C7H14O red precipitate forms
C C7H16O no change
D C7H16O red precipitate forms

21 Which statement is correct?

A 2,2-dimethylpropanoic acid is an isomer of propyl methanoate.


B 2-methylbutan-2-ol is an isomer of hexan-3-ol.
C 3-methylbutan-2-one is an isomer of pentanal.
D 3,3-dimethylbutan-2-one is an isomer of pentan-3-one.

© UCLES 2020 9701/11/M/J/20 [Turn over


8

22 But-1-ene and but-2-ene are treated separately with cold, dilute acidified manganate(VII) ions.

Four students, W, X, Y and Z, make statements about these alkenes and the diols formed from
them.

W One diol contains two primary alcohol groups.


X One diol contains a primary and a secondary alcohol group.
Y One diol contains two secondary alcohol groups.
Z Both alkenes exhibit cis-trans isomerism.

Which two students are correct?

A W and Y B W and Z C X and Y D X and Z

23 2-bromo-2-methylpentane is a tertiary halogenoalkane.

Which organic products are formed when 2-bromo-2-methylpentane reacts with a hot
concentrated ethanolic solution of sodium hydroxide?

A 2-methylpent-1-ene only
B 2-methylpent-1-ene and 2-methylpent-2-ene
C 2-methylpent-2-ene only
D 2-methylpent-2-ene and 4-methylpent-2-ene

24 Poly(propene) is an addition polymer.

What are the C–C–C bond angles along its polymer chain?

A They are all 109°.

B Half of them are 109° and half are 120°.

C Half of them are 90° and half are 180°.

D They are all 120°.

25 An alcohol has the molecular formula C5H12O. It has several isomers.

Which isomer forms a yellow precipitate with alkaline aqueous iodine?

A 2,2-dimethylpropan-1-ol
B 2-methylbutan-2-ol
C 3-methylbutan-2-ol
D pentan-3-ol

© UCLES 2020 9701/11/M/J/20


9

26 When compound X is heated under reflux with aqueous sodium hydroxide solution two products
are formed: sodium ethanoate and hexan-1-ol.

What is compound X?

A B C D

O O
O O O O
O O

27 What is the major product Z of the following reaction?

an excess of
dry HBr
Z
warm

A B C D

Br Br
Br Br

Br Br
Br Br

28 The structure of compound Q is shown.

compound Q

How many chiral centres are present in a molecule of Q?

A 4 B 5 C 6 D 7

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10

29 Compound X has the infra-red spectrum shown.

100

transmittance / %
50

0
4000 3000 2000 1500 1000 500
wavenumber / cm–1

What could be the identity of compound X?

A ethanoic acid
B ethanol
C ethylethanoate
D propanone

30 Which reaction produces an organic anion with a good yield?

A heating ethanenitrile under reflux with dilute sodium hydroxide


B heating ethanenitrile under reflux with dilute sulfuric acid
C heating ethane with sodium metal
D heating ethanol under reflux with dilute sodium hydroxide

© UCLES 2020 9701/11/M/J/20


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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

Use of the Data Booklet may be appropriate for some questions.

31 The definitions of many chemical terms can be illustrated by chemical equations.

Which terms can be illustrated by an equation that includes the formation of a positive ion?

1 first ionisation energy


2 heterolytic fission of a covalent bond
3 enthalpy change of atomisation

32 Which molecules have no overall dipole moment?

1 boron trifluoride
2 methane
3 phosphorus pentafluoride

33 Carbon exists in several different forms. Two of these forms are buckminsterfullerene and
graphene. Buckminsterfullerene is a fullerene allotrope of carbon.

Which statements about buckminsterfullerene and graphene are correct?

1 Both have delocalised electrons.


2 Buckminsterfullerene has a giant molecular structure.
3 The carbon atoms in graphene form a tetrahedral lattice.

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12

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

34 Carbon monoxide burns readily in oxygen to form carbon dioxide.

What does this information suggest?

1 The +4 oxidation state of carbon is more stable than the +2 state.


2 The standard enthalpy change of formation of carbon dioxide is more negative than the
standard enthalpy change of formation of carbon monoxide.
3 The value of the equilibrium constant for the reaction, 2CO(g) + O2(g) 2CO2(g), is likely
to be high.

35 The catalytic converters fitted to cars remove pollutants from the exhaust gases. Some of the
reactions that occur involve oxygen, which comes from the air.

Which pollutants in the exhaust gases will react with oxygen on the surface of the catalytic
converter?

1 NO2
2 unburnt fuel
3 CO

36 Chlorine reacts with sodium hydroxide in two different ways depending upon the temperature.

reaction 1 Cl 2 + 2OH– → Cl – + Cl O– + H2O

reaction 2 3Cl 2 + 6OH– → 5Cl – + Cl O3– + 3H2O

Which statements about these reactions are correct?

1 Reaction 2 requires a higher temperature than reaction 1.


2 The products of reaction 1 show chlorine in two different oxidation states.
3 The products of reaction 2 show oxygen in two different oxidation states.

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13

37 In which of the reactions is the organic compound oxidised by the given reagent?

1 CH3CHO + HCN reagent


2 CH3CH2CH2CHO + Tollens’ reagent
3 CH3CH2CHO + Fehling’s reagent

38 When the apparatus is set up as shown, an orange precipitate forms in test-tube Z.

Y Z
air

compound Q +
acidified potassium 2,4-dinitrophenylhydrazine
dichromate(VI) reagent

warm

What could compound Q be?

1 CH3CH2CH2OH
2 CH3CH(OH)CH3
3 (CH3)3COH

39 Chlorofluoroalkanes that diffuse into the stratosphere are broken down by ultraviolet radiation.

Radicals are generated that cause depletion of ozone.

What are these radicals?

1 chlorine radicals
2 fluorine radicals
3 alkyl radicals

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14

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

40 A mixture of the three isomers of C2H2Cl 2 is polymerised.

Which sequences will be seen within the polymer chains?

1 2 3

Cl H H H Cl H

C C C C C C

Cl Cl Cl Cl H H

© UCLES 2020 9701/11/M/J/20


9701/11 Cambridge International AS & A Level – Mark Scheme May/June 2020
PUBLISHED

Question Answer Marks

1 A 1

2 C 1

3 B 1

4 D 1

5 C 1

6 C 1

7 B 1

8 B 1

9 D 1

10 A 1

11 C 1

12 D 1

13 D 1

14 A 1

15 B 1

16 D 1

17 C 1

18 D 1

19 A 1

20 A 1

21 C 1

22 C 1

23 B 1

24 A 1

25 C 1

26 D 1

27 B 1

28 D 1

© UCLES 2020 Page 2 of 3


9701/11 Cambridge International AS & A Level – Mark Scheme May/June 2020
PUBLISHED

Question Answer Marks

29 A 1

30 A 1

31 B 1

32 A 1

33 D 1

34 A 1

35 C 1

36 B 1

37 C 1

38 B 1

39 D 1

40 A 1

© UCLES 2020 Page 3 of 3


2

Section A

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

Use of the Data Booklet may be appropriate for some questions.

1 In which carbon allotrope are all electrons localised?

A buckminsterfullerene
B diamond
C graphite
D graphene

2 A copper ore contains 3.00% of copper carbonate, CuCO3, by mass.

Which mass of copper would be obtained from 1 tonne of the ore?


A 1.91 kg B 3.71 kg C 15.4 kg D 58.4 kg

3 The catalysed formation of ammonia by the Haber process can be represented by the equation
shown.

N2(g) + 3H2(g) 2NH3(g) ∆H = –92 kJ mol–1

Which change in conditions will increase both the rate of formation and the equilibrium yield of
ammonia?

A decrease in the temperature


B increase in the temperature
C increase in the pressure
D increase in the surface area of the catalyst

4 Solid sulfur consists of S8 molecules.

Which equation represents the standard enthalpy of atomisation of sulfur?

A 1
S (s)
8 8
→ S(g)

B 1
S (g)
8 8
→ S(g)

C S8(s) → 8S(g)

D S8(g) → 8S(g)

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3

5 In this question you should use changes in oxidation numbers to balance a chemical equation.

The following reaction occurs when MnO2 is warmed with dilute H2SO4.

a MnO2 + b H+ → c Mn2+ + d MnO4– + e H2O

What is the ratio of c : d in the correctly balanced equation?

A 1:1 B 1:2 C 2:3 D 3:2

6 In this question you should assume air contains 21% oxygen.

What is the minimum volume of air required to ensure complete combustion of 10 cm3 of butane
gas, under room conditions?

A 14 cm3 B 27 cm3 C 65 cm3 D 310 cm3

7 When aqueous bromine is shaken with cyclohexane and allowed to stand, two layers form. The
top cyclohexane layer is coloured and the bottom aqueous layer is almost colourless.

What is the most likely explanation for this observation?

A Bromine is reduced to bromide ions in the bottom layer.


B Bromine molecules are non-polar.
C Bromine reacts with water but cannot react with cyclohexane.
D The product of the reaction between bromine and cyclohexane is coloured.

8 In which change are only temporary dipole-induced dipole forces overcome?

A C2H5OH(l) → C2H5OH(g)

B H2O(s) → H2O(l)

C O2(s) → O2(l)

D C4H10(l) → C4H10(s)

9 The complete combustion of 2 moles of an alkane produces 400 dm3 of carbon dioxide measured
at 301 K and 1 × 105 Pa. Carbon dioxide can be assumed to behave as an ideal gas under these
conditions.

What is the formula of the alkane?

A C8H18 B C16H34 C C20H42 D C40H82

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4

10 In which reaction does an element undergo the largest change in oxidation number?

A Cl 2 + 2OH– → OCl – + Cl – + H2O

B 3Cl 2 + 6OH– → Cl O3– + 5Cl – + 3H2O

C Cr2O72– + 6Fe2+ + 14H+ → 2Cr3+ + 6Fe3+ + 7H2O

D 3MnO42– + 4H+ → MnO2 + 2MnO4– + 2H2O

11 PCl 5 decomposes as shown.

PCl 5(g) PCl 3(g) + Cl 2(g)

1.0 mol of PCl 5(g), 1.0 mol of PCl 3(g) and 1.0 mol of Cl 2(g) are placed in a container of volume
1 dm3 at 250 °C and allowed to reach equilibrium.

At this temperature, the equilibrium mixture contains 1.8 moles of PCl 3.

What is the value of Kc at 250 °C?

A 1 B 1.8 C 9 D 16.2

12 The fifth to eighth ionisation energies of four elements in Period 3 of the Periodic Table are
shown.

Which row refers to chlorine?

ionisation energies / kJ mol–1


fifth sixth seventh eighth

A 6280 21 200 25 900 30 500


B 6990 8 490 27 100 31 700
C 6540 9 330 11 000 33 600
D 7240 8 790 12 000 13 800

13 Magnesium nitrate, Mg(NO3)2, decomposes when heated to give a white solid and a mixture of
gases. One of the gases released is an oxide of nitrogen, X.

7.4 g of anhydrous magnesium nitrate is heated until no further reaction takes place.

What mass of X is produced?

A 1.5 g B 2.3 g C 3.0 g D 4.6 g

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5

14 Which statement explains why iodine is less volatile than chlorine?

A Chlorine is more electronegative than iodine and so has more repulsion between its
molecules.
B The greater number of electrons in iodine leads to larger temporary dipole-induced dipole
forces.

C The I–I bond energy is smaller than the Cl –Cl bond energy.
D The iodine molecules have stronger permanent dipole-permanent dipole forces.

15 Ammonium carbonate is a crystalline solid. On gentle warming a reaction occurs, forming


ammonia as one product.

How are the carbonate ions behaving during this reaction?

A Brønsted-Lowry acid
B Brønsted-Lowry base
C oxidising agent
D reducing agent

16 One molecule of an oxide of element Z reacts with six molecules of water to produce an acidic
compound.

What is element Z?

A aluminium
B phosphorus
C silicon
D sulfur

17 Which property shows an increase from magnesium to barium?

A the first ionisation energy of the elements


B the oxidising power of the metals
C the solubility of the hydroxides
D the solubility of the sulfates

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6

18 A test-tube of HBr(g) and a separate test-tube of HI(g) are heated to the same temperature.

Which combination of observations is possible?

test-tube of HBr(g) test-tube of HI(g)

A a brown vapour appears no change


B a purple vapour appears no change
C no change a brown vapour appears
D no change a purple vapour appears

19 Most modern cars are fitted with catalytic converters in the exhaust system.

Which three gases are removed by a catalytic converter?

A carbon monoxide, hydrocarbons, nitrogen oxides


B carbon monoxide, carbon dioxide, nitrogen oxides
C carbon monoxide, nitrogen oxides, sulfur dioxide
D hydrocarbons, nitrogen oxides, sulfur dioxide

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7

20 Compound X is shown.

compound X
CO2H

OH

X is treated separately with NaOH(aq) and LiAl H4 to give Y and Z.

CO2H

NaOH(aq) LiAl H4
Y Z

OH

What are Y and Z?

Y Z
CO2Na CH2OH

OH OH
CO2Na CO2H

OH OH
CO2Na CH2OH

ONa OH
CO2Na CO2H

ONa OH

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8

21 The table shows the molecular formulae of three molecules P, Q and R. None of the molecules
are cyclic.

molecule molecular formula

P CH4O
Q CH2O2
R CH2O

Which molecules show a strong absorption between 1610 cm–1 and 1750 cm–1 in their infra-red
spectra?

A Q only B R only C Q and R only D P, Q and R

22 Which row correctly shows the type of mechanism of each of the two reactions?

C2H5Br + KCN CH3COCH3 + HCN

A electrophilic substitution electrophilic addition


B electrophilic substitution nucleophilic addition
C nucleophilic substitution electrophilic addition
D nucleophilic substitution nucleophilic addition

23 Ester X is shown.

ester X
CH3CO2(CH2)7CH3

Ester X is hydrolysed using aqueous sodium hydroxide.

What is the molecular formula of one of the products?

A C2H4O2 B C2H3O2Na C C8H16O D C8H17O2Na

24 Which reagent could be used to distinguish between propane-1,2-diol and ethane-1,2-diol?

A alkaline aqueous iodine

B aqueous acidified dichromate(VI)

C ethanol and a few drops of concentrated sulfuric acid


D sodium metal

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9

25 Which substance forms propanoic acid as one of the products when it reacts with hot
concentrated acidified potassium manganate(VII)?

A but-1-ene
B but-2-ene
C 2-methylpropene
D 2-methylbut-1-ene

26 The structure of damascenone is shown.

damascenone
O

Including damascenone, how many stereoisomers exist with this structural formula?

A 1 B 2 C 4 D 8

27 How many isomeric esters have the molecular formula C4H8O2?

A 2 B 3 C 4 D 5

28 Ethene reacts with aqueous bromine to give two products, CH2BrCH2Br and CH2BrCH2OH.

Which statement about these products is correct?

A Both products are obtained in this reaction by nucleophilic substitution.


B Both products are obtained in this reaction by nucleophilic addition.
C Both products can be hydrolysed to form the same organic compound.
D Both products can form hydrogen bonds with water.

29 PVC is used as a packaging material.

What holds the different polymer strands together in a piece of solid PVC?

A covalent bonds
B hydrogen bonds
C ionic bonds
D van der Waals’ forces

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10

30 The diagram shows the structure of buta-1,3-diene.

buta-1,3-diene

H H

C C H
H C C

H H

The addition reaction between buta-1,3-diene and two molecules of hydrogen bromide can
produce three structurally isomeric products.

How many of these products have at least one chiral centre?

A 0 B 1 C 2 D 3

© UCLES 2020 9701/12/M/J/20


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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

Use of the Data Booklet may be appropriate for some questions.

31 Scientists are trying to synthesise a new element with proton number 119. The element is
predicted to be a Group 1 element in Period 8 of the Periodic Table.

Which predictions are likely to be correct about this element?

1 The outermost occupied orbital of one atom of this element will be an s orbital.
2 The atomic radius will be the largest of the seven elements in Group 1.
3 It will have a greater first ionisation energy than element 118.

32 Which reactions would have the reaction profile shown?

energy

progress of reaction

1 NaOH + HCl → NaCl + H2O

2 CaCO3 → CaO + CO2

3 2MgO → 2Mg + O2

© UCLES 2020 9701/12/M/J/20 [Turn over


12

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

33 Which factors can lead to an increase in the rate of a reaction?

1 a lower activation energy


2 an increase in temperature
3 an increase in the concentration of a reactant

34 Sodium and fluorine are both reactive elements. Two atoms are described.

F Na

atomic number 9 11
nucleon number 19 23

Which statements about these two atoms, and the ions they can form, are correct?

1 One Na atom has two more protons than one F– ion.


2 One Na atom has two more neutrons than one F atom.
3 One Na+ ion has the same number of electrons as one F– ion.

35 In the atmosphere, which transformations can involve sulfur dioxide as either a reagent or a
catalyst?

1 NO2 to NO
2 NO to NO2
3 CO to CO2

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13

36 The bond ......P...... of the HBr molecule is ......Q...... than that of the HI molecule.

Which pairs of words correctly complete the above sentence?

P Q

1 energy greater
2 length less
3 polarity greater

37 Compound X has the structure shown.

compound X
OH

Which statements about compound X are correct?

1 X will decolourise cold, acidified KMnO4(aq).


2 X gives an orange precipitate with 2,4-DNPH reagent.
3 X does not react with Tollens’ reagent.

38 Propanal reacts with hydrogen cyanide.

Which absorptions are present in the infra-red spectrum of the product?

1 a weak absorption in the range 2200–2250 cm–1


2 a strong absorption in the range 3200–3600 cm–1
3 a strong absorption in the range 1040–1300 cm–1

39 Which alcohols cannot be dehydrated to form alkenes?

1 CH3OH
2 (CH3)3COH
3 CH3CH(OH)CH3

© UCLES 2020 9701/12/M/J/20 [Turn over


14

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

40 A reaction mechanism is shown.

H 2C CH2 H 2C CH2

H 2C CH2 H 2C CH2 + Br –

H 2C C Br H 2C C H

H OH
HO–

Which statements about this reaction are correct?

1 Heterolytic bond fission occurs.


2 It is a substitution reaction.
3 OH– behaves as an electrophile.

© UCLES 2020 9701/12/M/J/20


9701/12 Cambridge International AS & A Level – Mark Scheme May/June 2020
PUBLISHED

Question Answer Marks

1 B 1

2 C 1

3 C 1

4 A 1

5 D 1

6 D 1

7 B 1

8 C 1

9 A 1

10 B 1

11 D 1

12 C 1

13 D 1

14 B 1

15 B 1

16 B 1

17 C 1

18 D 1

19 A 1

20 A 1

21 C 1

22 D 1

23 B 1

24 A 1

25 A 1

26 B 1

27 C 1

28 C 1

© UCLES 2020 Page 2 of 3


9701/12 Cambridge International AS & A Level – Mark Scheme May/June 2020
PUBLISHED

Question Answer Marks

29 D 1

30 C 1

31 B 1

32 C 1

33 A 1

34 A 1

35 D 1

36 A 1

37 C 1

38 A 1

39 D 1

40 B 1

© UCLES 2020 Page 3 of 3


2

Section A

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

Use of the Data Booklet may be appropriate for some questions.

1 Which particle has equal numbers of protons and neutrons and an electronic structure of
1s22s22p63s23p6?
39 40 2+ 16 2 − 32
A 18 Ar B 20 Ca C 8O D 16 S

2 Which molecule contains six bonding electrons?

A NCl 3 B H2S C C2H4 D SF6

3 Solid carbon dioxide, CO2, is similar to solid iodine, I2, in its structure.

Which statement about solid CO2 and solid SiO2 is correct?

A Both solid CO2 and solid SiO2 exist in a lattice structure.


B Both solid CO2 and solid SiO2 have a simple molecular structure.
C Both solid CO2 and solid SiO2 have atoms joined by single covalent bonds.
D Both solid CO2 and solid SiO2 change spontaneously to gas at s.t.p..

4 The enthalpy changes of two reactions are shown.

K2CO3(s) + 2HCl (aq) → 2KCl (aq) + H2O(l) + CO2(g) ∆H = –34.0 kJ mol–1

KHCO3(s) + HCl (aq) → KCl (aq) + H2O(l) + CO2(g) ∆H = +32.8 kJ mol–1

What is the enthalpy change for the reaction shown?

2KHCO3(s) → K2CO3(s) + H2O(l) + CO2(g)

A –31.6 kJ mol–1
B 1.2 kJ mol–1
C 66.8 kJ mol–1
D 99.6 kJ mol–1

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3

5 Nitrogen reacts with oxygen to form nitrogen monoxide, NO, and nitrogen dioxide, NO2. Nitrogen
dioxide reacts with water and with hydroxide ions.

N2(g) + O2(g) → 2NO(g)

2NO(g) + O2(g) → 2NO2(g)

2NO2(g) + H2O(l) → HNO2(aq) + H+(aq) + NO3–(aq)

2NO2(g) + 2OH–(aq) → NO2–(aq) + NO3–(aq) + H2O(l)

What can be deduced using only the information from these equations?

A HNO2 is a strong acid.


B HNO3 is a weak acid.
C NO2 is a neutral gas.
D NO is a reducing agent.

6 Which solution has the lowest pH value?

A 0.01 mol dm–3 butanoic acid


B 0.01 mol dm–3 ethanoic acid
C 0.01 mol dm–3 hydrochloric acid
D 0.01 mol dm–3 sulfuric acid

7 The element sulfur produces a mass spectrum with the following peaks.

m / e value relative
of peak abundance

32 95.02
33 0.76
34 4.20
36 0.02

Which relative atomic mass of sulfur can be calculated from these data, given to four significant
figures?

A 32.07 B 32.08 C 32.09 D 32.10

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4

8 What is the electronic configuration of an isolated Ni2+ ion?

A 1s22s22p63s23p63d64s2
B 1s22s22p63s23p63d74s1
C 1s22s22p63s23p63d104s2
D 1s22s22p63s23p63d8

9 At 200 °C aluminium chloride is a gas with Mr = 267.

What is the number of covalent bonds, dative covalent bonds and Ione pairs of electrons in one
molecule of aluminium chloride at 200 °C?

covalent dative
Ione pairs
bonds covalent bonds

A 6 2 0
B 6 2 16
C 6 2 18
D 3 0 9

10 When solid KCl O3 is heated in the absence of air, a mixture of two chlorine compounds in the
mole ratio of 3 : 1 is formed. Chlorine is the only element whose oxidation number changes in this
reaction.

What could be the oxidation numbers of chlorine in the two compounds that are formed?

A +3 and –1 B +6 and +4 C +7 and –1 D +7 and +1

11 Two reactions are shown.

reaction 1 X2(g) + Y2(g) 2XY(g)


1 1
reaction 2 XY(g) 2
X2(g) + 2
Y2(g)

The equilibrium constant, Kp, for reaction 1 is 0.0052.

What is Kp for reaction 2?

A 2.6 × 10–3 B 13.9 C 192.3 D 384.6

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5

12 Compound T is a white crystalline solid.

When a sample of compound T is mixed with aqueous sodium hydroxide and heated, a gas is
produced which turns damp red litmus paper blue.

Further testing of a solution of compound T with aqueous barium chloride produces a dense
white precipitate which does not dissolve when dilute hydrochloric acid is added to the mixture.

What is the identity of compound T?

A ammonium carbonate
B ammonium sulfate
C sodium carbonate
D sodium sulfate

13 Which property explains the trend in volatility of the elements going down Group 17?

A decreasing covalent bond strength


B decreasing van der Waals’ forces
C increasing covalent bond strength
D increasing van der Waals’ forces

14 The statements apply to the elements in Group 2.

Which statement is correct?

A As atomic number increases, ionic radius increases.


B As atomic number increases, reducing ability decreases.
C As atomic number increases, first ionisation energy increases.
D As atomic radius increases, first ionisation energy increases.

15 Which element, when burned in oxygen, can form an oxide that is a reducing agent?

A Na B Mg C Al D S

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6

16 Nitrogen oxides are removed from the exhaust gases of internal combustion engines by the
action of a catalyst in a catalytic converter.

Which row is correct?

change in oxidation
type of catalyst
number of nitrogen

A decrease heterogeneous
B decrease homogeneous
C increase heterogeneous
D increase homogeneous

17 The addition of aqueous silver nitrate to aqueous barium chloride produces a white precipitate
which dissolves in an excess of dilute aqueous ammonia to form a colourless solution.

The addition of an excess of dilute nitric acid to the colourless solution produces a white
precipitate, Z.

What is Z?

A AgCl B BaCl 2 C Ba(NO3)2 D NH4NO3

18 Which property shows an increase from calcium to barium going down Group 2?

A the ease of decomposition of the carbonates


B the solubility of the hydroxides
C the solubility of the sulfates
D the volume of hydrogen given off when 1 g of the metal reacts with water

19 Element X is in Period 3. It reacts rapidly with water to form an alkaline solution.

Which statement about the chloride of element X is correct?

A It conducts electricity when molten.

B It has a melting point of less than 100 °C.


C It has covalent bonding.
D It reacts rapidly with cold water.

20 Structural and stereoisomerism should be considered when answering this question.

When trans-pent-2-ene reacts with HBr, how many different products can form?

A 1 B 2 C 3 D 4

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7

21 Ester P has the following structural formula.

ester P
O

CH3C

OCH2CH2CH(CH3)2

Which compounds are produced when P is hydrolysed using dilute hydrochloric acid?

A CH3COCl and (CH3)2CHCH2CH2OH


B CH3CH2OH and (CH3)2CHCH2CO2H
C CH3CO2H and (CH3)2CHCH2CO2H
D CH3CO2H and (CH3)2CHCH2CH2OH

22 There are many non-cyclic alcohols that cannot be oxidised by warm acidified MnO4– ions.
Alcohol X is the member of this set of alcohols with the lowest molecular mass.

How many moles of oxygen are required for the complete combustion of 1.0 mol of alcohol X?

A 3.5 mol B 4.5 mol C 6.0 mol D 6.5 mol

23 Butanoic acid can be produced from 1-bromopropane in two steps using reagents V and W as
shown.

reagent V reagent W
1-bromopropane compound Q butanoic acid

What could be reagents V and W?

V W

A KCN in ethanol HCl (aq)


B KCN in ethanol NaOH(aq)
C NH3 in ethanol HCl (aq)
D NaOH(aq) H+ / Cr2O72–(aq)

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8

24 Which statement about compound T and compound U is correct?

compound T compound U
O O

H 3C C H C

CH2CH2CH3 CH(CH3)CH2CH3

A T and U are stereoisomers.


B T can be distinguished from U by the use of alkaline aqueous iodine.
C T can be reduced by LiAl H4 but not by NaBH4.
D U can be formed by the oxidation of 3-methylbutan-1-ol.

25 The diagram shows the infrared spectrum of an organic compound.

What could be the identity of this compound?

A propan-1-ol
B propanal
C propanoic acid
D propanone

26 Which reagent reacts with both of the –OH groups in lactic acid, CH3CH(OH)CO2H?

A acidified potassium dichromate(VI)

B ethanol
C sodium
D sodium hydroxide

© UCLES 2020 9701/13/M/J/20


9

27 1,2-dibromopropane can be made from 1-bromopropane in two steps.

Which row is correct?

step 1 step 2

A addition substitution
B elimination addition
C hydrolysis elimination
D substitution hydrolysis

28 2-methylbut-2-ene reacts with HBr(g) to form two isomeric products. During the reaction two
positively charged intermediates can be made.

Which diagram shows the more stable of the two positively charged intermediates?

A B C D
Br
+ Br +
+
+

29 The ester ethyl methanoate is prepared in a school laboratory by reacting a carboxylic acid with
an alcohol.

During the reaction, only 50.0% of the alcohol is converted into the ester.

Which mass of alcohol is needed to prepare 10.0 g of the ester?

A 3.11 g B 8.65 g C 12.4 g D 32.2 g

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10

30 Compound X has the structure shown.

compound X
O

Which type of carbonyl group is present and how many chiral centres are there in one molecule
of X?

carbonyl chiral
group centres

A aldehyde 0
B aldehyde 1
C ketone 0
D ketone 1

© UCLES 2020 9701/13/M/J/20


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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

Use of the Data Booklet may be appropriate for some questions.

31 Which contain one mole of the underlined substance under room conditions?

1 a balloon containing 24.0 dm3 of helium


2 a block of calcium carbonate weighing 100.1 g
3 4000 cm3 of a 0.250 mol dm–3 solution of sulfuric acid

32 Buckminsterfullerene is a fullerene allotrope of carbon.

Which statements about buckminsterfullerene are correct?

1 Buckminsterfullerene is a giant covalent molecule.


2 Buckminsterfullerene has delocalised electrons.
3 Buckminsterfullerene has strong intramolecular bonds.

33 Gaseous sodium ions can be formed from sodium atoms.

Na(s) → Na+(g)

Which quantities are required to calculate the enthalpy change of formation of Na+(g)?

1 first ionisation energy of sodium


2 enthalpy change of atomisation of sodium
3 enthalpy change of formation of sodium

© UCLES 2020 9701/13/M/J/20 [Turn over


12

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

34 The Haber process is used in industry to form ammonia from hydrogen and nitrogen.

3H2 + N2 2NH3

Which statements about the activation energy for this process are correct?

1 The activation energy for the forward reaction is the same as the activation energy for the
reverse reaction.
2 The activation energy for the reverse reaction is decreased by the addition of iron.
3 The activation energy is the minimum energy that colliding particles must possess in order to
react.

35 Strontium nitrate is heated strongly for several minutes.

Which statements are correct?

1 A brown gas is produced.


2 A gas is produced that relights a glowing splint.
3 A white powder remains after heating.

36 When added to water, which oxides will not cause a change in pH?

1 Al 2O3
2 SiO2
3 P4O10

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13

37 Propanal reacts with hydrogen cyanide to form 2-hydroxybutanenitrile. A suitable catalyst for this
reaction is sodium cyanide.

NaCN
CH3CH2CHO + HCN CH3CH2CH(OH)CN

Which statements about this catalysed reaction of propanal with hydrogen cyanide are correct?

1 The sodium cyanide provides a stronger nucleophile than HCN.


2 The reaction can be classified as nucleophilic substitution.
3 The hydrogen cyanide molecule attacks the propanal molecule to form an intermediate ion.

38 A reaction mechanism is shown.

CH2 CH2

H2C CH2 H 2C CH2


+ Cl –

H 2C C Cl H 2C C H

H OH
HO–

Which statements about this reaction are correct?

1 It is a substitution reaction.
2 OH– behaves as a nucleophile.
3 Heterolytic bond fission is involved.

39 On complete combustion, a sample of X produces 44 g of carbon dioxide and 27 g of water.

On complete combustion, a sample of Y produces 44 g of carbon dioxide and 18 g of water.

On complete combustion, a sample of Z produces 22 g of carbon dioxide and 9 g of water.

Which substances could be straight chain alkanes?

1 X
2 Y
3 Z

© UCLES 2020 9701/13/M/J/20 [Turn over


14

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

40 Which pairs are structural isomers of each other?

1 CH3CH2CH2CH2CH2CO2H and CH3CH2CH2CO2CH2CH3

2 and

3 CH3CH2CH2CH(OH)CH2CH3 and CH3CH2CH(OH)CH2CH2CH3

© UCLES 2020 9701/13/M/J/20


9701/13 Cambridge International AS & A Level – Mark Scheme May/June 2020
PUBLISHED

Question Answer Marks

1 B 1

2 A 1

3 A 1

4 D 1

5 D 1

6 D 1

7 C 1

8 D 1

9 B 1

10 C 1

11 B 1

12 B 1

13 D 1

14 A 1

15 D 1

16 A 1

17 A 1

18 B 1

19 A 1

20 C 1

21 D 1

22 C 1

23 A 1

24 B 1

25 C 1

26 C 1

27 B 1

28 A 1

© UCLES 2020 Page 2 of 3


9701/13 Cambridge International AS & A Level – Mark Scheme May/June 2020
PUBLISHED

Question Answer Marks

29 C 1

30 D 1

31 A 1

32 C 1

33 B 1

34 C 1

35 A 1

36 B 1

37 D 1

38 A 1

39 D 1

40 B 1

© UCLES 2020 Page 3 of 3


2

Section A

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

Use of the Data Booklet may be appropriate for some questions.

1 Which statement is correct?

A Cl has a relative isotopic mass of 35.5.


B Cl 2 has a relative molecular mass of 70.

C ICl has a relative molecular mass of 162.4.


D NaCl has a relative molecular mass of 58.5.

2 Strontium metal can be extracted from strontium oxide, SrO, by reduction with aluminium. One of
the possible reactions is shown.

6SrO + 2Al  3Sr + Sr3Al 2O6

What is the maximum mass of strontium metal that can be produced from the reduction of 100 g
of strontium oxide using this reaction?

A 41.3 g B 42.3 g C 84.6 g D 169.2 g

3 A single 32P nucleus can be produced when a single 32


S nucleus joins with particle X. In the
process a proton is emitted.

What is particle X?

A a deuteron, 21H

B an electron
C a neutron
D a proton

4 In which of the following, when in liquid form, are there only intermolecular forces based on
temporary dipoles between the particles?

A bromine
B ethanol
C hydrogen chloride
D water

© UCLES 2020 9701/11/O/N/20


3

5 Copper has a high melting point.

What is the reason for the high melting point of copper?

A strong attractive forces between copper atoms only


B strong attractive forces between copper ions and delocalised electrons
C strong attractive forces between copper ions only
D strong attractive forces between copper atoms and delocalised electrons

6 Which pair of standard enthalpy changes are numerically equal?

A atomisation of CH4(g) and formation of CH4(g)


B combustion of CH3OH(l) and combustion of graphite + 2(combustion of H2(g))
C combustion of graphite and formation of CO2(g)
D neutralisation of HCl (aq) with NaOH(aq) and formation of H2O(l)

7 An energy cycle is drawn for the following reaction.

Br2(l) + 3F2(g)  2BrF3(l)

2Br(g) + 6F(g)

+698 kJ 2BrF3(g)

Br2(l) + 3F2(g) 2BrF3(l)

The standard enthalpy of formation of BrF3(l) = –301 kJ mol–1.

The enthalpy change of BrF3(l) to BrF3(g) is +44 kJ mol–1.

What is the average bond energy of the Br–F bond in BrF3?

A 152 kJ mol–1 B 202 kJ mol–1 C 304 kJ mol–1 D 404 kJ mol–1

8 In which reaction does the greatest change in the oxidation number of sulfur occur?

A S(s) + O2(g)  SO2(g)


1
B SO2(g) + O (g)
2 2
SO3(g)

C SO3(g) + H2SO4(l)  H2S2O7(l)

D H2S2O7(l) + H2O(l)  2H2SO4(l)

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4

9 The first stage in the chloride process for the manufacture of titanium consists of the following
reaction.

2TiO2 + 4Cl 2 + 3C  2TiCl 4 + 2CO + CO2

What is reduced in this reaction?

A carbon
B chlorine
C oxygen
D titanium

10 In aqueous solution, sulfuric acid dissociates as shown.

H2SO4  HSO4– + H+ This reaction goes to completion.


HSO4– SO42– + H+ This reaction reaches equilibrium with constant Kc.

Analysis of a 2.00 mol dm–3 solution of H2SO4 found the HSO4– concentration to be
1.988 mol dm–3.

What is Kc?

A 1.381  105 dm3 mol–1


B 82.34 dm3 mol–1

C 1.214  10–2 mol dm–3

D 7.244  10–5 mol dm–3

11 An autocatalytic reaction is a reaction in which one of the products catalyses the reaction.

Which curve would be obtained if the rate of an autocatalytic reaction is plotted against time?

A B C D

rate rate rate rate

0 0 0 0
0 time 0 time 0 time 0 time

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5

12 X and Y are two elements in Period 3 of the Periodic Table. They combine to form compound Z.

X forms a soluble acidic oxide. The oxidation number of X in this oxide is +4.

Y forms an amphoteric oxide.

What is the formula of compound Z?

A Al P B Al 2S3 C Si2P5 D SiS2

13 This question is about two elements in Group 2, Q and R.

Three of the statements shown are correct for metal Q.

The one remaining statement is correct for metal R.

Which statement applies to R?

A A saturated solution of the hydroxide of this metal has the higher pH value.
B This metal has a carbonate that is used in agriculture to reduce the acidity of soil.
C This metal has the greater atomic radius.
D This metal reacts more quickly with cold water.

14 The electronic arrangement for atoms of four elements is given.

Which element is the strongest oxidising agent?

A 1s22s22p5
B 1s22s22p63s2
C 1s22s22p63s23p5
D 1s22s22p63s23p64s2

15 A student mixes pairs of chemicals together in separate test-tubes.

● excess calcium (s) + water (l)


● barium chloride (aq) + strontium hydroxide (aq)
● calcium carbonate (s) + excess hydrochloric acid (aq)
● magnesium sulfate (aq) + barium nitrate (aq)

How many of the mixtures produce a white, solid product?

A 0 B 1 C 2 D 3

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6

16 With which compound does concentrated sulfuric acid react both as a strong acid and as an
oxidising agent?

A magnesium carbonate
B potassium chloride
C sodium bromide
D sulfur trioxide

17 Ammonia can undergo an acid–base reaction with hydrogen chloride to form ammonium chloride.

Which statement is correct?

A The ammonium ion is basic.


B The hydrogen atom from HCl donates a lone pair of electrons to the nitrogen atom.
C The H–N–H bond angle in ammonia is the same as the H–N–H bond angle in the ammonium
ion.
D The H–N–H bond angle in the ammonium ion is the same as the H–C–H bond angle in
methane.

18 What are the trends in the stated properties as Group 2 is descended from magnesium to
barium?

decomposition
temperature of the first ionisation energy
carbonate

A decreases increases
B decreases decreases
C increases increases
D increases decreases

19 Sulfur dioxide, SO2, reacts with calcium hydroxide in aqueous solution.

What is the main product that is first formed?

A Ca(HSO4)2 B CaS C CaSO3 D CaSO4

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7

20 Structural and stereoisomerism should be considered when answering this question.

Compounds X, Y and Z are shown.

X Y Z

HO HO Cl
H H
Cl Cl OH

How many other isomers of C3H7Cl O are there that are alcohols?

A 2 B 3 C 4 D 5

21 Two students each make a statement about 2-methylbut-1-ene.

Student 1 states that 2-methylbut-1-ene has geometrical isomers.

Student 2 states that 2-methylbut-1-ene reacts with HBr in an addition reaction to give
1-bromo-2-methylbutane as the main product.

Which students are correct?

A both 1 and 2
B 1 only
C 2 only
D neither 1 nor 2

22 Which statement is correct when referring to the complete combustion of PVC?

A A gas is made which contributes to global warming.


B Carbon dioxide and water are the only products.
C If water is used to clean the exhaust gases, the water becomes alkaline.
D There is no need to treat the exhaust gases as the products are non-hazardous.

23 Iodoethane, CH3CH2I, reacts with aqueous silver nitrate at 50 C. A precipitate forms during this
reaction.

Which row of the table is correct about this reaction?

type of organic reaction colour of precipitate

A electrophilic substitution cream


B electrophilic substitution yellow
C nucleophilic substitution cream
D nucleophilic substitution yellow

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8

24 A student converts 1-iodopropane, C3H7I, into butanoic acid, C3H7CO2H, by a two-stage chemical
synthesis.

In the first of the two stages, which reagent is reacted with 1-iodopropane?

A aqueous sodium hydroxide


B ethanolic ammonia
C ethanolic potassium cyanide
D ethanolic sodium hydroxide

25 1-chloro-1-methylcyclohexane is hydrolysed by heating with NaOH(aq).

CH3 CH3
+ OH– → + Cl –
Cl OH

The reaction pathway is shown.

energy Z

reaction pathway

One carbon atom in 1-chloro-1-methylcyclohexane is bonded to three other carbon atoms.

What is the charge on this carbon atom at point Z?

A 1– B – C + D 1+

26 An alcohol with the molecular formula C5H12O decolourises warm acidified potassium
manganate(VII). The alcohol also gives a yellow precipitate with alkaline aqueous iodine.

What could be the identity of the alcohol?

A 2-methylbutan-2-ol
B 3-methylbutan-2-ol
C pentan-1-ol
D pentan-3-ol

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9

27 Which pair of test results would prove that a substance, X, is a ketone?

A X has no reaction with Tollens’ reagent. X reacts with alkaline aqueous iodine.

B X is reduced by lithium aluminium hydride. X is oxidised by acidified dichromate(VI).

C X reacts with 2,4-DNPH reagent. X has no reaction with Fehling’s reagent.


D X reacts with hydrogen cyanide. X is reduced by lithium aluminium hydride.

28 Carvone is found in spearmint oil.

carvone
O

Which product is formed when carvone is reacted with NaBH4?

A B C D
OH O O OH

29 Which compound is chiral and reacts with Na2CO3 to give CO2?

A B C D

CH3 OH CH2Br CH(Br)CO2H


H CO2H
C HCO2CH
CH2
C CH3
H CO2H CH3

30 The skeletal formula of compound X is shown.

compound X
HO

What is the molecular formula of compound X?

A C10H18O B C10H20O C C11H22O D C11H24O

© UCLES 2020 9701/11/O/N/20 [Turn over


10

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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

Use of the Data Booklet may be appropriate for some questions.

31 Nitrogen forms a number of oxides. Their enthalpies of formation are given.

[NO(g)] = +90 kJ mol–1


[N2O(g)] = +82 kJ mol–1
[NO2(g)] = +33 kJ mol–1

Which statements are correct?

1 If N2O(g) is oxidised by O2(g) to NO2(g), 16 kJ is released per mole of N2O.


2 The decomposition of N2O(g) to N2(g) and O2(g) is exothermic.
3 The reaction between NO and oxygen is exothermic.

32 Which statements are correct?

1 enthalpy of combustion of H2 = enthalpy of formation of H2O


2 enthalpy of formation of H2 = –(enthalpy of atomisation of H2)
3 enthalpy of solution of HCl = enthalpy of hydration of H+ + enthalpy of hydration of Cl –

33 The units of Kc for an equilibrium reaction are mol–1 dm3.

What could be the equation for the equilibrium?

1 A(aq) + B(aq) C(s) + D(aq)


2 P(aq) + Q(aq) R(aq)
3 W(aq) + 2X(aq) Y(aq) + Z(aq)

© UCLES 2020 9701/11/O/N/20


11

34 Methanol, CH3OH, can be produced industrially by reacting CO with H2.

CO(g) + 2H2(g) CH3OH(g) H = –91 kJ mol–1

The process can be carried out at 4  103 kPa and 1150 K.

Which statements about this reaction are correct?

1 Increasing the temperature will increase the rate of reaction because more effective
collisions will occur.
2 Lowering the temperature will reduce the rate of reaction because the forward reaction is
exothermic.
3 Increasing the pressure will reduce the rate of reaction because there are a larger number of
moles on the left-hand side of the equation.

35 Which rows correctly show the relative electrical conductivities of the sets of three Period 3
elements?

greatest least
conductivity conductivity

1 sodium silicon chlorine


2 aluminium magnesium phosphorus
3 sulfur silicon phosphorus

36 Three test-tubes, X, Y and Z, each contain water.

● A small amount of NaCl is added to test-tube X.


● A small amount of SiCl 4 is added to test-tube Y.
● A small amount of Al Cl 3 is added to test-tube Z.

After a short time, two drops of universal indicator solution are added to each test-tube.

Which statements can be correct?

1 The pH in test-tube X is 7.
2 The pH in test-tube Y is 2.
3 The pH in test-tube Z is 2.

© UCLES 2020 9701/11/O/N/20 [Turn over


12

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

37 The structure of compound R is shown.

compound R

OH
O

Which statements about compound R are correct?

1 It has an Mr of 116.
2 It contains two groups that show strong absorptions between 1640 and 1740 cm–1 in its
infrared spectrum.
3 Its only infrared absorption between 2500 and 3000 cm–1 is sharp and strong.

38 During the bromination of methane, the free radical CH3• is generated. A possible termination
step of this reaction is the formation of C2H6 by the combination of two free radicals.

What could be produced in a termination step during the bromination of propane?

1 CH3CH2CH(CH3)CH2CH3
2 CH3CH(CH3)CH(CH3)2
3 CH3CH2CH2CH(CH3)2

© UCLES 2020 9701/11/O/N/20


13

39 Three reactions of primary alcohols are listed.

Which reactions give water as one of the products?

1 reaction with ethanoic acid


2 reaction with concentrated HBr
3 passing the alcohol vapour over heated Al 2O3

40 The diagram shows part of the structure of polymer X.

CH3 H CH3 H CH3 H

C C C C C C

H CO2CH3 H CO2CH3 H CO2CH3

Which reagents react with polymer X?

1 aqueous sulfuric acid


2 aqueous sodium hydroxide
3 sodium

© UCLES 2020 9701/11/O/N/20


9701/11 Cambridge International AS & A Level – Mark Scheme October/November
PUBLISHED 2020

Question Answer Marks

1 C 1

2 B 1

3 C 1

4 A 1

5 B 1

6 C 1

7 B 1

8 A 1

9 B 1

10 C 1

11 C 1

12 B 1

13 B 1

14 A 1

15 C 1

16 C 1

17 D 1

18 D 1

19 C 1

20 D 1

21 D 1

22 A 1

23 D 1

24 C 1

25 D 1

26 B 1

27 C 1

28 A 1

© UCLES 2020 Page 2 of 3


9701/11 Cambridge International AS & A Level – Mark Scheme October/November
PUBLISHED 2020

Question Answer Marks

29 D 1

30 A 1

31 A 1

32 D 1

33 A 1

34 D 1

35 B 1

36 A 1

37 B 1

38 C 1

39 A 1

40 B 1

© UCLES 2020 Page 3 of 3


2

Section A

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

Use of the Data Booklet may be appropriate for some questions.

1 What is the average oxidation number of sulfur in each compound?

Ca(HSO3)2 Na2S2O3

A 4 2
B 4 4
C 6 2
D 6 4

2 An ore of manganese contains 4% by mass of MnO2 and no other manganese compound.

Which mass of manganese would be obtained from 1 tonne of this ore?

A 25.3 kg B 40.0 kg C 63.3 kg D 632 kg

3 Which atomic orbitals are occupied in an atom of phosphorus?

A 1p 2s 2p B 2s 2p 2d C 2s 2p 3s D 2p 3s 3d

4 The structure of compound A is shown.

compound A
CH3 CH3
CH CH C CH C CH CH2OH

CH3 CH3

Some of the carbon atoms in compound A have a tetrahedral arrangement of bonds.

Some of the carbon atoms in compound A have a trigonal planar arrangement of bonds.

How many carbon atoms are there of each type?

tetrahedral trigonal planar

A 5 12
B 8 8
C 9 6
D 9 8

© UCLES 2020 9701/12/O/N/20


3

5 A white powder is known to be a mixture of magnesium oxide and aluminium oxide.

100 cm3 of 2 mol dm–3 NaOH(aq) is just enough to dissolve the aluminium oxide in x grams of the
mixture.

The reaction is shown.

Al 2O3 + 2OH– + 3H2O → 2Al (OH)4–

800 cm3 of 2 mol dm–3 HCl (aq) is just enough to dissolve all of the oxide in x grams of the mixture.

The reactions are shown.

Al 2O3 + 6H+ → 2Al 3+ + 3H2O


MgO + 2H+ → Mg2+ + H2O

How many moles of each oxide are present in x grams of the mixture?

aluminium magnesium
oxide oxide

A 0.05 0.25
B 0.05 0.50
C 0.10 0.25
D 0.10 0.50

6 A graph of pV against T is shown for a fixed mass of gas. (p = pressure, V = volume and
T = temperature in K.)

pV

Which gas gives this graph over the widest range of temperatures and pressures?

A hydrogen, H2
B hydrogen chloride, HCl
C hydrogen fluoride, HF
D oxygen, O2

© UCLES 2020 9701/12/O/N/20 [Turn over


4

7 A weather balloon is filled with 12.0 kg helium. The weather balloon reaches a height of 20 km,
the pressure inside the balloon is 6000 Pa and the temperature is 216 K.

What is the volume of the weather balloon at this height, correct to three significant figures?

A 897 dm3 B 1790 dm3 C 897 000 dm3 D 1 790 000 dm3

8 Which pair of enthalpy changes will always share the same sign (i.e. both are always exothermic
or both are always endothermic)?

A enthalpy change of atomisation and enthalpy change of neutralisation


B enthalpy change of atomisation and enthalpy change of solution
C enthalpy change of combustion and enthalpy change of hydration
D enthalpy change of solution and enthalpy change of hydration

9 Chlorine dioxide, Cl O2, reacts with sodium hydroxide in the reaction shown.

2Cl O2 + 2OH– → Cl O2– + Cl O3– + H2O

Which statement correctly describes this redox reaction?

A Chlorine atoms are oxidised and oxygen atoms are reduced.


B Chlorine atoms are reduced and oxygen atoms are oxidised.
C Some chlorine atoms are oxidised and some chlorine atoms are reduced.
D Some oxygen atoms are oxidised and some oxygen atoms are reduced.

10 Sulfur dioxide and oxygen react to form sulfur trioxide. The reaction is reversible.

2SO2(g) + O2(g) 2SO3(g) Kp = 2.96 × 10–9 Pa–1 at 700 °C

The reaction is allowed to reach equilibrium at 700 °C. The partial pressure of O2(g) is 375 kPa
and the partial pressure of SO3(g) is 20.3 kPa.

What is the partial pressure of SO2(g)?

A 19.3 kPa B 609 kPa C 18 300 kPa D 609 000 kPa

© UCLES 2020 9701/12/O/N/20


5

11 Ammonia is made by the Haber process. The reactants are nitrogen and hydrogen.

N2(g) + 3H2(g) 2NH3(g) ∆H is negative

What will increase the rate of the forward reaction?

A adding argon to the mixture but keeping the total volume constant
B decreasing the temperature
C increasing the total pressure by reducing the total volume at constant temperature
D removing ammonia as it is made but keeping the total volume of the mixture the same

12 Element X, in Period 3, has the following properties.

● Its oxide has a giant structure.


● It forms covalent bonds with chlorine.
● Its oxide will neutralise HCl (aq).

What is element X?

A Mg B Al C Si D P

13 Which row could refer to barium metal and barium hydroxide?

colour seen pH of a saturated


when the metal solution of
is burnt in O2 the hydroxide

A green flame 8
B green flame 13
C white flame 8
D white flame 13

© UCLES 2020 9701/12/O/N/20 [Turn over


6

14 AgNO3(aq) is added to a solution of a halide ion, X–(aq), and aqueous ammonia is then added.

The ionic equations for the two reactions that occur are shown.

Ag+(aq) + X–(aq) AgX(s) equilibrium 1


Ag+(aq) + 2NH3(aq) Ag(NH3)2+(aq) equilibrium 2

Which statement is correct?

A The position of equilibrium 1 lies to the left when X– = I–.


B Increasing the concentration of ammonia causes the position of equilibrium 1 to move to the
left.

C Kc for equilibrium 2 is larger when X– = Cl – than when X– = I–.


D Equilibrium 2 is a redox reaction.

15 Water and ammonia take part in a reaction that produces the ammonium ion.

Which statement about this reaction is correct?

A The ammonia molecule and the ammonium ion do not have dipole moments.

B The bond angle changes from 109.5° in the ammonia molecule to 107° in the ammonium ion.
C The reaction is a redox reaction.
D The water is acting as an acid.

16 Due to their similar ionic radii, the reactions of lithium and magnesium and their corresponding
compounds are very similar.

Which statement about the reactions of lithium or its compounds can be predicted from this
statement?

A Lithium burns very slowly in oxygen.


B Lithium carbonate decomposes on heating in a blue Bunsen burner flame, forming lithium
oxide and carbon dioxide.
C Lithium nitrate decomposes on heating, forming lithium nitrite, LiNO2, and oxygen.
D Lithium reacts very violently with cold water, producing hydrogen.

17 Which statement about Group 17 elements and their compounds is correct?

A Chlorine reacts with cold concentrated sodium hydroxide to form NaCl and NaCl O3.
B HCl is more thermally stable than HBr because chlorine is less electronegative than bromine.
C Iodide ions are oxidised to iodine by concentrated sulfuric acid.
D Silver iodide is soluble in dilute aqueous ammonia.

© UCLES 2020 9701/12/O/N/20


7

18 Which substance, when warmed with aqueous ammonium chloride, would produce an alkaline
gas?

A CH3CO2H B CH3CH2OH C CH3CO2CH3 D CH3CH2ONa

19 Compound X is the oxide of a Period 3 element. Compound X reacts with water to give an acidic
solution.

A solution is prepared by reacting 0.100 g of compound X with an excess of water. This solution is
neutralised by exactly 25.0 cm3 of 0.100 mol dm–3 sodium hydroxide solution.

What could be the identity of compound X?

A Al 2O3 B MgO C P4O10 D SO3

20 The unsaturated hydrocarbon octa-1,3,5,7-tetraene, C8H10, can display geometric isomerism.

octa-1,3,5,7-tetraene
CH2=CHCH=CHCH=CHCH=CH2

How many isomers exist?

A 2 B 3 C 4 D 8

21 What is the correct name for the compound shown?

HO

A 1,2,2-trimethylbutan-3-ol
B 2-ethyl-2-methylbutan-2-ol
C 3,3-dimethylpentan-2-ol
D 4-hydroxy-3,3-dimethylpentane

22 A polymer has the following repeat unit. It is made from two different monomers.

CH2 CHCl CH2 CH CH CH2

Which pair of monomers could be used to make this polymer?

A CH2=CHCl and CH2=CH2


B CH2=CHCl and CH2=CH–CH=CH2
C CH3–CH2Cl and CH3–CH=CH–CH3

D CH3–CH=CH–CH3 and CH2=CHCl

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8

23 Compound X contains two functional groups.

compound X
O

CH3 C CHO

Which reagent will react with only one of the functional groups?

A acidified potassium dichromate(VI)


B 2,4-DNPH reagent
C hydrogen cyanide
D NaBH4

24 Ethanol can be converted into ethene in a single reaction.

Ethanol can be converted into bromoethane in a single reaction.

Under standard laboratory conditions, is a catalyst used in these reactions?

ethanol to ethene ethanol to bromoethane

A yes yes
B yes no
C no yes
D no no

25 Diols in which both hydroxy groups are bonded to the same carbon atom can spontaneously
eliminate a molecule of water to produce a carbonyl compound.

Which compound, after complete hydrolysis, gives a silver mirror with Tollens’ reagent?

A 1,1-dibromobutane
B 1,2-dibromobutane
C 1,3-dibromobutane
D 2,2-dibromobutane

26 Which alcohol will give a yellow precipitate when warmed with alkaline aqueous iodine?

A (CH3)2CHCH2OH
B (CH3)3COH
C CH3CH2C(OH)(CH3)2
D CH3CH(OH)CH2CH3

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9

27 How many structural isomers are there of molecular formula C5H10O that give a red precipitate
with Fehling’s solution?

A 1 B 2 C 3 D 4

28 Which statement about the use of alkane fuels in internal combustion engines is correct?

A C8H18 is used as fuel in internal combustion engines and reacts with oxygen and nitrogen
from the air.
B In limited oxygen, CO is produced which oxidises SO2 to SO3 in the atmosphere.
C The catalytic converter removes polluting gases including NO2 and CO2.
D Unburnt hydrocarbons and NO2 can react in sunlight to produce photochemical smog.

29 Compound Z is shown.

compound Z

HO CO2H

HO O
OH

What is produced in good yield when compound Z is treated with an excess of sodium carbonate
solution at room temperature?

A B

HO CO2Na NaO CO2Na

O O

HO O NaO O
OH ONa

C D

NaO CO2H HO CO2Na

O O
+

NaO O HO OH HO
ONa OH

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10

30 The infra-red spectrum shown was obtained from compound G.

100

transmittance
/% 50

0
4000 3000 2000 1500 1000 500
–1
wavenumber / cm

What could be compound G?

A CH3COCH2OH
B CH3CH2CO2H
C CH3CO2CH3
D CH3CHCHCH3

© UCLES 2020 9701/12/O/N/20


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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

Use of the Data Booklet may be appropriate for some questions.

33 3 −
31 The symbol for a phosphorus ion is 15 P .

37 +
The symbol for a potassium ion is 19 K .

What do these two ions have in common?

1 the same number of electrons


2 the same number of neutrons
3 the same number of protons

32 The repeat unit of a polymer is shown.

H CN

C C

H CO2C2H5 n

Which types of intermolecular forces exist in the solid polymer?

1 temporary dipole – induced dipole interactions


2 permanent dipole – permanent dipole interactions
3 hydrogen bonds

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12

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

33 The diagram illustrates the enthalpy changes of a set of reactions.

∆H = –134 kJ mol–1
R S

∆H = +92 kJ mol–1

∆H = –75 kJ mol–1
T U

Which statements are correct?

1 The enthalpy change for the transformation U → R is + 42 kJ mol–1.

2 The enthalpy change for the transformation T → S is endothermic.

3 The enthalpy change for the transformation R → T is – 33 kJ mol–1.

34 Which statements about a reaction that has reached dynamic equilibrium are correct?

1 The rate of the forward reaction equals the rate of the reverse reaction.
2 There is no overall change in the concentrations of reactants and products.
3 There is no change in the measurable properties of the system.

35 Group 2 elements and their compounds show trends in their physical and chemical properties.
Barium is above radium in Group 2 of the Periodic Table.

Which statements are likely to be correct?

1 Barium hydroxide is less soluble than radium hydroxide.


2 Barium reacts less vigorously with water than radium does.
3 Barium sulfate is more soluble than radium sulfate.

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13

36 Which statements are correct?

1 The empirical formula of silicon(IV) oxide is SiO2.

2 The molecular formula of phosphorus(V) oxide is P2O5.

3 Silicon(IV) oxide and phosphorus(V) oxide are both simple molecular compounds.

37 Which reagents could be used, under suitable conditions, to oxidise CH3CH2CH2OH to


CH3CH2CHO?

1 acidified potassium manganate(VII)

2 acidified potassium dichromate(VI)

3 Tollens’ reagent

38 Which free radicals can be generated during a free-radical substitution reaction between chlorine
and ethane?

1 CH3•
2 CH2Cl CH2•
3 CH3CCl 2•

39 Which substances have molecular formula C4H8O?

1
O

2
O

OH
3

40 Which reactions produce pentanoic acid?

1 CH3CH2CH2CH(OH)CH3 + H+ / MnO4–(aq)
2 CH3OCO(CH2)3CH3 + HCl (aq)
3 CH3(CH2)3CN + H2SO4(aq)

© UCLES 2020 9701/12/O/N/20


9701/12 Cambridge International AS & A Level – Mark Scheme October/November
PUBLISHED 2020

Question Answer Marks

1 A 1

2 A 1

3 C 1

4 D 1

5 D 1

6 A 1

7 C 1

8 C 1

9 C 1

10 B 1

11 C 1

12 B 1

13 B 1

14 B 1

15 D 1

16 B 1

17 C 1

18 D 1

19 D 1

20 B 1

21 C 1

22 B 1

23 A 1

24 B 1

25 A 1

26 D 1

27 D 1

28 D 1

© UCLES 2020 Page 2 of 3


9701/12 Cambridge International AS & A Level – Mark Scheme October/November
PUBLISHED 2020

Question Answer Marks

29 A 1

30 C 1

31 B 1

32 B 1

33 D 1

34 A 1

35 A 1

36 D 1

37 B 1

38 C 1

39 A 1

40 C 1

© UCLES 2020 Page 3 of 3


2

Section A

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

Use of the Data Booklet may be appropriate for some questions.

1 Which statement is correct?

A Cl has a relative isotopic mass of 35.5.


B Cl 2 has a relative molecular mass of 70.

C ICl has a relative molecular mass of 162.4.


D NaCl has a relative molecular mass of 58.5.

2 Strontium metal can be extracted from strontium oxide, SrO, by reduction with aluminium. One of
the possible reactions is shown.

6SrO + 2Al  3Sr + Sr3Al 2O6

What is the maximum mass of strontium metal that can be produced from the reduction of 100 g
of strontium oxide using this reaction?

A 41.3 g B 42.3 g C 84.6 g D 169.2 g

3 A single 32P nucleus can be produced when a single 32


S nucleus joins with particle X. In the
process a proton is emitted.

What is particle X?

A a deuteron, 21H

B an electron
C a neutron
D a proton

4 In which of the following, when in liquid form, are there only intermolecular forces based on
temporary dipoles between the particles?

A bromine
B ethanol
C hydrogen chloride
D water

© UCLES 2020 9701/13/O/N/20


3

5 Copper has a high melting point.

What is the reason for the high melting point of copper?

A strong attractive forces between copper atoms only


B strong attractive forces between copper ions and delocalised electrons
C strong attractive forces between copper ions only
D strong attractive forces between copper atoms and delocalised electrons

6 Which pair of standard enthalpy changes are numerically equal?

A atomisation of CH4(g) and formation of CH4(g)


B combustion of CH3OH(l) and combustion of graphite + 2(combustion of H2(g))
C combustion of graphite and formation of CO2(g)
D neutralisation of HCl (aq) with NaOH(aq) and formation of H2O(l)

7 An energy cycle is drawn for the following reaction.

Br2(l) + 3F2(g)  2BrF3(l)

2Br(g) + 6F(g)

+698 kJ 2BrF3(g)

Br2(l) + 3F2(g) 2BrF3(l)

The standard enthalpy of formation of BrF3(l) = –301 kJ mol–1.

The enthalpy change of BrF3(l) to BrF3(g) is +44 kJ mol–1.

What is the average bond energy of the Br–F bond in BrF3?

A 152 kJ mol–1 B 202 kJ mol–1 C 304 kJ mol–1 D 404 kJ mol–1

8 In which reaction does the greatest change in the oxidation number of sulfur occur?

A S(s) + O2(g)  SO2(g)


1
B SO2(g) + O (g)
2 2
SO3(g)

C SO3(g) + H2SO4(l)  H2S2O7(l)

D H2S2O7(l) + H2O(l)  2H2SO4(l)

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4

9 The first stage in the chloride process for the manufacture of titanium consists of the following
reaction.

2TiO2 + 4Cl 2 + 3C  2TiCl 4 + 2CO + CO2

What is reduced in this reaction?

A carbon
B chlorine
C oxygen
D titanium

10 In aqueous solution, sulfuric acid dissociates as shown.

H2SO4  HSO4– + H+ This reaction goes to completion.


HSO4– SO42– + H+ This reaction reaches equilibrium with constant Kc.

Analysis of a 2.00 mol dm–3 solution of H2SO4 found the HSO4– concentration to be
1.988 mol dm–3.

What is Kc?

A 1.381  105 dm3 mol–1


B 82.34 dm3 mol–1

C 1.214  10–2 mol dm–3

D 7.244  10–5 mol dm–3

11 An autocatalytic reaction is a reaction in which one of the products catalyses the reaction.

Which curve would be obtained if the rate of an autocatalytic reaction is plotted against time?

A B C D

rate rate rate rate

0 0 0 0
0 time 0 time 0 time 0 time

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5

12 X and Y are two elements in Period 3 of the Periodic Table. They combine to form compound Z.

X forms a soluble acidic oxide. The oxidation number of X in this oxide is +4.

Y forms an amphoteric oxide.

What is the formula of compound Z?

A Al P B Al 2S3 C Si2P5 D SiS2

13 This question is about two elements in Group 2, Q and R.

Three of the statements shown are correct for metal Q.

The one remaining statement is correct for metal R.

Which statement applies to R?

A A saturated solution of the hydroxide of this metal has the higher pH value.
B This metal has a carbonate that is used in agriculture to reduce the acidity of soil.
C This metal has the greater atomic radius.
D This metal reacts more quickly with cold water.

14 The electronic arrangement for atoms of four elements is given.

Which element is the strongest oxidising agent?

A 1s22s22p5
B 1s22s22p63s2
C 1s22s22p63s23p5
D 1s22s22p63s23p64s2

15 A student mixes pairs of chemicals together in separate test-tubes.

● excess calcium (s) + water (l)


● barium chloride (aq) + strontium hydroxide (aq)
● calcium carbonate (s) + excess hydrochloric acid (aq)
● magnesium sulfate (aq) + barium nitrate (aq)

How many of the mixtures produce a white, solid product?

A 0 B 1 C 2 D 3

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6

16 With which compound does concentrated sulfuric acid react both as a strong acid and as an
oxidising agent?

A magnesium carbonate
B potassium chloride
C sodium bromide
D sulfur trioxide

17 Ammonia can undergo an acid–base reaction with hydrogen chloride to form ammonium chloride.

Which statement is correct?

A The ammonium ion is basic.


B The hydrogen atom from HCl donates a lone pair of electrons to the nitrogen atom.
C The H–N–H bond angle in ammonia is the same as the H–N–H bond angle in the ammonium
ion.
D The H–N–H bond angle in the ammonium ion is the same as the H–C–H bond angle in
methane.

18 What are the trends in the stated properties as Group 2 is descended from magnesium to
barium?

decomposition
temperature of the first ionisation energy
carbonate

A decreases increases
B decreases decreases
C increases increases
D increases decreases

19 Sulfur dioxide, SO2, reacts with calcium hydroxide in aqueous solution.

What is the main product that is first formed?

A Ca(HSO4)2 B CaS C CaSO3 D CaSO4

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7

20 Structural and stereoisomerism should be considered when answering this question.

Compounds X, Y and Z are shown.

X Y Z

HO HO Cl
H H
Cl Cl OH

How many other isomers of C3H7Cl O are there that are alcohols?

A 2 B 3 C 4 D 5

21 Two students each make a statement about 2-methylbut-1-ene.

Student 1 states that 2-methylbut-1-ene has geometrical isomers.

Student 2 states that 2-methylbut-1-ene reacts with HBr in an addition reaction to give
1-bromo-2-methylbutane as the main product.

Which students are correct?

A both 1 and 2
B 1 only
C 2 only
D neither 1 nor 2

22 Which statement is correct when referring to the complete combustion of PVC?

A A gas is made which contributes to global warming.


B Carbon dioxide and water are the only products.
C If water is used to clean the exhaust gases, the water becomes alkaline.
D There is no need to treat the exhaust gases as the products are non-hazardous.

23 Iodoethane, CH3CH2I, reacts with aqueous silver nitrate at 50 C. A precipitate forms during this
reaction.

Which row of the table is correct about this reaction?

type of organic reaction colour of precipitate

A electrophilic substitution cream


B electrophilic substitution yellow
C nucleophilic substitution cream
D nucleophilic substitution yellow

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8

24 A student converts 1-iodopropane, C3H7I, into butanoic acid, C3H7CO2H, by a two-stage chemical
synthesis.

In the first of the two stages, which reagent is reacted with 1-iodopropane?

A aqueous sodium hydroxide


B ethanolic ammonia
C ethanolic potassium cyanide
D ethanolic sodium hydroxide

25 1-chloro-1-methylcyclohexane is hydrolysed by heating with NaOH(aq).

CH3 CH3
+ OH– → + Cl –
Cl OH

The reaction pathway is shown.

energy Z

reaction pathway

One carbon atom in 1-chloro-1-methylcyclohexane is bonded to three other carbon atoms.

What is the charge on this carbon atom at point Z?

A 1– B – C + D 1+

26 An alcohol with the molecular formula C5H12O decolourises warm acidified potassium
manganate(VII). The alcohol also gives a yellow precipitate with alkaline aqueous iodine.

What could be the identity of the alcohol?

A 2-methylbutan-2-ol
B 3-methylbutan-2-ol
C pentan-1-ol
D pentan-3-ol

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9

27 Which pair of test results would prove that a substance, X, is a ketone?

A X has no reaction with Tollens’ reagent. X reacts with alkaline aqueous iodine.

B X is reduced by lithium aluminium hydride. X is oxidised by acidified dichromate(VI).

C X reacts with 2,4-DNPH reagent. X has no reaction with Fehling’s reagent.


D X reacts with hydrogen cyanide. X is reduced by lithium aluminium hydride.

28 Carvone is found in spearmint oil.

carvone
O

Which product is formed when carvone is reacted with NaBH4?

A B C D
OH O O OH

29 Which compound is chiral and reacts with Na2CO3 to give CO2?

A B C D

CH3 OH CH2Br CH(Br)CO2H


H CO2H
C HCO2CH
CH2
C CH3
H CO2H CH3

30 The skeletal formula of compound X is shown.

compound X
HO

What is the molecular formula of compound X?

A C10H18O B C10H20O C C11H22O D C11H24O

© UCLES 2020 9701/13/O/N/20 [Turn over


10

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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

Use of the Data Booklet may be appropriate for some questions.

31 Nitrogen forms a number of oxides. Their enthalpies of formation are given.

[NO(g)] = +90 kJ mol–1


[N2O(g)] = +82 kJ mol–1
[NO2(g)] = +33 kJ mol–1

Which statements are correct?

1 If N2O(g) is oxidised by O2(g) to NO2(g), 16 kJ is released per mole of N2O.


2 The decomposition of N2O(g) to N2(g) and O2(g) is exothermic.
3 The reaction between NO and oxygen is exothermic.

32 Which statements are correct?

1 enthalpy of combustion of H2 = enthalpy of formation of H2O


2 enthalpy of formation of H2 = –(enthalpy of atomisation of H2)
3 enthalpy of solution of HCl = enthalpy of hydration of H+ + enthalpy of hydration of Cl –

33 The units of Kc for an equilibrium reaction are mol–1 dm3.

What could be the equation for the equilibrium?

1 A(aq) + B(aq) C(s) + D(aq)


2 P(aq) + Q(aq) R(aq)
3 W(aq) + 2X(aq) Y(aq) + Z(aq)

© UCLES 2020 9701/13/O/N/20


11

34 Methanol, CH3OH, can be produced industrially by reacting CO with H2.

CO(g) + 2H2(g) CH3OH(g) H = –91 kJ mol–1

The process can be carried out at 4  103 kPa and 1150 K.

Which statements about this reaction are correct?

1 Increasing the temperature will increase the rate of reaction because more effective
collisions will occur.
2 Lowering the temperature will reduce the rate of reaction because the forward reaction is
exothermic.
3 Increasing the pressure will reduce the rate of reaction because there are a larger number of
moles on the left-hand side of the equation.

35 Which rows correctly show the relative electrical conductivities of the sets of three Period 3
elements?

greatest least
conductivity conductivity

1 sodium silicon chlorine


2 aluminium magnesium phosphorus
3 sulfur silicon phosphorus

36 Three test-tubes, X, Y and Z, each contain water.

● A small amount of NaCl is added to test-tube X.


● A small amount of SiCl 4 is added to test-tube Y.
● A small amount of Al Cl 3 is added to test-tube Z.

After a short time, two drops of universal indicator solution are added to each test-tube.

Which statements can be correct?

1 The pH in test-tube X is 7.
2 The pH in test-tube Y is 2.
3 The pH in test-tube Z is 2.

© UCLES 2020 9701/13/O/N/20 [Turn over


12

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

37 The structure of compound R is shown.

compound R

OH
O

Which statements about compound R are correct?

1 It has an Mr of 116.
2 It contains two groups that show strong absorptions between 1640 and 1740 cm–1 in its
infrared spectrum.
3 Its only infrared absorption between 2500 and 3000 cm–1 is sharp and strong.

38 During the bromination of methane, the free radical CH3• is generated. A possible termination
step of this reaction is the formation of C2H6 by the combination of two free radicals.

What could be produced in a termination step during the bromination of propane?

1 CH3CH2CH(CH3)CH2CH3
2 CH3CH(CH3)CH(CH3)2
3 CH3CH2CH2CH(CH3)2

© UCLES 2020 9701/13/O/N/20


13

39 Three reactions of primary alcohols are listed.

Which reactions give water as one of the products?

1 reaction with ethanoic acid


2 reaction with concentrated HBr
3 passing the alcohol vapour over heated Al 2O3

40 The diagram shows part of the structure of polymer X.

CH3 H CH3 H CH3 H

C C C C C C

H CO2CH3 H CO2CH3 H CO2CH3

Which reagents react with polymer X?

1 aqueous sulfuric acid


2 aqueous sodium hydroxide
3 sodium

© UCLES 2020 9701/13/O/N/20


9701/13 Cambridge International AS & A Level – Mark Scheme October/November
PUBLISHED 2020

Question Answer Marks

1 C 1

2 B 1

3 C 1

4 A 1

5 B 1

6 C 1

7 B 1

8 A 1

9 B 1

10 C 1

11 C 1

12 B 1

13 B 1

14 A 1

15 C 1

16 C 1

17 D 1

18 D 1

19 C 1

20 D 1

21 D 1

22 A 1

23 D 1

24 C 1

25 D 1

26 B 1

27 C 1

28 A 1

© UCLES 2020 Page 2 of 3


9701/13 Cambridge International AS & A Level – Mark Scheme October/November
PUBLISHED 2020

Question Answer Marks

29 D 1

30 A 1

31 A 1

32 D 1

33 A 1

34 D 1

35 B 1

36 A 1

37 B 1

38 C 1

39 A 1

40 B 1

© UCLES 2020 Page 3 of 3


2

Section A

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

Use of the Data Booklet may be appropriate for some questions.

1 The temperature of a sample of an inert gas is increased.

What effect does this have on the number of molecules with the most probable energy and on the
number of molecules with high energy?

number of molecules with number of molecules


the most probable energy with high energy

A decreases decreases
B decreases increases
C increases decreases
D increases increases

2 A sample of element X is analysed using mass spectrometry. The mass spectrum obtained is
shown.

56%

41%

% abundance

3%

112 113 114 115 116


m/e

What is the relative atomic mass of this sample of element X?

A 113.7 B 114.0 C 114.2 D 114.4

3 A washing powder contains sodium hydrogencarbonate, NaHCO3, as one of the ingredients.

In a titration, a solution containing 1.00 g of this washing powder requires 7.15 cm3 of
0.100 mol dm–3 sulfuric acid for complete reaction. The sodium hydrogencarbonate is the only
ingredient that reacts with the acid.

What is the percentage by mass of sodium hydrogencarbonate in the washing powder?

A 3.0% B 6.0% C 12.0% D 24.0%

© UCLES 2019 9701/11/M/J/19


3

4 The outermost electron in an atom of neon occupies a particular orbital.

Which row shows the relative energy and shape of this orbital?

energy of orbital relative


shape of orbital
to other occupied orbitals

A higher or equal

B higher or equal

C lower or equal

D lower or equal

5 In which species is there a lone pair of electrons?

A CH3 B CH3+ C CH3– D CH4

6 When an evacuated tube of volume 400 cm3 is filled with gas at 300 K and 101 kPa, the mass of
the tube increases by 0.65 g.

Assume the gas behaves as an ideal gas.

What could be the identity of the gas?

A argon
B helium
C krypton
D neon

7 Under which conditions will nitrogen behave most like an ideal gas?

temperature pressure

A low high
B high low
C low low
D high high

© UCLES 2019 9701/11/M/J/19 [Turn over


4

8 Two reactions and their enthalpy changes are shown.

2C(s) + 2H2(g) → C2H4(g) ∆H o = +52.2 kJ mol–1

C2H2(g) + H2(g) → C2H4(g) ∆H o = –175.8 kJ mol–1

These data can be used to calculate the enthalpy change for the reaction shown.

2C(s) + H2(g) → C2H2(g) ∆H o = X

What is the value of X?

A –228.0 kJ mol–1
B –123.6 kJ mol–1
C +123.6 kJ mol–1
D +228.0 kJ mol–1

9 Ethanedioic acid, HO2CCO2H, can be oxidised by KMnO4 in dilute sulfuric acid. The products of
this reaction are carbon dioxide, water, potassium sulfate and manganese(II) sulfate.

In this reaction each ethanedioic acid molecule loses two electrons as it is oxidised. A
half-equation for this process is shown.

HO2CCO2H → 2CO2 + 2H+ + 2e–

How many water molecules are produced when five ethanedioic acid molecules are oxidised by
KMnO4 in dilute sulfuric acid?

A 5 B 8 C 10 D 16

10 Hydrogen iodide gas decomposes reversibly producing iodine vapour and hydrogen.

2HI(g) I2(g) + H2(g) ∆H = +12 kJ mol–1

The position of the equilibrium for this reaction may be altered by changing the external
conditions.

Which row correctly describes the change in position of equilibrium?

effect of increasing effect of increasing


the pressure the temperature

A moves to the right moves to the right


B moves to the right moves to the left
C no change moves to the right
D no change moves to the left

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5

11 The reaction between sulfur dioxide and oxygen is reversible.

2SO2(g) + O2(g) 2SO3(g) Kc = 280 mol–1 dm3 at 1000 K

In an equilibrium mixture at 1000 K the sulfur trioxide concentration is 6.00 mol dm–3.

The sulfur dioxide concentration is twice the oxygen concentration.

What is the sulfur dioxide concentration?

A 0.175 mol dm–3


B 0.254 mol dm–3
C 0.318 mol dm–3
D 0.636 mol dm–3

12 1.15 g of a metallic element needs 300 cm3 of oxygen for complete reaction, under room
conditions, to form an oxide which contains O2– ions.

What could be the identity of this metallic element?

A calcium
B magnesium
C potassium
D sodium

13 The relative melting points of four consecutive elements in the Periodic Table are shown in the
graph.

The elements all have proton numbers less than 20.

Which element is in Group 16?

melting
point / K

B C
273
D
proton number

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6

14 Substance X reacts with water. A gas is given off and the pH of the solution increases. The
solution is then reacted with sulfuric acid and a white precipitate forms.

What could be substance X?

A barium
B barium oxide
C magnesium
D magnesium oxide

15 Solutions of 0.1 mol dm–3 Mg(NO3)2 and 0.1 mol dm–3 Ba(NO3)2 separately undergo a series of
reactions using pure reagents.

sodium
carbonate excess HCl (aq) excess
solution then boil NaOH(aq)
Mg(NO3)2(aq) M N P
sodium
carbonate excess HCl (aq) excess
solution then boil NaOH(aq)
Ba(NO3)2(aq) Q R S

M, N and P are magnesium compounds.

Q, R and S are barium compounds.

How many of M, N, P, Q, R and S are white precipitates?

A 2 B 3 C 4 D 5

16 Concentrated sulfuric acid is added to separate solid samples of sodium chloride, sodium
bromide and sodium iodide.

With which samples does sulfuric acid act as an oxidising agent?

A sodium chloride only


B sodium chloride and sodium bromide
C sodium bromide and sodium iodide
D sodium iodide only

17 The reaction of bromine with warm NaOH(aq) produces products with the same oxidation
numbers, in the same ratios, as the reaction of chlorine with hot NaOH(aq).

In one reaction between bromine and warm NaOH(aq), 30.2 g of a product containing sodium,
bromine and oxygen is produced.

Which mass of NaOH has reacted?

A 8.00 g B 10.2 g C 20.3 g D 48.0 g

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7

18 At 550 °C nitrogen dioxide reacts with unburnt hydrocarbon fragments such as CH3 in the
catalytic converter of a motor vehicle.

4CH3 + 7NO2 → 3 21 N2 + 4CO2 + 6H2O

Which row gives the energy change for this reaction and a possible reason for it?

energy change reason why the reaction is endothermic


of reaction or exothermic

A endothermic chemical energy is converted to heat energy


B endothermic the N≡N bond energy is very high
C exothermic CO2 and H2O have negative values
D exothermic double bonds are broken in NO2

19 Which statement is correct?

A Ammonia reacts with alkalis to form the ammonium ion.


B Ammonium chloride contains ionic, covalent and co-ordinate bonds.
C The ammonium ion reacts with acids to produce ammonia.

D The bond angle in the ammonium ion is approximately 107°.

20 The diagrams show two different compounds.

O O

1 2

What is

● the total number of structural isomers, including compound 2, that could be formed
by adding a second methyl group to the ring of compound 1,

● the number of π electrons in each compound?

number of number of
isomers π electrons

A 3 2
B 3 4
C 5 2
D 5 4

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8

21 Which compound has the molecular formula C6H10O?

A B C D
O
O
O
OH

22 What is the structural formula of the major product when hydrogen bromide reacts with
2-methylbut-2-ene?

A CH2BrCH(CH3)CH2CH3
B (CH3)2CBrCH2CH3
C (CH3)2CHCHBrCH3
D (CH3)2CHCH2CH2Br

23 Which reaction is most likely to involve the formation of a positively charged intermediate?

A 1-bromopentane and warm dilute NaOH(aq)


B 1-bromo-2,2-dimethylpropane and warm dilute NaOH(aq)
C 1-bromo-3-methylbutane and warm dilute NaOH(aq)
D 2-bromo-2-methylbutane and warm dilute NaOH(aq)

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9

24 The infra-red spectrum of a substance with empirical formula C2H4O is shown.

100

transmittance
50

Y
0
4000 3000 2000 1500 1000 500
–1
wavenumber / cm

Which bonds are responsible for peak X and peak Y?

peak X peak Y

A C–H C=C
B C–H C=O
C O–H C=C
D O–H C=O

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10

25 The structure of coniine is shown.

coniine

N CH2CH2CH3
H

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 1,1-dibromo-2-propylcyclopentane
B 1,2-dibromo-2-propylcyclopentane
C 1,4-dibromooctane
D 1,5-dibromooctane

26 Structural isomerism and stereoisomerism should be considered when answering this question.

3-methylhexan-3-ol reacts with hot, concentrated sulfuric acid to form several isomeric
compounds with the molecular formula C7H14.

3-methylhexan-3-ol

HO

How many isomeric compounds could be formed in this reaction?

A 3 B 4 C 5 D 6

27 An organic compound T undergoes the following reactions.

● T is oxidised by hot, acidified potassium manganate(VII).

● T reacts with sodium to give hydrogen.

What could be compound T?

A CH3CH2CH(OH)CH3
B CH3CH2CH2CHO
C (CH3)3COH
D CH3CH2COCH3

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11

28 Compound X is treated with two reagents successively, forming compound Z.

CHO a mild
oxidising
agent NaBH4
Y Z

COCH3

What could be Z?

A B C D

CO2H CH2OH CH2OH CO2H

CH(OH)CH3 CH(OH)CH3 CH(OH)CH3 CH(OH)CH3

29 Which reagent may be used to distinguish between propanone and ethanol?

A 2,4-dinitrophenylhydrazine
B bromine water
C Fehling’s reagent
D Tollens’ reagent

30 Which compound is chiral?

A 1-chloro-3-methylbutane
B 2-chloro-2-methylbutane
C 2-chloro-3-methylbutane
D 3-chloropentane

© UCLES 2019 9701/11/M/J/19 [Turn over


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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

Use of the Data Booklet may be appropriate for some questions.

31 An atom of calcium-48 can form a 2+ ion.

Which statements about this ion are correct?

1 It has 20 protons.
2 It has 28 neutrons.
3 It has 22 electrons.

32 Four elements, W, X, Y and Z, have electronic configurations as shown.

W X Y Z

2,4 2,6 2,8,2 2,8,8,1

Which formulae represent compounds that have boiling points below room temperature?

1 WX2
2 YX
3 Z2X

33 Which statements about enthalpy changes are correct?

1 The enthalpy change of atomisation is always positive.


2 The enthalpy change when a C–C bond is broken is positive.
3 The enthalpy change of neutralisation of a weak acid is always negative.

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13

34 Vanadium and pepsin can both act as catalysts. Vanadium is a metal. Pepsin is an enzyme.

Which statements are correct for both vanadium and pepsin?

1 They will speed up any chemical reaction.


2 They can lower the activation energy for a reaction.
3 They are not used up when they act as catalysts.

35 Which oxides, when placed in cold water for one day, will react with the water?

1 MgO
2 Al 2O3
3 SiO2

36 A mixture of magnesium carbonate and magnesium nitrate is heated strongly in a hard-glass


test-tube.

Which gases are formed?

1 carbon dioxide
2 nitrogen dioxide
3 oxygen

37 Which statements about poly(alkene)s are correct?

1 Poly(alkene)s do not react with Br2(aq) in the dark.

2 Disposal of poly(alkene)s by combustion can produce harmful products.

3 Poly(alkene)s do not readily biodegrade.

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14

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

38 Compound Y

● reacts with alkaline aqueous iodine to form a yellow precipitate

● changes the colour of warm, acidified potassium dichromate(VI) solution.

What could be compound Y?

OH
1

O
2
H

3
O

39 Carboxylic acids can be made by several different reactions.

Which statements are correct?

1 The acid hydrolysis of CH3CH2CN will make ethanoic acid.


2 The oxidation of CH3CH2CH2CH2OH will make butanoic acid.
3 The oxidation of CH3CH2CHO will make propanoic acid.

40 Carboxylic acids react with alcohols to produce esters.

Carboxylic acid X forms one ester only with molecular formula C5H10O2.

What could X be?

1 ethanoic acid
2 propanoic acid
3 butanoic acid

© UCLES 2019 9701/11/M/J/19


9701/11 Cambridge International AS/A Level – Mark Scheme May/June 2019
PUBLISHED

Question Answer Marks

1 B 1

2 D 1

3 C 1

4 A 1

5 C 1

6 A 1

7 B 1

8 D 1

9 B 1

10 C 1

11 D 1

12 D 1

13 C 1

14 A 1

15 B 1

16 C 1

17 D 1

18 C 1

19 B 1

20 D 1

21 A 1

22 B 1

23 D 1

24 B 1

25 D 1

26 C 1

27 A 1

28 A 1

© UCLES 2019 Page 2 of 3


9701/11 Cambridge International AS/A Level – Mark Scheme May/June 2019
PUBLISHED

Question Answer Marks

29 A 1

30 C 1

31 B 1

32 D 1

33 A 1

34 C 1

35 D 1

36 A 1

37 A 1

38 B 1

39 C 1

40 C 1

© UCLES 2019 Page 3 of 3


2

Section A

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

Use of the Data Booklet may be appropriate for some questions.

1 The Boltzmann distribution of molecular energies in a sample of aqueous hydrogen peroxide at


room temperature is shown.

molecules
proportion of
with sufficient
molecules with
energy to react
energy, E

0
0 molecular energy, E

Which diagram shows the Boltzmann distribution of molecular energies of aqueous hydrogen
peroxide maintained at room temperature when a catalyst, manganese(IV) oxide, is added?

A B

molecules
molecules with sufficient
proportion of proportion of
with sufficient energy to react
molecules with molecules with
energy to react
energy, E energy, E

0 0
0 molecular energy, E 0 molecular energy, E

C D
molecules molecules
with sufficient with sufficient
proportion of energy to react proportion of energy to react
molecules with molecules with
energy, E energy, E

0 0
0 molecular energy, E 0 molecular energy, E

2 Oxygen has three stable isotopes, 16O, 17O and 18O. All three isotopes are present in a sample of
oxygen gas, O2, which was analysed using a mass spectrometer.

How many peaks associated with the O2+ ion would be expected?

A 3 B 5 C 6 D 9

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3

3 The first eight successive ionisation energies for two elements of Period 3 of the Periodic Table
are shown in the graphs.

ionisation ionisation
energy energy

0 1 2 3 4 5 6 7 8 0 1 2 3 4 5 6 7 8
electron removed electron removed

What is the formula of the ionic compound formed from these elements?

A MgCl 2 B CaBr2 C Na2S D K2Se

4 A σ bond is made between two carbon atoms in a molecule of ethene.

Which diagram shows the orbital overlap that occurs to form this bond?

A B C D

5 The table shows some properties of four substances.

Which substance could be potassium iodide?

melting point electrical conductivity


of solid / °C when molten

A –66 poor
B –39 good
C 680 good
D 1600 poor

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4

6 X, Y and Z are all gases that behave ideally and react according to the equation shown.

X(g) + 2Y(g) → 2Z(g)

When 3.0 mol of X and 3.0 mol of Y are placed inside a container with a volume of 1.0 dm3, they
react to form the maximum amount of Z.

The final temperature of the reaction vessel is 120 °C.

What is the final pressure inside the reaction vessel?

A 4.49 × 106 Pa

B 9.80 × 106 Pa

C 1.47 × 107 Pa

D 1.96 × 107 Pa

7 Which pair of substances are both simple molecular?

A C60 and graphene


B C60 and iodine
C graphene and graphite
D graphite and iodine

8 A reaction pathway diagram is shown.

M N
reactants
energy O P
K L
products

progress of reaction

Which row is correct?

enthalpy change of activation energy of


the forward reaction the reverse reaction

A K M
B K O
C L O
D P M

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5

9 X is either chlorine or an oxide of chlorine.

X reacts with water, under suitable conditions, to form the two acids HCl and HCl O3 in the mole
ratio of 1 (HCl ) : 5 (HCl O3).

What could be X?

A Cl 2 B Cl 2O C Cl O2 D Cl 2O7

10 Ethyl ethanoate undergoes the following reaction.

CH3CO2C2H5 + H2O C2H5OH + CH3CO2H Kc = 0.27

Equal amounts of ethanoic acid and ethanol were mixed together and allowed to reach
equilibrium.

At equilibrium, the concentrations of both ethanoic acid and ethanol were 0.42 mol dm–3.

What is the concentration of ethyl ethanoate at equilibrium?

A 0.22 mol dm–3


B 0.65 mol dm–3
C 0.81 mol dm–3
D 1.54 mol dm–3

11 Which row is an example of heterogeneous catalysis?

reaction catalyst

A esterification sulfuric acid


B the Contact process divanadium pentoxide
C destruction of the ozone layer chlorine radicals
D atmospheric formation of sulfur trioxide nitrogen dioxide

12 Element Q readily oxidises in air. The oxide produced reacts with water to form a solution of very
low pH.

Where could element Q be found in the Periodic Table?

period group

A 2 1
B 2 14
C 3 14
D 3 15

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6

13 The eight elements sodium to argon are in the same period of the Periodic Table.

The equation corresponding to the first ionisation energy is shown.

X(g) → X+(g) + e–

For which of these eight elements is the electron in this equation removed from a filled orbital?

A Mg, Al, Si, P, S, Cl and Ar


B Al, Si, P, S, Cl and Ar only
C Mg, S, Cl and Ar only

D S, Cl and Ar only

14 Elements D and E are both in Period 3. Element D has the smallest atomic radius in Period 3.
There are only two elements in Period 3 which have a lower melting point than element E.
Elements D and E react together to form compound L.

Which compound could be L?

A MgCl 2 B MgS C Na2S D PCl 3

15 How many of the solutions shown, when added to separate portions of magnesium sulfate
solution, produce a white precipitate?

HCl (aq) NH3(aq) (NH4)2CO3(aq) Ba(NO3)2(aq)

A 0 B 1 C 2 D 3

16 A white solid, Z, is soluble in water. A sample of Z is heated with a Bunsen burner until there is no
further change. When the residue is shaken with water a solution is formed with no solid
remaining.

What could Z be?

A MgCO3 B Mg(NO3)2 C BaCO3 D Ba(NO3)2

17 An excess of chlorine was bubbled into 100 cm3 of hot 6.0 mol dm–3 sodium hydroxide.

How many moles of sodium chloride would be produced in the reaction?

A 0.3 B 0.5 C 0.6 D 1.2

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7

18 Ammonium sulfate, (NH4)2SO4, and ammonium nitrate, NH4NO3, are used as fertilisers.

These salts have different percentages by mass of nitrogen. They have the same effect as each
other on the pH of wet neutral soil.

Which row is correct?

higher percentage
effect on pH of soil
of nitrogen by mass

A ammonium nitrate decrease


B ammonium nitrate increase
C ammonium sulfate decrease
D ammonium sulfate increase

19 Which reaction gives a product that is an atmospheric pollutant causing acid rain?

A 3Mg(s) + SO2(g) → MgS(s) + 2MgO(s)

B (NH4)2SO4(s) + Ca(OH)2(s) → 2NH3(g) + CaSO4(s) + 2H2O(l)

C 2MnO4–(aq) + 5SO2(g) + 2H2O(l) → 2Mn2+(aq) + 4H+(aq) + 5SO42–(aq)

D 2FeSO4(s) → Fe2O3(s) + SO2(g) + SO3(g)

20 3-methylbut-1-ene can undergo different types of reaction.

Cl
1 2

Cl

Which row correctly identifies the reaction types?

reaction 1 reaction 2

A oxidation electrophilic addition


B oxidation nucleophilic addition
C reduction electrophilic addition
D reduction nucleophilic addition

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8

21 Compound X does not show cis-trans isomerism.

What could be the identity of compound X?

A 1,1,2-trichloropropene
B 1,2,3-trichloropropene
C 1-chlorobut-1-ene
D 1-chlorobut-2-ene

22 The diagram shows the repeat unit of an addition polymer.

C2H5 CH3

C C

CH3 C 2H 5 n

What is the correct name for the monomer that would form this polymer?

A cis-1,2-diethyl-1,2-dimethylethene
B cis-2-ethyl-3-methylpent-2-ene
C trans-2-ethyl-3-methylpent-2-ene
D trans-3,4-dimethylhex-3-ene

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9

23 A molecule of geraniol is shown.

geraniol

OH

What is formed when geraniol is reacted with an excess of cold, dilute, acidified manganate(VII)
ions?

A B
O

OH OH
HO HO HO HO
OH OH O O

C D
O

+ O + O
O OH OH
O
OH OH

24 Alcohol W cannot be made by reducing a carboxylic acid with LiAl H4. Alcohol W gives only one
product when dehydrated with concentrated sulfuric acid.

What could be the identity of W?

A butan-1-ol
B butan-2-ol
C propan-1-ol
D propan-2-ol

25 Which product can be made from bromoethane by an elimination reaction?

A ethanol
B ethene
C ethylamine
D propanenitrile

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10

26 Propene, bromine and hydrogen bromide are mixed in the dark.

A number of products are formed, some in very small quantities.

Which substance will not be present in the mixture of products?

A 1-bromopropane
B 2-bromopropane
C 1,1-dibromopropane
D 1,2-dibromopropane

27 Which reagent could be used to distinguish between ethanal and propanal?

A 2,4-dinitrophenylhydrazine

B I2 / NaOH(aq)
C K2Cr2O7 / H2SO4(aq)
D Tollens’ reagent

28 The diagram shows that a carboxylic acid P may be formed from X, Y or Z.

alcohol aldehyde
X Y

carboxylic
acid
P

nitrile
Z

Which row is correct?

the change in Mr
alcohol X is
is greatest for

A primary Y to P
B primary Z to P
C secondary Y to P
D secondary Z to P

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11

29 One molecule of compound R is shown.

compound R

H H H O

H C C C O C H

H H H

What is the name of compound R and how does its boiling point compare with that of butanoic
acid?

name of R boiling point of R

A methyl propanoate higher than butanoic acid


B methyl propanoate lower than butanoic acid
C propyl methanoate higher than butanoic acid
D propyl methanoate lower than butanoic acid

30 The diagram shows the infra-red spectrum of Q.

100

transmittance
50

0
4000 3000 2000 1500 1000 500
wavenumber / cm–1

What could be Q?

A butan-1-ol
B butanoic acid
C butanone
D 3-hydroxybutanal

© UCLES 2019 9701/12/M/J/19 [Turn over


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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

Use of the Data Booklet may be appropriate for some questions.

31 When O2 reacts with H2S the products are SO2 and H2O.

Mixture Y contains an equal number of the two molecules shown, and no other molecules.

16
8O = 188 O 1 32 1
1H – 16 S – 1H

Which statements about Y are correct?

1 The average Mr in Y is 34.


2 If some oxygen molecules are removed from Y, the average Mr of the mixture remains the
same.
3 When mixture Y is ignited, some H2S remains unreacted.

32 Which statements about an atom of 99Tc are correct?

1 It has 13 fewer protons than neutrons.


2 It forms 99Tc2+ which has 45 electrons.
3 It has 56 nucleons.

33 In which reactions are nitrogen atoms reduced?

1 2NO2 → N2 + 2O2

2 4NO2 → 2N2O + 3O2

3 4NO2 + 6H2O → 4NH3 + 7O2

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13

34 The manufacture of ammonia from nitrogen and hydrogen is an important industrial process.

Which of the following would leave the equilibrium constant, Kp, for the formation of ammonia
unchanged?

1 addition of an iron catalyst


2 addition of ammonia
3 an increase in pressure

35 Which reactions involving calcium and its compounds produce two gaseous products?

1 heating solid anhydrous calcium nitrate


2 heating solid anhydrous calcium carbonate
3 adding calcium metal to water

36 A small quantity of hot, concentrated sulfuric acid is added separately to solid samples of
potassium halides, KX.

Which potassium halides react and produce a mixture of products that include a halogen, X2?

1 potassium iodide
2 potassium bromide
3 potassium chloride

37 The diagram shows a compound used as a flame retardant.

Br
Br

Br

Br Br
Br

Which statements about this structure are correct?

1 The empirical formula is C2H3Br.


2 The C12 ring is not planar.
3 There are six chiral carbon atoms.

© UCLES 2019 9701/12/M/J/19 [Turn over


14

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

38 Halogenoalkanes can be hydrolysed using aqueous sodium hydroxide.

Which compounds tend to be hydrolysed by an SN1 mechanism?

1 CH3CH2CCl (CH3)CH2CH3
2 CH3CH2CBr(CH3)CH2CH3
3 CH3CH2CH(CH3)CH2CH2Br

39 In an organic synthesis, a 62% yield of product is achieved.

Which conversions are consistent with this information?

1 74.00 g of butan-2-ol → 44.64 g of butanone

2 74.00 g of butan-1-ol → 54.56 g of butanoic acid

3 74.00 g of 2-methylpropan-1-ol → 54.56 g of 2-methylpropanoic acid

40 An oxidising agent that can oxidise ethanal to ethanoic acid or ethanoate ions will also oxidise
methanoic acid, HCO2H, to carbon dioxide and water.

Which reagents, on heating, will react differently with HCO2H and CH3CO2H?

1 Na2CO3(aq)
2 Fehling’s reagent
3 dilute acidified KMnO4

© UCLES 2019 9701/12/M/J/19


9701/12 Cambridge International AS/A Level – Mark Scheme May/June 2019
PUBLISHED

Question Answer Marks

1 B 1

2 B 1

3 A 1

4 C 1

5 C 1

6 C 1

7 B 1

8 B 1

9 C 1

10 C 1

11 B 1

12 D 1

13 C 1

14 D 1

15 D 1

16 D 1

17 B 1

18 A 1

19 D 1

20 C 1

21 A 1

22 D 1

23 A 1

24 D 1

25 B 1

26 C 1

27 B 1

28 B 1

© UCLES 2019 Page 2 of 3


9701/12 Cambridge International AS/A Level – Mark Scheme May/June 2019
PUBLISHED

Question Answer Marks

29 D 1

30 C 1

31 A 1

32 D 1

33 A 1

34 A 1

35 D 1

36 B 1

37 A 1

38 B 1

39 A 1

40 C 1

© UCLES 2019 Page 3 of 3


2

Section A

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

Use of the Data Booklet may be appropriate for some questions.

1 Manganese and nitrogen can show a range of different oxidation states.

Calculate the sum of the oxidation states of Mn and N in each row of the table.

In which row is this sum the smallest?

manganese-containing nitrogen-containing
species species

A MnCl 4 N2
B MnCO3 NO2–
C K2MnO4 NH4+
D Mn(OH)3 NH2OH

© UCLES 2019 9701/13/M/J/19


3

2 The mass spectrum of an alloy of copper and gold is shown.

60 56.36
50

40
percentage
abundance 30 25.14
20 18.50

10

0
63 65 197
m/e

Which expression can be used to calculate the relative atomic mass, Ar, of copper present in this
sample?

(56.36 × 63) + (25.14 × 65)


A
(56.36 + 25.14 + 18.50)

(56.36 × 63) + (25.14 × 65) + (18.50 × 197)


B
(56.36 + 25.14 + 18.50)

(56.36 × 63) + (25.14 × 65)


C
(56.36 + 25.14)

(56.36 × 63) + (25.14 × 65)


D
(63 + 65)

3 Which atom has exactly three unpaired electrons?

A an isolated gaseous aluminium atom


B an isolated gaseous carbon atom
C an isolated gaseous chromium atom
D an isolated gaseous phosphorus atom

© UCLES 2019 9701/13/M/J/19 [Turn over


4

4 Element W is in period three of the Periodic Table and has a solid, white oxide, X. X is thermally
stable and has a very high melting point.

X is slightly soluble in water.

Which row describes the structure and bonding of X?

structure bonding

A giant covalent
three dimensional lattice
B strong double bonds covalent
within small molecules
C giant ionic
three dimensional lattice
D strong ionic bonds ionic
within small molecules

5 Ethane, CH3CH3, and fluoromethane, CH3F, have the same number of electrons in their
molecules.

Their boiling points are given.

CH3CH3 184.5 K
CH3F 194.7 K

What is responsible for this difference in boiling points?

A CH3F has a larger Mr than CH3CH3.


B CH3F has a permanent dipole, CH3CH3 does not.
C CH3F has a strong C–F bond, CH3CH3 does not.
D Hydrogen bonding occurs in CH3F, but not in CH3CH3.

© UCLES 2019 9701/13/M/J/19


5

6 The reaction pathway diagram for a chemical reaction is shown.

energy

progress of reaction

Which statement is correct?

A The activation energy of the forward reaction and the enthalpy change of the backward
reaction have the same sign.
B The activation energy of the forward reaction is more than twice the enthalpy change of the
backward reaction and opposite in sign.
C The enthalpy change of the forward reaction and the activation energy of the backward
reaction have the same sign.
D The enthalpy change of the forward reaction is more than twice the activation energy of the
backward reaction.

7 What changes in conditions or molecular properties make it more likely that gases approach ideal
behaviour?

A higher pressure
B lower temperature
C more polar molecules
D weaker intermolecular forces

8 Ethanol can be oxidised to ethanal by dilute acidified dichromate(VI) ions.

The oxidation reaction equation is C2H5OH → C2H4O + 2H+ + 2e–.

The reduction reaction equation is Cr2O72– + 14H+ + 6e– → 2Cr3+ + 7H2O.

Which equation is correct?

A Cr2O72– + 8H+ + 3C2H5OH → 2Cr3+ + 7H2O + 3C2H4O

B Cr2O72– + 12H+ + C2H5OH → 2Cr3+ + 7H2O + C2H4O

C Cr2O72– + 12H+ + 3C2H5OH → 2Cr3+ + 6H2O + 3C2H4O

D Cr2O72– + 14H+ + 3C2H5OH → 2Cr3+ + 6H2O + 3C2H4O

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6

9 What is the correct expression for Kc for the reaction shown?

I2(aq) + 2Fe2+(aq) 2I–(aq) + 2Fe3+(aq)

[2I−][2Fe3 + ] [I−]2[Fe3 + ]2 [I2][2Fe2 + ] [I2][Fe2 + ]2


A B C D
[I2][2Fe2 + ] [I2][Fe2 + ]2 [2I−][2Fe3 + ] [I−]2[Fe3 + ]2

10 X and Y react together to form Z in a reversible reaction.

The equilibrium yield of Z is lower at higher temperature.

The equilibrium yield of Z is lower at lower pressure.

Which equation could represent this reaction?

A X(g) + Y(g) Z(g) ∆H = –100 kJ mol–1

B X(g) + Y(g) Z(g) ∆H = +100 kJ mol–1

C X(s) + Y(g) 2Z(g) ∆H = –100 kJ mol–1

D X(s) + Y(g) 2Z(g) ∆H = +100 kJ mol–1

11 The volume of carbon dioxide collected by reacting 0.100 mol of magnesium carbonate with
50.0 cm3 of 1.00 mol dm–3 sulfuric acid is measured against time. The volume produced is plotted
against time and the line labelled P on the graph is obtained.

volume of
CO2 / cm3 P

0
0 time / s

The experiment is repeated using 0.100 mol of the same magnesium carbonate, and a different
sample of acid. All other conditions remain the same. Plotting these results gives the line labelled
Q.

Which sample of acid could give the line labelled Q?

A 100 cm3 of 0.500 mol dm–3 sulfuric acid


B 100 cm3 of 1.00 mol dm–3 sulfuric acid
C 200 cm3 of 0.500 mol dm–3 hydrochloric acid
D 200 cm3 of 1.00 mol dm–3 hydrochloric acid

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7

12 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 ionic radius

A sodium < sulfur sodium > sulfur


B sodium < sulfur sodium < sulfur
C sodium > sulfur sodium > sulfur
D sodium > sulfur sodium < sulfur

13 Which graph represents the variation in electronegativity for Period 3 elements?

A B

electronegativity electronegativity

Na Mg Al Si P S Cl Na Mg Al Si P S Cl
element element

C D

electronegativity electronegativity

Na Mg Al Si P S Cl Na Mg Al Si P S Cl
element element

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14 Dilute hydrochloric acid is added to solid barium carbonate and solid magnesium carbonate in
separate test-tubes.

Dilute sodium hydroxide is added to 0.1 mol dm–3 barium chloride and 0.1 mol dm–3 magnesium
chloride in separate test-tubes.

Which row is correct?

BaCO3(s) BaCl 2(aq) MgCO3(s) MgCl 2(aq)


+ HCl (aq) + NaOH(aq) + HCl (aq) + NaOH(aq)

A no change white ppt no change no change


B effervescence no change effervescence no change
C effervescence no change effervescence white ppt
D effervescence white ppt effervescence white ppt

15 River water in an agricultural area contains NH4+, CO32–, HCO3–, Cl − and NO3– ions. In a water
treatment plant, this water is treated by adding a calculated quantity of calcium hydroxide.

What is precipitated from the river water when calcium hydroxide is added?

A CaCl 2 B CaCO3 C Ca(NO3)2 D NH4OH

16 The solids sodium chloride and sodium iodide both react with concentrated sulfuric acid at room
temperature.

With NaCl , the products are NaHSO4 and HCl .


With NaI, the products are NaHSO4, HI, I2, SO2, H2O, S and H2S.

What is the explanation for this difference in products?

A Chloride ions will displace iodine from solution.


B Hydrogen chloride is more volatile than hydrogen iodide.
C Iodide ions are better reducing agents than chloride ions.

D Sulfuric acid is able to act as a dehydrating agent with NaI.

17 An aqueous solution of a calcium compound is treated with a mixture of dilute aqueous nitric acid
and aqueous silver nitrate. The resulting white precipitate dissolves when dilute aqueous
ammonia is added.

What is the relative molecular mass, Mr, of the calcium compound?

A 54.0 B 75.6 C 111.1 D 199.9

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9

18 Which statement about the ammonium ion is correct?

A It can act as a Brønsted-Lowry base.


B It can react with OH– to give ammonia.

C It is pyramidal with bond angles of 107°.


D The nitrogen atom is sp2 hybridised.

19 In a catalytic converter 5.6 g of carbon monoxide reacts with an excess of nitrogen monoxide.

What is produced in this reaction?

A 2.4 g of C and 6.0 g of NO2


B 2.4 g of C and 9.2 g of NO2
C 8.8 g of CO2 and 1.4 g of N2
D 8.8 g of CO2 and 2.8 g of N2

20 The Finkelstein reaction occurs when NaI in propanone reacts with a chloroalkane or
bromoalkane. The halogen is directly replaced by I. The reaction only works for primary
halogenoalkanes.

Which halogenoalkane produces compound X?

A (CH3)2CHCH(CH3)CH2CH2Br
B (CH3)2CHCH(CH3)CH2Br
C (CH3)2CHCH2CH2CH(CH3)Cl

D (CH3)2CHCH2CH(CH3)CH2Cl

21 The diagram shows the skeletal formula of compound Y.

Y
OH O
O OH

What is the empirical formula of Y?

A CHO B CH2O2 C C2HO2 D C4H4O4

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10

22 In polymer Z every carbon atom in the polymer chain is bonded to one hydrogen atom and one
methyl group.

Which alkene could be polymerised to make polymer Z?

A but-1-ene
B but-2-ene
C methylpropene
D propene

23 Which compound would produce a carboxylic acid and a ketone when treated with hot,
concentrated acidified manganate(VII) ions?

A B C D

24 Water is added to a sample of 2,3-dibromohexane.

Some of the 2,3-dibromohexane undergoes complete hydrolysis and some of it undergoes partial
hydrolysis.

What is not present in the mixture of products?

A CH3CH(OH)CHBrCH2CH2CH3
B CH3CH(OH)CH(OH)CH2CH2CH3
C CH3CH2CH(OH)CH(OH)CH2CH3
D CH3CH2CH2CH(OH)CHBrCH3

25 Which statement about the mechanism of an SN1 reaction of a halogenoalkane is correct?

A A nucleophile is substituted by an electrophile.


B One intermediate is formed from two reacting molecules.
C The intermediate is stabilised by adjacent alkyl groups.
D The intermediate is uncharged.

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11

26 Structural isomerism and stereoisomerism should be considered when answering this question.

Which isomer of C6H13OH gives the greatest number of different alkenes when it is dehydrated?

A B
CH3

CH3 CH CH CH2OH CH3 CH2 CH2 CH CH2 CH3

CH3 OH

C D
CH3 CH3

CH3 CH2 C CH2 CH3 CH3 C CH2 CH2OH

OH CH3

27 Compound Q reacts with 2,4-dinitrophenylhydrazine to give a precipitate.

Compound Q does not produce a precipitate when warmed with Fehling’s solution.

What could be the identity of compound Q?

A CH3COCH3
B CH2(OH)CH2CH3
C CH3CH2CO2H
D CH3CH2CHO

28 Structural isomerism only should be considered when answering this question.

A set of isomeric compounds, with molecular formula C5H10O, all react in a 1 : 1 ratio with an
excess of HCN by nucleophilic addition.

How many isomeric compounds are in the set?

A 5 B 6 C 7 D 8

29 Which pair of substances could react to give the ester CH3CH2CO2CH3?

A ethanol and ethanoic acid


B methanol and ethanoic acid
C methanol and propanoic acid
D propan-1-ol and methanoic acid

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12

30 An ester is shown.

O
O O

What is the structure of the carboxylic acid that would be obtained by acid hydrolysis of the ester
linkage?

A B
O O OH O
O
H OH HO O

C D

O O
O O
O O O
OH
HO
O

© UCLES 2019 9701/13/M/J/19


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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

Use of the Data Booklet may be appropriate for some questions.

209
31 Which deductions about the 83 Bi atom are correct?

1 It has 83 electrons.
2 It has 126 nucleons.
3 It has 83 neutrons.

32 Which statements are correct when referring to the two common isotopes of chlorine?

1 The isotopes have different masses.


2 The isotopes have different numbers of nucleons.
3 The isotopes have the same chemical reactions.

33 For which enthalpy changes is the value of ∆H always negative?

1 combustion
2 hydration
3 solution

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14

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

34 The diagram shows the Boltzmann distribution of molecular energies in one mole of a gas at two
temperatures, T1 and T2.

T1
T2

proportion of
molecules
with energy E

0
0 E1 E2
molecular energy, E

Which statements are correct?

1 The shaded area represents the proportion of molecules with energies between E1 and E2 at
temperature T2.
2 No particles have zero energy at either temperature.
3 T2 is a higher temperature than T1.

35 Which statements about sodium chloride are correct?

1 It is a product of the reaction between chlorine and cold aqueous sodium hydroxide.
2 It is a product of the reaction between chlorine and hot aqueous sodium hydroxide.
3 It is a product of the reaction between chlorine and aqueous sodium bromide.

36 Which gases will dissolve in water causing a lowering of the pH?

1 ammonia
2 sulfur dioxide
3 nitrogen dioxide

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15

37 Which compounds have optical isomers?

1 2 3
H O
CH3
C

H C OH O O
H C OH OH HO C CH CH C OH

H C OH CH
CH3 CH3
H C OH

38 Bromine reacts with ethene in an addition reaction.

Which statements about this reaction are correct?

1 It is the basis of a test for unsaturation in alkenes.


2 It leads to an increase in each of the H–C–H bond angles.
3 A nucleophile attacks the C=C bond in ethene.

39 An unknown organic compound Z reacts with sodium to give a combustible gas as one product.
Z does not give a yellow precipitate with alkaline aqueous iodine.

What is a possible identity of Z?

1 ethanoic acid
2 pentan-3-ol
3 propan-1-ol

40 An organic molecule X has a molecular formula of C5H10O2. Its infra-red spectrum has a strong
peak at 1250 cm–1, a strong peak at 1720 cm–1 but no strong peak above 3100 cm–1.

What could X be?

1 ethyl propanoate
2 methyl butanoate
3 1-hydroxypentan-3-one

© UCLES 2019 9701/13/M/J/19


9701/13 Cambridge International AS/A Level – Mark Scheme May/June 2019
PUBLISHED

Question Answer Marks

1 D 1

2 C 1

3 D 1

4 C 1

5 B 1

6 C 1

7 D 1

8 A 1

9 B 1

10 A 1

11 D 1

12 D 1

13 B 1

14 C 1

15 B 1

16 C 1

17 C 1

18 B 1

19 D 1

20 D 1

21 A 1

22 B 1

23 D 1

24 C 1

25 C 1

26 B 1

27 A 1

28 C 1

© UCLES 2019 Page 2 of 3


9701/13 Cambridge International AS/A Level – Mark Scheme May/June 2019
PUBLISHED

Question Answer Marks

29 C 1

30 A 1

31 D 1

32 A 1

33 B 1

34 A 1

35 A 1

36 C 1

37 B 1

38 D 1

39 A 1

40 B 1

© UCLES 2019 Page 3 of 3


2

Section A

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

Use of the Data Booklet may be appropriate for some questions.

1 The diagram shows the Boltzmann distribution of energies in a gas. The gas undergoes a
reaction with an activation energy, Ea. The peak of the distribution is labelled P.

proportion of
molecules with
energy E

0
0 Ea
molecular energy, E

If the same reaction is carried out in the presence of a catalyst, which statement is correct?

A The peak P is at a lower height and the position of Ea moves to the left.
B The peak P is at a lower height and the position of Ea moves to the right.
C The peak P remains at the same height and the position of Ea moves to the left.
D The peak P remains at the same height and the position of Ea moves to the right.

2 Diamond is a pure form of carbon. The mass of a diamond can be measured in carats. One carat
is 0.200 g of carbon.

Which expression gives the number of carats that contain 6.02 × 1023 carbon atoms?

A 0.200 × 12.0

B 0.200
12.0

C 12.0
0.200
0.200
D × 12.0
6.02 × 1023

3 Which molecule or ion contains the smallest bond angle?

A C2 H 4 B CH3COCH3 C NH4+ D NH3

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3

4 Four compounds are shown.

C2H4 C2H5OH CH3CHO CH3CO2H

How many of these compounds have an odd number of σ bonds?

A 1 B 2 C 3 D 4

5 Ethanal, CH3CHO, ethanol, C2H5OH, and methoxymethane, CH3OCH3, are three organic
compounds.

Which compound has the highest boiling point and what is the interaction that causes this boiling
point to be the highest?

highest boiling point interaction

A methoxymethane permanent dipole-dipole forces


B ethanal hydrogen bonds
C ethanol hydrogen bonds
D ethanal permanent dipole-dipole forces

6 What is the oxidation number of sulfur in each species?

H2S SO2 H2SO3

A –2 +4 +4
B –2 +4 +6
C +2 –4 +4
D +2 –4 +6

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4

7 The following data are needed for this question.

(N2H4(l)) = 50.6 kJ mol–1


(N2O4(g)) = 9.2 kJ mol–1
(H2O(g)) = –241.8 kJ mol–1

Hydrazine, N2H4(l), reacts with dinitrogen tetraoxide, N2O4(g), to form nitrogen gas and water
vapour.

2N2H4(l) + N2O4(g) → 3N2(g) + 4H2O(g)

What is the enthalpy change for this reaction?

A –1077.6 kJ mol–1
B –856.8 kJ mol–1
C –301.6 kJ mol–1
D –182.0 kJ mol–1

8 Sodium burns in oxygen giving out heat energy and forming the compound Na2O. The equation
for this reaction is shown.

2Na(s) + 1
2
O2(g) → Na2O(s)

Which statement about the reaction is correct?

A ∆H o for the reaction is equal to twice the bond energy of the Na–O bond.

B ∆H o for the reaction is positive.


C The equation represents the standard enthalpy change of combustion of sodium.
D The equation represents the standard enthalpy change of formation of sodium oxide.

9 In the chemical equation, w, x, y and z are all whole numbers.

wCl O3– + xMnO4– + yH+ → wCl O4– + xMnO2 + zH2O

When the equation is balanced, what are w, x and y?

w x y

A 1 1 2
B 2 2 2
C 2 3 8
D 3 2 2

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5

10 Two compounds X and Y react to produce compound Z. The reaction is reversible.

X + Y Z

When X and Y are mixed together in a closed system a dynamic equilibrium is gradually
established.

Which graph could represent the change in the rates of the forward and reverse reactions over
time?

A B
key
rate of
forward
rate rate reaction

rate of
reverse
reaction
0 time 0 time

C D

rate rate

0 time 0 time

11 The reaction between sulfur dioxide and oxygen is reversible.

2SO2(g) + O2(g) 2SO3(g) Kc = 280 mol–1 dm3 at 1000 K

In an equilibrium mixture at 1000 K the sulfur dioxide concentration is 0.200 mol dm–3 and the
oxygen concentration is 0.100 mol dm–3.

What is the sulfur trioxide concentration?

A 1.058 mol dm–3


B 1.120 mol dm–3
C 2.366 mol dm–3
D 5.600 mol dm–3

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6

12 Which oxide will cause an increase in pH when added to water?

A MgO B Al 2O3 C SiO2 D SO2

13 X, Y and Z are consecutive elements in Period 3 of the Periodic Table. Element Y has the highest
first ionisation energy and the lowest melting point of these three elements.

What are the identities of X, Y and Z?

X Y Z

A Na Mg Al
B Mg Al Si
C Al Si P
D Si P S

14 A 5.00 g sample of an anhydrous Group 2 metal nitrate loses 3.29 g in mass when heated
strongly.

Which metal is present?

A magnesium
B calcium
C strontium
D barium

15 Solutions P and Q each contain a different Group 2 ion at the same concentration. One contains
Mg2+, the other contains Ba2+. Tests are carried out on separate 5 cm3 samples of P and Q.

test 1: add 1 cm3 of 0.1 mol dm–3 Na2SO4(aq)

test 2: add 1 cm3 of 0.1 mol dm–3 NaOH(aq)

What are the results of these tests?

results in test 1 results in test 2

A more precipitate with Ba2+ more precipitate with Ba2+


B more precipitate with Ba2+ more precipitate with Mg2+
C more precipitate with Mg2+ more precipitate with Ba2+
D more precipitate with Mg2+ more precipitate with Mg2+

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7

16 Chlorine and bromine have different volatilities.

Which row identifies the more volatile of the two elements, and gives the correct explanation?

identity of the explanation for the


more volatile element difference in volatility
A bromine instantaneous dipole-induced dipole forces
are greater in bromine than they are in chlorine
B bromine instantaneous dipole-induced dipole forces
are greater in chlorine than they are in bromine
C chlorine instantaneous dipole-induced dipole forces
are greater in bromine than they are in chlorine
D chlorine instantaneous dipole-induced dipole forces
are greater in chlorine than they are in bromine

17 Sodium azide, NaN3, is dissolved in water. Acidified silver nitrate is added to the solution and a
white precipitate forms. Aqueous ammonia is then added to the white precipitate.

The azide ion, N3–, has similar chemical properties to the Cl – ion.

Which row of the table can be predicted from this information?

formula of observation on adding


white precipitate aqueous ammonia

A AgN3 colourless solution formed


B AgN3 precipitate remains
C Ag3N colourless solution formed
D Ag3N precipitate remains

18 Which type of reaction occurs when solid ammonium sulfate is heated with an excess of sodium
hydroxide solution?

A acid-base
B precipitation
C redox
D thermal decomposition

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19 Catalytic converters are fitted in the exhaust systems of many cars.

Which gas:

● causes acid rain if it is released into the air


● is removed from car exhaust fumes by a catalytic converter?

A carbon dioxide
B carbon monoxide
C hydrocarbon vapour
D nitrogen dioxide

20 Which substance reacts with trichloroethene to give a chiral product?

A Br2 B HCl C NaCN D NaOH

21 Alkanes are saturated hydrocarbons.

Which type of reaction are alkanes most likely to undergo?

A electrophilic addition
B electrophilic substitution
C free radical substitution
D nucleophilic addition

22 An alkene reacts with hot, concentrated, acidified potassium manganate(VII) to produce a single
organic product as shown.

hot, concentrated, O O
acidified KMnO4(aq)
alkene
OH

What is the structure of the alkene?

A B C D

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9

23 A tertiary bromoalkane, indicated here by C–Br , reacts with aqueous NaOH. The mechanism
has the reaction pathway shown.

C–Br + OH–
Y
energy

C–OH + Br –

progress of reaction

Which point in the diagram is correctly identified?

A X is C+


B X is HO C Br

C Y is C+


D Y is HO C Br

24 Bromoethane and chloroethane are added separately to water. Hydrolysis reactions occur.

Which compound hydrolyses more rapidly and what is the mechanism?

compound that
mechanism
hydrolyses more rapidly

A bromoethane electrophilic substitution


B bromoethane nucleophilic substitution
C chloroethane electrophilic substitution
D chloroethane nucleophilic substitution

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10

25 Alcohol X is oxidised to form compound Y.

The composition of Y is 54.54% carbon, 36.36% oxygen and 9.10% hydrogen. The Mr of Y is
88.0.

What could be the structure of alcohol X?

A CH3CH2CH(OH)CH3
B CH3CH2CH2CH2CH2OH
C CH3CH2CH2CH2OH
D CH3CH2CH(OH)CH2CH3

26 The diagram shows the structure of compound Z.

Z
O O

What is the product of the reaction between compound Z and an excess of NaBH4?

A B C D
OH OH OH OH O O O OH

27 Compound Q shows the following reactions.

● It gives an orange precipitate with 2,4-dinitrophenylhydrazine.


● It gives a red-brown precipitate with Fehling’s reagent.
● It gives a pale yellow precipitate with alkaline aqueous iodine.

What could be the identity of Q?

A ethanal
B propan-2-ol
C propanal
D propanone

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11

28 Tartaric acid, HO2CCH(OH)CH(OH)CO2H, is found in many plants.

A sample of tartaric acid reacts with an excess of LiAl H4 to form the organic product J.

What happens when NaOH(aq) is added to separate samples of tartaric acid and J?

A Both tartaric acid and J react.


B Only tartaric acid reacts.
C Only J reacts.
D Neither tartaric acid nor J react.

29 When CH2(OH)CH=CHCO2H is warmed with a little concentrated sulfuric acid, a cyclic compound
is formed.

What is the skeletal formula of the cyclic compound?

A B C D

O O

O O O O

O
O O

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12

30 The infra-red spectrum of compound P is shown.

100

transmittance
/% 50

0
4000 3000 2000 1500 1000 500
–1
wavenumber / cm

What could be compound P?

A methyl ethanoate
B propanal
C propanoic acid
D propan-2-ol

© UCLES 2019 9701/11/O/N/19


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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

Use of the Data Booklet may be appropriate for some questions.

31 A particular atom of germanium, Ge, has a nucleon number of 70.

70
Which statements about a 32 Ge atom are correct?

79 2+
1 It has the same number of electrons as a 34 Se ion.
68
2 It has the same number of neutrons as an atom of 30 Zn.
160
3 It has half as many protons as an atom of 64 Gd.

32 The first ionisation energy of chlorine is greater than that of sulfur.

Which factors contribute to this?

1 Chlorine has more protons in its nucleus than sulfur does.


2 Chlorine has greater electron shielding than sulfur does.
3 The covalent bonds in chlorine molecules are stronger than those in sulfur molecules.

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14

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

33 Liquids X and Y do not react with one another. They have identical boiling points.

When a particular volume of X is shaken with a similar volume of Y, they form a liquid mixture Z.

The average intermolecular forces in liquid Z are stronger than the average of the forces in X and
the forces in Y.

Which deductions from this information are correct?

1 The mixing of X and Y is exothermic.


2 The vapour pressure of liquid Z will be less than that of either liquid X or liquid Y at the same
temperature.
3 The boiling point of liquid Z will be lower than that of either liquid X or liquid Y at the same
pressure.

34 The stoichiometry of a catalysed reaction is shown by the equation below.

P (g) + Q (g) R (g) + S (l)

Two experiments are carried out in which the amount of R is measured. The results are shown in
the diagram.

experiment 1
amount experiment 2
of R

0
0 time

Which changes in the conditions could explain the results shown?

1 A lower pressure was used in experiment 2.


2 A different catalyst was used in experiment 2.
3 Product S was continuously removed from the reaction vessel in experiment 2.

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15

35 Which statements are correct?

1 Chloride ions are oxidised when concentrated sulfuric acid is added to NaCl (s).
2 A disproportionation reaction takes place when chlorine is added to cold NaOH(aq).
3 An acidic solution forms when chlorine is added to water.

36 Nitrogen gas is unreactive, whereas oxygen gas and chlorine gas are reactive.

Which statements help to explain this difference?

1 The two N atoms in an N2 molecule are held together by a very strong triple bond.
2 The triple bond between two N atoms is not polar. The bonds in O2 and Cl 2 are polar.

3 The atoms in N2 have a full outer shell of electrons. The atoms in O2 and Cl 2 do not have a
full outer shell of electrons.

37 The structure of tiglic acid is CH3CH=C(CH3)CO2H.

Which statements about the properties of one molecule of this acid are correct?

1 It contains two π bonds.


2 It contains four lone pairs of electrons.
3 It has all its atoms in the same plane.

38 Which compounds, on heating with an excess of concentrated sulfuric acid, produce only one
product with molecular formula C7H10?

1 2 3

OH
OH

OH

OH OH OH

39 Hydrogen cyanide reacts with propanone in the presence of potassium cyanide.

Which statements about this reaction are correct?

1 The cyanide ion is a catalyst for the reaction.

2 This is an addition reaction.

3 The intermediate behaves as a base.

© UCLES 2019 9701/11/O/N/19 [Turn over


16

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

40 Which compounds produce three different organic products when hydrolysed?

1 2 3

O O
O O
O O O
O
O O
O O

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.

To avoid the issue of disclosure of answer-related information to candidates, all copyright acknowledgements are reproduced online in the Cambridge
Assessment International Education Copyright Acknowledgements Booklet. This is produced for each series of examinations and is freely available to download
at www.cambridgeinternational.org after the live examination series.

Cambridge Assessment International Education is part of the Cambridge Assessment Group. Cambridge Assessment is the brand name of the University of
Cambridge Local Examinations Syndicate (UCLES), which itself is a department of the University of Cambridge.

© UCLES 2019 9701/11/O/N/19


9701/11 Cambridge International AS/A Level – Mark Scheme October/November
PUBLISHED 2019

Question Answer Mark

1 C 1

2 C 1

3 D 1

4 B 1

5 C 1

6 A 1

7 A 1

8 D 1

9 D 1

10 C 1

11 A 1

12 A 1

13 D 1

14 B 1

15 B 1

16 C 1

17 A 1

18 A 1

19 D 1

20 A 1

21 C 1

22 D 1

23 C 1

24 B 1

25 C 1

26 A 1

27 A 1

28 B 1

© UCLES 2019 Page 2 of 3


9701/11 Cambridge International AS/A Level – Mark Scheme October/November
PUBLISHED 2019

Question Answer Mark

29 C 1

30 D 1

31 A 1

32 D 1

33 B 1

34 B 1

35 C 1

36 D 1

37 B 1

38 B 1

39 A 1

40 D 1

© UCLES 2019 Page 3 of 3


2

Section A

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

Use of the Data Booklet may be appropriate for some questions.

1 The diagram shows a Boltzmann distribution of the energies of gaseous molecules and the
activation energies, Ea, of a reaction with and without a catalyst.

proportion of
molecules
with energy, E

0
0 Ea1 Ea2
molecular energy, E

Which statement about this distribution curve is correct?

A If the temperature of the gas is increased, the maximum of the curve becomes higher.
B If the temperature of the gas is increased, the maximum of the curve moves to the left.

C The fraction of molecules that react in the presence of a catalyst is shown by .

D The fraction of molecules that react in the absence of a catalyst is shown by .

2 In this question it should be assumed that (NH4)2CO3.H2O(s) dissolves in water without causing
an increase in volume.

Which mass of (NH4)2CO3.H2O(s) should be added to 800 cm3 of water to form a 0.100 mol dm–3
solution of NH4+ ions?

A 4.56 g B 7.13 g C 9.12 g D 14.3 g

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3

3 The graph shows the successive ionisation energies of element X and element Y.

Both elements are in Period 3.

key
element X
element Y
energy

0 1 2 3 4 5 6 7 8 9 10
successive
ionisation energies

Which statement is correct?

A An atom of element X needs one extra electron for a full outer shell; an atom of element Y
needs three extra electrons for a full outer shell.
B An atom of element Y has five electrons in the 3p subshell.
C Element X has an oxidation number of +7 in most of its compounds.
D When element X combines with element Y, the bonding is ionic.

4 Which statement about the electrons in a ground state carbon atom is correct?

A Electrons are present in four different energy levels.


B There are more electrons in p orbitals than there are in s orbitals.
C The occupied orbital of highest energy is spherical.
D The occupied orbital of lowest energy is spherical.

5 In this question you should assume the vapour behaves as an ideal gas.

0.175 g of a volatile liquid produces a vapour of volume 4.50 × 10–5 m3 at 100 °C and pressure of
1.013 × 105 Pa.

What is the Mr of the liquid?

A 31.9 B 87.1 C 119 D 127

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4

6 Which reaction is endothermic?

A Ca(OH)2(aq) + 2HCl (aq) → CaCl 2(aq) + 2H2O(l)

B 2Cl (g) → Cl 2(g)

C 2Ca(s) + O2(g) → 2CaO(s)

D CaCO3(s) → CaO(s) + CO2(g)

7 Which equation correctly represents the standard enthalpy change of atomisation of the given
element?

A 1
2
I2(g) → I(g)

B Na(s) → Na(g)

C Cl 2(g) → 2Cl (g)

D Na(g) → Na+(g) + e–

8 (NH4)2Cr2O7 decomposes when heated.

(NH4)2Cr2O7 → N2 + 4H2O + Cr2O3

Which element is oxidised and which element is reduced?

oxidised reduced

A chromium nitrogen
B hydrogen chromium
C nitrogen chromium
D nitrogen hydrogen

9 When lead(II) sulfide, PbS, is heated in air, sulfur dioxide and lead(II) oxide are formed.

What is the equation for the reaction between PbS and oxygen?

A PbS + 2O2 → SO2 + PbO2

B PbS + 2 21 O2 → SO3 + PbO2

C PbS + 1 21 O2 → SO2 + PbO

D PbS + 2O2 → SO3 + PbO

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5

10 The decomposition of SO3(g) is a dynamic equilibrium.

2SO3(g) 2SO2(g) + O2(g)

What happens when the pressure of the system is increased?

A The rate of reaction will decrease and the position of the equilibrium will move to the left.
B The rate of reaction will decrease and the position of the equilibrium will move to the right.
C The rate of reaction will increase and the position of the equilibrium will move to the left.
D The rate of reaction will increase and the position of the equilibrium will move to the right.

11 Hydrated aluminium ions undergo the following reaction.

[Al (H2O)6]3+(aq) + H2O(l) [Al (H2O)5OH]2+(aq) + H3O+(aq)

Which statement about this reaction is correct?

A H2O(l) and [Al (H2O)5OH]2+(aq) are a conjugate acid-base pair.


B H2O(l) is acting as an acid as it is donating H+ ions.
C If OH–(aq) is added, the equilibrium will move to the right.
D Kc varies as the pH is varied.

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6

12 Which diagram correctly shows the electronegativity of the elements Na, Mg, Al and Si plotted
against their first ionisation energies?

A B

Si Si

Al Al
electronegativity electronegativity
Mg Mg

Na Na

first ionisation energy first ionisation energy

C D

Na Na

Al Mg
electronegativity electronegativity
Mg Al

Si Si

first ionisation energy first ionisation energy

13 Which statement about the compounds of Group 2 elements magnesium to barium is correct?

A Carbonates of Group 2 elements produce bubbles when added to dilute nitric acid.
B Nitrates of Group 2 elements produce nitrogen and oxygen on heating.
C Oxides of Group 2 elements produce bubbles when added to dilute hydrochloric acid.
D The oxides of Group 2 elements are amphoteric.

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7

14 When equal volumes of saturated solutions of barium hydroxide and calcium hydroxide are
mixed, a white precipitate, Y, forms. The mixture is filtered and carbon dioxide is bubbled through
the filtrate, producing a second white precipitate, Z.

What are Y and Z?

Y Z

A Ba(OH)2 Ca(OH)2
B Ba(OH)2 CaCO3
C Ca(OH)2 BaCO3
D Ca(OH)2 Ba(OH)2

15 Chlorate(V) ions, Cl O3–, are produced in the redox reaction between chlorine and hot aqueous
sodium hydroxide. Oxidation numbers can be used to help balance the equation for this reaction.

vCl 2(g) + wOH–(aq) → xCl –(aq) + yCl O3–(aq) + zH2O(l)

What are the values of v, x and y in the balanced equation?

v x y

A 2 3 1
B 3 4 2
C 3 5 1
D 7 12 2

16 The properties of chlorine, bromine and their compounds are compared.

Which property is smaller for chlorine than for bromine?

A bond strength of the hydrogen-halide bond


B first ionisation energy
C solubility of the silver halide in NH3(aq)
D strength of the van der Waals’ forces between molecules of the element

17 Solid sodium iodide reacts with concentrated sulfuric acid to form more than one product that
contains sulfur.

What is the lowest oxidation number of sulfur in these products?

A –2 B 0 C +4 D +6

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8

18 Which emission from an internal combustion engine contributes to the erosion of marble statues?

A carbon monoxide
B nitrogen
C nitrogen dioxide
D unburnt hydrocarbons

19 Ammonia, carbon dioxide and water react together to form ammonium carbonate.

Which statement about this reaction is correct?

A It is a redox reaction.
B It is an acid-base reaction.
C The H–N–H bond angle decreases as a consequence of this reaction.
D The three substances react in a 1 : 1 : 1 ratio in this reaction.

20 Structural isomerism and stereoisomerism should be considered when answering this question.

How many isomers with the formula C5H10 have structures that involve π bonding?

A 3 B 4 C 5 D 6

21 The diagram shows the skeletal formula of phenazine.

phenazine

What is the empirical formula of phenazine?

A C6H4N B C6H6N C C12H8N2 D C12H12N2

22 An organic compound X reacts with hot, concentrated acidified potassium manganate(VII)


solution to give a single carbon-containing product.

What could be X?

A CH2C(CH3)2
B CH3CHCHCH3
C CH2CHCH2CH3
D CH3CH2CH2CH3

© UCLES 2019 9701/12/O/N/19


9

23 1-chloro-2-methylbutane reacts with sodium cyanide in ethanol in a nucleophilic substitution


reaction.

What is the most likely intermediate or transition state in this reaction?

A B
– –
H H H 3C CH2CH3

NC C Cl NC C Cl

CH(CH3)CH2CH3 CH3

C D
H 3C CH2CH3 H H

+C +C

CH3 CH(CH3)CH2CH3

24 Propan-1-ol can be reacted with acidified potassium dichromate(VI) to form propanoic acid,
reaction 1, or propanal, reaction 2.

O O
reaction 1 reaction 2
CH3CH2COH CH3CH2CH2OH CH3CH2CH
propan-1-ol

How can the reaction be carried out to ensure that reaction 2 occurs rather than reaction 1?

A An excess of acidified potassium dichromate(VI) is used.

B An excess of concentrated sulfuric acid is added.


C The reaction mixture is distilled immediately after mixing.
D The reaction mixture is heated under reflux.

25 What is the smallest amount of oxygen molecules needed for the complete combustion of 40.0 g
of methanol?

A 1.88 moles B 2.50 moles C 3.75 moles D 5.00 moles

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10

26 Compound X has stereoisomers and forms a precipitate when warmed with Fehling’s reagent.

What could be the structure of compound X?

A B C D
O

O O O

27 The diagram shows the structure of Y.

H H H

H C C C C C H

H O H O H

Two suggestions are made about Y.

1 Y can be oxidised by hot, acidified dichromate(VI) ions.

2 One mole of Y gives one mole of tri-iodomethane when it reacts with an excess of
alkaline aqueous iodine.

Which suggestions are correct?

A both 1 and 2
B 1 only
C 2 only
D neither 1 nor 2

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11

28 Esters can be prepared by the reaction of a carboxylic acid with an alcohol in the presence of
concentrated sulfuric acid.

Which row gives the correct names of the reagents that would be suitable to prepare ester Z?

Z
O

alcohol carboxylic acid

A butan-1-ol methyl propanoic acid


B propan-1-ol butanoic acid
C propan-2-ol butanoic acid
D propan-2-ol propanoic acid

29 Compound Q can be hydrolysed by HCl (aq). The two products of this hydrolysis have the same
empirical formula.

What could Q be?

A CH3CO2CH2CH2OH
B CH3CO2CH2CH2CO2H
C CH3CH2CO2CH2CH2CH3
D CH3CH2CH(OH)CH(OH)CH2CH3

© UCLES 2019 9701/12/O/N/19 [Turn over


12

30 Substance T was analysed and found to contain 62.07% carbon, 10.34% hydrogen and
27.59% oxygen.

The infra-red spectrum of substance T is shown.

100

transmittance
/% 50

0
4000 3000 2000 1500 1000 500
wavenumber / cm–1

Which substance could be T?

A B C D

HO O O
HO
OH
OH OH

© UCLES 2019 9701/12/O/N/19


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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

Use of the Data Booklet may be appropriate for some questions.

31 Which gaseous molecules are polar?

1 ammonia
2 hydrogen sulfide
3 boron trifluoride

32 A carbon monoxide molecule, CO, has three bonds between the carbon atom and the oxygen
atom.

Which features are present in one CO molecule?

1 two lone pairs of electrons


2 a co-ordinate (dative covalent) bond from oxygen to carbon

3 two π bonds

33 Carbon can exist as allotropes which include graphite, diamond and a fullerene.

Which statements are correct?

1 All three allotropes contain covalent bonds.


2 All three allotropes are giant molecular.
3 All three allotropes have delocalised electrons.

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14

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

34 The reaction pathway diagram for a reversible reaction is shown.

50
energy
/ kJ mol–1
20

progress of reaction

Which statements are correct?

1 The enthalpy change for the backward reaction is –20 kJ mol–1.


2 The forward reaction is endothermic.
3 The activation energy for the forward reaction is +70 kJ mol–1.

35 Silicon forms a tetrachloride, SiCl 4.

Which statements are correct?

1 In SiCl 4, the Si is δ+ and each Cl is δ–.


2 SiCl 4 is a liquid at room temperature.
3 SiCl 4 reacts with water to give an acidic solution and a precipitate.

36 Which statements about ammonia are correct?

1 An ammonia molecule has three bond pairs and one lone pair of electrons.
2 When ammonia is bubbled into water the pH of the solution increases.
3 Ammonia gas can be made by warming ammonium sulfate with aqueous hydrochloric acid.

© UCLES 2019 9701/12/O/N/19


15

37 Following fractional distillation of crude oil, which processes can be used to produce propene
from larger hydrocarbon molecules?

1 cracking
2 reduction
3 polymerisation

38 Bromoethane undergoes nucleophilic substitution reactions.

Which statements are correct?

1 Bromoethane reacts with aqueous NaOH to make ethanol.


2 Bromoethane reacts with ethanolic NH3 to make ethylamine.
3 Bromoethane reacts with ethanolic KCN to make ethanenitrile.

39 Which reagents, when used in excess, can convert Y into Z?

CH3CH(OH)CO2H → CH3CH(OH)CO2Na
Y Z

1 Na
2 Na2CO3
3 NaOH

40 Each of the compounds below is treated separately with an excess of NaBH4.

The product of each reaction is then heated with an excess of concentrated H2SO4.

Which compounds give only one final product with the molecular formula C7H10?

1 2 3

O
O

O H O H O H

© UCLES 2019 9701/12/O/N/19


9701/12 Cambridge International AS/A Level – Mark Scheme October/November
PUBLISHED 2019

Question Answer Marks

1 D 1

2 A 1

3 A 1

4 D 1

5 C 1

6 D 1

7 B 1

8 C 1

9 C 1

10 C 1

11 C 1

12 B 1

13 A 1

14 C 1

15 C 1

16 D 1

17 A 1

18 C 1

19 B 1

20 D 1

21 A 1

22 B 1

23 A 1

24 C 1

25 A 1

26 D 1

27 D 1

28 C 1

© UCLES 2019 Page 2 of 3


9701/12 Cambridge International AS/A Level – Mark Scheme October/November
PUBLISHED 2019

Question Answer Marks

29 B 1

30 A 1

31 B 1

32 A 1

33 D 1

34 A 1

35 A 1

36 B 1

37 D 1

38 B 1

39 C 1

40 C 1

© UCLES 2019 Page 3 of 3


2

Section A

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

Use of the Data Booklet may be appropriate for some questions.

1 The diagram shows the Boltzmann distribution of energies in a gas. The gas undergoes a
reaction with an activation energy, Ea. The peak of the distribution is labelled P.

proportion of
molecules with
energy E

0
0 Ea
molecular energy, E

If the same reaction is carried out in the presence of a catalyst, which statement is correct?

A The peak P is at a lower height and the position of Ea moves to the left.
B The peak P is at a lower height and the position of Ea moves to the right.
C The peak P remains at the same height and the position of Ea moves to the left.
D The peak P remains at the same height and the position of Ea moves to the right.

2 Diamond is a pure form of carbon. The mass of a diamond can be measured in carats. One carat
is 0.200 g of carbon.

Which expression gives the number of carats that contain 6.02 × 1023 carbon atoms?

A 0.200 × 12.0

B 0.200
12.0

C 12.0
0.200
0.200
D × 12.0
6.02 × 1023

3 Which molecule or ion contains the smallest bond angle?

A C2 H 4 B CH3COCH3 C NH4+ D NH3

© UCLES 2019 9701/13/O/N/19


3

4 Four compounds are shown.

C2H4 C2H5OH CH3CHO CH3CO2H

How many of these compounds have an odd number of σ bonds?

A 1 B 2 C 3 D 4

5 Ethanal, CH3CHO, ethanol, C2H5OH, and methoxymethane, CH3OCH3, are three organic
compounds.

Which compound has the highest boiling point and what is the interaction that causes this boiling
point to be the highest?

highest boiling point interaction

A methoxymethane permanent dipole-dipole forces


B ethanal hydrogen bonds
C ethanol hydrogen bonds
D ethanal permanent dipole-dipole forces

6 What is the oxidation number of sulfur in each species?

H2S SO2 H2SO3

A –2 +4 +4
B –2 +4 +6
C +2 –4 +4
D +2 –4 +6

© UCLES 2019 9701/13/O/N/19 [Turn over


4

7 The following data are needed for this question.

(N2H4(l)) = 50.6 kJ mol–1


(N2O4(g)) = 9.2 kJ mol–1
(H2O(g)) = –241.8 kJ mol–1

Hydrazine, N2H4(l), reacts with dinitrogen tetraoxide, N2O4(g), to form nitrogen gas and water
vapour.

2N2H4(l) + N2O4(g) → 3N2(g) + 4H2O(g)

What is the enthalpy change for this reaction?

A –1077.6 kJ mol–1
B –856.8 kJ mol–1
C –301.6 kJ mol–1
D –182.0 kJ mol–1

8 Sodium burns in oxygen giving out heat energy and forming the compound Na2O. The equation
for this reaction is shown.

2Na(s) + 1
2
O2(g) → Na2O(s)

Which statement about the reaction is correct?

A ∆H o for the reaction is equal to twice the bond energy of the Na–O bond.

B ∆H o for the reaction is positive.


C The equation represents the standard enthalpy change of combustion of sodium.
D The equation represents the standard enthalpy change of formation of sodium oxide.

9 In the chemical equation, w, x, y and z are all whole numbers.

wCl O3– + xMnO4– + yH+ → wCl O4– + xMnO2 + zH2O

When the equation is balanced, what are w, x and y?

w x y

A 1 1 2
B 2 2 2
C 2 3 8
D 3 2 2

© UCLES 2019 9701/13/O/N/19


5

10 Two compounds X and Y react to produce compound Z. The reaction is reversible.

X + Y Z

When X and Y are mixed together in a closed system a dynamic equilibrium is gradually
established.

Which graph could represent the change in the rates of the forward and reverse reactions over
time?

A B
key
rate of
forward
rate rate reaction

rate of
reverse
reaction
0 time 0 time

C D

rate rate

0 time 0 time

11 The reaction between sulfur dioxide and oxygen is reversible.

2SO2(g) + O2(g) 2SO3(g) Kc = 280 mol–1 dm3 at 1000 K

In an equilibrium mixture at 1000 K the sulfur dioxide concentration is 0.200 mol dm–3 and the
oxygen concentration is 0.100 mol dm–3.

What is the sulfur trioxide concentration?

A 1.058 mol dm–3


B 1.120 mol dm–3
C 2.366 mol dm–3
D 5.600 mol dm–3

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6

12 Which oxide will cause an increase in pH when added to water?

A MgO B Al 2O3 C SiO2 D SO2

13 X, Y and Z are consecutive elements in Period 3 of the Periodic Table. Element Y has the highest
first ionisation energy and the lowest melting point of these three elements.

What are the identities of X, Y and Z?

X Y Z

A Na Mg Al
B Mg Al Si
C Al Si P
D Si P S

14 A 5.00 g sample of an anhydrous Group 2 metal nitrate loses 3.29 g in mass when heated
strongly.

Which metal is present?

A magnesium
B calcium
C strontium
D barium

15 Solutions P and Q each contain a different Group 2 ion at the same concentration. One contains
Mg2+, the other contains Ba2+. Tests are carried out on separate 5 cm3 samples of P and Q.

test 1: add 1 cm3 of 0.1 mol dm–3 Na2SO4(aq)

test 2: add 1 cm3 of 0.1 mol dm–3 NaOH(aq)

What are the results of these tests?

results in test 1 results in test 2

A more precipitate with Ba2+ more precipitate with Ba2+


B more precipitate with Ba2+ more precipitate with Mg2+
C more precipitate with Mg2+ more precipitate with Ba2+
D more precipitate with Mg2+ more precipitate with Mg2+

© UCLES 2019 9701/13/O/N/19


7

16 Chlorine and bromine have different volatilities.

Which row identifies the more volatile of the two elements, and gives the correct explanation?

identity of the explanation for the


more volatile element difference in volatility
A bromine instantaneous dipole-induced dipole forces
are greater in bromine than they are in chlorine
B bromine instantaneous dipole-induced dipole forces
are greater in chlorine than they are in bromine
C chlorine instantaneous dipole-induced dipole forces
are greater in bromine than they are in chlorine
D chlorine instantaneous dipole-induced dipole forces
are greater in chlorine than they are in bromine

17 Sodium azide, NaN3, is dissolved in water. Acidified silver nitrate is added to the solution and a
white precipitate forms. Aqueous ammonia is then added to the white precipitate.

The azide ion, N3–, has similar chemical properties to the Cl – ion.

Which row of the table can be predicted from this information?

formula of observation on adding


white precipitate aqueous ammonia

A AgN3 colourless solution formed


B AgN3 precipitate remains
C Ag3N colourless solution formed
D Ag3N precipitate remains

18 Which type of reaction occurs when solid ammonium sulfate is heated with an excess of sodium
hydroxide solution?

A acid-base
B precipitation
C redox
D thermal decomposition

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8

19 Catalytic converters are fitted in the exhaust systems of many cars.

Which gas:

● causes acid rain if it is released into the air


● is removed from car exhaust fumes by a catalytic converter?

A carbon dioxide
B carbon monoxide
C hydrocarbon vapour
D nitrogen dioxide

20 Which substance reacts with trichloroethene to give a chiral product?

A Br2 B HCl C NaCN D NaOH

21 Alkanes are saturated hydrocarbons.

Which type of reaction are alkanes most likely to undergo?

A electrophilic addition
B electrophilic substitution
C free radical substitution
D nucleophilic addition

22 An alkene reacts with hot, concentrated, acidified potassium manganate(VII) to produce a single
organic product as shown.

hot, concentrated, O O
acidified KMnO4(aq)
alkene
OH

What is the structure of the alkene?

A B C D

© UCLES 2019 9701/13/O/N/19


9

23 A tertiary bromoalkane, indicated here by C–Br , reacts with aqueous NaOH. The mechanism
has the reaction pathway shown.

C–Br + OH–
Y
energy

C–OH + Br –

progress of reaction

Which point in the diagram is correctly identified?

A X is C+


B X is HO C Br

C Y is C+


D Y is HO C Br

24 Bromoethane and chloroethane are added separately to water. Hydrolysis reactions occur.

Which compound hydrolyses more rapidly and what is the mechanism?

compound that
mechanism
hydrolyses more rapidly

A bromoethane electrophilic substitution


B bromoethane nucleophilic substitution
C chloroethane electrophilic substitution
D chloroethane nucleophilic substitution

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10

25 Alcohol X is oxidised to form compound Y.

The composition of Y is 54.54% carbon, 36.36% oxygen and 9.10% hydrogen. The Mr of Y is
88.0.

What could be the structure of alcohol X?

A CH3CH2CH(OH)CH3
B CH3CH2CH2CH2CH2OH
C CH3CH2CH2CH2OH
D CH3CH2CH(OH)CH2CH3

26 The diagram shows the structure of compound Z.

Z
O O

What is the product of the reaction between compound Z and an excess of NaBH4?

A B C D
OH OH OH OH O O O OH

27 Compound Q shows the following reactions.

● It gives an orange precipitate with 2,4-dinitrophenylhydrazine.


● It gives a red-brown precipitate with Fehling’s reagent.
● It gives a pale yellow precipitate with alkaline aqueous iodine.

What could be the identity of Q?

A ethanal
B propan-2-ol
C propanal
D propanone

© UCLES 2019 9701/13/O/N/19


11

28 Tartaric acid, HO2CCH(OH)CH(OH)CO2H, is found in many plants.

A sample of tartaric acid reacts with an excess of LiAl H4 to form the organic product J.

What happens when NaOH(aq) is added to separate samples of tartaric acid and J?

A Both tartaric acid and J react.


B Only tartaric acid reacts.
C Only J reacts.
D Neither tartaric acid nor J react.

29 When CH2(OH)CH=CHCO2H is warmed with a little concentrated sulfuric acid, a cyclic compound
is formed.

What is the skeletal formula of the cyclic compound?

A B C D

O O

O O O O

O
O O

© UCLES 2019 9701/13/O/N/19 [Turn over


12

30 The infra-red spectrum of compound P is shown.

100

transmittance
/% 50

0
4000 3000 2000 1500 1000 500
–1
wavenumber / cm

What could be compound P?

A methyl ethanoate
B propanal
C propanoic acid
D propan-2-ol

© UCLES 2019 9701/13/O/N/19


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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

Use of the Data Booklet may be appropriate for some questions.

31 A particular atom of germanium, Ge, has a nucleon number of 70.

70
Which statements about a 32 Ge atom are correct?

79 2+
1 It has the same number of electrons as a 34 Se ion.
68
2 It has the same number of neutrons as an atom of 30 Zn.
160
3 It has half as many protons as an atom of 64 Gd.

32 The first ionisation energy of chlorine is greater than that of sulfur.

Which factors contribute to this?

1 Chlorine has more protons in its nucleus than sulfur does.


2 Chlorine has greater electron shielding than sulfur does.
3 The covalent bonds in chlorine molecules are stronger than those in sulfur molecules.

© UCLES 2019 9701/13/O/N/19 [Turn over


14

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

33 Liquids X and Y do not react with one another. They have identical boiling points.

When a particular volume of X is shaken with a similar volume of Y, they form a liquid mixture Z.

The average intermolecular forces in liquid Z are stronger than the average of the forces in X and
the forces in Y.

Which deductions from this information are correct?

1 The mixing of X and Y is exothermic.


2 The vapour pressure of liquid Z will be less than that of either liquid X or liquid Y at the same
temperature.
3 The boiling point of liquid Z will be lower than that of either liquid X or liquid Y at the same
pressure.

34 The stoichiometry of a catalysed reaction is shown by the equation below.

P (g) + Q (g) R (g) + S (l)

Two experiments are carried out in which the amount of R is measured. The results are shown in
the diagram.

experiment 1
amount experiment 2
of R

0
0 time

Which changes in the conditions could explain the results shown?

1 A lower pressure was used in experiment 2.


2 A different catalyst was used in experiment 2.
3 Product S was continuously removed from the reaction vessel in experiment 2.

© UCLES 2019 9701/13/O/N/19


15

35 Which statements are correct?

1 Chloride ions are oxidised when concentrated sulfuric acid is added to NaCl (s).
2 A disproportionation reaction takes place when chlorine is added to cold NaOH(aq).
3 An acidic solution forms when chlorine is added to water.

36 Nitrogen gas is unreactive, whereas oxygen gas and chlorine gas are reactive.

Which statements help to explain this difference?

1 The two N atoms in an N2 molecule are held together by a very strong triple bond.
2 The triple bond between two N atoms is not polar. The bonds in O2 and Cl 2 are polar.

3 The atoms in N2 have a full outer shell of electrons. The atoms in O2 and Cl 2 do not have a
full outer shell of electrons.

37 The structure of tiglic acid is CH3CH=C(CH3)CO2H.

Which statements about the properties of one molecule of this acid are correct?

1 It contains two π bonds.


2 It contains four lone pairs of electrons.
3 It has all its atoms in the same plane.

38 Which compounds, on heating with an excess of concentrated sulfuric acid, produce only one
product with molecular formula C7H10?

1 2 3

OH
OH

OH

OH OH OH

39 Hydrogen cyanide reacts with propanone in the presence of potassium cyanide.

Which statements about this reaction are correct?

1 The cyanide ion is a catalyst for the reaction.

2 This is an addition reaction.

3 The intermediate behaves as a base.

© UCLES 2019 9701/13/O/N/19 [Turn over


16

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

40 Which compounds produce three different organic products when hydrolysed?

1 2 3

O O
O O
O O O
O
O O
O O

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.

To avoid the issue of disclosure of answer-related information to candidates, all copyright acknowledgements are reproduced online in the Cambridge
Assessment International Education Copyright Acknowledgements Booklet. This is produced for each series of examinations and is freely available to download
at www.cambridgeinternational.org after the live examination series.

Cambridge Assessment International Education is part of the Cambridge Assessment Group. Cambridge Assessment is the brand name of the University of
Cambridge Local Examinations Syndicate (UCLES), which itself is a department of the University of Cambridge.

© UCLES 2019 9701/13/O/N/19


9701/13 Cambridge International AS/A Level – Mark Scheme October/November
PUBLISHED 2019

Question Answer Marks

1 C 1

2 C 1

3 D 1

4 B 1

5 C 1

6 A 1

7 A 1

8 D 1

9 D 1

10 C 1

11 A 1

12 A 1

13 D 1

14 B 1

15 B 1

16 C 1

17 A 1

18 A 1

19 D 1

20 A 1

21 C 1

22 D 1

23 C 1

24 B 1

25 C 1

26 A 1

27 A 1

28 B 1

© UCLES 2019 Page 2 of 3


9701/13 Cambridge International AS/A Level – Mark Scheme October/November
PUBLISHED 2019

Question Answer Marks

29 C 1

30 D 1

31 A 1

32 D 1

33 B 1

34 B 1

35 C 1

36 D 1

37 B 1

38 B 1

39 A 1

40 D 1

© UCLES 2019 Page 3 of 3


2

Section A

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

Use of the Data Booklet may be appropriate for some questions.

1 This question refers to isolated gaseous atoms.

In which atom are all electrons paired?

A Ba B Br C S D Si

2 Which compound has a boiling point that is influenced by hydrogen bonding?

A CH3CHO B CH3OCH3 C HCO2CH3 D HCO2H

3 Which fuel would produce the largest mass of CO2 when 10 kg of the fuel undergo complete
combustion?

A biodiesel, C17H34O2
B ethanol, C2H6O
C octane, C8H18
D propane, C3H8

4 The diagram shows the Boltzmann distribution of energies in a gas. The gas can take part in a
reaction with an activation energy, Ea. The gas is maintained at a constant temperature.

proportion of
molecules with
a given energy

0
0 Ea
molecular energy

Which statement is correct?

A If a catalyst is added, peak P will be lower and Ea will move to the left.
B If a catalyst is added, peak P will be lower and Ea will move to the right.
C If a catalyst is added, peak P will be the same and Ea will move to the left.
D If a catalyst is added, peak P will be the same and Ea will move to the right.

© UCLES 2018 9701/11/M/J/18


3

5 Which molecule has no overall dipole?

A CH3Cl B CH2Cl 2 C CHCl 3 D CCl 4

6 Which solid contains more than one type of bonding?

A iodine
B silicon dioxide
C sodium chloride
D zinc

7 Enthalpy changes of combustion can be used to determine enthalpy changes of formation. The
following equation represents the enthalpy change of formation of butane.

4C(s) + 5H2(g) → C4H10(g)

By using the following standard enthalpy of combustion data, what is the value of the standard
enthalpy change of formation, , of butane?

substance

C(s) –394
H2(g) –286
C4H10(g) –2877

A –5883 kJ mol–1
B –129 kJ mol–1
C +129 kJ mol–1
D +2197 kJ mol–1

8 Ethanedioate ions, C2O42–, react with a suitable reagent to form CO2. A half-equation for this
reaction is shown.

C2O42– → 2CO2 + 2e–

Which row is correct?

oxidation state of
type of reaction
carbon in C2O42–

A +3 oxidation
B +3 reduction
C +5 oxidation
D +5 reduction

© UCLES 2018 9701/11/M/J/18 [Turn over


4

9 Oxidation numbers should be used to answer this question.

A redox reaction takes place between hydroxylammonium ions, [NH3OH]+, and acidified iron(III)
ions, Fe3+. The products are iron(II) ions, Fe2+, H+ ions, water and a compound of nitrogen.

The mole ratio of reacting hydroxylammonium ions to reacting iron(III) ions is 1 : 2.

Which nitrogen-containing compound could be formed in the reaction?

A NH3 B N2O C NO D NO2

10 Element X has a higher first ionisation energy than element Y.

Two students state what they believe is one factor that helps to explain this.

student 1 “X has a higher first ionisation energy than Y because an atom of X has more
protons in its nucleus than an atom of Y.”

student 2 “X has a higher first ionisation energy than Y because X has a smaller atomic
radius than Y.”

Only one of the two students is correct.

What could X and Y be?

X Y

A carbon boron
B magnesium aluminium
C oxygen nitrogen
D oxygen sulfur

11 Hydrogen ions catalyse the hydrolysis of esters.

Which statement is correct?

A The hydrogen ions act as a heterogeneous catalyst.


B The hydrogen ions are in the same phase as the reactants.
C The hydrogen ions are used up in the reaction.
D The hydrogen ions have no effect on the activation energy of the reaction.

© UCLES 2018 9701/11/M/J/18


5

12 Silicon is heated in an excess of chlorine, producing compound J.

Excess water is added to the sample of J produced.

Which row is correct?

Is HCl produced
structure of J when water is
added to J?

A giant molecular no
B giant molecular yes
C simple molecular no
D simple molecular yes

13 Which element has the second smallest atomic radius in its group and the third lowest first
ionisation energy in its period?

A boron
B calcium
C magnesium
D sodium

14 Chlorine reacts with cold aqueous sodium hydroxide to produce sodium chloride, water and
compound X.

Chlorine reacts with hot aqueous sodium hydroxide to produce sodium chloride, water and
compound Y.

What are the oxidation states of chlorine in compound X and compound Y?

X Y

A –1 –5
B –1 +5
C +1 –5
D +1 +5

15 In which reaction does ammonia behave as a Brønsted-Lowry base?

A NH3 + CH3CH2Br → CH3CH2NH2 + HBr

B NH3 + H2O + CO2 → (NH4)HCO3

C 2NH3 + 2Na → 2NaNH2 + H2

D 4NH3 + 3O2 → 2N2 + 6H2O

© UCLES 2018 9701/11/M/J/18 [Turn over


6

16 Aqueous silver nitrate is added to a solution of potassium iodide.

Aqueous ammonia is then added.

What would be observed?

A a cream precipitate that dissolves on addition of aqueous ammonia


B a cream precipitate that does not dissolve on addition of aqueous ammonia
C a yellow precipitate that dissolves on addition of aqueous ammonia
D a yellow precipitate that does not dissolve on addition of aqueous ammonia

17 Oxides of nitrogen are present in the environment due to natural and man-made sources.

Which row is correct?

natural source of nitrogen oxides man-made source of nitrogen oxides

A electrical discharges in the atmosphere internal combustion engines


B electrical discharges in the atmosphere as a by-product of the Haber process
C decomposition of dead plants in rivers internal combustion engines
D decomposition of dead plants in rivers as a by-product of the Haber process

18 When 3.00 g of an anhydrous nitrate of a Group 2 metal is decomposed, 1.53 g of gas is


produced.

What is the nitrate compound?

A beryllium nitrate
B calcium nitrate
C magnesium nitrate
D strontium nitrate

19 Which row correctly describes one property of barium and one property of barium oxide?

observation when pH of solution obtained when


barium metal is a spatula measure of BaO is
added to water added to 100 cm3 of water

A a few gas bubbles 8


form on the metal surface
B a few gas bubbles 13
form on the metal surface
C rapid effervescence is seen 8
D rapid effervescence is seen 13

© UCLES 2018 9701/11/M/J/18


7

20 Fructose is a sugar with more than one chiral centre. The fructose molecule is shown with X, Y
and Z indicating three carbon atoms.

OH

H C H

X C O

HO C H

H C OH

Y H C OH

H C H

Z OH

fructose

Which carbon atoms are chiral centres?

A X, Y and Z B X and Y only C X only D Y only

21 Which pair of alcohols are isomers of each other?

A butan-1-ol and 2,2-dimethylpropan-1-ol


B butan-2-ol and 2-methylpropan-2-ol
C pentan-1-ol and 2-methylpropan-2-ol
D propan-2-ol and 2-methylpropan-2-ol

22 Sodium methoxide, Na+CH3O–, reacts with 2-chloro-2-methylpropane in a nucleophilic


substitution reaction. The nucleophile is the CH3O– ion.

Which row is correct?

intermediate or
product
transition state

A (CH3)3C+ (CH3)3COCH3
B (CH3)3C+ (CH3)3CCH2OH
C [HOCH2- - -C(CH3)3- - -Cl ]– HOCH2C(CH3)3
D [H3CO- - -C(CH3)3- - -Cl ]– H3COC(CH3)3

© UCLES 2018 9701/11/M/J/18 [Turn over


8

23 Which alcohol can be dehydrated to give two products which are structural isomers of each
other?

A B C D

H H H H H H CH3 H H H H CH3

H C C C C OH H C C C OH H C C C OH H C C OH

H H H H H H H H CH3 H H CH3

24 Which reagent could detect the presence of alcohol in a mixture consisting mainly of alkanes and
alkenes?

A Na
B Br2 (in CCl 4)
C KMnO4(aq)
D 2,4-dinitrophenylhydrazine

25 Compound Q

● contains a chiral centre,


● gives a positive result with Fehling’s reagent,
● gives a positive result with alkaline aqueous iodine.

What could compound Q be?

A 1-hydroxybutanone
B 2-hydroxybutanal
C 3-hydroxybutanal
D 3-hydroxybutanone

© UCLES 2018 9701/11/M/J/18


9

26 What is the mechanism for the reaction of ethanal, CH3CHO, with hydrogen cyanide, HCN, in the
presence of NaCN?

O O– O

A CH3 C H CH3 C H CH3 C + H–

CN– CN CN


O O H C N OH

B CH3 C H CH3 C H CH3 C H + CN–

CN– CN CN

O H C N OH OH
+
C CH3 C H CH3 C H CH3 C H

CN– CN

D initiation HCN H• + •CN

O O•

propagation CH3 C + • CN CH3 C H

H CN

O• OH

CH3 C H + H CN CH3 C H + • CN

CN CN

O• OH

termination CH3 C H + H• CH3 C H

CN CN

© UCLES 2018 9701/11/M/J/18 [Turn over


10

27 Ethyl propanoate is refluxed with aqueous sodium hydroxide. The alcohol produced is then
reacted with methyl propanoic acid to make a second ester.

What is the structural formula of this second ester?

A B
O O

CH3 CH2 O C CH CH3 CH3 CH2 CH2 O C CH CH3

CH3 CH3

C D
O O

CH3 C O CH2 CH CH3 CH3 CH2 C O CH2 CH CH3

CH3 CH3

28 Which reagent could be used to carry out the following reaction?

O
O
OH

A a solution containing acidified dichromate(VI) ions

B a solution containing dilute, acidified manganate(VII) ions

C a solution containing hot, concentrated, acidified manganate(VII) ions

D concentrated sulfuric acid

29 Four reactions of propanoic acid to form salts and other products are shown.

Which reaction does not show the formulae of all the correct products?

A B
CH3CH2CO2– K+(aq) + H2O(l) (CH3CH2CO2–)2Mg2+(aq) + H2(g)

KOH Mg(s)

CH3CH2CO2H(aq)
propanoic
Na2CO3 acid Ca(OH)2

C D
CH3CH2CO2– Na+(aq) + CO2(g) (CH3CH2CO2–)2Ca2+(aq) + H2O(l)

© UCLES 2018 9701/11/M/J/18


11

30 Compound X contains three carbon atoms. Part of a simplified infra-red spectrum of compound X
is shown.

100

transmittance
50

0
4000 3000 2000 1500 1000 500
wavenumber / cm–1

Which compound could be X?

A CH3CH2CHO
B CH3CH2CO2H
C CH3CH2CH2OH
D CH3CO2CH3

© UCLES 2018 9701/11/M/J/18 [Turn over


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 B C D
1, 2 and 3 1 and 2 2 and 3 1 only
are only are only are is
correct correct correct correct

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

Use of the Data Booklet may be appropriate for some questions.

31 One mole of sulfuric acid is used to make an aqueous solution. The solution contains H2SO4
molecules, H+ ions, SO42– ions and HSO4– ions.

Which statements are correct?

1 The solution contains 6.02 × 1023 sulfur atoms.


2 The solution contains an exactly equal number of H+ ions and HSO4– ions.
3 One mole of SO42– ions contains two moles of electrons.

32 Which statements are correct?

1 The hydrogen bonds in ice are more regularly arranged than in water.
2 The solidification of water to form ice is exothermic.
3 Pure water is less dense than ice.

33 Calcium reacts with water to form calcium hydroxide and hydrogen.

Ca(s) + 2H2O(l) → Ca(OH)2(s) + H2(g)

The standard enthalpy change for this reaction is – 414 kJ mol–1.

What further information is needed in order to calculate the standard enthalpy change of
formation of calcium hydroxide, Ca(OH)2(s)?

1 for H2O(l)
2 for H2(g)
3 first and second ionisation energies of Ca

© UCLES 2018 9701/11/M/J/18


13

34 Which statements are correct when a reversible reaction is at equilibrium?

1 All species are at equal concentration.


2 The concentrations of all species remain constant.
3 The rate of the forward reaction equals the rate of the reverse reaction.

35 Each of the three mixtures shown can result in a chemical reaction.

Which mixtures result in a redox reaction?

1 bromine + hydrogen
2 sodium chloride + concentrated sulfuric acid
3 potassium iodide + silver nitrate

36 Which statements correctly describe an oxide of nitrogen acting as an atmospheric pollutant?

1 Nitrogen monoxide, NO, reacts with oxygen to form nitrogen dioxide which contributes to
acid rain.
2 Nitrogen dioxide reacts with sulfur dioxide to form sulfur trioxide which reacts with water to
form sulfuric acid.
3 Nitrogen oxides react with unburnt hydrocarbons in sunlight to form other pollutants.

37 Polymer Z contains the length of polymer chain shown below.

This short length of chain is found many times within the chains of polymer Z, although it is not
the repeat unit.

– CH2 – CHCl – CH2 –

What could be the name of polymer Z?

1 poly(2-chloropropene)
2 poly(chloroethene)
3 PVC

© UCLES 2018 9701/11/M/J/18 [Turn over


14

The responses A to D should be selected on the basis of

A B C D
1, 2 and 3 1 and 2 2 and 3 1 only
are only are only are is
correct correct correct correct

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

38 Limonene is found in lemons.

limonene

Limonene is heated with concentrated acidified potassium manganate(VII).

Which compounds are produced?

1 CH3COCH2CH2CH(CH2CO2H)2
2 CO2
3 CH3COCH2CH2CH(COCH3)CH2CO2H

39 Chlorofluoroalkanes have been used as the refrigerant in refrigerators but care has to be taken in
disposing of old refrigerators.

Which statements about chlorofluoroalkanes are correct?

1 C–Cl bonds more readily undergo homolytic fission than C–F bonds.
2 Care is taken in the disposal of old refrigerators because of possible ozone depletion.
3 C2H4Cl F is more volatile than C2H6.

40 The Mr of compound X is 72. The composition by mass of X is 66.7% carbon, 11.1% hydrogen
and 22.2% oxygen. X gives an orange precipitate with 2,4-dinitrophenylhydrazine reagent.
X does not react with Fehling’s reagent.

What can be deduced from this information?

1 X is a carbonyl compound.
2 X is a ketone.
3 X is butanone.

© UCLES 2018 9701/11/M/J/18


9701/11 Cambridge International AS/A Level – Mark Scheme May/June 2018
PUBLISHED

Question Answer Marks

1 A 1

2 D 1

3 C 1

4 C 1

5 D 1

6 A 1

7 B 1

8 A 1

9 B 1

10 D 1

11 B 1

12 D 1

13 C 1

14 D 1

15 B 1

16 D 1

17 A 1

18 D 1

19 D 1

20 B 1

21 B 1

22 A 1

23 B 1

24 A 1

25 C 1

26 B 1

27 A 1

28 A 1

© UCLES 2018 Page 2 of 4


9701/11 Cambridge International AS/A Level – Mark Scheme May/June 2018
PUBLISHED

Question Answer Marks

29 C 1

30 C 1

31 D 1

32 B 1

33 D 1

34 C 1

35 D 1

36 A 1

37 C 1

38 C 1

39 B 1

40 A 1

© UCLES 2018 Page 3 of 4


2

Section A

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

Use of the Data Booklet may be appropriate for some questions.

1 Which feature is present in both ethene and poly(ethene)?

A bond angles of 109°

B π covalent bonds

C σ covalent bonds
D sp3 orbitals

2 The electronic configuration of an atom of sulfur is 1s22s22p63s23p4.

How many valence shell and unpaired electrons are present in one sulfur atom?

valence shell unpaired


electrons electrons

A 2 1
B 4 2
C 6 0
D 6 2

3 In which pair does the second substance have a lower boiling point than the first substance?

A C2H6 and C2H5Cl


B CH3OCH3 and C2H5OH
C Ne and Ar
D CH3NH2 and C2H6

4 Compound J burns in excess oxygen to give carbon dioxide and water only. When a 3.00 g
sample of compound J is burnt in excess oxygen, 4.40 g of carbon dioxide and 1.80 g of water are
formed.

What is the empirical formula of J?

A CH B CHO C CH2 D CH2O

© UCLES 2018 9701/12/M/J/18


3

5 The gases X and Y react to form Z.

X(g) + Y(g) Z(g)

An equilibrium mixture of these three gases is compressed at constant temperature.

What will be the changes in the mole fraction of Z and in Kp?

mole fraction of Z Kp

A increase increase
B increase no change
C no change increase
D no change no change

6 Which gas is likely to deviate most from ideal gas behaviour?

A HCl B He C CH4 D N2

7 The enthalpy change of reaction 1 is –114 kJ mol–1.

2NaOH(aq) + H2SO4(aq) → Na2SO4(aq) + 2H2O(l) reaction 1

By using this information, what is the most likely value for the enthalpy change of reaction 2?

Ba(OH)2(aq) + 2HCl (aq) → BaCl 2(aq) + 2H2O(l) reaction 2

A –57 kJ mol–1 B –76 kJ mol–1 C –114 kJ mol–1 D –228 kJ mol–1

8 Sulfur reacts with concentrated nitric acid in a redox reaction.

S + 4HNO3 → SO2 + 4NO2 + 2H2O

What are the changes in oxidation number of sulfur and of nitrogen in this reaction?

sulfur nitrogen

A +2 –3
B +2 –1
C +4 –3
D +4 –1

© UCLES 2018 9701/12/M/J/18 [Turn over


4

9 Materials can be classified by their chemical structures. Four common types of structure are
metallic, ionic, simple molecular and giant molecular.

Some physical properties of four substances are shown in the table.

Which substance has a simple molecular structure?

melting point effect of electrical


/ °C adding water conductivity

A 64 reacts good when solid


B 113 insoluble always poor
C 767 soluble good when solid
D 1600 insoluble always poor

10 In a particular reversible reaction the yield of product is increased

● if the temperature is increased;


● if the pressure is decreased.

Which equation could describe this reversible reaction?

A CH4(g) + H2O(g) 3H2(g) + CO(g) ∆H = +206 kJ mol–1

B 4NH3(g) + 3O2(g) 2N2(g) + 6H2O(g) ∆H = –227 kJ mol–1

C 2NO2(g) N2O4(g) ∆H = –58 kJ mol–1

D 3O2(g) 2O3(g) ∆H = +143 kJ mol–1

11 A chemical company used a catalyst in a chemical process. The company has now decided not
to use the catalyst but to increase the temperature so that the rate of the reaction is the same as
it was when the catalyst was used.

Which statement about the new conditions compared to the original conditions is correct?

A The activation energy has been decreased.


B The activation energy has been increased.
C There are fewer successful collisions per unit time.
D There are more successful collisions per unit time.

12 Which oxide does not react with cold, dilute sodium hydroxide to produce a salt?

A Al 2O3 B P4O10 C SO2 D SiO2

© UCLES 2018 9701/12/M/J/18


5

13 The graphs show trends in four physical properties of elements in Period 3, excluding argon.

Which graph has electronegativity on the y-axis?

A B

Na Mg Al Si P S Cl Na Mg Al Si P S Cl

C D

Na Mg Al Si P S Cl Na Mg Al Si P S Cl

14 In this question, X represents an atom of chlorine, bromine or iodine.

Which explanation for the variation in volatility down Group 17 is correct?

A Instantaneous dipole-induced dipole forces between molecules become stronger.


B Permanent dipole-permanent dipole forces between molecules become stronger.
C The bond energy of the X2 molecules decreases.

D The first ionisation energy X(g) → X+(g) + e– decreases.

15 To manufacture cement, 1000 million tonnes of limestone are decomposed each year. To
manufacture lime for agriculture, 200 million tonnes of limestone are decomposed each year.

What is the total mass of carbon dioxide in million tonnes produced from these two processes in
a year?

A 440 B 528 C 660 D 880

© UCLES 2018 9701/12/M/J/18 [Turn over


6

16 In Group 2 of the Periodic Table, the properties of the elements and their compounds show
regular change down the group.

Which property shows a decrease from magnesium to barium?

A the decomposition temperature of the carbonates


B the decomposition temperature of the nitrates
C the solubility of the hydroxides
D the solubility of the sulfates

17 When concentrated sulfuric acid is added to solid sodium bromide, bromine gas is produced,
along with a number of other products. However when concentrated sulfuric acid is added to solid
sodium chloride only hydrogen chloride and sodium hydrogensulfate are produced.

What is the reason for this difference?

A Bromine is less volatile than chlorine.


B Hydrochloric acid is a weak acid.
C Sulfuric acid is not an oxidising agent.
D The bromide ion is a stronger reducing agent than the chloride ion.

18 The dative covalent bond can be represented by an arrow, . The arrow points towards the
atom receiving the lone pair.

Which diagram of an ammonium ion is correct?

A B C D

H + H – H + H –

H N H H N H H N H H N H

H H H H

19 Sulfur dioxide can be catalytically oxidised by an oxide of nitrogen in the atmosphere.

Which reaction shows the regeneration of the catalyst?

A N2 + 2O2 2NO2

B 4NH3 + 5O2 → 4NO + 6H2O

C N2 + O2 → 2NO

D NO + 1
O
2 2
→ NO2

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7

20 Compound Y is treated with an excess of hydrogen gas in the presence of a nickel catalyst. The
product is fully saturated.

compound Y

What is the number of chiral carbon atoms in the product?

A 5 B 6 C 7 D 8

21 Which equation represents a valid propagation step in the chlorination of ethane?

A C2H6 + Cl • → C2H5Cl + H•

B C2H5Cl + Cl • → C2H4Cl • + HCl

C C2H5Cl + H• → C2H5• + HCl

D C2H5• + Cl • → C2H5Cl

22 Maleic acid is used in the food industry and for stabilising drugs. It is the cis-isomer of butenedioic
acid and has the structural formula HO2CCH=CHCO2H.

What is the product formed from the reaction of maleic acid with cold, dilute, acidified
manganate(VII) ions?

A HO2CCH(OH)CH(OH)CO2H
B HO2CCO2H
C HO2CCH2CH(OH)CO2H
D HO2CCOCOCO2H

23 Primary halogenoalkanes undergo hydrolysis reactions.

Which reaction would occur most rapidly if they are all warmed to the same temperature?

A C2H5Br with H2O


B C2H5Br with NaOH(aq)
C C2H5Cl with H2O
D C2H5Cl with NaOH(aq)

© UCLES 2018 9701/12/M/J/18 [Turn over


8

24 Structural isomerism and stereoisomerism should be considered when answering this question.

A colourless liquid, C5H11Cl , exists as a mixture of two optical isomers.

When heated with sodium hydroxide in ethanol, a mixture of only two alkenes is formed.

What could the colourless liquid be?

A (CH3CH2)2CHCl
B CH3CH2CH2CHCl CH3
C (CH3)2CHCHCl CH3
D CH3CH2CCl (CH3)2

25 When warm water is added to halogenoalkane X, an SN1 reaction occurs.

AgNO3(aq) is then added; a yellow precipitate is formed.

What could be X?

A 1-chlorobutane
B 1-iodobutane
C 2-chloro-2-methylpropane
D 2-iodo-2-methylpropane

26 Which alcohol will react with an acidified solution of potassium dichromate(VI) to produce a
ketone containing six carbon atoms?

A 2,2-dimethylbutan-1-ol
B 2-methylpentan-3-ol
C 3,3-dimethylpentan-2-ol
D 3-methylpentan-3-ol

27 Which statement about butanone is correct?

A Butanone can be dehydrated by concentrated sulfuric acid to give CH2=CHCH=CH2.


B Butanone gives a positive result with Tollens’ reagent.
C Butanone reacts with HCN by an electrophilic addition mechanism.
D Butanone reacts with NaBH4 to give a chiral product.

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9

28 Ethanal, CH3CHO, is used to make product R in a three-stage synthesis.

HCN H2SO4(aq), conc. H2SO4


/ NaCN reflux (a few drops)
CH3CHO product P product Q product R

Two molecules of Q react to give one molecule of R plus two molecules of water.

R has two ester functional groups in each molecule. R does not react with sodium.

What is the empirical formula of R?

A CHO B C3H4O2 C C3H5O2 D C6H10O5

29 The ester ethyl butanoate can be hydrolysed using an excess of dilute sodium hydroxide solution.

Which substance is a product of this reaction?

A CH3CH2CH2CO2Na
B CH3CO2Na
C CH3CH2ONa
D H2O

30 The infra-red spectrum of an organic compound is shown.

100

transmittance
% 50

0
4000 3000 2000 1500 1000 500
wavenumber / cm–1

Which compound could give this spectrum?

A CH3CH2CO2H
B CH3CH(OH)CH3
C CH3COCH3
D CH3COCH2OH

© UCLES 2018 9701/12/M/J/18 [Turn over


10

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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

Use of the Data Booklet may be appropriate for some questions.

31 For complete combustion, 1 mol of an organic compound X requires 2.5 mol of O2.

Which compounds could be X?

1 C2H5OH
2 C2H2
3 CH3CHO

32 In which pairs do both species have the same number of electrons?


35
1 Cl and 37Cl
35
2 Cl – and 40Ar
40
3 Ar and 40K+

33 For which reactions does the value of ∆H o represent both a standard enthalpy change of
combustion and a standard enthalpy change of formation?

1 C(s) + O2(g) → CO2(g)

2 2C(s) + O2(g) → 2CO(g)

3 CO(g) + 1
O (g)
2 2
→ CO2(g)

© UCLES 2018 9701/12/M/J/18


11

34 The temperature of a reversible gas phase reaction is increased.

Which statements are always correct?

1 More product is present at equilibrium.


2 The average speed of the particles increases.
3 There are more successful collisions per unit time.

35 Three samples of chlorine gas each contain 0.710 g of chlorine. Each sample is reacted with a
reagent.

● In the first reaction a sample is reacted completely with hydrogen gas.


● In the second reaction a sample is reacted completely with cold NaOH(aq).
● In the third reaction a sample is reacted completely with hot NaOH(aq).

Which masses of the named products would be formed?

1 Exactly 0.730 g of HCl form in the first reaction.


2 Exactly 0.585 g of NaCl form in the second reaction.
3 Exactly 0.975 g of NaCl form in the third reaction.

36 Solid barium oxide is added to some ammonium sulfate solution in a test-tube and the mixture is
warmed. A piece of damp red litmus paper is held over the mouth of the test-tube.

Which observations would be made?

1 The damp litmus paper initially turns from red to blue.


2 A white precipitate forms in the test-tube.
3 A brown gas is evolved with strong heating.

37 Which compounds show geometrical (cis-trans) isomerism?

1 CH3CH=C(CH3)C2H5
2 CH3CH=CHCH2CH2CH3
3 C2H5CH=CHC2H5

38 Which pairs of compounds may be distinguished from each other by testing with alkaline aqueous
iodine?

1 ethane-1,2-diol and ethanol


2 propan-2-ol and methylpropan-2-ol
3 ethanol and butan-2-ol

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12

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

39 The diagram shows an experimental set-up which can be used in several different experiments.

silica, alumina
or baked clay
liquid X on
mineral wool gas collected
support

strong
gentle heat
trough of
heat
water

Which processes could be demonstrated by using the above apparatus?

1 oxidation of ethanol (liquid X)


2 dehydration of ethanol (liquid X)
3 cracking of paraffin (liquid X)

40 The ester C2H5CO2CH2CH2CH3 can be made in a school or college laboratory by a sequence of


four reactions or fewer using compound Z as the only organic material.

What might be the identity of compound Z?

1 CH3CH2CH2OH
2 CH3CH2CHO
3 CH3COCH3

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.

To avoid the issue of disclosure of answer-related information to candidates, all copyright acknowledgements are reproduced online in the Cambridge
International Examinations Copyright Acknowledgements Booklet. This is produced for each series of examinations and is freely available to download at
www.cie.org.uk after the live examination series.

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 2018 9701/12/M/J/18


9701/12 Cambridge International AS/A Level – Mark Scheme May/June 2018
PUBLISHED

Question Answer Marks

1 C 1

2 D 1

3 D 1

4 D 1

5 B 1

6 A 1

7 C 1

8 D 1

9 B 1

10 A 1

11 B 1

12 D 1

13 D 1

14 A 1

15 B 1

16 D 1

17 D 1

18 C 1

19 D 1

20 A 1

21 B 1

22 A 1

23 B 1

24 C 1

25 D 1

26 B 1

27 D 1

28 B 1

© UCLES 2018 Page 2 of 3


9701/12 Cambridge International AS/A Level – Mark Scheme May/June 2018
PUBLISHED

Question Answer Marks

29 A 1

30 C 1

31 C 1

32 A 1

33 D 1

34 C 1

35 A 1

36 B 1

37 A 1

38 B 1

39 C 1

40 B 1

© UCLES 2018 Page 3 of 3


2

Section A

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

Use of the Data Booklet may be appropriate for some questions.

1 Why is the boiling point of ammonia, NH3, higher than the boiling point of phosphine, PH3?

A Ammonia molecules are polar; phosphine molecules are not.


B Ammonia molecules have significant hydrogen bonding; phosphine molecules do not.
C N–H covalent bonds are stronger than P–H covalent bonds.
D There is one lone pair in each ammonia molecule but no lone pair in each phosphine
molecule.

1
2 Neutrons are passed through an electric field. The mass of one neutron relative to 12
the mass of
a 12C atom and any deflection in the electric field is recorded.

Which row is correct?

mass of behaviour of beam of


neutron neutrons in an electric field

A 0 deflected
B 1 deflected
C 0 not deflected
D 1 not deflected

3 The table refers to the electron distribution in the second shell of an atom with eight protons.

Which row is correct for this atom?

orbital shape orbital shape

number of number of
orbital type orbital type
electrons electrons

A p 2 s 4
B p 4 s 2
C s 2 p 4
D s 4 p 2

© UCLES 2018 9701/13/M/J/18


3

4 Which statement describes the bond between carbon and hydrogen in an ethene molecule?

A a π bond between an s orbital and an sp2 orbital

B a π bond between an s orbital and an sp3 orbital

C a σ bond between an s orbital and an sp2 orbital

D a σ bond between an s orbital and an sp3 orbital

5 Aspirin, C9H8O4, Mr = 180.0, can be made by a reaction between 2-hydroxybenzoic acid, C7H6O3,
Mr = 138.0, and ethanoic anhydride, C4H6O3, Mr = 102.0. The balanced equation for the reaction
is shown.

C7H6O3 + C4H6O3 → C9H8O4 + C2H4O2

If a reaction mixture consists of 10.0 g of each of the two reactants, what is the maximum mass of
aspirin that can be produced?

A 5.7 g B 10.0 g C 13.0 g D 17.6 g

6 Which diagram correctly describes the behaviour of a fixed mass of an ideal gas? (T is measured
in K.)

A B C D

constant p constant T constant T constant T

V p pV pV

0 0 0 0
0 T 0 V 0 p 0 V

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4

7 Anhydrous copper(II) chloride, CuCl 2, combines with water to form CuCl 2.2H2O. The standard
enthalpy changes of formation for this reaction are shown in the table.

H2O –286
CuCl 2 –206
CuCl 2.2H2O –808

What is the standard enthalpy change of the reaction shown?

CuCl 2 + 2H2O → CuCl 2.2H2O

A –1586 kJ mol–1
B –316 kJ mol–1
C –110 kJ mol–1
D –30 kJ mol–1

8 Xenon hexafluoride, XeF6, reacts with water.

XeF6 + 3H2O → XeO3 + 6HF

Which statement is correct?

A Hydrogen is reduced in this reaction.


B Hydrogen is the only element oxidised in this reaction.
C The only element oxidised in this reaction is xenon.
D This is not a redox reaction.

9 Hydrogen is produced industrially from methane as shown in the equation.

CH4(g) + H2O(g) CO(g) + 3H2(g) ∆H o = +205 kJ mol–1

Which conditions would most favour the formation of hydrogen?

pressure temperature

A high high
B high low
C low high
D low low

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5

10 The chemical equilibrium shown is formed when ammonia is produced in the Haber process.

N2 + 3H2 2NH3

The following concentrations are found to be present at equilibrium under certain conditions.

N2 H2 NH3

0.200 mol dm–3 0.300 mol dm–3 0.600 mol dm–3

What is the numerical value of Kc under these conditions?

A 0.0150 B 6.0 C 10.0 D 66.7

11 The enzyme maltase speeds up the reaction between maltose and water.

maltase
maltose + water glucose

Maltase shows specificity.

Which statement describes the specificity of maltase?

A Maltase is a biological catalyst and it is a type of protein.


B Maltase is most effective between pH 6.1 and pH 6.8.
C Maltase lowers the activation energies of the reactions it catalyses.
D Maltase only speeds up a small number of chemical reactions.

12 Which description of the bonding and acid / base nature of aluminium oxide is correct?

bonding acid / base nature

A simple covalent amphoteric


B giant covalent basic only
C ionic amphoteric
D ionic basic only

13 X and Y are elements of the third period.

X and Y are individually heated in excess chlorine. Each product is purified and then separately
added to water, producing two solutions. Both solutions have a pH of less than 5.

What could be X and Y?

A Na and P B Mg and Al C Mg and Si D Si and P

© UCLES 2018 9701/13/M/J/18 [Turn over


6

14 An ore contains magnesium carbonate and barium carbonate. A sample of the ore is dissolved in
nitric acid.

How could this solution be processed into a magnesium compound and a separate barium
compound?

A Add HCl (aq), filter off the solid barium chloride.


B Add HCl (aq), filter off the solid magnesium chloride.
C Add H2SO4(aq), filter off the solid barium sulfate.
D Add H2SO4(aq), filter off the solid magnesium sulfate.

15 When calcium and calcium hydride, CaH2, react separately with water, they each produce a white
solid and a colourless gas. The white solid is the same compound in each reaction.

Which statement is correct?

A Both Ca and CaH2 produce H2.


B Both Ca and CaH2 produce O2.
C Ca produces H2 and CaH2 produces O2.
D Ca produces O2 and CaH2 produces H2.

16 When concentrated sulfuric acid is added to solid sodium chloride, HCl is formed but not Cl 2.

When concentrated sulfuric acid is added to solid sodium iodide, I2 is formed.

Which statement explains these observations?

A Sulfuric acid is an oxidising agent and chloride ions are more easily oxidised.
B Sulfuric acid is an oxidising agent and iodide ions are more easily oxidised.
C Sulfuric acid is a reducing agent and chloride ions are more easily reduced.
D Sulfuric acid is a reducing agent and iodide ions are more easily reduced.

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7

17 Silver chloride and silver iodide form equilibria when added to water.

AgCl(s) Ag+(aq) + Cl –(aq) Kc = K1

AgI(s) Ag+(aq) + I–(aq) Kc = K2

Each equilibrium position lies well to the left.

Silver iodide will not dissolve in aqueous ammonia. Silver chloride will dissolve in aqueous
ammonia. Another equilibrium is formed.

Ag+(aq) + 2NH3(aq) Ag(NH3)2+(aq) Kc = K3

The position of this equilibrium lies to the right.

What is the order of magnitude for these three equilibrium constants?

A K1 > K2 > K3
B K2 > K1 > K3
C K3 > K1 > K2
D K3 > K2 > K1

18 Elements and their compounds are important as catalysts.

In which process is a compound used, rather than an element?

A catalytic converters
B Contact process
C Haber process
D hydrogenation of alkenes

19 The gaseous products of heating a mixture of Ca(OH)2 and NH4Cl are passed through solid CaO.
This absorbs water vapour and a gas, W, is collected.

A sample of W is oxidised by Cl 2(g) to produce two gases, X and Y.

X is an element. Y is acidic.

Y reacts with W to produce Z.

What are X and Z?

X Z

A N2 CaCl 2
B N2 NH4Cl
C O2 CaCl 2
D O2 NH4Cl

© UCLES 2018 9701/13/M/J/18 [Turn over


8

20 Molecule G is shown.

How many chiral centres are present in each molecule of G?

A 1 B 2 C 3 D 4

21 Sibirene, C15H24, is reacted with an excess of HBr(g). The major product is X.

excess HBr(g)
X

sibirene

What is the skeletal formula of X?

A B

Br
Br
Br Br

C D

Br
Br Br Br

© UCLES 2018 9701/13/M/J/18


9

22 Which statement is not correct?

A Combustion of PVC produces a highly acidic gas.


B PVC molecules are saturated.
C The empirical formula of PVC is the same as the empirical formula of its monomer.
D The repeat unit of PVC is (CHCl CHCl ) .

23 The presence of a halogen in an organic compound may be detected by warming the organic
compound with aqueous silver nitrate.

Which compound would be the quickest to produce a precipitate?

A B C D
Cl F F Cl

Cl Cl F Br

Cl F I F

24 Halogenoalkanes react with NaOH(aq) either by an SN1 mechanism or by an SN2 mechanism.


The mechanism followed by the reaction depends on the structure of the halogenoalkane.

This question is about the reaction of 3-bromo-3-ethylpentane, (C2H5)3CBr.

Which statement is correct?

A The mechanism is SN1, due to the stabilisation of an intermediate anion by three alkyl
groups.
B The mechanism is SN1, due to the stabilisation of an intermediate cation by three alkyl
groups.
C The mechanism is SN2, due to the stabilisation of an intermediate anion by three alkyl
groups.
D The mechanism is SN2, due to the stabilisation of an intermediate cation by three alkyl
groups.

25 Which compound is a secondary alcohol that can be dehydrated to form an alkene with Mr = 70?

A B C D

OH
OH OH OH

© UCLES 2018 9701/13/M/J/18 [Turn over


10

26 When 0.0075 mol of alcohol X are completely burnt in excess oxygen and the gases produced
are passed through an excess of limewater (calcium hydroxide solution), 3.0 g of calcium
carbonate are produced.

When X is warmed with acidified potassium dichromate(VI) there is a colour change from orange
to green.

What could be the identity of X?

A CH3CH(OH)CH2CH3
B (CH3)3COH
C CH3CH2CH2OH
D CH3CH(OH)CH3

27 Considering only structural isomers, what is the number of alcohols of each type with the formula
C5H12O?

primary secondary tertiary

A 3 3 2
B 4 2 2
C 4 3 1
D 5 2 1

28 A student carried out a two-stage synthesis in which CH3CH2CH2Br was converted into
CH3CH2CH2CO2H.

Which compound could have been formed by the first stage of this synthesis?

A CH3CH2CH2OH
B CH3CH2CH2CHO
C CH3CH2CN
D CH3CH2CH2CN

29 An ester X has the structural formula CH3CO2CH(CH3)CH2CH3. X can be prepared by heating an


alcohol Y, under reflux, with ethanoic acid and an acid catalyst.

What is the correct name for Y?

A butan-1-ol
B butan-2-ol
C butan-3-ol
D methylpropan-2-ol

© UCLES 2018 9701/13/M/J/18


11

30 Compound S can be extracted from natural compounds. Reacting S with hot, concentrated
KMnO4 produces the organic product, T. Some of the absorptions found in the infra-red spectra of
S and T are described.

S has no strong absorption between 1670 and 1740 cm–1.

T has a strong absorption at 1720 cm–1 but has no strong, broad absorption between 2500 and
3000 cm–1.

From this information, what could be the formulae of S and T?

S T

A CH3(CH2)5CH=CH2 CH3(CH2)5CO2H

B CH3COCH2CH2COCH(CH3)2

CH3CO
C CH3COCH(COCH3)CH2CH2CH(COCH3)CH3

D HO2CCH2CH2COCH2COCH3

© UCLES 2018 9701/13/M/J/18 [Turn over


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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

Use of the Data Booklet may be appropriate for some questions.

31 Complete combustion of a sample of a hydrocarbon gave 0.132 g of carbon dioxide and 0.054 g
of water.

Which formulae could correctly represent this hydrocarbon?

1 CH2=CH2
2 CH3CH=CH2
3 CH3CH=CHCH3

32 Which statements are correct?

1 Magnesium carbonate decomposes at a lower temperature than calcium carbonate.


2 Calcium hydroxide is more soluble in water than magnesium hydroxide.
3 Calcium is a stronger reducing agent than magnesium.

33 Ammonia and chlorine react as shown.

8NH3 + 3Cl 2 → N2 + 6NH4Cl

Which statements are correct?

1 Each nitrogen atom is oxidised.


2 Each chlorine atom is reduced.
3 Ammonia behaves as a base.

© UCLES 2018 9701/13/M/J/18


13

34 The diagram shows the reaction pathway for a reversible reaction.

energy 90
/ kJ mol–1
30

extent of reaction

Which statements are correct?

1 The forward reaction is exothermic.


2 The enthalpy change for the forward reaction is –30 kJ mol–1.
3 The enthalpy change for the backward reaction is +90 kJ mol–1.

35 The structure of metals is considered to be positive ions surrounded by delocalised electrons.

The melting points of the metals in Period 3 increase with increasing atomic number.

Which statements help to explain this trend from sodium to aluminium?

1 The charge on the metal ion increases.


2 There are more delocalised electrons per metal ion.
3 The radius of the metal ion decreases.

36 Under room conditions, 600 cm3 of a gas, X, has a mass of 0.700 g.

What could X be?

1 carbon monoxide
2 ethene
3 nitrogen

37 Which compounds, on reaction with NaBH4, form a compound with a chiral carbon atom?

1 CH3CH2CH2COCH3
2 CH2CHCOCH2CH3
3 CH3CH2COCH2CH3

© UCLES 2018 9701/13/M/J/18 [Turn over


14

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

38 Compound Y is a straight chain molecule with formula CnH2n+1X. X is a halogen. The Mr of Y


is 137. The halogen atom is on the second carbon atom in the chain.

Which statements are correct?

1 Y contains a chiral centre.


2 Y can eliminate HX to form two structurally isomeric alkenes.
3 Y can eliminate HX to form two geometrically isomeric alkenes.

39 Propanone and hydrogen cyanide react together by the mechanism shown.

H 3C H3C O– H 3C OH
C O C H CN C + CN–

H 3C H3 C CN H 3C CN
CN–

Which statements about this mechanism are correct?

1 CN– is an electrophile.
2 It is an addition reaction.
3 Heterolytic bond breaking is involved.

40 Acrolein is an organic compound with the molecular formula C3H4O. It is used in water treatment
and as a herbicide. When acrolein reacts with 2,4-dinitrophenylhydrazine an orange precipitate is
obtained. Reaction of acrolein with Tollens’ reagent produces a silver mirror.

Which statements are correct?

1 Acrolein reacts with alkaline aqueous iodine to produce a yellow precipitate.


2 Acrolein can be reduced to a primary alcohol.
3 Acrolein decolourises bromine water.

© UCLES 2018 9701/13/M/J/18


9701/13 Cambridge International AS/A Level – Mark Scheme May/June 2018
PUBLISHED

Question Answer Marks

1 B 1

2 D 1

3 B 1

4 C 1

5 C 1

6 A 1

7 D 1

8 D 1

9 C 1

10 D 1

11 D 1

12 C 1

13 D 1

14 C 1

15 A 1

16 B 1

17 C 1

18 B 1

19 B 1

20 C 1

21 D 1

22 D 1

23 C 1

24 B 1

25 B 1

26 A 1

27 C 1

28 D 1

© UCLES 2018 Page 2 of 3


9701/13 Cambridge International AS/A Level – Mark Scheme May/June 2018
PUBLISHED

Question Answer Marks

29 B 1

30 B 1

31 A 1

32 A 1

33 C 1

34 B 1

35 A 1

36 A 1

37 B 1

38 A 1

39 C 1

40 C 1

© UCLES 2018 Page 3 of 3


2

Section A

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

Use of the Data Booklet may be appropriate for some questions.

1 The first four ionisation energies for element X are shown in the table.

ionisation energy 1st 2nd 3rd 4th


value / kJ mol–1 577 1980 2960 6190

Which ion of X is produced by removing an electron from a filled shell?

A X+ B X2+ C X3+ D X4+

2 What is a basic assumption of the kinetic theory, as applied to an ideal gas?

A Collisions between gas molecules are elastic.


B Each gas molecule occupies a finite volume.
C Gases consist of particles that experience the force of gravity.
D Gas molecules attract each other with weak intermolecular forces.

3 A sample of the hydrocarbon C6H12 is completely burned in dry oxygen and the product gases are
collected as shown.

product gases,
H2O + CO2 + excess of O2 excess of O2

P Q

anhydrous soda lime


calcium chloride (to absorb CO2)
(to absorb H2O)

The increases in mass of the collecting vessels P and Q are MP and MQ, respectively.

What is the ratio MP / MQ?

A 0.41 B 0.82 C 1.2 D 2.4

© UCLES 2018 9701/11/O/N/18


3

4 5.0 g samples of the carbonates of barium, copper, lithium and magnesium are decomposed to
the metal oxides and carbon dioxide.

For which compound is there the greatest loss in mass?

A barium carbonate

B copper(II) carbonate

C lithium carbonate
D magnesium carbonate

5 In this question you should assume methane behaves as an ideal gas.

The gas laws can be summarised in the ideal gas equation below.

pV = nRT

The volume of a sample of methane is measured at a temperature of 60 °C and a pressure of


103 kPa. The volume measured is 5.37 × 10–3 m3.

What is the mass of the sample of methane, given to two significant figures?

A 0.0032 g B 0.018 g C 3.2 g D 18 g

6 A butane burner is used to heat water. The Mr of butane is 58.

● of butane is –2877 kJ mol–1.

● 250 g of water is heated from 12 °C to 100 °C.


● The burner transfers 47% of the heat released from the burning fuel to the water.

Assume that the butane undergoes complete combustion and none of the water evaporates.

What is the minimum mass of butane that must be burnt?

A 0.068 g B 1.85 g C 3.94 g D 4.48 g

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7 Nitric acid is known to take part in the oxidation of atmospheric sulfur dioxide. One possible
reaction is shown.

SO2 + HNO3 → NO+ + HSO4–

Which row shows the correct changes in oxidation numbers of nitrogen and sulfur?

nitrogen sulfur

A –3 +3
B –2 +2
C –2 +3
D –1 +2

8 A transition metal ion, M2+, reacts with acidified dichromate(VI) ions to form M4+ ions, Cr3+ ions,
and H2O.

Which equation correctly represents this reaction?

A Cr2O72– + 14H+ + M2+ → 2Cr3+ + 7H2O + M4+

B Cr2O72– + 14H+ + 2M2+ → 2Cr3+ + 7H2O + 2M4+

C Cr2O72– + 14H+ + 3M2+ → 2Cr3+ + 7H2O + 3M4+

D Cr2O72– + 14H+ + 6M2+ → 2Cr3+ + 7H2O + 6M4+

9 In this question you should assume that all gases behave ideally.

Hydrogen and iodine react reversibly in the following reaction. The system reaches dynamic
equilibrium.

H2(g) + I2(g) 2HI(g) ∆H = –9.5 kJ mol–1

Which statement must be true for the Kp of this equilibrium to be constant?

A The partial pressures of H2, I2 and HI are equal.


B The external pressure is constant.
C The forward and reverse reactions have stopped.
D The temperature is constant.

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10 0.200 mol of sulfur dioxide and 0.200 mol of oxygen are placed in a 1.00 dm3 sealed container.
The gases are allowed to react until equilibrium is reached.

2SO2 + O2 2SO3

At equilibrium there is 0.100 mol of SO3 in the container.

What is the value of Kc?

A 0.150 mol dm–3


B 0.800 mol dm–3
C 1.25 mol–1 dm3
D 6.67 mol–1 dm3

11 Two reactions are shown.

reaction 1 N2(g) + 3H2(g) 2NH3(g)


reaction 2 2O3(g) 3O2(g)

In reaction 1, a finely powdered iron catalyst is used.

In reaction 2, a vaporised tetrachloromethane catalyst in ultraviolet light is used.

Which statement about the catalysts used is correct?

A Both reaction 1 and reaction 2 use a heterogeneous catalyst.


B Both reaction 1 and reaction 2 use a homogeneous catalyst.
C Reaction 1 uses a heterogeneous catalyst and reaction 2 uses a homogeneous catalyst.
D Reaction 1 uses a homogeneous catalyst and reaction 2 uses a heterogeneous catalyst.

12 Sodium and sulfur are burned separately in oxygen.

Each reaction has a distinctive coloured flame.

Which row is correct?

Na + O2 S + O2

A white blue
B white yellow
C yellow blue
D yellow yellow

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13 X and Y are elements in Period 3 of the Periodic Table.

● The oxide of X is a solid at room temperature. This oxide has a giant structure.
● The chloride of X does not react with water.
● Argon is the only element in Period 3 with a lower melting point than Y.

What could be the formula of a compound formed between elements X and Y?

A Al 2S3 B MgS C NaCl D PCl 5

14 Which row describes the structure and bonding of SiO2 and SiCl 4?

SiO2 SiCl 4
bonding structure bonding structure

A covalent giant covalent giant


B covalent giant covalent simple
C ionic giant covalent giant
D ionic giant covalent simple

15 A sample of anhydrous calcium nitrate is placed in a test-tube and heated in a roaring Bunsen
flame until it decomposes. The description of the gas in the test-tube is then noted. A glowing
splint is then put into the test-tube and any changes are noted.

Which observations are correct?

description of the result of


gas in the test-tube glowing splint test

A brown the splint goes out


B brown the splint relights
C colourless the splint goes out
D colourless the splint relights

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16 Which row correctly describes the properties of the halogens as Group 17 is descended from
chlorine to iodine?

strength as
volatility
oxidising agent

A decreases decreases

B decreases increases

C increases decreases

D increases increases

17 Reaction 1: chlorine reacts with cold aqueous sodium hydroxide to form solution Z.

Reaction 2: solution Z is heated and forms Cl O3–(aq) and Cl –(aq).

Which equations represent reaction 1 and reaction 2?

A reaction 1 2Cl 2 + 4OH– → Cl O2– + 3Cl – + 2H2O


reaction 2 3Cl O2– → 2Cl O3– + Cl –

B reaction 1 2Cl 2 + 4OH– → Cl O2– + 3Cl – + 2H2O


reaction 2 3Cl O– → Cl O3– + 2Cl –

C reaction 1 Cl 2 + 2OH– → Cl O– + Cl – + H2O


reaction 2 2Cl O– + 2OH– → Cl O3– + Cl – + H2O

D reaction 1 Cl 2 + 2OH– → Cl O– + Cl – + H2O


reaction 2 3Cl O– → Cl O3– + 2Cl –

18 Which statement explains the observation that magnesium hydroxide dissolves in aqueous
ammonium chloride, but not in aqueous sodium chloride?

A The ionic radius of the NH4+ ion is similar to that of Mg2+ but not that of Na+.
B NH4Cl dissociates less fully than NaCl.
C The Na+ and Mg2+ ions have the same number of electrons.
D The NH4+ ion can donate a proton.

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19 Transition elements and their compounds are widely used as catalysts.

What is the identity and what is the oxidation number of the element present in the catalyst used
in the Contact process?

element oxidation number

A iron 0
B iron +3
C vanadium 0
D vanadium +5

20 What is true of every nucleophile?

A It attacks a double bond.


B It donates a lone pair of electrons.
C It is a single atom.
D It is negatively charged.

21 X has the molecular formula C5H12O. X has a branched carbon skeleton and a secondary alcohol
functional group.

How many structural isomers fit this description of X?

A 1 B 2 C 3 D 4

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22 A new jet fuel has been produced that is a mixture of different structural isomers of compound Q.

Which skeletal formula represents a structural isomer of Q?

A B

C D

23 The conversion of propene to propan-2-ol can be carried out in two stages represented by the
equations shown.

reaction 1 CH3CH=CH2(g) + HI(g) → CH3CHICH3(l)

reaction 2 CH3CHICH3(l) + KOH(aq) → CH3CH(OH)CH3(aq) + K+(aq) + I–(aq)

How can these two reactions be described?

reaction 1 reaction 2

A addition elimination
B addition substitution
C elimination substitution
D substitution elimination

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24 An organic molecule W contains 3 carbon atoms. It requires 4.5 molecules of oxygen for
complete combustion.

What could W be?

A propane
B propanoic acid
C propanone
D propan-1-ol

25 Compound J, C15H23Br2Cl, is reacted with an excess of a hot concentrated solution of


sodium hydroxide in ethanol. One of the products is X.

excess NaOH
Cl
Br in ethanol
X
Br

compound J

What could be the skeletal formula of X?

A B C D

26 Sodium reacts with 1 mol of compound Y to produce 1 mol of H2(g).

Which compound could Y be?

A CH3CH2CH2CH2OH
B (CH3)3COH
C CH3CH2CH2CO2H
D CH3CH(OH)CO2H

27 Which compound shows optical isomerism and gives a positive test with alkaline aqueous iodine?

A CH3COCH(OH)CH3
B CH3COCH2CH2OH
C HOCH2CH(CH3)CHO
D (CH3)2C(OH)CHO

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28 Ethanedioic acid, HO2CCO2H, is reduced using an excess of lithium aluminium hydride, LiAl H4.

What is the organic product of the reaction?

A ethanol
B ethane-1,2-diol
C ethanedial, OHCCHO
D methane

29 The diester shown can be hydrolysed by heating with an excess of aqueous sodium hydroxide.

O H H H H

H C O C C C O C C H

H H H O H

What would the products of this reaction be?

O H H H O H

A H C HO C C C OH HO C C H

OH H H H H

O H H H O H

B H C NaO C C C ONa HO C C H

OH H H H H

O H H H O H

C H C HO C C C OH NaO C C H

ONa H H H H

O H H H O H

D H C NaO C C C ONa NaO C C H


ONa H H H H

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12

30 J is a branched-chain alcohol, C5H12O. J is heated under reflux with an excess of Cr2O72– / H+ until
no further reaction occurs. An organic compound K is formed in good yield.

The infra-red spectrum of K is shown.

100

transmittance
%
50

0
4000 3000 2000 1500 1000 500
wavenumber / cm–1

What are the structures of the branched-chain alcohol J and compound K?

J K

A CH3CH(CH3)CH2CH2OH CH3CH(CH3)CH2CHO
B CH3CH2CH(OH)CH2CH3 CH3CH2COCH2CH3
C CH3CH(CH3)CH(OH)CH3 CH3CH(CH3)COCH3
D CH3CH(CH3)CH2CH2OH CH3CH(CH3)CH2COOH

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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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

Use of the Data Booklet may be appropriate for some questions.

31 Which ions contain one or more unpaired electrons?

1 Cu2+
2 Mn3+
3 V3+

32 Which molecules and ions have a bond angle of 120°?

1 BF3
2 CH3–
3 NH3

33 Which statements are correct for all exothermic reactions?

1 ∆H for the reaction is negative.


2 On a reaction pathway diagram the products are shown lower than the reactants.
3 The reaction will occur without heating.

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14

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

34 The factors affecting the rate of reaction between aqueous sodium thiosulfate and hydrochloric
acid can be investigated. The ionic equation for the reaction is shown.

S2O32–(aq) + 2H+(aq) → H2O(l) + S(s) + SO2(aq)

Which of the following can be used to investigate the rate of this reaction?

1 change of mass
2 change of appearance caused by formation of a precipitate
3 change of electrical conductivity

35 Which reaction routes can be used to make a pure sample of barium sulfate?

heat dilute dilute filter, wash


1 Ba metal product product 2 product 3
in O2 HCl H2SO4 and dry

strong solid an excess dilute filter, wash


2 Ba(NO3)2 product 2 product 3
heat in air product of water H2SO4 and dry

dilute dilute filter, wash


3 Ba(OH)2 product product 2
HNO3 H2SO4 and dry

36 Which properties increase from magnesium to barium?

1 ionic radius of the cation M2+


2 screening of outermost electrons by inner shells
3 solubility of the hydroxides, M(OH)2, in water

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15

37 2-methylpropene can react in more than one way with chlorine.

One of the reactions follows the pathway shown.

CH3 CH3 CH3


+
CH2 C + Cl 2 → Cl CH2 C + Cl – → Cl CH2 C + HCl

CH3 CH3 CH2


2-methylpropene intermediate product

Which statements about this mechanism are correct?

1 The intermediate has all carbon atoms in the same plane.


2 There is an electrophilic attack on the double bond.
3 It is a free radical mechanism.

38 The halogenoalkanes listed below all react with NaOH(aq).

Which reactions proceed mainly by an SN1 mechanism?

1 1-iodopropane
2 2-iodo-2-methylpropane
3 2-bromo-2-methylbutane

39 3-oxobutanoic acid can be synthesised in a two-step process.

O O
X Y
OH
3-oxobutanoic acid

What could be the structure of X?

1 OH

Cl O
2
OH

Br O
3
H

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16

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

40 Ethanal reacts with HCN in the presence of KCN.

Which changes in bonding occur during this reaction?

1 A carbon-carbon bond is formed.


2 A carbon-hydrogen bond is broken.
3 A carbon-nitrogen bond is broken.

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.

To avoid the issue of disclosure of answer-related information to candidates, all copyright acknowledgements are reproduced online in the Cambridge
International Examinations Copyright Acknowledgements Booklet. This is produced for each series of examinations and is freely available to download at
www.cie.org.uk after the live examination series.

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 2018 9701/11/O/N/18


9701/11 Cambridge International AS/A Level – Mark Scheme October/November
PUBLISHED 2018

Question Answer Marks

1 D 1

2 A 1

3 A 1

4 C 1

5 C 1

6 C 1

7 B 1

8 C 1

9 D 1

10 D 1

11 C 1

12 C 1

13 C 1

14 B 1

15 B 1

16 A 1

17 D 1

18 D 1

19 D 1

20 B 1

21 A 1

22 C 1

23 B 1

24 D 1

25 B 1

26 D 1

27 A 1

28 B 1

© UCLES 2018 Page 2 of 3


9701/11 Cambridge International AS/A Level – Mark Scheme October/November
PUBLISHED 2018

Question Answer Marks

29 C 1

30 C 1

31 A 1

32 D 1

33 B 1

34 C 1

35 A 1

36 A 1

37 B 1

38 C 1

39 A 1

40 B 1

© UCLES 2018 Page 3 of 3


2

Section A

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

Use of the Data Booklet may be appropriate for some questions.

1 Which statement about enthalpy changes is correct?

A Enthalpy changes of atomisation are always negative.


B Enthalpy changes of combustion are always positive.
C Enthalpy changes of formation are always positive.
D Enthalpy changes of neutralisation are always negative.

2 Beams of charged particles are deflected by an electrical field. The angle of deflection of a
particle is proportional to its charge / mass ratio.

In an experiment protons are deflected by an angle of +15°. In another experiment under identical
conditions 2H– ions are deflected by an angle of Y°.

What is the value of Y?

A –30.0 B –7.5 C +7.5 D +30.0

3 Rubidium and bromine form ions that are isoelectronic. Each ion has 36 electrons.

Which row is correct?

bromine
rubidium radii
/ bromide radii

A atomic < ionic atomic < ionic


B atomic < ionic atomic > ionic
C atomic > ionic atomic < ionic
D atomic > ionic atomic > ionic

4 In which set do all the molecules have all their atoms arranged in one plane?

A Al Cl 3, BF3, PH3
B Al Cl 3, CO2, NH3
C BF3, C2H4, C3H6
D C2H4, CO2, H2O

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5 Flask X contains 5 dm3 of helium at 12 kPa pressure and flask Y contains 10 dm3 of neon at 6 kPa
pressure.

If the flasks are connected at constant temperature, what is the final pressure?

A 8 kPa B 9 kPa C 10 kPa D 11 kPa

6 Exactly 1.00 g of a metallic element reacts completely with 300 cm3 of oxygen at 298 K and 1 atm
pressure to form an oxide which contains O2– ions.

The volume of one mole of gas at this temperature and pressure is 24.0 dm3.

What could be the identity of the metal?

A calcium
B magnesium
C potassium
D sodium

7 Ethanol is increasingly being used as a fuel for cars.

The standard enthalpy change of formation of carbon dioxide is –393 kJ mol–1.


The standard enthalpy change of formation of water is –286 kJ mol–1.
The standard enthalpy change of formation of ethanol is –277 kJ mol–1.

What is the standard enthalpy change of combustion of ethanol?

A –1921 kJ mol–1
B –1367 kJ mol–1
C –956 kJ mol–1
D – 402 kJ mol–1

8 Ammonium metavanadate, NH4VO3, can be used to make a solution containing VO2Cl, which
contains chloride ions.

What is the change in the oxidation number of vanadium in this reaction?

A –1 B 0 C +1 D +2

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9 In this question, all pressures are measured in atm.

The equation represents the equilibrium between three gaseous substances X, Y and Z.

X + 3Y 2Z

At temperature T1, the numerical value of Kp, the equilibrium constant, is 2.

At a higher temperature T2, the partial pressures at equilibrium are as shown.

X Y Z

2 3 5

Which row is correct?

the numerical the forward


value of Kp at T2 reaction is

A 54 / 25 endothermic
B 54 / 25 exothermic
C 25 / 54 endothermic
D 25 / 54 exothermic

10 In a chemical system the particles involved have a range of energies. This can be shown on a
graph called the Boltzmann distribution.

Which statement correctly explains the effect of a catalyst on the particles in a chemical system?

A A catalyst enables particles with a lower energy to collide successfully.


B A catalyst increases the number of particles with higher energies.
C A catalyst increases the number of particles with the most probable energy value.
D A catalyst increases the value of the most probable particle energy.

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11 Nitrogen and hydrogen can react together to form ammonia.

The formation of ammonia is exothermic.

The rate and yield of the reaction can be altered by changing the conditions under which the
reaction is carried out.

Which row shows the effects of adding iron to the mixture and increasing the temperature?

adding iron increasing the temperature

A has no effect on the equilibrium yield reduces the equilibrium yield


B increases the equilibrium yield increases the equilibrium yield
C increases the equilibrium yield increases the rate
D increases the rate has no effect on the equilibrium yield

12 The melting points of the Period 3 elements phosphorus to argon are shown in the table.

element P S Cl Ar
mp / K 317 392 172 84

Which factor explains the changes in melting points from phosphorus to argon?

A the changes in electronegativity from phosphorus to argon


B the changes in first ionisation energy from phosphorus to argon
C the increase in the number of electrons in each atom from phosphorus to argon
D the number of atoms in each molecule of the element from phosphorus to argon

13 Which observations are made when a sample of silicon chloride, SiCl 4, is added to a beaker of
water?

A No visible change is observed.


B Steamy fumes and a precipitate are both observed.
C The appearance of a precipitate is the only observation.
D The appearance of steamy fumes is the only observation.

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14 A 4.00 g sample of an anhydrous Group 2 metal nitrate is heated strongly until there is no further
change. A solid residue of mass 1.37 g is formed.

Which metal is present?

A barium
B calcium
C magnesium
D strontium

15 In which row are all statements comparing magnesium and barium correct?

fourth ionisation energy reaction with water


magnesium barium magnesium barium

A higher lower faster slower


B higher lower slower faster
C lower higher faster slower
D lower higher slower faster

16 Which statement about the halogens is correct?

A Iodine cannot behave as an oxidising agent.


B The volatility of the elements increases from chlorine to iodine because of the increase in
molecular size down the group.
C When an equimolar mixture of chlorine and hydrogen is exploded, only one product is
formed.
D When concentrated sulfuric acid is added to solid sodium bromide, hydrogen sulfide is one of
the products.

17 Chlorine reacts with both hot and cold sodium hydroxide to form products containing chlorine.

Cold sodium hydroxide forms sodium chlorate(X) and hot sodium hydroxide forms sodium
chlorate(Y). X and Y are oxidation numbers.

Which equation is correct?

A Y=X–6 B Y=X–4 C Y=X+4 D Y=X+6

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18 The product of the Contact process is Z.

Which reaction or process leads to the formation of a gas that can neutralise an aqueous solution
of Z?

A atmospheric lightning
B combustion of fuel in an internal combustion engine
C the Haber process
D thermal decomposition of Group 2 nitrates

19 If ammonium cyanate is heated in the absence of air, the only product of the reaction is urea,
CO(NH2)2. No other products are formed in the reaction.

What is the formula of the cyanate ion present in ammonium cyanate?

A CON2– B CON22– C OCN– D OCN2–

20 There are three structural isomers with the formula C5H12.

Which formulae correctly represent these three structural isomers?

A CH3CH2CH2CH2CH3 CH3CH(CH3)CH2CH3 C(CH3)4


B CH3CH2CH2CH2CH3 CH3CH(CH3)CH2CH3 CH3CH2CH(CH3)CH3

21 The diagram shows a molecule that has σ bonds and π bonds.

CH2 CH CH2 C O CH2 CH CH2

How many σ bonds are present in this molecule?

A 15 B 17 C 18 D 21

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22 Polyethene is made by the polymerisation of ethene.

Which statement is correct?

A The monomer and the polymer have different empirical formulae.


B The monomer can be oxidised without heat whereas the polymer cannot.
C The monomer can be used as a fuel whereas the polymer cannot.
D The monomer has greater van der Waals’ forces than the polymer.

23 Compound P reacts separately with KOH(aq) and HBr.

CH2CHCH2CH2Cl
compound P

What are the mechanisms of these two reactions?

KOH (aq) HBr

A nucleophilic addition electrophilic addition


B nucleophilic addition free radical substitution
C nucleophilic substitution electrophilic addition
D nucleophilic substitution free radical substitution

© UCLES 2018 9701/12/O/N/18


9

24 Which statement about compound Q is correct?

CH3C CHCH2CH3

CO2CH3

H CH3

A It could be polymerised to give a polymer with the repeat unit C C .

CO2CH3 CH2CH3

Cl Cl

B It reacts with chlorine by a free radical mechanism to give CH3CH C CH CH3 .

CO2CH3 H

OH OH

C It reacts with cold, dilute acidified manganate(VII) to give CH3C C CH2CH3 .

CO2CH3 H

Br Br

D It reacts with bromine via a free radical mechanism to give CH3 C C CH2CH3 .

CO2CH3 H

25 A halogenoalkane has the molecular formula C5H11Br. The halogenoalkane does not form an
alkene when treated with ethanolic sodium hydroxide.

What could be the halogenoalkane?

A 1-bromo-2-methylbutane
B 2-bromo-2-methylbutane
C 3-bromopentane
D bromodimethylpropane

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26 The reactions of four organic compounds are given in the table.

Which compound could be propan-2-ol?

reagent / observations

when oxidised with Cr2O72– / H+, gives when added to ethanoic acid, and a
an organic product with a boiling point few drops of conc. H2SO4, gives a
greater than the original compound sweet-smelling compound

A no no
B no yes
C yes no
D yes yes

27 Compound X has the empirical formula C2H3O.

Compound X reacts with 2,4-dinitrophenylhydrazine reagent to give an orange precipitate and


also decolourises warmed acidified potassium manganate(VII) solution.

What could be the identity of X?

A B

O H H O H O H

C C C C H C C C C H

H H H H H O H

C D

HO O O H H H H O
H C H
C C C C C C
H C C C
HO H H H H H
H H

28 Compound Y gives methanol and sodium ethanoate on treatment with aqueous sodium
hydroxide.

What is the structure of Y?

A CH3CO2CH3
B HCO2C2H5
C HO2CCH2CHO
D HOCH2CH2COOH

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11

29 Which compound can be used to make propanoic acid by treatment with a single reagent?

A CH2=CHCH2CH3
B CH3CH2CH2CN
C CH3CH(OH)CN
D CH3CH(OH)CH3

30 The infra-red spectrum of compound L is shown.

100

transmittance
%
50

0
4000 3000 2000 1500 1000 500
wavenumber / cm–1

What could be the structure of L?

A HOCH2COCH2OH
B HOCH2CH(OH)CHO
C HOCH2CH(OH)CH2OH
D HOCH2CH2COOH

© UCLES 2018 9701/12/O/N/18 [Turn over


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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

Use of the Data Booklet may be appropriate for some questions.

31 Zinc reacts with hydrochloric acid according to the following equation.

Zn + 2HCl → ZnCl 2 + H2

Which statements are correct?

1 A 3.27 g sample of zinc reacts with an excess of hydrochloric acid to give 0.0500 mol of zinc
chloride.
2 A 6.54 g sample of zinc reacts completely with exactly 100 cm3 of 1.00 mol dm–3 hydrochloric
acid.
3 A 13.08 g sample of zinc reacts with an excess of hydrochloric acid to give 9.60 dm3 of
hydrogen, measured at room conditions.

32 The melting point of chlorine is lower than the melting point of iodine.

Which statements help to explain this difference?

1 Iodine has more electrons than chlorine and so has stronger van der Waals’ forces.
2 An iodine molecule is more polar than a chlorine molecule.
3 The covalent bonds between iodine atoms are stronger than the covalent bonds between
chlorine atoms.

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13

33 Aqueous iron(II) sulfate can take part in redox reactions.

6FeSO4 + 7H2SO4 + Na2Cr2O7 → 3Fe2(SO4)3 + Cr2(SO4)3 + Na2SO4 + 7H2O

Which redox changes occur during this reaction?

1 Fe(II) is oxidised to Fe(III).

2 Cr(VI) is reduced to Cr(III).


3 Oxygen is reduced to water.

34 The equation represents an equilibrium.

4NH3(g) + 5O2(g) 4NO(g) + 6H2O(g) ∆H = –900 kJ mol–1

What would increase the concentration of NO at equilibrium?

1 a reduction in the reaction temperature


2 the use of a suitable catalyst
3 an increase in the total pressure

35 A sample containing x mol of Al 2Cl 6 is dissolved in water to give solution W.

In order to precipitate all of the aluminium as its hydroxide, y mol of sodium hydroxide are
required.

More of the alkali is added to re-dissolve the precipitate, giving solution Z.

Which statements are correct?

1 the initial pH of solution W is below 7


2 y = 3x
3 Z contains x mol of aluminium

36 Which statements concerning calcium hydroxide are correct?

1 It is less soluble in water than strontium hydroxide.


2 When it is added to water an alkaline solution is formed.
3 It is used in agriculture to lower soil pH.

37 Which bromopropenes would react with cold bromine in the dark to form a product containing a
chiral carbon atom?

1 CHBr=CHCH3
2 CH2=CHCH2Br
3 CH2=CBrCH3

© UCLES 2018 9701/12/O/N/18 [Turn over


14

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

38 Halogenoalkanes can undergo reaction with hydroxide ions.

RBr + OH– → ROH + Br –

The reaction of some halogenoalkanes proceeds by the SN1 mechanism.

Which statements about the SN1 mechanism are correct?

1 A carbocation is formed which is stabilised by the inductive effect of the alkyl groups present.
2 Only tertiary halogenoalkanes are hydrolysed in this way.
3 The intermediate formed includes a carbon atom with five bonds attached to it.

39 Which statements about 2-methylbutan-1-ol are correct?

1 It can give HCl (g) on reaction with PCl 5.


2 It can be oxidised to give an aldehyde.
3 It displays optical isomerism.

40 The compound cis-hex-3-enal is responsible for the characteristic smell of cut grass.

O
cis-hex-3-enal

Which reagents will react with cis-hex-3-enal?

1 sodium
2 sodium borohydride
3 Fehling’s reagent

© UCLES 2018 9701/12/O/N/18


9701/12 Cambridge International AS/A Level – Mark Scheme October/November
PUBLISHED 2018

Question Answer Marks

1 D 1

2 B 1

3 C 1

4 D 1

5 A 1

6 A 1

7 B 1

8 B 1

9 D 1

10 A 1

11 A 1

12 D 1

13 B 1

14 B 1

15 B 1

16 C 1

17 C 1

18 C 1

19 C 1

20 A 1

21 C 1

22 B 1

23 C 1

24 C 1

25 D 1

26 B 1

27 A 1

28 A 1

© UCLES 2018 Page 2 of 3


9701/12 Cambridge International AS/A Level – Mark Scheme October/November
PUBLISHED 2018

Question Answer Marks

29 A 1

30 C 1

31 D 1

32 D 1

33 B 1

34 D 1

35 D 1

36 B 1

37 D 1

38 D 1

39 A 1

40 C 1

© UCLES 2018 Page 3 of 3


2

Section A

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

Use of the Data Booklet may be appropriate for some questions.

1 The first four ionisation energies for element X are shown in the table.

ionisation energy 1st 2nd 3rd 4th


value / kJ mol–1 577 1980 2960 6190

Which ion of X is produced by removing an electron from a filled shell?

A X+ B X2+ C X3+ D X4+

2 What is a basic assumption of the kinetic theory, as applied to an ideal gas?

A Collisions between gas molecules are elastic.


B Each gas molecule occupies a finite volume.
C Gases consist of particles that experience the force of gravity.
D Gas molecules attract each other with weak intermolecular forces.

3 A sample of the hydrocarbon C6H12 is completely burned in dry oxygen and the product gases are
collected as shown.

product gases,
H2O + CO2 + excess of O2 excess of O2

P Q

anhydrous soda lime


calcium chloride (to absorb CO2)
(to absorb H2O)

The increases in mass of the collecting vessels P and Q are MP and MQ, respectively.

What is the ratio MP / MQ?

A 0.41 B 0.82 C 1.2 D 2.4

© UCLES 2018 9701/13/O/N/18


3

4 5.0 g samples of the carbonates of barium, copper, lithium and magnesium are decomposed to
the metal oxides and carbon dioxide.

For which compound is there the greatest loss in mass?

A barium carbonate

B copper(II) carbonate

C lithium carbonate
D magnesium carbonate

5 In this question you should assume methane behaves as an ideal gas.

The gas laws can be summarised in the ideal gas equation below.

pV = nRT

The volume of a sample of methane is measured at a temperature of 60 °C and a pressure of


103 kPa. The volume measured is 5.37 × 10–3 m3.

What is the mass of the sample of methane, given to two significant figures?

A 0.0032 g B 0.018 g C 3.2 g D 18 g

6 A butane burner is used to heat water. The Mr of butane is 58.

● of butane is –2877 kJ mol–1.

● 250 g of water is heated from 12 °C to 100 °C.


● The burner transfers 47% of the heat released from the burning fuel to the water.

Assume that the butane undergoes complete combustion and none of the water evaporates.

What is the minimum mass of butane that must be burnt?

A 0.068 g B 1.85 g C 3.94 g D 4.48 g

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4

7 Nitric acid is known to take part in the oxidation of atmospheric sulfur dioxide. One possible
reaction is shown.

SO2 + HNO3 → NO+ + HSO4–

Which row shows the correct changes in oxidation numbers of nitrogen and sulfur?

nitrogen sulfur

A –3 +3
B –2 +2
C –2 +3
D –1 +2

8 A transition metal ion, M2+, reacts with acidified dichromate(VI) ions to form M4+ ions, Cr3+ ions,
and H2O.

Which equation correctly represents this reaction?

A Cr2O72– + 14H+ + M2+ → 2Cr3+ + 7H2O + M4+

B Cr2O72– + 14H+ + 2M2+ → 2Cr3+ + 7H2O + 2M4+

C Cr2O72– + 14H+ + 3M2+ → 2Cr3+ + 7H2O + 3M4+

D Cr2O72– + 14H+ + 6M2+ → 2Cr3+ + 7H2O + 6M4+

9 In this question you should assume that all gases behave ideally.

Hydrogen and iodine react reversibly in the following reaction. The system reaches dynamic
equilibrium.

H2(g) + I2(g) 2HI(g) ∆H = –9.5 kJ mol–1

Which statement must be true for the Kp of this equilibrium to be constant?

A The partial pressures of H2, I2 and HI are equal.


B The external pressure is constant.
C The forward and reverse reactions have stopped.
D The temperature is constant.

© UCLES 2018 9701/13/O/N/18


5

10 0.200 mol of sulfur dioxide and 0.200 mol of oxygen are placed in a 1.00 dm3 sealed container.
The gases are allowed to react until equilibrium is reached.

2SO2 + O2 2SO3

At equilibrium there is 0.100 mol of SO3 in the container.

What is the value of Kc?

A 0.150 mol dm–3


B 0.800 mol dm–3
C 1.25 mol–1 dm3
D 6.67 mol–1 dm3

11 Two reactions are shown.

reaction 1 N2(g) + 3H2(g) 2NH3(g)


reaction 2 2O3(g) 3O2(g)

In reaction 1, a finely powdered iron catalyst is used.

In reaction 2, a vaporised tetrachloromethane catalyst in ultraviolet light is used.

Which statement about the catalysts used is correct?

A Both reaction 1 and reaction 2 use a heterogeneous catalyst.


B Both reaction 1 and reaction 2 use a homogeneous catalyst.
C Reaction 1 uses a heterogeneous catalyst and reaction 2 uses a homogeneous catalyst.
D Reaction 1 uses a homogeneous catalyst and reaction 2 uses a heterogeneous catalyst.

12 Sodium and sulfur are burned separately in oxygen.

Each reaction has a distinctive coloured flame.

Which row is correct?

Na + O2 S + O2

A white blue
B white yellow
C yellow blue
D yellow yellow

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6

13 X and Y are elements in Period 3 of the Periodic Table.

● The oxide of X is a solid at room temperature. This oxide has a giant structure.
● The chloride of X does not react with water.
● Argon is the only element in Period 3 with a lower melting point than Y.

What could be the formula of a compound formed between elements X and Y?

A Al 2S3 B MgS C NaCl D PCl 5

14 Which row describes the structure and bonding of SiO2 and SiCl 4?

SiO2 SiCl 4
bonding structure bonding structure

A covalent giant covalent giant


B covalent giant covalent simple
C ionic giant covalent giant
D ionic giant covalent simple

15 A sample of anhydrous calcium nitrate is placed in a test-tube and heated in a roaring Bunsen
flame until it decomposes. The description of the gas in the test-tube is then noted. A glowing
splint is then put into the test-tube and any changes are noted.

Which observations are correct?

description of the result of


gas in the test-tube glowing splint test

A brown the splint goes out


B brown the splint relights
C colourless the splint goes out
D colourless the splint relights

© UCLES 2018 9701/13/O/N/18


7

16 Which row correctly describes the properties of the halogens as Group 17 is descended from
chlorine to iodine?

strength as
volatility
oxidising agent

A decreases decreases

B decreases increases

C increases decreases

D increases increases

17 Reaction 1: chlorine reacts with cold aqueous sodium hydroxide to form solution Z.

Reaction 2: solution Z is heated and forms Cl O3–(aq) and Cl –(aq).

Which equations represent reaction 1 and reaction 2?

A reaction 1 2Cl 2 + 4OH– → Cl O2– + 3Cl – + 2H2O


reaction 2 3Cl O2– → 2Cl O3– + Cl –

B reaction 1 2Cl 2 + 4OH– → Cl O2– + 3Cl – + 2H2O


reaction 2 3Cl O– → Cl O3– + 2Cl –

C reaction 1 Cl 2 + 2OH– → Cl O– + Cl – + H2O


reaction 2 2Cl O– + 2OH– → Cl O3– + Cl – + H2O

D reaction 1 Cl 2 + 2OH– → Cl O– + Cl – + H2O


reaction 2 3Cl O– → Cl O3– + 2Cl –

18 Which statement explains the observation that magnesium hydroxide dissolves in aqueous
ammonium chloride, but not in aqueous sodium chloride?

A The ionic radius of the NH4+ ion is similar to that of Mg2+ but not that of Na+.
B NH4Cl dissociates less fully than NaCl.
C The Na+ and Mg2+ ions have the same number of electrons.
D The NH4+ ion can donate a proton.

© UCLES 2018 9701/13/O/N/18 [Turn over


8

19 Transition elements and their compounds are widely used as catalysts.

What is the identity and what is the oxidation number of the element present in the catalyst used
in the Contact process?

element oxidation number

A iron 0
B iron +3
C vanadium 0
D vanadium +5

20 What is true of every nucleophile?

A It attacks a double bond.


B It donates a lone pair of electrons.
C It is a single atom.
D It is negatively charged.

21 X has the molecular formula C5H12O. X has a branched carbon skeleton and a secondary alcohol
functional group.

How many structural isomers fit this description of X?

A 1 B 2 C 3 D 4

© UCLES 2018 9701/13/O/N/18


9

22 A new jet fuel has been produced that is a mixture of different structural isomers of compound Q.

Which skeletal formula represents a structural isomer of Q?

A B

C D

23 The conversion of propene to propan-2-ol can be carried out in two stages represented by the
equations shown.

reaction 1 CH3CH=CH2(g) + HI(g) → CH3CHICH3(l)

reaction 2 CH3CHICH3(l) + KOH(aq) → CH3CH(OH)CH3(aq) + K+(aq) + I–(aq)

How can these two reactions be described?

reaction 1 reaction 2

A addition elimination
B addition substitution
C elimination substitution
D substitution elimination

© UCLES 2018 9701/13/O/N/18 [Turn over


10

24 An organic molecule W contains 3 carbon atoms. It requires 4.5 molecules of oxygen for
complete combustion.

What could W be?

A propane
B propanoic acid
C propanone
D propan-1-ol

25 Compound J, C15H23Br2Cl, is reacted with an excess of a hot concentrated solution of


sodium hydroxide in ethanol. One of the products is X.

excess NaOH
Cl
Br in ethanol
X
Br

compound J

What could be the skeletal formula of X?

A B C D

26 Sodium reacts with 1 mol of compound Y to produce 1 mol of H2(g).

Which compound could Y be?

A CH3CH2CH2CH2OH
B (CH3)3COH
C CH3CH2CH2CO2H
D CH3CH(OH)CO2H

27 Which compound shows optical isomerism and gives a positive test with alkaline aqueous iodine?

A CH3COCH(OH)CH3
B CH3COCH2CH2OH
C HOCH2CH(CH3)CHO
D (CH3)2C(OH)CHO

© UCLES 2018 9701/13/O/N/18


11

28 Ethanedioic acid, HO2CCO2H, is reduced using an excess of lithium aluminium hydride, LiAl H4.

What is the organic product of the reaction?

A ethanol
B ethane-1,2-diol
C ethanedial, OHCCHO
D methane

29 The diester shown can be hydrolysed by heating with an excess of aqueous sodium hydroxide.

O H H H H

H C O C C C O C C H

H H H O H

What would the products of this reaction be?

O H H H O H

A H C HO C C C OH HO C C H

OH H H H H

O H H H O H

B H C NaO C C C ONa HO C C H

OH H H H H

O H H H O H

C H C HO C C C OH NaO C C H

ONa H H H H

O H H H O H

D H C NaO C C C ONa NaO C C H


ONa H H H H

© UCLES 2018 9701/13/O/N/18 [Turn over


12

30 J is a branched-chain alcohol, C5H12O. J is heated under reflux with an excess of Cr2O72– / H+ until
no further reaction occurs. An organic compound K is formed in good yield.

The infra-red spectrum of K is shown.

100

transmittance
%
50

0
4000 3000 2000 1500 1000 500
wavenumber / cm–1

What are the structures of the branched-chain alcohol J and compound K?

J K

A CH3CH(CH3)CH2CH2OH CH3CH(CH3)CH2CHO
B CH3CH2CH(OH)CH2CH3 CH3CH2COCH2CH3
C CH3CH(CH3)CH(OH)CH3 CH3CH(CH3)COCH3
D CH3CH(CH3)CH2CH2OH CH3CH(CH3)CH2COOH

© UCLES 2018 9701/13/O/N/18


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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

Use of the Data Booklet may be appropriate for some questions.

31 Which ions contain one or more unpaired electrons?

1 Cu2+
2 Mn3+
3 V3+

32 Which molecules and ions have a bond angle of 120°?

1 BF3
2 CH3–
3 NH3

33 Which statements are correct for all exothermic reactions?

1 ∆H for the reaction is negative.


2 On a reaction pathway diagram the products are shown lower than the reactants.
3 The reaction will occur without heating.

© UCLES 2018 9701/13/O/N/18 [Turn over


14

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

34 The factors affecting the rate of reaction between aqueous sodium thiosulfate and hydrochloric
acid can be investigated. The ionic equation for the reaction is shown.

S2O32–(aq) + 2H+(aq) → H2O(l) + S(s) + SO2(aq)

Which of the following can be used to investigate the rate of this reaction?

1 change of mass
2 change of appearance caused by formation of a precipitate
3 change of electrical conductivity

35 Which reaction routes can be used to make a pure sample of barium sulfate?

heat dilute dilute filter, wash


1 Ba metal product product 2 product 3
in O2 HCl H2SO4 and dry

strong solid an excess dilute filter, wash


2 Ba(NO3)2 product 2 product 3
heat in air product of water H2SO4 and dry

dilute dilute filter, wash


3 Ba(OH)2 product product 2
HNO3 H2SO4 and dry

36 Which properties increase from magnesium to barium?

1 ionic radius of the cation M2+


2 screening of outermost electrons by inner shells
3 solubility of the hydroxides, M(OH)2, in water

© UCLES 2018 9701/13/O/N/18


15

37 2-methylpropene can react in more than one way with chlorine.

One of the reactions follows the pathway shown.

CH3 CH3 CH3


+
CH2 C + Cl 2 → Cl CH2 C + Cl – → Cl CH2 C + HCl

CH3 CH3 CH2


2-methylpropene intermediate product

Which statements about this mechanism are correct?

1 The intermediate has all carbon atoms in the same plane.


2 There is an electrophilic attack on the double bond.
3 It is a free radical mechanism.

38 The halogenoalkanes listed below all react with NaOH(aq).

Which reactions proceed mainly by an SN1 mechanism?

1 1-iodopropane
2 2-iodo-2-methylpropane
3 2-bromo-2-methylbutane

39 3-oxobutanoic acid can be synthesised in a two-step process.

O O
X Y
OH
3-oxobutanoic acid

What could be the structure of X?

1 OH

Cl O
2
OH

Br O
3
H

© UCLES 2018 9701/13/O/N/18 [Turn over


16

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

40 Ethanal reacts with HCN in the presence of KCN.

Which changes in bonding occur during this reaction?

1 A carbon-carbon bond is formed.


2 A carbon-hydrogen bond is broken.
3 A carbon-nitrogen bond is broken.

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.

To avoid the issue of disclosure of answer-related information to candidates, all copyright acknowledgements are reproduced online in the Cambridge
International Examinations Copyright Acknowledgements Booklet. This is produced for each series of examinations and is freely available to download at
www.cie.org.uk after the live examination series.

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 2018 9701/13/O/N/18


9701/13 Cambridge International AS/A Level – Mark Scheme October/November
PUBLISHED 2018

Question Answer Marks

1 D 1

2 A 1

3 A 1

4 C 1

5 C 1

6 C 1

7 B 1

8 C 1

9 D 1

10 D 1

11 C 1

12 C 1

13 C 1

14 B 1

15 B 1

16 A 1

17 D 1

18 D 1

19 D 1

20 B 1

21 A 1

22 C 1

23 B 1

24 D 1

25 B 1

26 D 1

27 A 1

28 B 1

© UCLES 2018 Page 2 of 3


9701/13 Cambridge International AS/A Level – Mark Scheme October/November
PUBLISHED 2018

Question Answer Marks

29 C 1

30 C 1

31 A 1

32 D 1

33 B 1

34 C 1

35 A 1

36 A 1

37 B 1

38 C 1

39 A 1

40 B 1

© UCLES 2018 Page 3 of 3


2

Section A

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

Use of the Data Booklet may be appropriate for some questions.

1 Which molecule contains six bonding electrons?

A C2H4 B H2S C NCl 3 D SF6

2 The mass spectrum of a sample of lithium shows that it contains two isotopes, 6Li and 7Li.

The isotopic abundances are shown in the table.

isotope isotopic abundance


6
Li 7.42%
7
Li 92.58%

What is the relative atomic mass of this sample of lithium, given to three significant figures?

A 6.07 B 6.50 C 6.90 D 6.93

3 A sports medal has a total surface area of 150 cm2. It was evenly coated with silver by
electrolysis. Its mass increased by 0.216 g.

How many atoms of silver were deposited per cm2 on the surface of the medal?

A 8.0 × 1018 B 1.8 × 1019 C 8.7 × 1020 D 1.2 × 1021

4 Which property of an atom does not affect its first ionisation energy?

A the atomic radius


B the number of electron shells
C the number of neutrons
D the number of protons

5 Which molecule has the largest overall dipole?

A B C D

H CH3 CH3 Cl H3 C Cl

C C O C O C C C

H CH3 CH3 Cl Cl CH3

© UCLES 2017 9701/11/M/J/17


3

6 The complete combustion of 2 moles of a straight chain alkane produces 400 dm3 of
carbon dioxide measured at 301 K and 1 × 105 Pa. Carbon dioxide can be assumed to behave as
an ideal gas under these conditions.

What is the formula of the straight chain alkane?

A C8H18 B C16H34 C C20H42 D C40H82

7 Which expression gives the standard enthalpy change of combustion of methane?

A (CH4) + (CO2) – 2 (H2O)


B (CO2) + 2 (H2O) + (CH4)
C (CH4) + 2 (H2O) – (CO2)
D (CO2) + 2 (H2O) – (CH4)

8 Solutions containing chlorate(I) ions are used as household bleaches and disinfectants. These
solutions decompose on heating as shown.

3Cl O– → Cl O3– + 2Cl –

Which oxidation state is shown by chlorine in each of these three ions?

Cl O– Cl O3– Cl –

A +1 +3 –1
B –1 +3 +1
C +1 +5 –1
D –1 +5 +1

9 When K2MnO4 is dissolved in water, the following reaction occurs.

a MnO42–(aq) + b H2O(l) → c MnO4–(aq) + d MnO2(s) + e OH–(aq)

What are the values of a and c in the balanced chemical equation?

a c

A 2 1
B 3 2
C 4 3
D 5 4

© UCLES 2017 9701/11/M/J/17 [Turn over


4

10 Methanol can be produced from hydrogen and carbon monoxide.

2H2(g) + CO(g) CH3OH(g)

What is the expression for K p for this reaction?

(2pH2 )2 × pCO
A Kp =
pCH3 OH

( pH2 )2 × pCO
B Kp =
pCH3 OH

pCH3OH
C Kp =
( pH2 )2 × pCO

pCH3 OH
D Kp =
pCO × (2 pH2 )2

11 When 4 g of powdered calcium carbonate, Mr = 100, were added to 100 cm3 of 0.10 mol dm–3
hydrochloric acid the volume of carbon dioxide produced was recorded.

time / s 30 60 90 120 150 180 210 240


total volume of carbon
40 70 88 101 110 116 120 120
dioxide given off / cm3

Which row gives the correct explanations about these results?

why the rate of the


why the reaction stops
reaction changes with time
A fewer collisions between the calcium carbonate is used up
reacting molecules occur
B fewer collisions between the hydrochloric acid is used up
reacting molecules occur
C more collisions between the calcium carbonate is used up
reacting molecules occur
D more collisions between the hydrochloric acid is used up
reacting molecules occur

© UCLES 2017 9701/11/M/J/17


5

12 Why is the second ionisation energy of sodium larger than the second ionisation energy of
magnesium?

A The attraction between the nucleus and the outer electron is greater in Na+ than in Mg+.
B The nuclear charge of Na+ is greater than that of Mg+.
C The outer electron of Na+ is more shielded than the outer electron of Mg+.
D The outer electron of Na is in the same orbital as the outer electron of Mg.

13 Which graph correctly shows the relative melting points of the elements Mg, Al, Si and P plotted
against their relative electronegativities?

A B

Si
Al

melting point Mg melting point Mg Al


Si

P P

electronegativity electronegativity

C D
Si

Al

melting point Al Mg melting point Mg

Si
P P

electronegativity electronegativity

© UCLES 2017 9701/11/M/J/17 [Turn over


6

14 An excess of MgO is shaken with water. The resulting mixture is filtered into test-tube X.

An excess of BaO is shaken with water. The resulting mixture is filtered into test-tube Y.

Which oxide reacts more readily with water and which filtrate has the lower pH?

oxide reacts more test-tube with


readily with water filtrate of lower pH

A barium oxide X
B barium oxide Y
C magnesium oxide X
D magnesium oxide Y

15 Samples of magnesium carbonate, MgCO3, are placed in crucibles R and S. The sample in
crucible R is heated until there is no further loss in mass, and then allowed to cool. The sample in
crucible S is left unheated.

Dilute hydrochloric acid is then added to both crucibles.

On adding the dilute hydrochloric acid, which observations are correct?

R S

A gas produced gas produced


B gas produced no gas produced
C no gas produced gas produced
D no gas produced no gas produced

16 Which statement about nitrogen or its compounds is correct?

A In the Haber process the temperature is kept high to give a good equilibrium yield of
ammonia.
B Nitrogen gas is unreactive because of the strong nitrogen-nitrogen double bond.
C Nitrogen monoxide will react with carbon monoxide under suitable conditions.
D The formula of ammonium sulfate is NH4SO4.

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7

17 When concentrated sulfuric acid reacts with sodium iodide the products include sulfur, iodine,
hydrogen sulfide and sulfur dioxide.

Which statement is correct?

A Hydrogen sulfide is the product of a reduction reaction.


B Iodide ions are stronger oxidising agents than sulfate ions.
C Sulfur atoms from the sulfuric acid are both oxidised and reduced.
D Sulfur atoms from the sulfuric acid are oxidised to make sulfur dioxide.

18 A solution of sodium hydroxide reacts with 3 mol of chlorine under certain conditions. The reaction
produces 5 mol of sodium chloride and 1 mol of X, the only other chlorine-containing product.

What is the formula of compound X?

A NaCl O B NaCl O2 C NaCl O3 D NaCl O4

19 Redox reactions are common in the chemistry of Group 17.

Which statement is correct?

A Br – ions will reduce Cl 2 but not I2.

B Cl 2 will oxidise Br – ions but not I– ions.

C F2 is the weakest oxidising agent out of F2, Cl 2, Br2 and I2.

D I– ions are the weakest reducing agent out of F –, Cl –, Br – and I–.

20 Structural isomerism and stereoisomerism should be considered when answering this question.

Each of the following carbonyl compounds is reacted with NaBH4. The product of each reaction is
heated with Al 2O3 at 600 °C, generating one product or a mixture of isomers.

Which carbonyl compound will produce the most isomers?

A butanal
B butanone
C pentan-3-one
D propanone

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8

21 The drug cortisone has the formula shown.

OH

OH
O O

In addition to those chiral centres marked by an asterisk (*), how many other chiral centres are
present in the cortisone molecule?

A 0 B 1 C 2 D 3

22 An alkene is reacted with acidified manganate(VII) ions, MnO4–. The desired organic product has
a relative molecular mass greater than that of the alkene by 34.

What conditions should be used?

A cold, concentrated MnO4–


B cold, dilute MnO4–
C hot, concentrated MnO4–
D hot, dilute MnO4–

23 The diagram shows a short length of an addition polymer chain.

H H H H

C C C C

H H H H

The polymer has a relative molecular mass of approximately 10 000.

Approximately how many monomer units are joined together in each polymer molecule?

A 180 B 360 C 625 D 710

© UCLES 2017 9701/11/M/J/17


9

24 Lactide is an intermediate in the manufacture of a synthetic fibre.

O O

O O

lactide

Which compound, on heating with an acid catalyst, can produce lactide?

A hydroxyethanoic acid
B 2-hydroxybutanoic acid
C 2-hydroxypropanoic acid
D 3-hydroxypropanoic acid

25 Diols in which both hydroxy groups are bonded to the same carbon atom spontaneously eliminate
a molecule of water to produce a carbonyl compound.

Which compound is hydrolysed to form a product that gives a positive reaction with
2,4-dinitrophenylhydrazine but not with Fehling’s reagent?

A 1,1-dibromopropane
B 1,2-dibromopropane
C 1,3-dibromopropane
D 2,2-dibromopropane

26 X and Y are the reagents required to convert 1-bromopropane into butanoic acid.

H H H H H H H H H O
X Y
H C C C Br H C C C CN H C C C C

H H H H H H H H H OH

What are the correct identities of X and Y?

X Y

A NH3 HCl (aq)


B KCN in C2H5OH NaOH(aq)
C KCN in C2H5OH HCl (aq)
D HCN NaOH(aq)

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10

27 Q is a compound with the molecular formula C4H10O. Q can be oxidised with acidified
potassium dichromate(VI). Q cannot be made by reducing a carboxylic acid with LiAl H4.

What is the structure of Q?

A CH3CH(OH)CH2CH3
B CH3CH2CH2CH2OH
C (CH3)3COH
D (CH3)2CHCH2OH

28 A sample of 2.30 g of ethanol was mixed with an excess of aqueous acidified potassium
dichromate(VI). The reaction mixture was then boiled under reflux for one hour. The required
organic product was then collected by distillation. The yield of product was 60.0%.

Which mass of product was collected?

A 1.32 g B 1.38 g C 1.80 g D 3.00 g

29 Which compound gives a positive test with alkaline aqueous iodine and does not show optical
isomerism?

A CH3COCH2CH2OH
B CH3CH2CH(OH)CHO
C CH3COCH(OH)CH3
D (CH3)2C(OH)CHO

30 Citral is found in lemongrass oil. It can react to give compound W.

CHO
an excess of hot, concentrated
V W
H2 / Ni acidified manganate(VII)
under reflux

citral

What could compound W be?

A B C D

CHO CO2H CO2H


O
CO2H
CO2H

© UCLES 2017 9701/11/M/J/17


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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

Use of the Data Booklet may be appropriate for some questions.

31 Beams of charged particles are deflected by an electric field. In identical conditions the angle of
deflection of a particle is proportional to its charge / mass ratio.

In an experiment, protons are deflected by an angle of +15°. In another experiment under


identical conditions, particle Y is deflected by an angle of –5°.

What could be the composition of particle Y?

protons neutrons electrons

1 1 2 2
2 3 3 5
3 4 5 1

32 Graphene, graphite and the fullerene C60 are allotropes of carbon.

Which statements are correct for all three of these allotropes of carbon?

1 Delocalised electrons are present in the structure.

2 All bond angles are 120°.


3 It has a giant molecular crystalline lattice structure.

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12

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

33 A reaction between carbon and oxygen is shown.

C(s) + 1
2
O2(g) → CO(g)

How can the enthalpy change of this reaction be described correctly?

1 enthalpy change of formation


2 enthalpy change of combustion
3 enthalpy change of atomisation

34 Which changes can be used to measure the rates of chemical reactions?

1 the decrease in concentration of a reactant per unit time


2 the rate of appearance of a product
3 the increase in total volume per unit time at constant pressure

35 Which statements describe a trend in Period 3 between every pair of adjacent elements from
sodium to chlorine?

1 The atomic radius decreases.


2 The 1st ionisation energy decreases.
3 The melting point decreases.

36 X is either nitrogen or sulfur and forms pollutant oxide Y in a car engine.

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 molecules.

Which statements about X, Y and Z can be correct?

1 The oxidation number of X increases by two from Y to Z.


2 Y has an unpaired electron in its molecule.
3 Y is a polar molecule.

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13

37 P and Q are a pair of cis-trans isomers.

What must be the same for P and Q?

1 their empirical formula


2 their functional groups
3 their skeletal formula

38 The following statements are about the reaction of NaOH(aq) with the three chloroalkanes
shown.

CH3CH2CHCl CH3 (CH3)2CHCH2Cl (CH3)3CCl

Which statements are correct?

1 (CH3)2CHCH2Cl reacts with NaOH(aq) by an SN2 mechanism.


2 The tertiary chloroalkane reacts more quickly than the others because the carbon atom
bonded to the Cl atom is more positive in this molecule.
3 The Cl atoms in the three chloroalkanes are attacked by OH–.

39 For which reactions are the colour changes described correctly?

reagents colour change

1 pentanal + hot, acidified potassium dichromate(VI) orange to green


2 pentan-2-one + warm Fehling’s reagent no change
3 cyclohexane + cold, acidified potassium manganate(VII) purple to colourless

40 Which statements about ethanol and ethanoic acid are correct?

1 Both react with a suitable reagent to form an ester.


2 Both react with sodium.
3 Both are soluble in water.

© UCLES 2017 9701/11/M/J/17


9701/11 Cambridge International AS/A Level – Mark Scheme May/June 2017
PUBLISHED

Question Answer Marks

1 C 1

2 D 1

3 A 1

4 C 1

5 B 1

6 A 1

7 D 1

8 C 1

9 B 1

10 C 1

11 B 1

12 A 1

13 B 1

14 A 1

15 C 1

16 C 1

17 A 1

18 C 1

19 A 1

20 B 1

21 D 1

22 B 1

23 B 1

24 C 1

25 D 1

26 C 1

27 A 1

28 C 1

© UCLES 2017 Page 2 of 3


9701/11 Cambridge International AS/A Level – Mark Scheme May/June 2017
PUBLISHED

Question Answer Marks

29 A 1

30 B 1

31 B 1

32 D 1

33 D 1

34 A 1

35 D 1

36 A 1

37 B 1

38 D 1

39 B 1

40 A 1

© UCLES 2017 Page 3 of 3


2

Section A

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

Use of the Data Booklet may be appropriate for some questions.

1 In which species are the numbers of protons, neutrons and electrons all different?

19 − 23 + 31 32 2 −
A 9F B 11 Na C 15 P D 16 S

2 Which would contain 9.03 × 1023 oxygen atoms?

A 0.25 mol aluminium oxide


B 0.75 mol sulfur dioxide
C 1.5 mol sulfur trioxide
D 3.0 mol water

3 In some fireworks there is a reaction between powdered aluminium and powdered barium nitrate.
Heat is evolved, an unreactive gas is produced, and all nitrogen atoms are reduced.

What is the equation for this reaction?

A 2Al + Ba(NO3)2 → Al 2O3 + BaO + 2NO

B 4Al + 4Ba(NO3)2 → 2Al 2O3 + 4Ba(NO2)2 + O2

C 10Al + 3Ba(NO3)2 → 5Al 2O3 + 3BaO + 3N2

D 10Al + 18Ba(NO3)2 → 10Al (NO3)3 + 18BaO + 3N2

4 Which organic compound has the highest boiling point?

A C(CH3)4
B CH3CH2CH2CH2CH3
C CH3COCH2CH3
D CH3CH(OH)CH2CH3

5 At a temperature of 2500 K and a pressure of 1.00 × 10–4 Pa a sample of 0.321 g of sulfur vapour
has a volume of 2.08 × 106 m3.

What is the molecular formula of sulfur under these conditions?

A S B S2 C S4 D S8

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3

6 Which reaction involves a decrease in the bond angle at a carbon atom?

A bromoethane refluxed with ethanolic sodium hydroxide


B complete combustion of methane in air
C ethanol heated with conc. H2SO4
D polymerisation of ethene

7 In the high temperatures of car engines, nitrogen reacts with oxygen to give nitrogen monoxide.

1
2
N2(g) + 1
2
O2(g) → NO(g) ∆H o = +90 kJ mol–1

This reaction has activation energy Ea.

Which reaction pathway diagram could correctly represent this reaction?

A B

Ea NO(g)
Ea
1
2 N2(g) +
1
2 O2(g)
1
2 N2(g) +
1
2 O2(g)
∆H o
energy energy
∆H o NO(g)

extent of reaction extent of reaction

C D

NO(g) NO(g)
Ea Ea
1
2 N2(g) +
1
2 O2(g)
∆H o 1
2 N2(g) +
1
2 O2(g)
∆H o
energy energy

extent of reaction extent of reaction

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4

8 A reaction sequence is shown.

1 2 3 4
SO2 SO3 H2SO4 H2S SO2

In each stage of this sequence the sulfur is oxidised, reduced or neither oxidised nor reduced.

Which row is correct?

1 2 3 4

A neither oxidised reduced reduced


B oxidised neither reduced reduced
C oxidised neither reduced oxidised
D oxidised oxidised reduced oxidised

9 Hydrogen and carbon dioxide gases are mixed at 800 K. A reversible reaction takes place.

H2(g) + CO2(g) H2O(g) + CO(g)

At equilibrium, the partial pressures of H2 and CO2 are both 10.0 kPa. Kp is 0.288 at 800 K.

What is the partial pressure of CO in the equilibrium mixture?

A 5.37 kPa B 18.6 kPa C 28.8 kPa D 347 kPa

10 A reaction involved in the Contact process is shown.

2SO2(g) + O2(g) 2SO3(g) ∆H o = –197 kJ mol–1

The reaction is investigated at 200 kPa and 700 K and the value of the equilibrium constant, Kp, is
found to be Y. The reaction is then investigated at 1000 kPa and 700 K and the value of Kp is
found to be Z.

Which statement comparing Y and Z is correct?

A Y and Z are the same.


B Y is greater than Z.
C Z is 2.2 times greater than Y.
D Z is 5.0 times greater than Y.

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5

11 The Boltzmann distribution for the hydrogenation of an alkene at a particular temperature in the
absence of a catalyst is shown.

proportion
of molecules Ea
with energy E

0
0
molecular energy E

Which row correctly describes the effects of adding nickel to the reaction vessel?

the shape of the


activation energy, Ea
Boltzmann distribution

A changes decreases
B changes increases
C does not change decreases
D does not change increases

12 The elements magnesium and sulfur each form doubly charged ions.

How do the atomic radii and ionic radii of these elements compare?

atomic ionic atomic ionic


radius radius radius radius

A Mg > Mg2+ S > S2–


B Mg > Mg2+ S < S2–
C Mg < Mg2+ S > S2–
D Mg < Mg2+ S < S2–

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6

13 Which graph correctly shows relative electronegativity plotted against relative atomic radius for
the elements Na, Mg, Al and Si?

A B
Si

Al Al
electronegativity Mg electronegativity Mg

Si Na Na

atomic radius atomic radius

C D
Na Si

Mg Al
electronegativity Al electronegativity Mg
Si Na

atomic radius atomic radius

14 Trends are seen in the physical and chemical properties of the elements of Group 2 and their
compounds.

Which property shows a decrease from magnesium to barium?

A the rate of the reaction between the element and dilute hydrochloric acid
B the solubility of the hydroxides
C the solubility of the sulfates
D the temperature of decomposition of the carbonates

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7

15 Calcium oxide is added to water and the resulting mixture is filtered.

This filtrate is X.

When carbon dioxide is bubbled through filtrate X, a white precipitate is formed.

Which equation for this reaction of filtrate X with carbon dioxide is correct?

A CaO + CO2 → CaCO3

B Ca(OH)2 + CO2 → CaO + H2CO3

C 2CaO + H2O + CO2 → CaCO3 + Ca(OH)2

D Ca(OH)2 + CO2 → CaCO3 + H2O

16 Element X reacts with cold, dilute, aqueous sodium hydroxide to form two different
chlorine-containing products, Y and Z.

What are the oxidation states of chlorine in Y and Z?

Y Z

A 0 +1
B 0 +5
C –1 +1
D –1 +5

17 A powder is known to be either a single sodium halide or a mixture of two sodium halides. A
sample of the powder was dissolved in water.

Aqueous silver nitrate was added, and a pale yellow precipitate was formed. When concentrated
aqueous ammonia was then added, this precipitate partly dissolved leaving a darker yellow
precipitate.

What might the powder be?

A sodium bromide only


B sodium iodide only
C a mixture of sodium chloride and sodium bromide
D a mixture of sodium chloride and sodium iodide

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8

18 The ammonium ion is formed by the following reaction.

NH3 + H+ → NH4+

Which statement about the species involved in this reaction is correct?

A The ammonia molecule contains a dative covalent bond.


B The ammonium ion is a Brønsted-Lowry base as it has accepted a proton.

C The H–N–H bond angle changes from 107° in ammonia to 90° in the ammonium ion.
D The number of electrons surrounding each nitrogen atom does not change.

19 A chemist took 2.00 dm3 of nitrogen gas, measured under room conditions, and reacted it with a
large volume of hydrogen gas to produce ammonia. Only 15.0% of the nitrogen gas reacted to
produce ammonia.

Which mass of ammonia was formed?

A 0.213 g B 0.425 g C 1.42 g D 2.83 g

20 A carbonyl compound X will react with HCN in the presence of NaCN to make a compound with
Mr 85. Compound X does not react with Fehling’s reagent.

What is X?

A butanal
B butanone
C propanal
D propanone

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9

21 Geraniol and linalool are compounds found in some flower fragrances.

CH3 CH3
HO
C CH2OH C
H 2C C H 2C C H

H 2C H H 2C CH2
CH CH

C C
H 3C CH3 H 3C CH3

geraniol linalool

Which statement is correct?

A They are chain isomers of each other.


B They are geometrical isomers of each other.
C They are optical isomers of each other.
D They are positional isomers of each other.

22 Which equation represents the initiation step of the substitution reaction between methane and
chlorine?

A CH4 → CH3• + H•

B CH4 → CH3– + H+

C Cl 2 → 2Cl •

D Cl 2 → Cl + + Cl –

23 Aqueous sodium hydroxide reacts with 1-bromopropane to give propan-1-ol.

What should be included in a diagram of the first step in the mechanism?

A a curly arrow from a lone pair on the OH– ion to the Cδ+ atom of 1-bromopropane

B a curly arrow from the Cδ+ atom of 1-bromopropane to the OH– ion
C a curly arrow from the C–Br bond to the C atom
D the homolytic fission of the C–Br bond

© UCLES 2017 9701/12/M/J/17 [Turn over


10

24 A sample of 2.76 g of ethanol was mixed with an excess of aqueous acidified potassium
dichromate(VI). The reaction mixture was then boiled under reflux for one hour. The required
organic product was then collected by distillation.

The yield of product was 75.0%.

Which mass of product was collected?

A 1.26 g B 1.98 g C 2.07 g D 2.70 g

25 Compound X is a single, pure, optical isomer. X is heated with an excess of concentrated H2SO4.
Only one organic product is formed.

What could X be?

A B C D
OH
OH CH2OH
HO

26 2-bromo-2-methylpropane undergoes nucleophilic substitution when heated under reflux with an


aqueous solution of sodium hydroxide.

Which row is correct?

mechanism for
reason
this reaction
A SN1 the hydroxide ion is helped in its approach to
the central carbon atom by the methyl groups
B SN1 the intermediate carbocation is stabilised
by the inductive effect of the methyl groups
C SN2 the hydroxide ion is hindered in its approach to
the central carbon atom by the methyl groups
D SN2 the intermediate carbocation is destabilised
by the inductive effect of the methyl groups

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11

27 H2NNHC6H3(NO2)2 is the structural formula of 2,4-DNPH.

Many, but not all, organic reactions need to be heated before reaction occurs.

Which reaction occurs at a good rate at room temperature (20 °C)?

A C10H22 → C8H18 + C2H4

B CH3CH2CH2Br + NH3 → CH3CH2CH2NH2 + HBr

C CH3CH2OH + KBr → CH3CH2Br + KOH

D (CH3)2CO + H2NNHC6H3(NO2)2 → (CH3)2C=NNHC6H3(NO2)2 + H2O

28 A carboxylic acid, P, has no possible chain isomers. It reacts with an alcohol, Q, that has only
one positional isomer.

What could be the ester formed from a reaction between P and Q?

A butyl propanoate
B ethyl butanoate
C pentyl ethanoate
D propyl pentanoate

29 Which compound is chiral and reacts with Na2CO3 to give CO2?

A B C D

CH3 OH CH2Br CH(Br)CO2H


H CO2H
C HCO2CH
CH2
C CH3
H CO2H CH3

30 Which compound, when hydrolysed, gives propanoic acid and propan-2-ol?

A CH3CH2CO2CH2CH(CH3)CH3
B (CH3)2CHCO2CH2CH3
C CH3CH2CO2CH(CH3)CH3
D CH3CH2CH2CO2CH(CH3)CH3

© UCLES 2017 9701/12/M/J/17 [Turn over


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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

Use of the Data Booklet may be appropriate for some questions.

31 An isolated gaseous atom of element X has paired electrons in at least one of its 3d orbitals and
has a filled 4s subshell.

What could be the identity of element X?

1 iron
2 gallium
3 copper

32 Which allotropes of carbon have a giant molecular structure?

1 buckminsterfullerene
2 diamond
3 graphite

33 Which statements about endothermic reactions are correct?

1 On the reaction pathway diagram the products of the reaction are lower than the reactants.
2 There is a net transfer of heat energy from the surroundings to the reacting system.
3 the total bond energies of the reactants > the total bond energies of the products

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13

34 The rate of chemical reactions can be increased by the addition of a suitable catalyst.

For which reactions can a heterogeneous catalyst be used?

1 N2 + 3H2 2NH3
2 2SO2 + O2 2SO3
3 2NO + 2CO N2 + 2CO2

35 Which chlorides, when added to water, can produce a solution with a pH of less than 5?

1 SiCl 4
2 Al Cl 3

3 MgCl 2

36 Acid rain continues to be a problem.

Which statements about acid rain are correct?

1 Acid rain is formed when oxides of nitrogen or oxides of sulfur react with water in the
atmosphere.
2 Acid rain causes an increase in the concentration of heavy metal ions in water courses.
3 Nitrogen dioxide will catalyse the formation of SO3 from SO2 in the atmosphere.

37 Which compounds contain a chiral centre?

1 2-hydroxybutanoic acid
2 3-hydroxybutanoic acid
3 4-hydroxybutanoic acid

38 The diagram shows the monomer used to make polyvinyl chloride, PVC.

H H

C C

H Cl

Assuming that one particular molecule of the polymer forms from n molecules of the monomer
(where n is many thousands), which statements are correct?

1 The relative molecular mass of this polymer molecule is approximately 62.5n.


2 There are n chiral carbon atoms in this polymer molecule.

3 There are 5n σ bonds in one polymer molecule.

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14

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

39 An organic compound, X, has the following skeletal formula.

OH

Which statements about X are correct?

1 X is a primary alcohol.
2 X will dehydrate to give a single alkene.
3 X will undergo a substitution reaction with chloride ions.

40 2,2,4-trimethylpentanal is used in the manufacture of adhesives.

Which reagents would 2,2,4-trimethylpentanal react with?

1 2,4-dinitrophenylhydrazine reagent
2 Tollens' reagent
3 alkaline aqueous iodine

© UCLES 2017 9701/12/M/J/17


9701/12 Cambridge International AS/A Level – Mark Scheme May/June 2017
PUBLISHED

Question Answer Marks

1 B 1

2 B 1

3 C 1

4 D 1

5 A 1

6 D 1

7 C 1

8 C 1

9 A 1

10 A 1

11 C 1

12 B 1

13 B 1

14 C 1

15 D 1

16 C 1

17 D 1

18 D 1

19 B 1

20 D 1

21 D 1

22 C 1

23 A 1

24 D 1

25 D 1

26 B 1

27 D 1

28 A 1

© UCLES 2017 Page 2 of 3


9701/12 Cambridge International AS/A Level – Mark Scheme May/June 2017
PUBLISHED

Question Answer Marks

29 D 1

30 C 1

31 B 1

32 C 1

33 C 1

34 A 1

35 B 1

36 A 1

37 B 1

38 B 1

39 A 1

40 B 1

© UCLES 2017 Page 3 of 3


2

Section A

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

Use of the Data Booklet may be appropriate for some questions.

1 The ion Y3– contains 18 electrons and has a mass number of 31.

How many protons and neutrons does Y3– contain?

protons neutrons

A 15 16
B 15 18
C 18 13
D 21 10

2 A 0.216 g sample of an aluminium compound X reacts with an excess of water to produce a


single hydrocarbon gas. This gas burns completely in O2 to form H2O and CO2 only. The volume
of CO2 at room temperature and pressure is 108 cm3.

What is the formula of X?

A Al 2C3 B Al 3C2 C Al 3C4 D Al 4C3

3 Which equation correctly describes the complete combustion of an alkene, CnH2n?

A CnH2n + 3
2
nO2 → nCO2 + 2nH2O

B CnH2n + 3
2
nO2 → nCO2 + nH2O

C CnH2n + 2nO2 → nCO2 + nH2O

D CnH2n + 2nO2 → nCO2 + 2nH2O

© UCLES 2017 9701/13/M/J/17


3

4 Two conversions are shown.

NH4+ → NH3

C2H4 → C2H6

Which similar feature do these two conversions have?

A change in oxidation state of an element


B decrease in bond angle
C formation of a lone pair of electrons

D loss of a π bond

5 All gases listed are at the same pressure.

Which gas will most closely approach ideal behaviour?

A ammonia at 100 K
B ammonia at 500 K
C neon at 100 K
D neon at 500 K

6 The following data are needed for this question.

(CO(g)) = –111 kJ mol–1


(CO2(g)) = –394 kJ mol–1
(Fe2O3(s)) = –822 kJ mol–1

Carbon monoxide reacts with iron(III) oxide.

3CO(g) + Fe2O3(s) → 3CO2(g) + 2Fe(s)

What is the enthalpy change when 55.8 g of iron are produced by this reaction?

A –27.0 kJ B –13.5 kJ C +13.5 kJ D +27.0 kJ

7 Vanadium reacts with dilute sulfuric acid to form V2(SO4)3 and hydrogen gas.

What happens to vanadium atoms in this reaction?

A They lose three electrons and are oxidised.


B They lose three electrons and are reduced.
C They lose two electrons and are oxidised.
D They lose two electrons and are reduced.

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4

8 Na2S2O3 reacts with HCl as shown.

Na2S2O3(aq) + 2HCl (aq) → 2NaCl (aq) + H2O(l) + SO2(g) + S(s)

When calculating the oxidation number of sulfur in Na2S2O3, the average oxidation number of the
two sulfur atoms should be found.

What is the oxidation number of sulfur in each of Na2S2O3, SO2, and S?

Na2S2O3 SO2 S

A +2 +2 +1
B +2 +4 0
C +4 +4 0
D +5 +4 0

9 Ammonia is produced by the Haber process.

N2 + 3H2 2NH3 ∆H o = –92 kJ mol–1

A fault in the temperature control during the process resulted in the temperature changing to
600 °C for two hours.

What effect did this have on the ammonia production during this time?

A Ammonia was formed faster. The equilibrium yield decreased.


B Ammonia was formed faster. The equilibrium yield increased.
C Ammonia was formed slower. The equilibrium yield decreased.
D Ammonia was formed slower. The equilibrium yield increased.

10 For the reaction shown, an equilibrium is established at a temperature of 700 K.

The equilibrium constant, Kp, for the reaction is 9.80 kPa. The partial pressure of N2O4 at
equilibrium is 80.0 kPa.

N2O4(g) 2NO2(g)

What is the partial pressure of NO2 at equilibrium?

A 8.16 kPa B 28.0 kPa C 66.6 kPa D 784 kPa

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5

11 The diagram shows the Boltzmann distribution of the energy of gaseous molecules at a particular
temperature.

proportion
of molecules
with energy E Y

X
0
0
molecular energy E

Which statement is correct?

A If the temperature of the gas is raised, the height of the maximum of the curve increases.
B If the temperature of the gas is raised, the maximum of the curve moves to the right.
C The length of the line labelled X shows the activation energy for the reaction.
D The length of the line labelled Y shows the enthalpy change of the reaction.

12 Magnesium chloride, MgCl 2, and silicon tetrachloride, SiCl 4, are separately added to water.

What are the approximate pH values of the solutions formed?

MgCl 2 SiCl 4

A 0–3 0–3
B 0–3 6–7
C 6–7 0–3
D 6–7 6–7

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6

13 Which graph correctly shows the relative melting points of the elements Mg, Al, Si and P plotted
against their relative first ionisation energies?

A B

Si
Al
Si
melting point Mg Al melting point Mg

P
P

first ionisation energy first ionisation energy

C D

Si Si

Al
melting point Al Mg melting point Mg
P
P

first ionisation energy first ionisation energy

14 The table gives information about calcium carbonate and calcium hydroxide.

Which row is correct?

calcium hydroxide
calcium carbonate can be manufactured
is more soluble than using calcium
calcium hydroxide carbonate as a
starting material

A no no
B no yes
C yes no
D yes yes

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7

15 Which row correctly describes the reactions of calcium and strontium with water?

substance reduced substance oxidised more vigorous reaction

A calcium or strontium water calcium + water


B calcium or strontium water strontium + water
C water calcium or strontium calcium + water
D water calcium or strontium strontium + water

16 Chlorine gas is added to cold, aqueous sodium hydroxide.

In a separate experiment, chlorine gas is added to hot, aqueous sodium hydroxide.

Which oxidation states of chlorine are found in the reactants and products of the two reactions
that take place?

A 0, –1, +1 and +5
B 0, –1 and +1 only
C 0, –1 and +5 only
D 0, +1 and +5 only

17 A test-tube of HBr(g) and a separate test-tube of HI(g) are heated to the same temperature.

Which combination of observations is possible?

test-tube of HBr(g) test-tube of HI(g)

A a brown vapour appears no change


B a purple vapour appears no change
C no change a brown vapour appears
D no change a purple vapour appears

18 Ammonia exists as simple covalent molecules, NH3. Ammonia can react with suitable reagents to
form products containing ammonium ions, NH4+. Ammonia can also react with suitable reagents
to form products containing amide ions, NH2–.

Which of these nitrogen-containing species are present in an aqueous solution of ammonia?

A ammonia molecules and amide ions only


B ammonia molecules and ammonium ions only
C ammonia molecules only
D ammonium ions only

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8

19 What would be produced when 60 g of nitrogen monoxide react with an excess of carbon
monoxide in a catalytic converter?

A 12 g of carbon and 92 g of nitrogen dioxide


B 24 g of carbon and 92 g of nitrogen dioxide
C 88 g of carbon dioxide and 28 g of nitrogen
D 88 g of carbon dioxide and 56 g of nitrogen

20 Structural isomerism and stereoisomerism should be considered when answering this question.

Which formula identifies a single substance?

A CH3CHCl CH2CHO
B CH3CHCHCH3
C CH2Cl CH2CHCl 2
D C4H10

21 Structural isomerism and stereoisomerism should be considered when answering this question.

If a molecule contains two non-identical chiral carbon atoms, four optical isomers exist.

How many isomers are there with

● molecular formula C7H14O and


● a five-membered ring and
● a tertiary alcohol group?

A 4 B 5 C 9 D 13

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9

22 The formulae of three compounds are shown.

C3H7CHO C2H5COCH3 CH2CHCH2CH2OH

Only one of these compounds will decolourise bromine water. Only one of these compounds will
produce a silver mirror with Tollens’ reagent.

Which row shows the correct results?

decolourises forms a silver mirror


bromine water with Tollens’ reagent

A C3H7CHO C2H5COCH3
B C2H5COCH3 C3H7CHO
C CH2CHCH2CH2OH C2H5COCH3
D CH2CHCH2CH2OH C3H7CHO

23 Carboxylic acids may be prepared by several different methods.

In which reaction would propanoic acid be formed?

A adding ammonium propanoate to dilute sulfuric acid


B heating ethyl propanoate with aqueous sodium hydroxide

C heating propan-2-ol with acidified potassium manganate(VII) under reflux

D heating propyl ethanoate with dilute sulfuric acid

24 The diagram represents the structure of a polymer.

OH OH OH OH OH OH

C C C C C C

H H H H H H

By which method might this polymer be made?

A polymerise ethene followed by hydration


B polymerise ethene followed by oxidation with cold, acidified KMnO4
C polymerise 1,2-dichloroethene followed by hydrolysis
D polymerise 1,2-dichloroethene followed by oxidation with cold, acidified KMnO4

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10

25 Bromine reacts with ethene in the dark.

Which description of the organic intermediate in this reaction is correct?

A It has a negative charge.


B It is a free radical.
C It is a nucleophile.
D It is an electrophile.

26 Which statement about butan-1-ol, butan-2-ol, and 2-methylbutan-2-ol is not correct?

A They all react with methanoic acid to form an ester.


B They all react with sodium.
C They can all be dehydrated to form an alkene.
D They can all be oxidised to a carbonyl compound.

27 Which compound will react with acidified potassium dichromate(VI) and with alkaline aqueous
iodine?

A CH3COCH2CH3
B CH3CH(OH)CH2CH3
C CH3CH2CH2CHO
D CH3CH2CH2CH2OH

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11

28 Chlorogenic acid is found in green coffee beans and is used in treatments for weight loss.

HO CO2H

O R = C6H5O2 and takes


no part in the reaction
with sodium carbonate.
HO O R
OH
chlorogenic acid

What is produced in good yield when chlorogenic acid is treated with an excess of sodium
carbonate solution at room temperature?

A B

HO CO2Na NaO CO2Na

O O

HO O R NaO O R
OH ONa

C D

NaO CO2H HO CO2Na

O O
+

NaO O R HO OH HO R
ONa OH

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12

29 Butanoic acid can be produced from 1-bromopropane using reagents X and Y as shown.

reagent X reagent Y
1-bromopropane compound Q butanoic acid

What could be reagents X and Y?

X Y

A KCN in ethanol HCl (aq)


B KCN in ethanol NaOH(aq)
C NH3 in ethanol HCl (aq)
D NaOH(aq) H+ / Cr2O72–(aq)

30 How many esters with the molecular formula C5H10O2 can be made by reacting a primary alcohol
with a carboxylic acid?

A 4 B 5 C 6 D 8

© UCLES 2017 9701/13/M/J/17


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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

Use of the Data Booklet may be appropriate for some questions.

31 Which statements about the atoms 23Na and 24Mg are correct?

1 They have the same number of filled electron orbitals.


2 They have the same number of neutrons.
3 They are both reducing agents.

32 Which compounds contain covalent bonds?

1 aluminium chloride
2 ammonia
3 calcium fluoride

33 Ethylene glycol, HOCH2CH2OH, is used as a de-icer. It allows ice to melt at temperatures below
0 °C.

Which statements are correct?

1 Ethylene glycol changes the extensive network of hydrogen bonds in ice.


2 Ethylene glycol molecules form hydrogen bonds with other ethylene glycol molecules.
3 Ethylene glycol molecules will dissolve in the water formed from the ice.

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14

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

34 A student carried out two experiments using MnO2 as a catalyst to decompose hydrogen
peroxide. The equation for this reaction is shown.

2H2O2(aq) → 2H2O(l) + O2(g)

The student’s results are recorded in the table.

mass MnO2 conditions vol H2O2 final vol O2 time taken

experiment 1 0.25 g room conditions 10.0 cm3 480 cm3 200 s


experiment 2 0.25 g room conditions 10.0 cm3 480 cm3 500 s

Which statements are correct?

1 The activation energy was the same for both experiments.


2 The concentration of the hydrogen peroxide solution used was 4.0 mol dm–3.
3 The MnO2 used in experiment 1 was in larger pieces than the MnO2 used in experiment 2.

35 The formula of a solid magnesium compound is Mg(NO3)2.6H2O. When the solid compound is
heated in a hard-glass test-tube, one or more changes are observed.

Which statements are correct?

1 Strong heating produces a basic residue.


2 Strong heating produces a brown gas.
3 Gentle heating produces colourless droplets of liquid on the upper parts of the test-tube.

36 Sulfur dioxide is an atmospheric pollutant.

What might result from the release of sulfur dioxide gas into the atmosphere?

1 reduction of NO2 to NO
2 depletion of aquatic life
3 corrosion of limestone statues

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15

37 Which mechanisms are represented in this sequence of reactions?

CH3CH2CH3 → CH3CH2CH2Cl → CH3CH2CH2OH → CH3CHCH2 → CH3CHBrCH2Br

1 electrophilic addition
2 nucleophilic substitution
3 free radical substitution

38 Which compounds, on heating with ethanolic NaOH, produce more than one product with
molecular formula C4H8?

1 2-bromobutane
2 2-bromo-2-methylpropane
3 1-bromo-2-methylpropane

39 Substance M is refluxed with aqueous sodium hydroxide. One of the products of this reaction
reacts with alkaline aqueous iodine to give a pale yellow precipitate.

Which compounds could be substance M?

1 CH3CO2CH3
2 CH3CO2CH2CH3
3 HCO2CH(CH3)2

40 Propanal will react with hydrogen cyanide to form 2-hydroxybutanenitrile. A suitable catalyst for
this reaction is sodium cyanide.

NaCN
CH3CH2CHO + HCN CH3CH2CH(OH)CN

Which statements about this reaction of propanal with hydrogen cyanide are correct?

1 The CN– ion attacks the propanal molecule to form an intermediate ion.
2 The product of the reaction has a chiral carbon atom.
3 The CN– ion is a stronger electrophile than the HCN molecule.

© UCLES 2017 9701/13/M/J/17


9701/13 Cambridge International AS/A Level – Mark Scheme May/June 2017
PUBLISHED

Question Answer Marks

1 A 1

2 D 1

3 B 1

4 B 1

5 D 1

6 B 1

7 A 1

8 B 1

9 A 1

10 B 1

11 B 1

12 C 1

13 C 1

14 B 1

15 D 1

16 A 1

17 D 1

18 B 1

19 C 1

20 C 1

21 C 1

22 D 1

23 A 1

24 C 1

25 D 1

26 D 1

27 B 1

28 A 1

© UCLES 2017 Page 2 of 3


9701/13 Cambridge International AS/A Level – Mark Scheme May/June 2017
PUBLISHED

Question Answer Marks

29 A 1

30 C 1

31 C 1

32 B 1

33 A 1

34 B 1

35 A 1

36 A 1

37 A 1

38 D 1

39 C 1

40 B 1

© UCLES 2017 Page 3 of 3


2

Section A

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

Use of the Data Booklet may be appropriate for some questions.

1 Which formula represents the empirical formula of a compound?

A C2H4O B C2H4O2 C C6H12 D H2O2

2 The relative first ionisation energies of four elements with consecutive atomic numbers below 20
are shown on the graph.

One of the elements reacts with hydrogen to form a covalent compound with formula HX.

Which element could be X?

first
ionisation
energy
/ kJ mol–1

D
C

atomic number

3 In which structure are three atoms bonded together in a straight line?

A poly(ethene), ] ( CH2CH2 )n
B propane, C3H8
C silicon tetrachloride, SiCl4
D sulfur hexafluoride, SF6

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3

4 In the sodium chloride lattice the number of chloride ions that surround each sodium ion is called
the co-ordination number of the sodium ions.

What are the co-ordination numbers of the sodium ions and the chloride ions in the
sodium chloride lattice?

sodium ions chloride ions

A 4 6
B 6 4
C 6 6
D 8 6

5 A fluorescent light tube has an internal volume of 400 cm3 and an internal pressure of 200 kPa.

It is filled with 0.03 moles of an ideal gas.

What is the temperature of the gas inside the fluorescent light tube?

A 3.21 × 10–1 K

B 3.21 × 102 K

C 3.21 × 105 K

D 3.21 × 108 K

6 One of the reactions in a lead / acid cell is shown.

Pb(s) + PbO2(s) + 4H+(aq) + 2SO42–(aq) → 2PbSO4(s) + 2H2O(l)

Which statement about this reaction is correct?

A Lead is both oxidised and reduced.


B Lead is neither oxidised nor reduced.
C Lead is oxidised only.
D Lead is reduced only.

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4

7 Iodine and propanone react according to the following equation.

I2(aq) + CH3COCH3(aq) → CH3COCH2I(aq) + HI(aq)

If the concentration of propanone is increased, keeping the total reaction volume constant, the
rate of the reaction also increases.

What could be the reason for this?

A A greater proportion of collisions is successful at the higher concentration.


B The particles are further apart at the higher concentration.
C The particles have more energy at the higher concentration.
D There are more collisions between reactant particles per second at the higher concentration.

8 Sulfur can be oxidised in two ways.

S(s) + O2(g) → SO2(g) ∆H o = –296.5 kJ mol–1

2S(s) + 3O2(g) → 2SO3(g) ∆H o = –791.4 kJ mol–1

Sulfur trioxide can be made from sulfur dioxide and oxygen.

2SO2(g) + O2(g) → 2SO3(g)

What is the standard enthalpy change for this reaction?

A –1384.4 kJ mol–1
B –989.8 kJ mol–1
C –494.9 kJ mol–1
D –198.4 kJ mol–1

9 Hydrogen iodide dissociates into hydrogen and iodine.

2HI(g) H2(g) + I2(g)

In an experiment, b mol of hydrogen iodide were put into a sealed vessel at pressure p. At
equilibrium, x mol of the hydrogen iodide had dissociated.

Which expression for Kp is correct?

A x2 B x 2p2 C x 2p2 D x2
( b − x )2 ( b − x )2 4 b( b − x ) 4( b − x )2

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5

10 The diagram shows the distribution of molecular energies in a sample of gas at a temperature T1.
The activation energy for an uncatalysed reaction of this gas, Ea(uncat), is shown.

T1
proportion Ea(uncat)
of molecules
with a given
energy

0
0 molecular energy E

Which diagram correctly shows the new distribution and new activation energy, Ea(cat), when the
temperature is increased to T2, and a catalyst is used that increases the rate of the reaction?

A B
T1 T1 Ea(cat)
proportion Ea(uncat) proportion Ea(uncat)
T2 T2
of molecules Ea(cat) of molecules
with a given with a given
energy energy

0 0
0 molecular energy E 0 molecular energy E

C D
T1 Ea(cat) T1
proportion Ea(uncat) proportion Ea(uncat)
of molecules of molecules Ea(cat)
with a given with a given
energy T2 energy T2

0 0
0 molecular energy E 0 molecular energy E

11 200 g of water are at 25 °C.

The water is heated to 75 °C by burning 2 g of ethanol.

What is the amount of energy transferred to the water?

A 0.418 kJ B 10.4 kJ C 41.8 kJ D 62.7 kJ

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6

12 The elements Cl , Mg, Si and S are all in Period 3.

What is the correct sequence of the melting points of these elements, from lowest to highest?

lowest highest
melting point melting point

A Cl S Mg Si
B Cl S Si Mg
C Mg Si S Cl
D Si Mg S Cl

13 An element Y reacts according to the following sequence.

burns an excess of
in O2 HCl (aq) NaOH(aq) NaOH(aq)
Y white solid solution white precipitate solution

What could be element Y?

A Al B Ca C Mg D P

14 Which compound would most usually be added to soil to reduce its acidity?

A aluminium hydroxide
B calcium hydroxide
C magnesium hydroxide
D sodium hydroxide

15 The mineral dolomite is a mixture of magnesium carbonate and calcium carbonate.

An aqueous reagent, X, was added to a small sample of dolomite. Effervescence was seen and a
white solid, Y, was formed.

What could be the correct identity of reagent X and solid Y?

reagent X solid Y

A hydrochloric acid calcium chloride


B hydrochloric acid magnesium chloride
C sulfuric acid calcium sulfate
D sulfuric acid magnesium sulfate

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7

16 Which fertiliser contains the greatest percentage of nitrogen by mass?

A ammonium nitrate, NH4NO3


B ammonium sulfate, (NH4)2SO4
C diammonium hydrogen phosphate, (NH4)2HPO4
D urea, CO(NH2)2

17 71.0 g of chlorine, Cl 2, react with an excess of sodium hydroxide solution at a particular


temperature. The reaction produces exactly 35.5 g of product X.

What is product X?

A H2O B NaCl C NaCl O D NaCl O3

18 Compound Q is a white crystalline solid which dissolves easily in water. When concentrated
sulfuric acid is added to a dry sample of Q steamy white fumes are formed which, when passed
through aqueous silver nitrate solution, form a white precipitate. This precipitate is soluble in
dilute ammonia solution.

What could be the identity of compound Q?

A AgCl B NaBr C NaCl D PbBr2

19 The strengths of the covalent bonds within halogen molecules, and the van der Waals’ forces
between halogen molecules, vary going down Group 17 from chlorine to bromine to iodine.

Which row shows these correctly?

strength of strength of
covalent bonds van der Waals’ forces

A decreases decreases
B decreases increases
C increases decreases
D increases increases

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8

20 The structural formula of compound Q is shown.

How many stereoisomers exist with this structural formula?

A 1 B 2 C 4 D 8

21 What is the name of compound X?

OH

compound X

A trans-2-hydroxyhex-3-ene
B trans-2-hydroxyhexene
C trans-5-hydroxyhex-3-ene
D trans-5-hydroxyhexene

22 Many, but not all, organic reactions need to be heated before a reaction occurs.

Which reaction occurs quickly at room temperature, 20 °C?

A C2H4 + Br2 → C2H4Br2

B C2H4 + H2O → CH3CH2OH

C CH3CH2OH → C2H4 + H2O

D CH3CH2OH + HBr → CH3CH2Br + H2O

© UCLES 2017 9701/11/O/N/17


9

23 A section of an addition polymer chain is shown.

CH CH2 CH2 CH

Cl Cl

Which monomer could be used to make this polymer?

A CH2CHCH2Cl
B CH2CHCl
C CH3CHCHCl
D CHCl CHCH2CH2Cl

24 Which organic reaction is an example of nucleophilic substitution?

A CH3CH2Br + NaOH → CH2CH2 + H2O + NaBr

B CH3CH2Br + NaOH → CH3CH2OH + NaBr

C CH2CH2 + HCl → C2H5Cl

D C2H6 + Cl 2 → C2H5Cl + HCl

25 Citric acid can be converted into tricarballylic acid in two stages. An intermediate, Q, is formed.

CH2 CO2H CH2 CO2H


stage 1 stage 2
HO C CO2H Q CH CO2H

CH2 CO2H CH2 CO2H

citric acid tricarballylic acid

Which reagents are needed for each stage?

stage 1 stage 2

A concentrated H2SO4 H2(g) and Ni


B concentrated H2SO4 LiAl H4
C LiAl H4 H2SO4(aq)
D NaOH(aq) H2(g) and Ni

© UCLES 2017 9701/11/O/N/17 [Turn over


10

26 Glucose can be used to prepare sorbitol, a compound used as a sugar substitute.

H OH OH OH OH
OH OH
O HO
OH OH OH OH

glucose sorbitol

Which reagent may be used for this conversion?

A acidified potassium dichromate(VI)


B sodium borohydride
C sodium hydroxide
D Tollens’ reagent

27 3-methylbutanone is treated with alkaline aqueous iodine. The mixture of products is then
acidified.

Which compound is present in the final mixture of products?

A 3-methylbutanoic acid
B butanoic acid
C methylpropanoic acid
D propanoic acid

28 At room temperature, propanoic acid was reacted to produce sodium propanoate. No gas was
produced during the reaction.

What could the propanoic acid have reacted with?

A NaHCO3(aq) B NaOH(aq) C Na2CO3(aq) D Na2SO4(aq)

© UCLES 2017 9701/11/O/N/17


11

29 Ethene is reacted with steam in the presence of concentrated H3PO4. The product of this reaction
is added to acidified potassium dichromate(VI) and heated under reflux for one hour. The final
organic product is collected and labelled X.

But-2-ene is treated with hot, concentrated, acidified potassium manganate(VII). The final
organic product is collected and labelled Y.

Which statement is correct?

A One molecule of X has more carbon atoms than one molecule of Y.


B One molecule of Y has more carbon atoms than one molecule of X.
C X and Y have different functional groups.
D X is the same compound as Y.

30 A sample of the ester CH3CH2CH2CO2CH2CH3 is hydrolysed. The product mixture is then treated
with hot, acidified KMnO4.

What are the final carbon-containing products?

A CH3CH2CO2H only
B CH3CO2H + CH3CH2CO2H
C CH3CO2H + CH3CH2CH2CO2H
D CH3CH2OH + CH3CH2CH2CO2H

© UCLES 2017 9701/11/O/N/17 [Turn over


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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

Use of the Data Booklet may be appropriate for some questions.

31 The definitions of many chemical terms can be illustrated by chemical equations.

Which terms can be illustrated by an equation that includes the formation of a positive ion?

1 first ionisation energy


2 heterolytic fission of a covalent bond
3 enthalpy change of atomisation

32 A student makes sodium chloride by reacting together 0.025 mol of sodium carbonate with an
excess of 0.2 mol dm–3 hydrochloric acid.

Na2CO3 + 2HCl → 2NaCl + H2O + CO2

Which statements about the quantities of substance are correct?

1 600 cm3 of carbon dioxide are produced at room temperature and pressure.
2 250 cm3 of the hydrochloric acid are needed to exactly neutralise the sodium carbonate.
3 1.46 g of sodium chloride are produced.

© UCLES 2017 9701/11/O/N/17


13

33 One way of recovering tin from old printed circuit boards is to dissolve it in a mixture of
concentrated hydrochloric acid and concentrated nitric acid. The tin dissolves because it reacts
with the mixture of these concentrated acids.

Sn + 4HCl + 2HNO3 → SnCl 4 + NO2 + NO + 3H2O

Which statements about this reaction are correct?

1 Nitrogen is present in three different oxidation states in the reactants and products.
2 The oxidation state of tin increases from 0 to +4.
3 The oxidation state of chlorine remains the same.

34 The following reaction takes place in a suitable solvent.

Na+NH2– + NH4+Cl – → Na+Cl – + 2NH3

Which statements explain why this reaction should be classified as a Brønsted-Lowry acid-base
reaction?

1 The ammonium ion acts as a proton donor.


2 Na+Cl – is a salt.
3 Ammonia is a nucleophile.

35 Which statements about the elements barium and calcium and their compounds are correct?

1 Barium nitrate decomposes at a higher temperature than calcium nitrate.


2 Barium hydroxide is more soluble in water than is calcium hydroxide.
3 Calcium is more reactive with water than is barium.

36 Which statements explain why nitrogen gas is unreactive?

1 Nitrogen atoms are highly electronegative.


2 Nitrogen molecules are non-polar.
3 The triple bond between nitrogen atoms is very strong.

37 In which molecules do all the carbon atoms lie in the same plane?

1 2,3-dimethylbut-2-ene
2 propane
3 cyclohexane

© UCLES 2017 9701/11/O/N/17 [Turn over


14

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

38 A reaction pathway diagram is shown.

energy

progress of reaction

Which reactions would have this reaction pathway diagram?

1 (CH3)3CBr + NaOH → (CH3)3COH + NaBr

2 CH3CH2CH2Br + NaOH → CH3CH2CH2OH + NaBr

3 (CH3)3CCH2CH2Cl + 2NH3 → (CH3)3CCH2CH2NH2 + NH4Cl

39 The compounds below are used to make perfumes.

Which compounds will produce a yellow precipitate with alkaline aqueous iodine?

1 2 3
OH
OH
HO O

OH

OH

© UCLES 2017 9701/11/O/N/17


9701/11 Cambridge International AS/A Level – Mark Scheme October/November
PUBLISHED 2017

Question Answer Marks

1 A 1

2 A 1

3 D 1

4 C 1

5 B 1

6 A 1

7 D 1

8 D 1

9 D 1

10 C 1

11 C 1

12 A 1

13 A 1

14 B 1

15 C 1

16 D 1

17 D 1

18 C 1

19 B 1

20 C 1

21 A 1

22 A 1

23 B 1

24 B 1

25 A 1

26 B 1

27 C 1

28 B 1

© UCLES 2017 Page 2 of 3


9701/11 Cambridge International AS/A Level – Mark Scheme October/November
PUBLISHED 2017

Question Answer Marks

29 D 1

30 C 1

31 B 1

32 B 1

33 A 1

34 D 1

35 B 1

36 C 1

37 B 1

38 D 1

39 C 1

40 A 1

© UCLES 2017 Page 3 of 3


2

Section A

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

Use of the Data Booklet may be appropriate for some questions.

1 In which pair do the atoms contain the same number of neutrons?


11
A B and 12C
7
B Li and 9Be
24
C Mg and 28Si
14
D N and 16O

2 Two hydrocarbons have the formulae CWHX and CYHZ. W, X, Y and Z represent different whole
numbers.

W = Y
X Z

Which row is correct when comparing the two hydrocarbons?

empirical molecular relative


formula formula molecular mass

A different same different


B different same same
C same different different
D same different same

3 The airbags in cars contain sodium azide, NaN3, and an excess of potassium nitrate, KNO3.

In a car accident, the reactions shown occur, producing nitrogen. This causes the airbag to inflate
rapidly.

2NaN3 → 2Na + 3N2

10Na + 2KNO3 → K2O + 5Na2O + N2

How many moles of nitrogen gas are produced in total when 1 mol of sodium azide, NaN3,
decomposes in an airbag?

A 1.5 B 1.6 C 3.2 D 4.0

© UCLES 2017 9701/12/O/N/17


3

4 Ethane burns in oxygen to produce carbon dioxide and water vapour.

Which bond angles are present in the molecules of ethane and its combustion products?

ethane combustion products

A 90° 104.5° and 180°


B 90° 109.5° and 120°
C 109.5° 104.5° and 180°
D 109.5° 109.5° and 180°

5 A sample of an ideal gas is contained at a constant temperature of 300 K in a gas syringe.

pV
The pressure is increased and a graph of against pressure is plotted.
RT
Which graph correctly represents the results?

B
pV
RT C

D
p

6 In calculating the enthalpy change, ∆H, of an experiment involving solutions, the mass of the
solution, m, specific heat capacity of the solution, c, and the temperature change, ∆T, are
needed.

∆T = Tfinal – Tinitial

Which expression for ∆H is correct?


− mc
A ∆H = mc B ∆H = C ∆H = mc∆T D ∆H = –mc∆T
∆T ∆T

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7 The following data are needed for this question.

(P4O10(s)) = –3012 kJ mol–1

(H2O(l)) = –286 kJ mol–1

(H3PO4(s)) = –1279 kJ mol–1

What is ∆H o for the reaction shown?

P4O10(s) + 6H2O(l) → 4H3PO4(s)

A –9844 kJ mol–1
B –388 kJ mol–1
C –97 kJ mol–1
D +2019 kJ mol–1

8 Which statement is always correct for an oxidation reaction?

A It involves the gain of oxygen by an element.


B For one reactant to be oxidised a different reactant must be reduced.
C The element or ion being oxidised will gain electrons.
D The oxidation number of the element being oxidised will increase.

9 Nitrogen dioxide, NO2, is a brown gas.

Dinitrogen tetroxide, N2O4, is a colourless gas.

An equilibrium is established between NO2 and N2O4 in a closed vessel.

2NO2(g) N2O4(g) ∆H = –57 kJ mol–1


brown colourless

Which row describes the effects of changing conditions on the colour of an equilibrium mixture of
NO2 and N2O4?

increasing the pressure increasing the temperature

A colour becomes darker colour becomes darker


B colour becomes darker colour becomes lighter
C colour becomes lighter colour becomes darker
D colour becomes lighter colour becomes lighter

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10 A large excess of marble chips was reacted with 25 cm3 of 1.0 mol dm–3 hydrochloric acid at 40 °C.

How will the result be different when the reaction is repeated with 60 cm3 of 0.5 mol dm–3
hydrochloric acid at 40 °C?

A The reaction is faster and less of the products are made.


B The reaction is faster and more of the products are made.
C The reaction is slower and less of the products are made.
D The reaction is slower and more of the products are made.

11 Which change alters the activation energy of a given reaction?

A adding a suitable catalyst


B changing the particle size of the reactants
C changing the pressure at which the reaction is carried out
D changing the temperature at which the reaction is carried out

12 The relative magnitude of the property X of five elements is shown. P, Q, R, S and T are all in
Period 3 and have consecutive atomic numbers.

Q
P
X

S T

atomic number

Which row shows a correct pairing of property X and element R?

property X element R

A electrical conductivity Al
B electronegativity Si
C melting point Al
D second ionisation energy Si

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13 Element Z has a giant structure.

The chloride of Z reacts with water to give a solution with a pH less than 5.

Which row shows two elements which could be Z?

A aluminium, magnesium
B aluminium, silicon
C phosphorus, magnesium
D phosphorus, silicon

14 Radium is an element below barium in Group 2 of the Periodic Table.

Which equation shows what happens when solid radium nitrate, Ra(NO3)2, is heated strongly?

A Ra(NO3)2(s) → RaO(s) + N2O(g) + 2O2(g)

B 2Ra(NO3)2(s) → 2RaO(s) + 2N2(g) + 5O2(g)

C 2Ra(NO3)2(s) → 2RaO(s) + 4NO2(g) + O2(g)

D 4Ra(NO3)2(s) → 2Ra2O(s) + 8NO2(g) + 3O2(g)

15 Exactly 3.705 kg of substance Y are needed to neutralise 100 moles of HCl (aq).

What could be substance Y?

A Ca B CaO C Ca(OH)2 D CaCO3

16 In an experiment, 0.125 mol of chlorine gas, Cl 2, is reacted with an excess of cold, aqueous
sodium hydroxide. One of the products is a compound of sodium, oxygen and chlorine.

Which mass of this product is formed?

A 9.31 g B 13.3 g C 18.6 g D 26.6 g

17 Sodium bromide reacts with concentrated sulfuric acid.

Which observation will be made?

A A coloured vapour is produced.


B A purple solid is formed.
C A strong smell of H2S is detected.
D Yellow sulfur is formed.

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18 The reaction of nitrogen and oxygen to produce oxides of nitrogen happens at high temperatures
in car engines or lightning strikes during thunderstorms.

What is the main reason for these reactions requiring such high temperatures?

A the lack of reactivity of nitrogen, due to the half-filled 2p subshell in the nitrogen atom
B the lack of reactivity of nitrogen, due to the strength of the bond in N2
C the lack of reactivity of oxygen, due to electron-electron repulsion in one of its 2p orbitals
D the lack of reactivity of oxygen, due to the strength of the bond in O2

19 X is a mixture of two compounds of Group 2 elements.

X undergoes thermal decomposition to produce a white solid and only two gaseous products.
One of the gaseous products relights a glowing splint.

What could be the components of mixture X?

A MgCl 2 and CaCO3


B MgCO3 and Ca(NO3)2
C Mg(NO3)2 and Ca(NO3)2
D MgO and CaO

20 Which compound does not exhibit stereoisomerism?

A CH3CHCl CH2CHO
B CH3CHCHCH3
C CH2Cl CH2CCl 2H

D CHCl CHCl

21 The diagram shows the skeletal formula of citric acid.

O OH
O O

HO OH
OH
citric acid

What is the molecular formula of citric acid?

A C6H8O7 B C6H4O7 C C8H8O7 D C10H8O7

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22 Which compound would produce two different carboxylic acids when treated with hot,
concentrated, acidified manganate(VII) ions?

A B C D

23 Which types of bond are broken and formed in the addition polymerisation of alkenes?

type of type of
bond broken bond formed

A π only σ only
B π only σ and π
C σ and π σ only
D σ and π σ and π

24 2,3-dimethylpent-2-ene, (CH3)2C=C(CH3)CH2CH3, is treated with cold, dilute KMnO4. The product


of this reaction is treated with an excess of concentrated H2SO4 at 180 °C, giving a mixture of
isomeric hydrocarbons with molecular formula C7H12.

What is the name of one of the isomeric hydrocarbons?

A 2,3-dimethylpenta-1,2-diene
B cis-2,3-dimethylpenta-1,3-diene
C 2,3-dimethylpenta-1,4-diene
D 3,4-dimethylpenta-1,3-diene

25 Equal volumes of aqueous silver nitrate were added to separate small volumes of bromoethane
and iodoethane in two test-tubes. The test-tubes were shaken.

Which row about the observations made for bromoethane is correct?

colour of precipitate rate of reaction

A cream faster than for iodoethane


B cream slower than for iodoethane
C yellow faster than for iodoethane
D yellow slower than for iodoethane

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26 Many, but not all, organic reactions need to be heated before a reaction occurs.

Which reaction occurs quickly at room temperature (20 °C)?

A CH3OH + PCl 5 → CH3Cl + POCl 3 + HCl

B CH3CH2Br + KCN → CH3CH2CN + KBr

C CH3CH2OH → C2H4 + H2O

D CH3CH2CN + 2H2O → CH3CH2CO2H + NH3

27 When compound X is warmed with dilute, acidified potassium dichromate(VI) there is no colour
change. X does not give an orange precipitate with 2,4-dinitrophenylhydrazine reagent.

What could X be?

A butan-2-ol
B ethanal
C methylpropan-2-ol
D propanone

28 What are the only structures formed when butan-2-ol is heated with concentrated H2SO4?

CH3CH2 H CH3 H

A C C C C

H H H CH3

CH3 CH3 CH3 H H H

B C C C C C C

H H H CH3 CH3CH2 H

H H H H

C C C C C

CH3CH2 H CH3 CH3

CH3 H CH3CH2 H H H

D C C C C C C

CH3 H H H CH3 CH3

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29 Compound G

● has a chiral centre,


● gives a positive result with alkaline aqueous iodine,
● does not give a silver mirror with Tollens’ reagent.

What could compound G be?

A 1-hydroxybutan-2-one
B 2-hydroxybutanal
C 3-hydroxybutanal
D 3-hydroxybutan-2-one

30 An ester with an odour of banana has the following formula.

CH3CO2CH2CHCH2CH3

CH3

Which pair of reactants, under suitable conditions, will produce this ester?

A CH3CH2CHCH2CO2H + CH3OH

CH3

B CH3CH2CHCO2H + CH3CH2OH

CH3

C CH3CO2H + CH3CH2CHCH2OH

CH3

D CH3CO2H + CH3CHCH2CH2OH

CH3

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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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

Use of the Data Booklet may be appropriate for some questions.

31 In 2011 an international group of scientists agreed to add two new elements to the Periodic
Table. Both elements had been made artificially and are called flerovium, Fl, and livermorium, Lv.

Fl Lv

proton number 114 116


nucleon number 289 292

From the information about atoms in the table, which statements are correct?

1 One atom of Lv has one more neutron than one atom of Fl.
2 One Fl 2– ion has the same number of electrons as one atom of Lv.
3 One Lv+ ion has the same number of electrons as one Fl – ion.

32 The chlorine oxide free radical, Cl O•, is produced by the reaction between chlorine atoms and
ozone.

Cl • + O3 → Cl O• + O2

Which features are present in the chlorine oxide free radical?

1 an odd number of electrons


2 a single covalent bond
3 a dative covalent bond from oxygen to chlorine

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The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

33 Hydrogen sulfide can be oxidised to form sulfur dioxide.

2H2S + 3O2 → 2SO2 + 2H2O

Which statements are correct?

1 The oxidation number of sulfur increases by 6.


2 The oxidation number of oxygen increases by 2.
3 The oxidation number of hydrogen decreases.

34 Methanoic acid, HCO2H, and hydrocyanic acid, HCN, can both behave as acids.

A solution of methanoic acid has a lower pH than a solution of hydrocyanic acid of the same
concentration.

Which statements explain this?

1 HCO2H molecules dissociate more fully than HCN molecules do.


2 Each HCO2H molecule has two hydrogen atoms; each HCN molecule only has one.
3 Methanoic acid is a weaker acid than hydrocyanic acid.

35 Which statements correctly describe a trend on going down Group 2?

1 Reactivity of the elements increases.


2 First ionisation energy of the elements decreases.
3 The hydroxides become more soluble in water.

36 Modern cars are fitted with catalytic converters to reduce atmospheric pollution caused by
unwanted reactions during the combustion of the fuel.

Which statements are correct?

1 Carbon monoxide is oxidised to carbon dioxide in a catalytic converter.


2 Catalytic converters have a very large surface area.
3 Nitrogen dioxide is reduced to nitrogen monoxide in a catalytic converter.

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37 Which statements are correct for an SN2 mechanism?

1 One bond is being broken at the same time as another bond is being formed.
2 The formation of the intermediate involves the collision of two molecules or ions.
3 A carbon atom in the transition state is bonded, either fully or partially, to five atoms.

38 Bromoethane is heated under reflux with concentrated aqueous NaOH.

Which statements are correct?

1 The major product is a primary alcohol.


2 The major reaction is hydrolysis by an SN2 mechanism.
3 The major product would be the same if the NaOH is dissolved in ethanol.

39 Compound M is an important ingredient in perfume.

O O

compound M

M reacts with HCN.

Which statements about this reaction are correct?

1 A small amount of NaOH will speed up the reaction.


2 The reaction is initiated by the transfer of a proton to one of the C=O groups.
3 Both of the C=O groups react with HCN.

40 Carboxylic acids can be converted into their salts by a number of reactions at room temperature.

Which reactions would produce sodium butanoate and a gas?

1 sodium carbonate + butanoic acid


2 sodium + butanoic acid
3 sodium hydroxide + butanoic acid

© UCLES 2017 9701/12/O/N/17


9701/12 Cambridge International AS/A Level – Mark Scheme October/November
PUBLISHED 2017

Question Answer Marks

1 A 1

2 C 1

3 B 1

4 C 1

5 C 1

6 D 1

7 B 1

8 D 1

9 C 1

10 D 1

11 A 1

12 A 1

13 B 1

14 C 1

15 C 1

16 A 1

17 A 1

18 B 1

19 C 1

20 C 1

21 A 1

22 B 1

23 A 1

24 B 1

25 B 1

26 A 1

27 C 1

28 B 1

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9701/12 Cambridge International AS/A Level – Mark Scheme October/November
PUBLISHED 2017

Question Answer Marks

29 D 1

30 C 1

31 A 1

32 B 1

33 D 1

34 D 1

35 A 1

36 B 1

37 A 1

38 B 1

39 D 1

40 B 1

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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.

Use of the Data Booklet may be appropriate for some questions.

1 Which formula represents the empirical formula of a compound?

A C2H4O B C2H4O2 C C6H12 D H2O2

2 The relative first ionisation energies of four elements with consecutive atomic numbers below 20
are shown on the graph.

One of the elements reacts with hydrogen to form a covalent compound with formula HX.

Which element could be X?

first
ionisation
energy
/ kJ mol–1

D
C

atomic number

3 In which structure are three atoms bonded together in a straight line?

A poly(ethene), ] ( CH2CH2 )n
B propane, C3H8
C silicon tetrachloride, SiCl4
D sulfur hexafluoride, SF6

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4 In the sodium chloride lattice the number of chloride ions that surround each sodium ion is called
the co-ordination number of the sodium ions.

What are the co-ordination numbers of the sodium ions and the chloride ions in the
sodium chloride lattice?

sodium ions chloride ions

A 4 6
B 6 4
C 6 6
D 8 6

5 A fluorescent light tube has an internal volume of 400 cm3 and an internal pressure of 200 kPa.

It is filled with 0.03 moles of an ideal gas.

What is the temperature of the gas inside the fluorescent light tube?

A 3.21 × 10–1 K

B 3.21 × 102 K

C 3.21 × 105 K

D 3.21 × 108 K

6 One of the reactions in a lead / acid cell is shown.

Pb(s) + PbO2(s) + 4H+(aq) + 2SO42–(aq) → 2PbSO4(s) + 2H2O(l)

Which statement about this reaction is correct?

A Lead is both oxidised and reduced.


B Lead is neither oxidised nor reduced.
C Lead is oxidised only.
D Lead is reduced only.

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7 Iodine and propanone react according to the following equation.

I2(aq) + CH3COCH3(aq) → CH3COCH2I(aq) + HI(aq)

If the concentration of propanone is increased, keeping the total reaction volume constant, the
rate of the reaction also increases.

What could be the reason for this?

A A greater proportion of collisions is successful at the higher concentration.


B The particles are further apart at the higher concentration.
C The particles have more energy at the higher concentration.
D There are more collisions between reactant particles per second at the higher concentration.

8 Sulfur can be oxidised in two ways.

S(s) + O2(g) → SO2(g) ∆H o = –296.5 kJ mol–1

2S(s) + 3O2(g) → 2SO3(g) ∆H o = –791.4 kJ mol–1

Sulfur trioxide can be made from sulfur dioxide and oxygen.

2SO2(g) + O2(g) → 2SO3(g)

What is the standard enthalpy change for this reaction?

A –1384.4 kJ mol–1
B –989.8 kJ mol–1
C –494.9 kJ mol–1
D –198.4 kJ mol–1

9 Hydrogen iodide dissociates into hydrogen and iodine.

2HI(g) H2(g) + I2(g)

In an experiment, b mol of hydrogen iodide were put into a sealed vessel at pressure p. At
equilibrium, x mol of the hydrogen iodide had dissociated.

Which expression for Kp is correct?

A x2 B x 2p2 C x 2p2 D x2
( b − x )2 ( b − x )2 4 b( b − x ) 4( b − x )2

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10 The diagram shows the distribution of molecular energies in a sample of gas at a temperature T1.
The activation energy for an uncatalysed reaction of this gas, Ea(uncat), is shown.

T1
proportion Ea(uncat)
of molecules
with a given
energy

0
0 molecular energy E

Which diagram correctly shows the new distribution and new activation energy, Ea(cat), when the
temperature is increased to T2, and a catalyst is used that increases the rate of the reaction?

A B
T1 T1 Ea(cat)
proportion Ea(uncat) proportion Ea(uncat)
T2 T2
of molecules Ea(cat) of molecules
with a given with a given
energy energy

0 0
0 molecular energy E 0 molecular energy E

C D
T1 Ea(cat) T1
proportion Ea(uncat) proportion Ea(uncat)
of molecules of molecules Ea(cat)
with a given with a given
energy T2 energy T2

0 0
0 molecular energy E 0 molecular energy E

11 200 g of water are at 25 °C.

The water is heated to 75 °C by burning 2 g of ethanol.

What is the amount of energy transferred to the water?

A 0.418 kJ B 10.4 kJ C 41.8 kJ D 62.7 kJ

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12 The elements Cl , Mg, Si and S are all in Period 3.

What is the correct sequence of the melting points of these elements, from lowest to highest?

lowest highest
melting point melting point

A Cl S Mg Si
B Cl S Si Mg
C Mg Si S Cl
D Si Mg S Cl

13 An element Y reacts according to the following sequence.

burns an excess of
in O2 HCl (aq) NaOH(aq) NaOH(aq)
Y white solid solution white precipitate solution

What could be element Y?

A Al B Ca C Mg D P

14 Which compound would most usually be added to soil to reduce its acidity?

A aluminium hydroxide
B calcium hydroxide
C magnesium hydroxide
D sodium hydroxide

15 The mineral dolomite is a mixture of magnesium carbonate and calcium carbonate.

An aqueous reagent, X, was added to a small sample of dolomite. Effervescence was seen and a
white solid, Y, was formed.

What could be the correct identity of reagent X and solid Y?

reagent X solid Y

A hydrochloric acid calcium chloride


B hydrochloric acid magnesium chloride
C sulfuric acid calcium sulfate
D sulfuric acid magnesium sulfate

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16 Which fertiliser contains the greatest percentage of nitrogen by mass?

A ammonium nitrate, NH4NO3


B ammonium sulfate, (NH4)2SO4
C diammonium hydrogen phosphate, (NH4)2HPO4
D urea, CO(NH2)2

17 71.0 g of chlorine, Cl 2, react with an excess of sodium hydroxide solution at a particular


temperature. The reaction produces exactly 35.5 g of product X.

What is product X?

A H2O B NaCl C NaCl O D NaCl O3

18 Compound Q is a white crystalline solid which dissolves easily in water. When concentrated
sulfuric acid is added to a dry sample of Q steamy white fumes are formed which, when passed
through aqueous silver nitrate solution, form a white precipitate. This precipitate is soluble in
dilute ammonia solution.

What could be the identity of compound Q?

A AgCl B NaBr C NaCl D PbBr2

19 The strengths of the covalent bonds within halogen molecules, and the van der Waals’ forces
between halogen molecules, vary going down Group 17 from chlorine to bromine to iodine.

Which row shows these correctly?

strength of strength of
covalent bonds van der Waals’ forces

A decreases decreases
B decreases increases
C increases decreases
D increases increases

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20 The structural formula of compound Q is shown.

How many stereoisomers exist with this structural formula?

A 1 B 2 C 4 D 8

21 What is the name of compound X?

OH

compound X

A trans-2-hydroxyhex-3-ene
B trans-2-hydroxyhexene
C trans-5-hydroxyhex-3-ene
D trans-5-hydroxyhexene

22 Many, but not all, organic reactions need to be heated before a reaction occurs.

Which reaction occurs quickly at room temperature, 20 °C?

A C2H4 + Br2 → C2H4Br2

B C2H4 + H2O → CH3CH2OH

C CH3CH2OH → C2H4 + H2O

D CH3CH2OH + HBr → CH3CH2Br + H2O

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23 A section of an addition polymer chain is shown.

CH CH2 CH2 CH

Cl Cl

Which monomer could be used to make this polymer?

A CH2CHCH2Cl
B CH2CHCl
C CH3CHCHCl
D CHCl CHCH2CH2Cl

24 Which organic reaction is an example of nucleophilic substitution?

A CH3CH2Br + NaOH → CH2CH2 + H2O + NaBr

B CH3CH2Br + NaOH → CH3CH2OH + NaBr

C CH2CH2 + HCl → C2H5Cl

D C2H6 + Cl 2 → C2H5Cl + HCl

25 Citric acid can be converted into tricarballylic acid in two stages. An intermediate, Q, is formed.

CH2 CO2H CH2 CO2H


stage 1 stage 2
HO C CO2H Q CH CO2H

CH2 CO2H CH2 CO2H

citric acid tricarballylic acid

Which reagents are needed for each stage?

stage 1 stage 2

A concentrated H2SO4 H2(g) and Ni


B concentrated H2SO4 LiAl H4
C LiAl H4 H2SO4(aq)
D NaOH(aq) H2(g) and Ni

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26 Glucose can be used to prepare sorbitol, a compound used as a sugar substitute.

H OH OH OH OH
OH OH
O HO
OH OH OH OH

glucose sorbitol

Which reagent may be used for this conversion?

A acidified potassium dichromate(VI)


B sodium borohydride
C sodium hydroxide
D Tollens’ reagent

27 3-methylbutanone is treated with alkaline aqueous iodine. The mixture of products is then
acidified.

Which compound is present in the final mixture of products?

A 3-methylbutanoic acid
B butanoic acid
C methylpropanoic acid
D propanoic acid

28 At room temperature, propanoic acid was reacted to produce sodium propanoate. No gas was
produced during the reaction.

What could the propanoic acid have reacted with?

A NaHCO3(aq) B NaOH(aq) C Na2CO3(aq) D Na2SO4(aq)

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11

29 Ethene is reacted with steam in the presence of concentrated H3PO4. The product of this reaction
is added to acidified potassium dichromate(VI) and heated under reflux for one hour. The final
organic product is collected and labelled X.

But-2-ene is treated with hot, concentrated, acidified potassium manganate(VII). The final
organic product is collected and labelled Y.

Which statement is correct?

A One molecule of X has more carbon atoms than one molecule of Y.


B One molecule of Y has more carbon atoms than one molecule of X.
C X and Y have different functional groups.
D X is the same compound as Y.

30 A sample of the ester CH3CH2CH2CO2CH2CH3 is hydrolysed. The product mixture is then treated
with hot, acidified KMnO4.

What are the final carbon-containing products?

A CH3CH2CO2H only
B CH3CO2H + CH3CH2CO2H
C CH3CO2H + CH3CH2CH2CO2H
D CH3CH2OH + CH3CH2CH2CO2H

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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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

Use of the Data Booklet may be appropriate for some questions.

31 The definitions of many chemical terms can be illustrated by chemical equations.

Which terms can be illustrated by an equation that includes the formation of a positive ion?

1 first ionisation energy


2 heterolytic fission of a covalent bond
3 enthalpy change of atomisation

32 A student makes sodium chloride by reacting together 0.025 mol of sodium carbonate with an
excess of 0.2 mol dm–3 hydrochloric acid.

Na2CO3 + 2HCl → 2NaCl + H2O + CO2

Which statements about the quantities of substance are correct?

1 600 cm3 of carbon dioxide are produced at room temperature and pressure.
2 250 cm3 of the hydrochloric acid are needed to exactly neutralise the sodium carbonate.
3 1.46 g of sodium chloride are produced.

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33 One way of recovering tin from old printed circuit boards is to dissolve it in a mixture of
concentrated hydrochloric acid and concentrated nitric acid. The tin dissolves because it reacts
with the mixture of these concentrated acids.

Sn + 4HCl + 2HNO3 → SnCl 4 + NO2 + NO + 3H2O

Which statements about this reaction are correct?

1 Nitrogen is present in three different oxidation states in the reactants and products.
2 The oxidation state of tin increases from 0 to +4.
3 The oxidation state of chlorine remains the same.

34 The following reaction takes place in a suitable solvent.

Na+NH2– + NH4+Cl – → Na+Cl – + 2NH3

Which statements explain why this reaction should be classified as a Brønsted-Lowry acid-base
reaction?

1 The ammonium ion acts as a proton donor.


2 Na+Cl – is a salt.
3 Ammonia is a nucleophile.

35 Which statements about the elements barium and calcium and their compounds are correct?

1 Barium nitrate decomposes at a higher temperature than calcium nitrate.


2 Barium hydroxide is more soluble in water than is calcium hydroxide.
3 Calcium is more reactive with water than is barium.

36 Which statements explain why nitrogen gas is unreactive?

1 Nitrogen atoms are highly electronegative.


2 Nitrogen molecules are non-polar.
3 The triple bond between nitrogen atoms is very strong.

37 In which molecules do all the carbon atoms lie in the same plane?

1 2,3-dimethylbut-2-ene
2 propane
3 cyclohexane

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14

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

38 A reaction pathway diagram is shown.

energy

progress of reaction

Which reactions would have this reaction pathway diagram?

1 (CH3)3CBr + NaOH → (CH3)3COH + NaBr

2 CH3CH2CH2Br + NaOH → CH3CH2CH2OH + NaBr

3 (CH3)3CCH2CH2Cl + 2NH3 → (CH3)3CCH2CH2NH2 + NH4Cl

39 The compounds below are used to make perfumes.

Which compounds will produce a yellow precipitate with alkaline aqueous iodine?

1 2 3
OH
OH
HO O

OH

OH

© UCLES 2017 9701/13/O/N/17


15

40 The reaction of ethanal, CH3CHO, with HCN to form 2-hydroxypropanenitrile is catalysed by


NaCN.

What are features of the intermediate of this reaction?

1 It is chiral.
2 It has a single negative charge on one of its atoms.
3 It is a nucleophile.

© UCLES 2017 9701/13/O/N/17


9701/13 Cambridge International AS/A Level – Mark Scheme October/November
PUBLISHED 2017

Question Answer Marks

1 A 1

2 A 1

3 D 1

4 C 1

5 B 1

6 A 1

7 D 1

8 D 1

9 D 1

10 C 1

11 C 1

12 A 1

13 A 1

14 B 1

15 C 1

16 D 1

17 D 1

18 C 1

19 B 1

20 C 1

21 A 1

22 A 1

23 B 1

24 B 1

25 A 1

26 B 1

27 C 1

28 B 1

© UCLES 2017 Page 2 of 3


9701/13 Cambridge International AS/A Level – Mark Scheme October/November
PUBLISHED 2017

Question Answer Marks

29 D 1

30 C 1

31 B 1

32 B 1

33 A 1

34 D 1

35 B 1

36 C 1

37 B 1

38 D 1

39 C 1

40 A 1

© UCLES 2017 Page 3 of 3


2

Section A

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

Use of the Data Booklet may be appropriate for some questions.

1 Which equation shows the reaction that occurs during the standard enthalpy change of
atomisation of bromine?

A Br2(l) → 2Br(g)

B Br2(g) → 2Br(g)
1
C 2
Br2(l) → Br(g)
1
D 2
Br2(g) → Br(g)

2 What is the correct number of bonds of each type in the Al 2Cl 6 molecule?

co-ordinate
covalent
(dative covalent)

A 6 1
B 6 2
C 7 0
D 7 1

3 Tetraethyl lead, Pb(C2H5)4, has been used as a petrol additive.

What is the percentage by mass of carbon in tetraethyl lead?

A 10.2 B 14.9 C 29.7 D 32.0

© UCLES 2016 9701/11/M/J/16


3

4 When nuclear reactions take place, the elements produced are different from the elements that
reacted. Nuclear equations, such as the one below, are used to represent the changes that
occur.

235 1 144 89
92 U + 0n → 56 Ba + 36 Kr + 3 01 n

The nucleon (mass) number total is constant at 236 and the proton number total is constant
at 92.

2
In another nuclear reaction, uranium-238 is reacted with deuterium atoms, 1 H. An isotope of a
new element, J, is formed as well as two neutrons.

238 2
92 U + 1H → J + 2 01 n

What is isotope J?
238 238 240 240
A Np B Pu C Np D Pu

5 Dicarbon monoxide, C2O, is found in dust clouds in space. The structure of this molecule is
C=C=O. The molecule contains no unpaired electrons.

How many lone pairs of electrons are present in a molecule of C2O?

A 1 B 2 C 3 D 4

6 A white powder is known to be a mixture of magnesium oxide and aluminium oxide.

100 cm3 of 2 mol dm–3 NaOH(aq) is just sufficient to cause the aluminium oxide in x grams of the
mixture to dissolve.

The reaction occurring is Al 2O3 + 2OH– + 3H2O → 2Al (OH)4–.

800 cm3 of 2 mol dm–3 HCl (aq) is just sufficient to cause all of the oxide in x grams of the mixture
to dissolve.

The reactions occurring are Al 2O3 + 6H+ → 2Al 3+ + 3H2O


and MgO + 2H+ → Mg2+ + H2O.

How many moles of each oxide are present in x grams of the mixture?

aluminium magnesium
oxide oxide

A 0.05 0.25
B 0.05 0.50
C 0.10 0.25
D 0.10 0.50

© UCLES 2016 9701/11/M/J/16 [Turn over


4

7 At room temperature and pressure, H2O is a liquid and H2S is a gas.

What is the reason for this difference?

A O has higher first and second ionisation energies than S.


B The covalent bond between O and H is stronger than the covalent bond between S and H.
C There is significant hydrogen bonding between H2O molecules but not between H2S
molecules.
D The instantaneous dipole-induced dipole forces between H2O molecules are stronger than
the instantaneous dipole-induced dipole forces between H2S molecules.

8 Gaseous phosphorus pentachloride can be decomposed into gaseous phosphorus trichloride and
chlorine by heating. The table gives the bond energies.

bond bond energy / kJ mol–1

P–Cl (in both chlorides) 330


Cl –Cl 242

What is the enthalpy change for the decomposition of PCl 5 to PCl 3 and Cl 2?

A –418 kJ mol–1
B –88 kJ mol–1
C +88 kJ mol–1
D +418 kJ mol–1

9 An aqueous solution was prepared containing a mixture of 1.0 mol of AgNO3 and 1.0 mol of
FeSO4 in 1.00 dm3 of water. When equilibrium was established, there was 0.44 mol of Ag+(aq) in
the mixture.

Ag+(aq) + Fe2+(aq) Ag(s) + Fe3+(aq)

What is the numerical value of Kc?

A 0.62 B 1.40 C 1.62 D 2.89

10 The equation for the reaction between carbon monoxide and hydrogen is shown.

CO(g) + 3H2(g) CH4(g) + H2O(g)

What are the units of Kp for this reaction?

A kPa B kPa–1 C kPa2 D kPa–2

© UCLES 2016 9701/11/M/J/16


5

11 Enzymes are biological catalysts. Many enzymes show specificity. An example of an enzyme
which shows specificity is glucokinase. Glucokinase is involved in the metabolism of glucose.

What does specificity mean in this context?

A Glucokinase is most effective as a catalyst over a narrow pH range.


B Glucokinase is most effective as a catalyst over a narrow range of temperatures.
C Glucokinase only operates on a narrow range of substrate molecules.
D Glucokinase provides an alternative route for the reactions it catalyses.

12 Why is the ionic radius of a chloride ion larger than the ionic radius of a sodium ion?

A A chloride ion has one more occupied electron shell than a sodium ion.
B Chlorine has a higher proton number than sodium.
C Ionic radius increases regularly across the third period.
D Sodium is a metal, chlorine is a non-metal.

13 Elements D and E are both in Period 3. Element D has the smallest atomic radius in Period 3.
There are only two elements in Period 3 which have a lower melting point than element E.
Elements D and E react together to form compound L.

Which compound could be L?

A MgCl 2 B MgS C Na2S D PCl 3

14 X and Y are both Group 2 metals.

X and Y both form hydroxide compounds, but X(OH)2 is more soluble in water than Y(OH)2.

If a piece of metal Y is put into cold water a very slow reaction occurs, and only a very few, small
hydrogen bubbles can be seen.

What could be the identities of X and Y?

X Y

A barium magnesium
B barium strontium
C calcium strontium
D magnesium calcium

© UCLES 2016 9701/11/M/J/16 [Turn over


6

15 The solids sodium chloride and sodium iodide both react with concentrated sulfuric acid at room
temperature.

With NaCl , the products are NaHSO4 and HCl .


With NaI, the products are NaHSO4, HI, I2, SO2, H2O, S and H2S.

What is the best explanation for this difference in products?

A Chloride ions will displace iodine from solution.


B Hydrogen chloride is more volatile than hydrogen iodide.
C Iodide ions are better reducing agents than chloride ions.

D Sulfuric acid is able to act as a dehydrating agent with NaI.

16 In some areas lime, Ca(OH)2, is added to soil to improve crop growth.

Which statement correctly describes a reason why lime improves crop growth?

A Lime acts as a catalyst which speeds up the release of nitrates into the soil.
B Lime is an effective pesticide and protects the plants from damage.
C Lime is used to reduce the acidity of the soil.
D Lime lowers the pH of the soil.

17 A piece of rock has a mass of 2.00 g. It contains calcium carbonate, but no other basic
substances. It neutralises exactly 36.0 cm3 of 0.500 mol dm–3 hydrochloric acid.

What is the percentage of calcium carbonate in the 2.00 g piece of rock?

A 22.5% B 45.0% C 72.0% D 90.1%

18 Which statement about the ammonia molecule and/or the ammonium ion is correct?

A Ammonia molecules are basic because they can donate H+ ions.


B Ammonium ions are basic because they can accept H+ ions.
C If ammonium ions are heated with NaOH(aq), ammonia molecules are formed.

D The bond angle in NH4+ is 2.5° less than the bond angle in NH3.

19 Which reaction does not contribute to the problem of acid rain?

A the combustion of fossil fuels


B the oxidation of sulfur dioxide to sulfur trioxide catalysed by nitrogen dioxide
C the reaction between nitrogen monoxide and carbon monoxide in a catalytic converter
D the reaction of sulfur trioxide with water

© UCLES 2016 9701/11/M/J/16


7

20 The diagrams show two different compounds.

O O

1 2

What is

● the total number of structural isomers, including compound 2, that could be formed
by adding a second methyl group to the ring of compound 1,

● the number of π electrons in each compound?

number of number of
isomers π electrons

A 3 2
B 3 4
C 5 2
D 5 4

21 The structural formula of compound X is shown below.

CH3CH2CH2OC

compound X

What is the name of compound X and how does its boiling point compare with that of butanoic
acid?

name of X boiling point of X

A methyl propanoate higher than butanoic acid


B methyl propanoate lower than butanoic acid
C propyl methanoate higher than butanoic acid
D propyl methanoate lower than butanoic acid

© UCLES 2016 9701/11/M/J/16 [Turn over


8

22 Which pair of reagents will take part in a redox reaction?

A CH3CHCH2 + Br2
B CH3CH2CH2OH + concentrated H3PO4
C CH3COCH3 + HCN
D HCO2C2H5 + dilute H2SO4

23 The first propagation step in the reaction between methane and chlorine is shown.

CH4 + Cl • → CH3• + HCl

How many different first propagation steps are possible in the reaction between pentane and
chlorine?

A 2 B 3 C 4 D 5

24 Alcohol Y gives product Z after mild oxidation. Z gives a positive result with Tollens’ reagent and
with 2,4-dinitrophenylhydrazine reagent.

What could be the identity of alcohol Y?

A butan-1-ol
B butan-2-ol
C butan-2,3-diol
D 2-methylbutan-2-ol

25 A student prepares pentan-1-ol by the alkaline hydrolysis of 1-iodopentane. She gently warms the
reaction mixture for 20 minutes.

CH3CH2CH2CH2CH2I + OH– → CH3CH2CH2CH2CH2OH + I–

When the student uses 1-chloropentane to prepare the same alcohol she has to change the
condition of the reaction.

Which change in condition should she use and what is the correct reason for its use?

change in condition reason

A heat under reflux C–Cl bond is more polar than the C–I bond
B heat under reflux C–Cl bond is stronger than the C–I bond
C room temperature C–Cl bond is more polar than the C–I bond
D room temperature C–Cl bond is shorter than the C–I bond

© UCLES 2016 9701/11/M/J/16


9

26 Malic acid is found in apples.

OH

H C CH2CO2H

CO2H

malic acid

Which reagent will react with all three –OH groups present in the malic acid molecule?

A ethanol in the presence of concentrated sulfuric acid


B potassium hydroxide
C sodium
D sodium carbonate

27 Cyclic esters are also known as lactones. Delta lactone is used as a solvent and in the
manufacture of polyesters.

delta lactone

From which compound could delta lactone be made by a single reaction?

A HOCH2CH2CH2CH2CHO
B HOCH2CH2CH2CH2CO2H
C HOCH2CH2CH2CH2CH2OH
D HOCH2CH2CH2CH2CH2CO2H

28 Which reagent cannot be used to distinguish between ethanal and propanone?

A acidified sodium dichromate(VI) solution


B alkaline aqueous iodine

C cold acidified potassium manganate(VII) solution


D Fehling’s reagent

© UCLES 2016 9701/11/M/J/16 [Turn over


10

29 The ester CH3CH2CH2CO2CH2CH(CH3)2 was hydrolysed under acidic conditions.

What are the organic products of this hydrolysis?

A butanoic acid and 2-methylpropan-1-ol


B butanoic acid and 2-methylpropan-2-ol
C butan-1-ol and 2-methylpropanoic acid
D propanoic acid and 2-methylpropan-1-ol

30 Geranyl ethanoate is present in ginger and cocoa, and is used in shampoos and soaps as a
perfume. It reacts with an excess of bromine in an organic solvent to give X, a bromo-derivative.

O
Br2
O bromo-derivative

geranyl ethanoate X

Including geranyl ethanoate, how many cis-trans isomers are there of geranyl ethanoate, and
how many chiral centres are there in X?

chiral centres
cis-trans isomers
in X

A 2 3
B 2 4
C 4 3
D 4 4

© UCLES 2016 9701/11/M/J/16


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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

31 X is a particle with 18 electrons and 20 neutrons.

What could be the symbol of X?


38
1 18 Ar

40 2+
2 20 Ca

39 +
3 19 K

32 What are basic assumptions of the kinetic theory as applied to an ideal gas?

1 Gas particles are in continuous random motion.


2 Gas particles experience no intermolecular forces.
3 The volume of each gas particle is zero.

33 Bromine reacts with water.

Br2 + H2O HOBr + HBr

Which oxidation states of bromine are present in the equilibrium mixture?

1 +3
2 0
3 –1

© UCLES 2016 9701/11/M/J/16 [Turn over


12

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

34 A little water is added to each of the following compounds and the mixture warmed.

For which compounds will an acidic gas be evolved?

1 aluminium chloride
2 silicon tetrachloride
3 phosphorous pentachloride

35 The element astatine, At, is below iodine in Group 17 of the Periodic Table.

Which statements concerning At are likely to be correct?

1 It is a dark-coloured solid at room temperature.


2 It is a more powerful oxidising agent than iodine.
3 Its hydride is thermally stable.

36 Which types of reaction can occur with 1-bromobutane?

1 elimination
2 hydrolysis
3 free radical substitution

© UCLES 2016 9701/11/M/J/16


13

37 The equation shows a gas phase reaction.

X(g) → 2Y(g)

The diagram shows the Boltzmann distribution of a fixed mass of X(g) at temperature T in the
absence of a catalyst. The line EA indicates the activation energy.

proportion of
molecules
with a given
energy

0
0 EA
molecular energy

Which diagrams correctly show the effect of the following changes made separately and
independently?

1 adding a catalyst

proportion of
molecules
with a given
energy

0
0 EA
molecular energy

2 increasing the pressure of X(g)

proportion of
molecules
with a given
energy

0
0 EA
molecular energy

3 increasing the temperature of X(g)

proportion of temperature T '


molecules (T ' > T )
with a given
temperature T
energy

0
0 EA
molecular energy

© UCLES 2016 9701/11/M/J/16 [Turn over


14

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

38 The diagram shows the structure of cyclohexene.

cyclohexene

Which structures could be formed by addition reactions with cyclohexene as the only reactant?

1 2 3

n n

39 Several steps are involved in the synthesis of 2-hydroxypropanoic acid from ethanol.

C2H5OH → → → CH3CH(OH)CO2H

Which statements concerning this synthesis are correct?

1 The chain length can be increased during a step involving reaction between HCN and an
aldehyde.
2 The carboxyl group can be made by hydrolysis of a nitrile by boiling with NaOH(aq) and then
acidifying.
3 The ethanol should be first oxidised by heating it under reflux with an excess of acidified
potassium dichromate(VI).

© UCLES 2016 9701/11/M/J/16


15

40 The diagram shows the structure of an addition polymer, X.

CH3 H CH3 H CH3 H

C C C C C C

H CO2CH3 H CO2CH3 H CO2CH3

Which reagents react with polymer X?

1 aqueous sulfuric acid


2 aqueous sodium hydroxide
3 sodium

© UCLES 2016 9701/11/M/J/16


Page 2 Mark Scheme Syllabus Paper
Cambridge International AS/A Level – May/June 2016 9701 11

Question Question
Key Key
Number Number

1 C 21 D
2 B 22 A
3 C 23 B
4 A 24 A
5 C 25 B

6 D 26 C
7 C 27 B
8 D 28 B
9 D 29 A
10 D 30 A

11 C 31 A
12 A 32 A
13 D 33 C
14 A 34 A
15 C 35 D

16 C 36 A
17 B 37 B
18 C 38 B
19 C 39 B
20 D 40 B

© Cambridge International Examinations 2016


2

Section A

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

Use of the Data Booklet may be appropriate for some questions.

1 The diagram shows the Boltzmann distribution of energies in 1 mole of a gas. The gas can take
part in a reaction with an activation energy, Ea.

proportion of molecules
with a given energy

0
0 Ea
molecular energy

Which statement correctly describes the effect of an increase in temperature?

A Peak P will be higher and fewer molecules will have energy > Ea.
B Peak P will be higher and more molecules will have energy > Ea.
C Peak P will be lower and fewer molecules will have energy > Ea.
D Peak P will be lower and more molecules will have energy > Ea.

2 Four electronic configurations are shown below. Three of these configurations belong to atoms of
the elements chlorine, sodium and vanadium.

Which electronic configuration belongs to an atom of another element?

A 1s22s22p63s1
B 1s22s22p63s23p5
C 1s22s22p63s23p63d34s2
D 1s22s22p63s23p63d64s2

© UCLES 2016 9701/12/M/J/16


3

3 Elements X and Y are in the same group of the Periodic Table.

The table shows the first six ionisation energies of X and Y in kJ mol–1.

1st 2nd 3rd 4th 5th 6th

X 800 1600 2400 4300 5400 10 400


Y 1000 1800 2700 4800 6000 12 300

What could be the identities of X and Y?

X Y

A antimony, Sb arsenic, As
B arsenic, As antimony, Sb
C selenium, Se tellurium, Te
D tellurium, Te selenium, Se

4 In China, the concentration of blood glucose, C6H12O6, is measured in mmol / l . In Pakistan, the
concentration of blood glucose is measured in mg / dl .

The unit l is a litre (1 dm3). The unit dl is a decilitre (0.1 dm3).

A blood glucose concentration of 18.5 mmol / l indicates a health problem.

What is 18.5 mmol / l converted to mg / dl ?

A 33.3 mg / dl B 178 mg / dl C 333 mg / dl D 3330 mg / dl

5 Each of the four species in this question are isolated and gaseous.

Which species is not planar?

A BF3 B CH3+ C C2H4 D NH3

6 Argon is a gas used to fill electric light bulbs.

Under which conditions of pressure and temperature will argon behave most like an ideal gas?

pressure temperature

A high high
B high low
C low high
D low low

© UCLES 2016 9701/12/M/J/16 [Turn over


4

7 0.10 g of the volatile liquid X formed 0.025 dm3 of vapour at 100 °C and atmospheric pressure.

1 mol of vapour occupies 22.4 dm3 at 0 °C and atmospheric pressure.

What is the relative molecular mass of X?

A 0.025 × 273 × 22.4


0.10 × 373

B 0.025 × 373 × 22.4


0.10 × 273

C 0.10 × 273 × 22.4


0.025 × 373

D 0.10 × 373 × 22.4


0.025 × 273

8 The equation for the complete combustion of propan-1-ol is shown.

CH3CH2CH2OH(l) + 4 21 O2(g) → 3CO2(g) + 4H2O(l)

Standard enthalpy changes of formation are given.

compound CH3CH2CH2OH(l) CO2(g) H2O(l)


∆Hfo –303 kJ mol–1 –394 kJ mol–1 –286 kJ mol–1

What is the standard enthalpy change of combustion of propan-1-ol, in kJ mol–1?

A –394 – 286 – 303

B 303 – (4 × 286) – (3 × 394)


C 394 + 286 – 303

D (3 × 394) + (4 × 286) + 303

9 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 change in oxidation number of chlorine when forming the Cl O– ion from aqueous
chlorine?

A –1 B 0 C +1 D +2

© UCLES 2016 9701/12/M/J/16


5

10 When solid ammonium chloride dissociates at a certain temperature in a 0.500 dm3 container,
ammonia and hydrogen chloride are formed.

NH4Cl (s) NH3(g) + HCl (g)

The initial amount of ammonium chloride was 1.00 mol, and when the system had reached
equilibrium there was 0.300 mol of ammonium chloride.

What is the numerical value of Kc for this reaction under these conditions?

A 0.490 B 1.63 C 1.96 D 3.27

11 Which stage in the free radical substitution of ethane by chlorine has the lowest activation
energy?

A Cl 2 → 2Cl ●

B Cl ● + C2H6 → C2H5● + HCl

C C2H5● + Cl 2 → C2H5Cl + Cl ●

D Cl ● + C2H5● → C2H5Cl

12 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 ionic radius

A sodium < sulfur sodium > sulfur


B sodium < sulfur sodium < sulfur
C sodium > sulfur sodium > sulfur
D sodium > sulfur sodium < sulfur

13 Solid aluminium chloride sublimes at 178 oC.

Which structure best represents the species in the vapour at this temperature?

A B C D

Cl Cl Cl Cl Cl Cl Cl Cl Al 3+(Cl –)3
Al
Al Al Al Al

Cl Cl Cl Cl
Cl Cl Cl

© UCLES 2016 9701/12/M/J/16 [Turn over


6

14 A 0.005 mol sample of anhydrous calcium carbonate was completely thermally decomposed to
give 100 cm3 of gas measured at a certain temperature and pressure.

In a separate experiment carried out at the same temperature and pressure, a 0.005 mol sample
of anhydrous calcium nitrate was completely thermally decomposed. The volume of gaseous
products was measured.

What total volume of gaseous products was produced from the calcium nitrate?

A 50 cm3 B 100 cm3 C 200 cm3 D 250 cm3

15 Ammonia gas, NH3, and hydrogen sulfide gas, H2S, react together to form the salt ammonium
sulfide, (NH4)2S. Ammonium sulfide dissolves in water to produce an orange alkaline solution.

(NH4)2S(aq) NH3(aq) + NH4SH(aq)

The addition of NaOH(aq) to this solution produces a gas, X.


The addition of HCl (aq) to a separate portion of this solution produces a gas, Y.

What are the identities of X and Y?

X Y

A H2S H2S
B H2S NH3
C NH3 H2S
D NH3 NH3

16 A solid, T, was placed in an excess of the liquid U.

A colourless gas was given off and a white precipitate was seen. The precipitate was not T.

What could be the identities of T and U?

T U

A BaCO3 H2O
B Ca dilute H2SO4
C Mg dilute H2SO4
D SrCO3 dilute HCl

© UCLES 2016 9701/12/M/J/16


7

17 Nitrogen(II) oxide, NO, nitrogen(IV) oxide, NO2, carbon monoxide, CO, and unburnt
hydrocarbons are present in the exhaust gases of internal combustion engines. When catalytic
converters are used to remove these compounds from the exhaust gases, redox reactions occur.

What happens to each compound in the catalytic converter?

NO NO2 CO hydrocarbons

A oxidised oxidised reduced oxidised


B oxidised oxidised oxidised oxidised
C reduced reduced oxidised oxidised
D reduced reduced reduced reduced

18 An excess of chlorine gas, Cl 2, is passed through 60 cm3 of cold aqueous 0.1 mol dm–3 sodium
hydroxide. In a separate experiment an excess of chlorine gas is passed through 60 cm3 of hot
aqueous 0.1 mol dm–3 sodium hydroxide until no further reaction takes place.

How much more sodium chloride will be produced by the reaction with hot NaOH than with cold
NaOH?

A 0.002 moles
B 0.003 moles
C 0.005 moles
D 0.006 moles

19 Fluorine and iodine are Group 17 elements. Their melting points are different due to differing
strengths of van der Waals’ forces between molecules.

Which row is correct?

strength of van der Waals’


melting point
forces between molecules

A F2 > I2 F2 > I2
B F2 > I2 F 2 < I2
C F2 < I2 F 2 < I2
D F2 < I2 F 2 > I2

© UCLES 2016 9701/12/M/J/16 [Turn over


8

20 Chlorofluorocarbons damage the ozone layer by undergoing reactions with a free radical
mechanism. The first stage of this is initiation.

Which equation is most likely to be the initiation stage when chlorofluoromethane is involved in
such a reaction?

A B

H H H H

F C H C H + F F C H F C H + Cl

Cl Cl Cl

C D

H H H

F C H F C H + H F C H C H + Cl + F

Cl Cl Cl

21 Synthetic resins can be made by polymerisation of a variety of monomers including


prop-2-en-1-ol, CH2=CHCH2OH.

Which structure represents the repeat unit in poly(prop-2-en-1-ol)?

A CH2 CH2 CH2 O

B CH2 CH

CH2OH

C CH C

CH2OH

D CH2 CH2 CH

OH

© UCLES 2016 9701/12/M/J/16


9

22 Oct-1-ene, CH3(CH2)5CH=CH2, can be thermally cracked.

Which combination of compounds W, X, Y and Z can be obtained by thermally cracking


oct-1-ene?

CH2=CH2 CH3CH=CH2 CH3CH2CH3 CH2=CHCH=CH2


W X Y Z

A W, X, Y and Z
B W, X and Y only
C W, X and Z only
D W and X only

23 A cycloalkene with the molecular formula C7H12 was oxidised by hot concentrated acidified
MnO4–. The only organic product was 2-methylhexane-1,6-dioic acid.

What is the identity of the cycloalkene?

CH3 CH3 CH3 CH3

A B C D

CH3

24 1-chloro-1-methylcyclohexane is hydrolysed by heating with NaOH(aq).

CH3 CH3
+ OH– → + Cl –
Cl OH

The reaction pathway is shown.

energy Z

reaction pathway

One carbon atom in 1-chloro-1-methylcyclohexane is bonded to three other carbon atoms.

What is the charge on this carbon atom at point Z?

A δ+ B + C δ– D –

© UCLES 2016 9701/12/M/J/16 [Turn over


10

25 Malic acid is found in apples.

OH

H C CH2CO2H

CO2H

malic acid

Which reagent will react with only one of the – OH groups in the malic acid molecule?

A ethanoic acid in the presence of concentrated sulfuric acid


B sodium
C sodium hydrogen carbonate
D sodium hydroxide

26 Which organic compound would not give either a yellow precipitate when treated with alkaline
aqueous iodine or an orange precipitate when treated with 2,4-dinitrophenylhydrazine reagent?

A propanal
B propan-1-ol
C propan-2-ol
D propanone

27 In which reaction is the organic compound oxidised?

A CH3CH2CH2CHO + Tollens’ reagent


B CH3CH2CH2CHO + LiAl H4
C CH3CH2CH2OH + concentrated H3PO4
D CH3CO2C2H5 + dilute H2SO4

28 How many of the following compounds produce a carboxylic acid on heating under reflux with an
excess of hot acidified K2Cr2O7?

CH3CH2CHO
CH3COCH3
CH3CH2CH2OH
CH3CH(OH)CH3

A 1 B 2 C 3 D 4

© UCLES 2016 9701/12/M/J/16


11

29 How many isomeric esters, including structural isomers and stereoisomers, can be made with the
molecular formula C5H10O2, if methanoic acid is one of the two reactants used?

A 2 B 3 C 4 D 5

30 Compound X, C4H8O2, has an unbranched carbon chain. An aqueous solution of X has an


approximate pH of 3.

Compound Y, C3H8O, is a secondary alcohol.

X and Y are reacted together in the presence of a little concentrated sulfuric acid to form Z as the
major organic product.

What is the structural formula of Z?

A (CH3)2CHCO2CH2CH2CH3
B CH3(CH2)2CO2CH(CH3)2
C CH3(CH2)2CO2(CH2)2CH3
D (CH3)2CHCO2CH(CH3)2

© UCLES 2016 9701/12/M/J/16 [Turn over


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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

31 In an experiment, 10 cm3 of an organic compound, J, in the gaseous state was sparked with an
excess of oxygen. 20 cm3 of carbon dioxide and 5 cm3 of nitrogen were obtained among the
products. All gas volumes were measured at the same temperature and pressure.

What could be the identity of J?

1 C2H6N2
2 C2H3N
3 C2H7N

32 Three elements, X, Y and Z, have electronic configurations as shown.

X Y Z

2,6 2,8,1 2,8,7

Which formulae represent compounds that conduct electricity in the liquid state?

1 YZ
2 Y2X
3 Z2X

© UCLES 2016 9701/12/M/J/16


13

33 In this question, all gases can be assumed to behave ideally.

A chemist heats a mixture of nitrogen and oxygen gases in a sealed container at a constant
temperature until the mixture reaches a dynamic equilibrium containing N2(g), O2(g) and NO(g).

N2(g) + O2(g) 2NO(g)

The chemist repeats the experiment at the same temperature using the same initial amounts of
N2(g) and O2(g), but at a much higher pressure.

Which statements about the second experiment at higher pressure are correct?

1 At higher pressure, there are more particles per unit volume.


2 The composition of the equilibrium mixture does not change.
3 There are more collisions per second so equilibrium is reached faster.

34 An ethanol burner can be used to heat water. If appropriate measurements are taken, a value for
the enthalpy of combustion of ethanol can be calculated. The equation

heat transferred = –mc∆T

is used as part of the calculation.

Which symbols are correctly described?

1 ∆T is the change in temperature of the water.


2 m is the mass of water used in the experiment.
3 c is the specific heat capacity of ethanol.

© UCLES 2016 9701/12/M/J/16 [Turn over


14

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

35 The first ionisation energies of twenty successive elements in the Periodic Table are represented
in the graph.

The letters given are not the normal symbols for these elements.

2500

2000

1500
first ionisation
_
energy / kJ mol 1
1000

500

0
A B C D E F G H I J K L M N O P Q R S T
element

Which statements about this graph are correct?

1 Elements B, J and R are in Group 18 of the Periodic Table.


2 Atoms of elements D and L contain two electrons in their outer shells.
3 Atoms of elements G and O contain a half-filled p subshell.

36 Which properties increase in the sequence hydrogen chloride, hydrogen bromide and hydrogen
iodide?

1 thermal stability
2 bond length
3 ease of oxidation

© UCLES 2016 9701/12/M/J/16


15

37 The diagram shows a compound used as a flame retardant.

Br
Br

Br

Br Br
Br

Which statements about this structure are correct?

1 The empirical formula is C2H3Br.


2 The C12 ring is not planar.
3 There are six chiral carbon atoms.

38 One of the active ingredients in tea-tree oil is terpinen-4-ol.

In the diagram of the skeletal formula of terpinen-4-ol, three of the carbon atoms are labelled 1, 2
and 3.

Which of the labelled carbon atoms are chiral?

1
HO
3

terpinen-4-ol

© UCLES 2016 9701/12/M/J/16 [Turn over


16

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

39 Propanal reacts with hydrogen cyanide to form 2-hydroxybutanenitrile. A suitable catalyst for this
reaction is sodium cyanide.

NaCN
CH3CH2CHO + HCN CH3CH2CH(OH)CN

Which statements about the reaction of propanal with hydrogen cyanide are correct?

1 The sodium cyanide provides a stronger nucleophile than HCN.


2 The reaction can be classified as nucleophilic substitution.
3 The hydrogen cyanide molecule attacks the propanal molecule to form an intermediate ion.

40 Which syntheses will be successful?

1 CH3CH2CH3 from CH3CH=CH2 + LiAl H4


2 CH3CH(OH)CH3 from CH3COCH3 + NaBH4
3 CH3CH2CH2OH from CH3CH2CHO + NaBH4

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.

To avoid the issue of disclosure of answer-related information to candidates, all copyright acknowledgements are reproduced online in the Cambridge
International Examinations Copyright Acknowledgements Booklet. This is produced for each series of examinations and is freely available to download at
www.cie.org.uk after the live examination series.

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 2016 9701/12/M/J/16


Page 2 Mark Scheme Syllabus Paper
Cambridge International AS/A Level – May/June 2016 9701 12

Question Question
Key Key
Number Number

1 D 21 B
2 D 22 A
3 A 23 A
4 C 24 B
5 D 25 A

6 C 26 B
7 D 27 A
8 B 28 B
9 C 29 D
10 C 30 B

11 D 31 C
12 D 32 B
13 A 33 A
14 D 34 B
15 C 35 A

16 B 36 C
17 C 37 A
18 A 38 D
19 C 39 D
20 B 40 C

© Cambridge International Examinations 2016


2

Section A

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

Use of the Data Booklet may be appropriate for some questions.

1 Enthalpy changes, ∆H, can be positive or negative.

Which row is correct?

∆H positive ∆H negative

A atomisation bond breaking


B bond breaking neutralisation
C bond making combustion
D combustion bond making

2 What will make it more likely that a gas will approach ideal behaviour?

A higher pressure
B lower temperature
C more polar molecules
D weaker intermolecular forces

3 Which mass of urea, CO(NH2)2, contains the same mass of nitrogen as 101.1 g of potassium
nitrate?

A 22 g B 30 g C 44 g D 60 g

© UCLES 2016 9701/13/M/J/16


3

4 The relative atomic mass of copper is 63.5.

Which chart is a correct mass spectrum that would lead to this value?

A B
100%
abundance abundance 50%

33%
17%

61 62 63 64 65 66 61 62 63 64 65 66
m/e m/e

C D

abundance abundance
74% 33% 33%
22%
26%
12%

61 62 63 64 65 66 61 62 63 64 65 66
m/e m/e

5 Which isolated gaseous atom has a total of five electrons occupying spherically shaped orbitals?

A boron
B fluorine
C sodium
D potassium

6 Carbon and silicon have the same outer electronic structure.

Why is a Si–Si bond weaker than a C–C bond?

A Silicon atoms have a larger atomic radius than carbon atoms.


B Silicon has a greater nuclear charge than carbon.
C Silicon has a smaller first ionisation energy than carbon.
D Silicon is more metallic than carbon.

© UCLES 2016 9701/13/M/J/16 [Turn over


4

7 Methyl isocyanate, CH3NCO, is a toxic liquid which is used in the manufacture of some
pesticides.

What is the approximate angle between the bonds formed by the N atom in a molecule of methyl
isocyanate?

A B C D

N C O N C O N C O
H3C N C O
H 3C H 3C H3C

104° 109° 120° 180°

8 Methanol may be prepared by the reaction between carbon monoxide and hydrogen.

CO(g) + 2H2(g) → CH3OH(g)

The relevant average bond energies are given below.

E (C ≡ O) 1077 kJ mol–1
E (C – O) 360 kJ mol–1
E (C – H) 410 kJ mol–1
E (H – H) 436 kJ mol–1
E (O – H) 460 kJ mol–1

What is the enthalpy change of this reaction?

A –537 kJ mol–1
B –101 kJ mol–1
C +101 kJ mol–1
D +537 kJ mol–1

9 The equilibrium constant, Kc, for the reaction shown is 2 mol–2 dm6, at 600 K.

N2(g) + 3H2(g) 2NH3(g)

What is the concentration of NH3 at equilibrium, at 600 K, when the equilibrium concentrations of
N2 and H2 are both 2 mol dm–3?

A 8 mol dm–3 B 16 mol dm–3 C 32 mol dm–3 D 32 mol dm–3

© UCLES 2016 9701/13/M/J/16


5

10 Sulfur dioxide is used as a preservative in wine making.

The following equations describe the reactions that occur when sulfur dioxide dissolves in water.

H2O + SO2 HSO3– + H+


HSO3– + H+ SO32– + 2H+

Which statement about these two reactions is correct?

A HSO3– acts as a base.


B SO2 acts as an oxidising agent.
C SO32– acts as an acid.
D SO32– acts as a reducing agent.

11 Catalysts are an important feature of many industrial processes and biochemical reactions.

Which row correctly describes the effect of a catalyst on a reversible chemical reaction?

position of equilibrium effect on value of ∆H

A moved to right decreased


B unaffected decreased
C unaffected increased
D unaffected unaffected

12 The oxide and chloride of an element X are separately mixed with water. The two resulting
solutions have the same effect on litmus.

What could element X be?

A Al B Ca C Na D P

13 Each pair below consists of a sample of two separate elements. Each element is in its standard
state at room temperature and pressure.

Which pair of elements has chemical bonds of the same type between their atoms?

A aluminium and phosphorus


B chlorine and argon
C magnesium and silicon
D sulfur and chlorine

© UCLES 2016 9701/13/M/J/16 [Turn over


6

14 Solutions of Mg(NO3)2 and Ba(NO3)2 separately undergo a series of reactions.

sodium
carbonate excess excess
solution HCl (aq) NaOH(aq)
Mg(NO3)2(aq) M N P
sodium
carbonate excess excess
solution HCl (aq) NaOH(aq)
Ba(NO3)2(aq) Q R S

M, N and P are magnesium compounds.

Q, R and S are barium compounds.

How many of M, N, P, Q, R and S are white precipitates?

A 2 B 3 C 4 D 5

15 Anhydrous magnesium nitrate, Mg(NO3)2 , will decompose when heated, giving a white solid and
a mixture of two gases X and Y.

Y is oxygen.

What is the ratio mass of X released ?


mass of Y released
A 1 B 1 C 1 D 1
0.174 0.267 0.348 3.43

16 Steam is passed over heated magnesium to give compound J and hydrogen.

What is not a property of compound J?

A It has an Mr of 40.3.
B It is basic.
C It is a white solid.
D It is very soluble in water.

© UCLES 2016 9701/13/M/J/16


7

17 Two students, P and Q, were asked to draw bar charts to represent how some properties of the
halogens and their compounds differ in magnitude. Their diagrams are shown. The bar charts
show trends only and not actual values.

student P student Q

∆H o
I Cl Br I
0
solubility Br
Cl

solubility of AgX(s) in NH3(aq) ∆H o for H2(g) + X2(g) → 2HX(g)

Which of the students have drawn bar charts which show the trends correctly?

A both P and Q
B P only
C Q only
D neither P nor Q

18 In a series of nine experiments to test the reactivity of the halogens, an aqueous solution of each
halogen was added to an equal volume of an aqueous solution containing halide ions as shown
in the table below.

solution sodium chloride (aq) sodium bromide (aq) sodium iodide (aq)

chlorine (aq) experiment 1 experiment 2 experiment 3


bromine (aq) experiment 4 experiment 5 experiment 6
iodine (aq) experiment 7 experiment 8 experiment 9

The nine resulting mixtures were then shaken with hexane. The nine tubes were corked and left
to stand so that the aqueous and organic solvents could separate into layers.

How many test-tubes contained a purple upper layer?

A 1 B 2 C 3 D 5

19 Which statement does not describe an effect of acid rain on the environment?

A Acid rain causes erosion of stone buildings.


B Acid rain causes ozone depletion.
C Acid rain increases the corrosion of some metals.
D Acid rain increases the leaching away of essential nutrients and minerals from soils.

© UCLES 2016 9701/13/M/J/16 [Turn over


8

20 What is the correct name of the molecule with the skeletal formula shown?

HO

A 1,2,2-trimethylbutan-3-ol
B 2-ethyl-2-methylbutan-2-ol
C 3,3-dimethylpentan-2-ol
D 4-hydroxy-3,3-dimethylpentane

21 The diagram shows the structure of 1,3-butadiene.

H H

C C H
H C C

H H

1,3-butadiene

The addition reaction between 1,3-butadiene and two molecules of hydrogen bromide can
produce three structurally isomeric products.

How many of these products have at least one chiral centre?

A 0 B 1 C 2 D 3

22 An ester with an aroma of pineapples can be synthesised in the laboratory from butanal using this
reaction scheme.

X
NaBH4

conc. H2SO4
CH3(CH2)2CHO ester

Cr2O72– / H+
Y

What is the structural formula of the ester?

A CH3(CH2)2CO2(CH2)2CH3
B CH3(CH2)2CO2(CH2)3CH3
C CH3(CH2)3CO2(CH2)2CH3
D CH3(CH2)3CO2(CH2)3CH3

© UCLES 2016 9701/13/M/J/16


9

23 When heated with chlorine, the hydrocarbon 2,2-dimethylbutane undergoes free radical
substitution.

In a propagation step a free radical X• is formed.

CH3

CH3CH2 C CH3 + Cl • → X• + HCl

CH3

How many different structures of X• are possible?

A 2 B 3 C 4 D 5

24 Vitamin A contains retinol.

OH

retinol

Under appropriate conditions, acidified KMnO4(aq) can be used to break apart C=C bonds.

After these bonds have been broken, further oxidation of the fragments may occur.

Under which conditions is the acidified KMnO4(aq) used and what do the final oxidation products
include?

conditions final oxidation products

A cold, dilute aldehydes and carboxylic acids


B cold, dilute ketones and carboxylic acids
C hot, concentrated aldehydes and carboxylic acids
D hot, concentrated ketones and carboxylic acids

© UCLES 2016 9701/13/M/J/16 [Turn over


10

25 A reaction pathway diagram is shown.

energy

extent of reaction

The four reactions that follow are all exothermic.

Which reaction would not have such a pathway?

A CH3I + NaCN → CH3CN + NaI

CH3 CH3
B + 2NH3 → + NH4Br
Br NH2

C + HBr → Br

conc. H2SO4 OH
D CH3 + H2O
heat
CH3

26 Which volume of oxygen, at room temperature and pressure, is needed for complete combustion
of 1.0 mol of methylpropan-1-ol?

A 108 dm3 B 144 dm3 C 156 dm3 D 288 dm3

27 An unknown organic compound reacts with sodium to give a combustible gas as one product but
does not give a yellow precipitate with alkaline aqueous iodine.

What is a possible identity of the unknown organic compound?

A propanal
B propan-1-ol
C propan-2-ol
D propanone

© UCLES 2016 9701/13/M/J/16


11

28 Which reaction will give 2-chloropropane in the best yield?

A propane gas with chlorine gas in the presence of ultraviolet light


B propan-2-ol with dilute NaCl (aq)
C propan-2-ol with SOCl 2(l)
D propene with dilute HCl (aq)

29 The ester, CH3CH2CO2CH3, is hydrolysed by boiling with aqueous sodium hydroxide.

Which compound is one of the products?

A ethanol
B propan-1-ol
C sodium methanoate
D sodium propanoate

30 Caprolactone is a cyclic ester. It is being used increasingly for the manufacture of specialist
polymers.

caprolactone

From which compound could caprolactone be made by a single reaction?

A OHCCH2CH2CH2CH2CHO
B HOCH2CH2CH2CH2CH2CH2OH
C HOCH2CH2CH2CH2CH2CO2H
D HO2CCH2CH2CH2CH2CO2H

© UCLES 2016 9701/13/M/J/16 [Turn over


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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

31 Compound X is made from two elements. One element has the second highest value of first
ionisation energy in its group and the other element has the third highest value of first ionisation
energy in its group.

Which compounds could be compound X?

1 calcium chloride
2 magnesium bromide
3 potassium sulfide

32 Water has some unusual physical properties compared to other hydrides of Group 16 elements.
Some of these properties are due to hydrogen bonds. These intermolecular forces are much
stronger in water than they are in H2S, for example.

Which statements are correct?

1 Hydrogen bonds cause the melting point of ice to be higher than expected.
2 Hydrogen bonds cause the surface tension of water to be higher than expected.
3 Hydrogen bonds cause the viscosity of water to be higher than expected.

© UCLES 2016 9701/13/M/J/16


13

33 The diagram shows the Boltzmann distribution of molecular energies in one mole of a gas at two
temperatures, T1 and T2.

T1
T2

proportion of
molecules
with a
given energy

E1 E2
molecular energy

Which statements are correct?

1 The shaded area represents the proportion of molecules with energies between E1 and E2 at
temperature T2.
2 No particles have zero energy at either temperature.
3 T2 is a lower temperature than T1.

34 When KCl O3 is heated, the following reaction occurs.

4KCl O3 → 3KCl O4 + KCl

Which statements are correct?

1 The oxidation state of Cl in KCl O3 is +5.


2 The oxidation state of some Cl atoms decreases by 6.
3 The reaction involves disproportionation.

35 Why is the first ionisation energy of aluminium less than that of magnesium?

1 The outer electron in the aluminium atom is more shielded from the nuclear charge.
2 The outer electron in the aluminium atom is in a higher energy orbital.
3 The outer electron in the aluminium atom is further from the nucleus.

36 Ammonia is a colourless gas that is produced by the Haber process.

Which statements about ammonia are correct?

1 An ammonia molecule has three bond pairs and one lone pair of electrons.
2 If ammonia is bubbled into water the pH of the solution will increase.
3 Ammonia gas can be made by warming ammonium sulfate with aqueous hydrochloric acid.

© UCLES 2016 9701/13/M/J/16 [Turn over


14

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

37 Halogenoalkanes show trends in their physical and chemical properties.

Which properties steadily increase from C2H5Cl to C2H5Br to C2H5I ?

1 the polarity of the carbon-halogen bond


2 the boiling point of the halogenoalkane
3 the rate of reaction of the halogenoalkane with nucleophiles

38 Ethanal and hydrogen cyanide react together to form a compound used in the production of
acrylic fibres. The reaction mechanism involves cyanide ions.


CH3 H 3C O H 3C OH
C O C H CN C + CN–

H CN– H CN H CN

Which statements about this mechanism are correct?

1 CN– acts as a catalyst.


2 CN– is a nucleophile.
3 It is an addition reaction.

© UCLES 2016 9701/13/M/J/16


15

39 Which compounds will give an orange precipitate with 2,4-dinitrophenylhydrazine reagent?

CH3
O
H
HO O
1 O HO
[R is an inert group]
HO O OR

HO NHCH3

streptomycin

CH3 CH3

CH3 CH3
O
RO O
[R is an inert group]

2 CH3
O O

OH

O CH3
OH
avermectin B1b

O
H 3C N OCH3
[R is an inert group]
3
O O

R
cocaine

40 The structural formulae of two compounds are shown below.

O O

CH3CH2CH2CH2CH2C CH3CH2CH2CH2CH2OC

OH H

Which statements about these compounds are correct?

1 The two compounds are structural isomers of each other.


2 The empirical formula of both compounds is C3H6O.
3 Both compounds are carboxylic acids.

© UCLES 2016 9701/13/M/J/16


Page 2 Mark Scheme Syllabus Paper
Cambridge International AS/A Level – May/June 2016 9701 13

Question Question
Key Key
Number Number

1 B 21 C
2 D 22 B
3 B 23 B
4 C 24 D
5 C 25 A

6 A 26 B
7 C 27 B
8 B 28 C
9 C 29 D
10 A 30 C

11 D 31 A
12 D 32 A
13 D 33 B
14 B 34 A
15 A 35 A

16 D 36 B
17 C 37 C
18 D 38 A
19 B 39 D
20 C 40 B

© Cambridge International Examinations 2016


2

Section A

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

Use of the Data Booklet may be appropriate for some questions.

1 The diagram represents, for a given temperature, the Boltzmann distribution of the kinetic
energies of the molecules in a mixture of two gases that react together. The activation energy for
the reaction, Ea , is marked.

proportion of
molecules
with a
given energy
0
0 Ea molecular
energy

The dotted curves below show the Boltzmann distribution for the same reaction at a higher
temperature. On these diagrams, H represents the activation energy at the higher temperature.

Which diagram is correct?

A B

proportion of proportion of
molecules molecules
with a with a
given energy given energy
0 0
0 Ea molecular 0 Ea molecular
energy H energy
H
C D

proportion of proportion of
molecules molecules
with a with a
given energy given energy
0 0
0 Ea molecular 0 Ea molecular
energy energy
H H

© UCLES 2016 9701/11/O/N/16


3

2 In the ideal gas equation, pV = nRT, what are the units of n and T ?

n T

A no units °C
B no units K
C mol °C
D mol K

3 The reaction between acidified dichromate(VI) ions, Cr2O72–, and aqueous Fe2+ ions results in the
dichromate(VI) ions being reduced to Cr3+ ions.

What is the correct equation for this reaction?

A Cr2O72– + Fe2+ + 14H+ → 2Cr3+ + Fe3+ + 7H2O

B Cr2O72– + 2Fe2+ + 14H+ → 2Cr3+ + 2Fe3+ + 7H2O

C Cr2O72– + 3Fe2+ + 14H+ → 2Cr3+ + 3Fe3+ + 7H2O

D Cr2O72– + 6Fe2+ + 14H+ → 2Cr3+ + 6Fe3+ + 7H2O

4 Sodium azide, NaN3 is an explosive used to inflate airbags in cars when they crash. It consists of
positive sodium ions and negative azide ions.

What are the numbers of electrons in the sodium ion and the azide ion?

sodium ion azide ion

A 10 20
B 10 22
C 12 20
D 12 22

5 The 68Ge isotope is medically useful because it undergoes a natural radioactive process to give
an isotope of a different element, 68X, which can be used to detect tumours. This transformation
of 68Ge occurs when an electron enters the nucleus and changes a proton into a neutron.

Which statement about the composition of an atom of 68X is correct?

A It has 4 electrons in its outer p orbitals.


B It has 13 electrons in its outer shell.
C It has 37 neutrons.
D Its proton number is 32.

© UCLES 2016 9701/11/O/N/16 [Turn over


4

6 Histamine is produced in the body to help fight infection. Its shape allows it to fit into receptors
which expand blood vessels.

H H H N C

xN N
yC C C
z H
C
H H H
H
histamine

What are the bond angles x, y and z in histamine, from the smallest to the largest?

smallest largest
bond angle bond angle

A x y z
B y x z
C y z x
D z y x

7 The approximate percentage composition of the atmospheres on four different planets is given in
the table below.

Which mixture of gases has the greatest density?

major gases /
planet % by number of molecules
H2 He CH4

A Jupiter 89.8 10.2 0.0


B Neptune 80.0 19.0 1.0
C Saturn 96.3 3.3 0.4
D Uranus 82.5 15.2 2.3

8 An important reaction in the manufacture of nitric acid is the catalytic oxidation of ammonia.

4NH3(g) + 5O2(g) 4NO(g) + 6H2O(g)

For every mole of O2 that reacts in this way, 181.8 kJ of energy are released.

A factory makes 2.50 × 105 mol of NO every day.

How much energy, in kJ, is released every day?

A 3.64 × 107 B 4.55 × 107 C 5.68 × 107 D 2.27 × 108

© UCLES 2016 9701/11/O/N/16


5

9 Sodium chromate(VI), Na2CrO4, is manufactured by heating chromite, FeCr2O4, with sodium


carbonate in an oxidising atmosphere. Chromite contains Cr2O42– ions.

2FeCr2O4 + 4Na2CO3 + 3 21 O2 → 4Na2CrO4 + Fe2O3 + 4CO2

What happens in this reaction?

A Chromium and iron are the only elements oxidised.


B Chromium, iron and carbon are oxidised.
C Only chromium is oxidised.
D Only iron is oxidised.

10 The table shows the partial pressures in an equilibrium mixture formed by the Haber process.

substance partial pressure / kPa

nitrogen 7000 3H2(g) + N2(g) 2NH3(g)


hydrogen 8000
ammonia 4000

What is the numerical value of the equilibrium constant, Kp, for this reaction?

A 4.46 × 10–9

B 4.76 × 10–5

C 7.14 × 10–5

D 2.24 × 108

11 An autocatalytic reaction is a reaction in which one of the products catalyses the reaction.

Which curve would be obtained if the rate of an autocatalytic reaction is plotted against time?

A B C D

rate rate rate rate

0 0 0 0
0 time 0 time 0 time 0 time

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12 1.15 g of a metallic element needs 300 cm3 of oxygen for complete reaction, at 298 K and 1 atm
pressure, to form an oxide which contains O2– ions.

What could be the identity of this metallic element?

A calcium
B magnesium
C potassium
D sodium

13 The diagram shows the melting points of eight elements with consecutive atomic numbers.

Which element could be sodium?

D
melting
point / K
C
A

B
atomic number

14 The properties of chlorine, bromine and their compounds are compared.

Which property is smaller for chlorine than for bromine?

A bond strength of the hydrogen-halide bond


B first ionisation energy
C solubility of the silver halide in NH3(aq)
D strength of the van der Waals’ forces between molecules of the element

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7

15 At 550 °C nitrogen dioxide reacts with unburnt hydrocarbon fragments such as CH3• in the
catalytic converter of a motor vehicle.

4CH3• + 7NO2 → 3 21 N2 + 4CO2 + 6H2O

The following table lists types of energy change for this reaction and possible reasons for them.

Which row gives the energy change for this reaction and the reason for it?

energy change reason why the reaction is endothermic


of reaction or exothermic

A endothermic chemical energy is converted to heat energy


B endothermic the N≡N bond energy is very high
C exothermic CO2 and H2O have large negative values
D exothermic double bonds are broken in NO2

16 Magnesium nitrate, Mg(NO3)2, will decompose when heated to give a white solid and a mixture of
gases. One of the gases released is an oxide of nitrogen, X.

7.4 g of anhydrous magnesium nitrate is heated until no further reaction takes place.

What mass of X is produced?

A 1.5 g B 2.3 g C 3.0 g D 4.6 g

17 Compound T is a white crystalline solid.

When a sample of T was mixed with aqueous sodium hydroxide and heated, a pungent smelling
gas was produced which turned damp red litmus paper blue. This same gas produced dense
white smoke with hydrogen chloride gas.

Further testing of a solution of T with barium chloride solution produced a dense white precipitate
which did not dissolve when dilute hydrochloric acid was added to the mixture.

What is the identity of compound T?

A ammonium carbonate
B ammonium sulfate
C sodium carbonate
D sodium sulfate

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18 Which row of the table gives correct comparisons between the solubilities of calcium and barium
hydroxide and the thermal stabilities of calcium and barium carbonate?

solubility thermal stability


calcium hydroxide barium hydroxide calcium carbonate barium carbonate

A higher lower higher lower


B higher lower lower higher
C lower higher higher lower
D lower higher lower higher

19 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) Y –(aq) Z –(aq)

X2(aq) no reaction no reaction no reaction


Y2(aq) X2 formed no reaction Z2 formed
Z2(aq) X2 formed no reaction no reaction

Which row of the following table contains the ions X –, Y – and Z – in order of their decreasing
strength as reducing agents?

strongest weakest

A X– Y– Z–
B X– Z– Y–
C Y– Z– X–
D Z– X– Y–

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9

20 In 1865 Kekulé suggested a ring structure for benzene, C6H6, in which a hydrogen atom is
attached to each carbon atom.

H C H
C C

C C
H C H

Kekulé structure

In this structure all of the bonds remain in the places shown. Assuming this is the structure of
benzene, how many isomers of dichlorobenzene, C6H4Cl 2, would exist?

A 3 B 4 C 5 D 6

21 The diagram shows the structure of vitamin A.

H 3C CH3 CH3 CH3

OH

CH3
vitamin A

How many chiral centres are present in one vitamin A molecule?

A 0 B 1 C 2 D 3

22 PVC is difficult to dispose of. Two possible methods are burying it in landfill sites and disposal by
combustion.

Which row of the table is correct?

rate of biodegradation gases produced when


of PVC in landfill sites PVC combusts

A fast CO2, H2O, HCl


B fast CO2, H2O, Cl 2
C slow CO2, H2O, Cl 2
D slow CO2, H2O, HCl

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23 Part of the structure of a fungicide, strobilurin, is shown. R and R' are inert groups.

O OCH3

R'
R

strobilurin

In this reaction, strobilurin is warmed with aqueous sulfuric acid producing compound X.
Compound X is then treated with hydrogen in the presence of a nickel catalyst producing
compound Y.

What could be the structure of compound Y?

A B

O OH HO OCH3

R' R'
R R

C D

OH O OH
OH OH
R' R'
R R
OH

24 Chloroethane can be used to make sodium propanoate.

chloroethane → Q → sodium propanoate

The intermediate, Q, is hydrolysed with boiling aqueous sodium hydroxide to give sodium
propanoate.

Which reagent would produce the intermediate, Q, from chloroethane?

A concentrated ammonia solution


B dilute sulfuric acid
C hydrogen cyanide in water
D potassium cyanide in ethanol

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11

25 X, Y and Z are three isomeric alcohols.

X CH3CH2CH2CH2CH2OH
Y CH3CH2CH(OH)CH2CH3
Z (CH3)2C(OH)CH2CH3

Two or more of these alcohols react with mild oxidising agents.

One of these alcohols, when dehydrated, will give a pair of cis-trans isomers with molecular
formula C5H10.

Which row is correct?

reacts with mild gives cis-trans


oxidising reagents isomers

A X, Y and Z Y only
B X, Y and Z Z only
C X and Y only Y only
D X and Y only Z only

26 Propanone reacts with an aqueous mixture of HCN and NaCN by a nucleophilic addition
mechanism.

The first stage of the mechanism involves attack by cyanide ions.

Which diagram correctly represents this?

A B

CH3 CH3
– δ+ δ– – δ+ δ–
N C C O N C C O

CH3 CH3

C D

CH3 CH3
– δ+ δ– – δ+ δ–
C N C O N C C O

CH3 CH3

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27 P, Q and R are carbonyl compounds.

CH2 CH2 CH2


O C C O O C C O O C C O

H 3C H H H H3 C CH3
P Q R

Fehling’s solution can be used to help identify these compounds.

Which compounds form a red-brown precipitate on warming with Fehling’s solution?

A P, Q and R B P and Q only C P only D Q only

28 Which reaction would not give ethanoic acid?

A heating ethanenitrile under reflux with dilute sodium hydroxide


B heating ethanenitrile under reflux with dilute sulfuric acid

C heating ethanal under reflux with acidified sodium dichromate(VI)

D heating ethanol under reflux with acidified sodium dichromate(VI)

29 Which formula represents an ester that will form propanoic acid on hydrolysis with dilute sulfuric
acid?

A B C D

O O O O

O O O O

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13

30 A solvent, X, used in printing inks has a molecular formula C6H10O4. It may be made by reacting
ethane-1,2-diol with ethanoic acid in the presence of an acid catalyst.

H H

HO C C OH

H H

ethane-1,2-diol

What is the structure of solvent X?

A B

H H O O H H O

HO C C O C C O C C O C

H H CH3 H 3C H H CH3

C D

O H H O O H H O

C C C C C C C O C

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

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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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

31 A sample of boron contains aluminium as the only impurity. A mass spectrum of the mixture
shows three lines corresponding to three ions, X+, Y+ and Z+.

ion X+ Y+ Z+

m/e 10 11 27
percentage 15.52 74.48 10.00
abundance

Which statements are correct?

1 There are more electrons in Z+ than in X+.


2 The Ar of boron in the sample is 10.83 to four significant figures.
3 There are more protons in Y+ than in X+.

32 Which elements can form π bonds in their compounds?

1 carbon
2 oxygen
3 nitrogen

33 For which enthalpy changes is the value of ∆H always negative?

1 combustion
2 hydration
3 solution

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15

34 In the manufacture of sulfuric acid, the following exothermic reaction occurs.

2SO2(g) + O2(g) 2SO3(g)

Which changes will move the position of the equilibrium to the right?

1 increasing the pressure


2 increasing the temperature
3 using twice as much catalyst

35 Water is added to anhydrous aluminium chloride to make a 0.1 mol dm–3 solution.

Which observations are correct?

1 The reaction is endothermic.


2 The solution is acidic.
3 The solution contains the ion [Al (H2O)6]3+.

36 Catalytic converters are used to modify exhaust emissions from motor vehicles.

Which reactions occur in catalytic converters?

1 C8H18 + 12 21 O2 → 8CO2 + 9H2O

2 2NO + 2CO → N2 + 2CO2

3 NO + SO3 → NO2 + SO2

37 Which compounds would produce a carboxylic acid and a ketone when treated with hot,
concentrated, acidified KMnO4?

1 2 3

38 Bromoethane reacts with NaOH in different ways depending on the solvent used.

Which statements about these reactions are correct?

solvent used main organic product

1 water ethane-1,2-diol
2 ethanol ethene
3 water ethanol

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The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

39 Several structural isomers of C3H6O3 are listed below.

HOCH2COCH2OH
HOCH2CH(OH)CHO
HOCH2CH2CO2H
CH3CH(OH)CO2H

Which statements about these structural isomers are correct?

1 One mole of each reacts with two moles of sodium.


2 Only one of the isomers contains a tertiary alcohol group.
3 They all contain a primary alcohol group.

40 When onions are peeled in air, the reaction shown is thought to occur.

2CH3CH2C + 2H2O + 2[O] → H2SO4 + H2S + 2CH3CH2CHO

S O

Which tests would give a positive reaction with the organic product?

1 warming with Tollens’ reagent

2 warming with acidified potassium manganate(VII)


3 warming with alkaline aqueous iodine

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.

To avoid the issue of disclosure of answer-related information to candidates, all copyright acknowledgements are reproduced online in the Cambridge
International Examinations Copyright Acknowledgements Booklet. This is produced for each series of examinations and is freely available to download at
www.cie.org.uk after the live examination series.

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 2016 9701/11/O/N/16


Page 2 Mark Scheme Syllabus Paper
Cambridge International AS/A Level – October/November 2016 9701 11

Question Question
Key Key
Number Number
1 C 21 A
2 D 22 D
3 D 23 A
4 B 24 D
5 C 25 C

6 A 26 D
7 D 27 B
8 C 28 A
9 A 29 A
10 A 30 B

11 C 31 B
12 D 32 A
13 C 33 B
14 D 34 D
15 C 35 C

16 D 36 B
17 B 37 A
18 D 38 C
19 B 39 D
20 B 40 B

© UCLES 2016
2

Section A

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

Use of the Data Booklet may be appropriate for some questions.

1 The molecules of a gas at a constant temperature, T1, have the distribution of molecular energies
shown in the diagram.

proportion of
molecules
with a given T1
energy

0
0
molecular energy

When the temperature is increased to T2, the distribution of molecular energies changes.

Which diagram correctly shows this change?

A B

T2 T2
proportion of proportion of
molecules molecules
with a given T1 with a given T1
energy energy

0 0
0 molecular energy
0
molecular energy

C D

T2 T2
proportion of proportion of
molecules molecules
with a given T1 with a given T1
energy energy

0 0
0 molecular energy 0 molecular energy

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3

2 The diagram shows the pathways of a reaction, with and without a catalyst.

Which letter represents the overall energy change for the reaction?

B
A
D
energy reactants
C

products

extent of reaction

3 People are advised to eat less than 6.00 g of salt (sodium chloride) per day for health reasons.

Which mass of sodium is present in 6.00 g of sodium chloride?

A 0.261 g B 2.36 g C 3.64 g D 3.88 g

4 When copper reacts with a 50% solution of nitric acid, nitrogen monoxide is evolved and a blue
solution results.

The balanced equation for this reaction is shown.

p Cu + q HNO3 → r Cu(NO3)2 + s H2O + t NO

What are the values of the integers p, q, r, s and t ?

p q r s t

A 1 4 1 2 2
B 2 6 2 3 2
C 2 8 2 4 4
D 3 8 3 4 2

5 What is the electronic configuration of an isolated Ni2+ ion?

A 1s22s22p63s23p63d64s2
B 1s22s22p63s23p63d84s2
C 1s22s22p63s23p63d104s2
D 1s22s22p63s23p63d8

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6 When solid aluminium chloride is heated, Al 2Cl 6 is formed.

Which bonding is present in Al 2Cl 6?

A covalent and co-ordinate (dative covalent)


B covalent only
C ionic and co-ordinate (dative covalent)
D ionic only

7 In which hydride is the H–X–H bond angle the smallest?

A BH3 B CH4 C C2H6 D NH3

8 In an experiment, a sample of a pure gas is put into a gas syringe at a temperature of 300 K and
pressure of 16 kPa. The gas is compressed until the volume occupied by the gas is halved.

After compression, the temperature of the gas in the syringe is 375 K and the pressure is 40 kPa.

Which statement is correct?

A Intermolecular forces between the gas molecules are significant.


B It is possible to calculate the number of moles of gas present using these data alone.
C The gas is behaving ideally.
D The pressures used are too high for ideal gas behaviour.

9 In a calorimetric experiment 1.60 g of a fuel are burnt. 45.0% of the energy released is absorbed
by 200 g of water. The temperature of the water rises from 18.0 °C to 66.0 °C.

What is the total energy released per gram of fuel burnt (to 3 significant figures)?

A 25 100 J B 55 700 J C 89 200 J D 143 000 J

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10 Nitrogen reacts with hydrogen to produce ammonia.

N2(g) + 3H2(g) 2NH3(g)

A mixture of 2.00 mol of nitrogen, 6.00 mol of hydrogen and 2.40 mol of ammonia is allowed to
reach equilibrium in a sealed vessel of volume 1 dm3. It was found that 2.32 mol of nitrogen were
present in the equilibrium mixture.

What is the value of Kc?

(1.76)2
A
(2.32)(6.96)3

(1.76)2
B
(2.32)(6.32)3

(2.08)2
C
(2.32)(6.32)3

(2.40)2
D
(2.32)(6.00)3

11 Lithium reacts with nitrogen at room temperature to form solid Li3N.

Three vessels of equal volume are connected by taps, A and B, as shown.

evacuated N2(g) + 3H2(g) 2NH3(g)


A B
Li

At the start, A and B are closed, the left-hand vessel is evacuated, the middle vessel has the
indicated reaction at equilibrium and the right-hand vessel contains lithium only.

Which action would allow the equilibrium mixture to contain the most ammonia?

A Keep both A and B closed.


B Open both A and B.
C Open A only.
D Open B only.

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12 The graph below shows the variation of the first ionisation energy with proton number for some
elements. The letters used are not the usual symbols for the elements.

first ionisation W
energy / kJ mol–1
U
V
R
T

S
Q

proton number

Which statement about the elements is correct?

A P and X are in the same period in the Periodic Table.


B The general increase from Q to X is due to increasing atomic radius.
C The small decrease from R to S is due to decreased shielding.
D The small decrease from U to V is due to repulsion between paired electrons.

13 Which element shows the greatest tendency to form covalent compounds?

A boron
B magnesium
C neon
D potassium

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14 Elements Y and Z are both in Period 3.

When the chloride of Y is added to water, it reacts and a solution of pH 2 is produced.

When the chloride of Z is added to water, it dissolves and a solution of pH 7 is produced.

Which statement explains these observations?

A Both chlorides hydrolyse in water.


B Y is magnesium and Z is sodium.
C Y is phosphorus and Z is aluminium.
D Y is silicon and Z is sodium.

15 When chlorine reacts with hot aqueous sodium hydroxide, two chlorine-containing ions are
formed. One of these is the chloride ion, Cl –.

What is the other ion?

A Cl O– B Cl O2– C Cl O3– D Cl O4–

16 J is a salt of one of the halogens chlorine, bromine, iodine or astatine.

The reaction scheme shows a series of reactions using a solution of J as the starting reagent.

HNO3(aq) an excess of a colourless


J(aq) a precipitate
AgNO3(aq) dilute NH3(aq) solution

an excess of
HNO3(aq)

a precipitate

What could J be?

A sodium chloride
B sodium bromide
C potassium iodide
D potassium astatide

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17 When heated, magnesium nitrate decomposes.

Which equation for the thermal decomposition of magnesium nitrate is correct?

A Mg(NO3)2 → MgO + NO2 + NO + O2

B 2Mg(NO3)2 → 2MgO + 4NO + 3O2

C 2Mg(NO3)2 → 2MgO + 4NO2 + O2

D 3Mg(NO3)2 → Mg2N3 + MgO + 3NO + 7O2

18 Chlorine and bromine have different volatilities.

Which row identifies the more volatile of the two elements, and gives the correct explanation?

identity of the explanation for the


more volatile element difference in volatility
A bromine instantaneous dipole-induced dipole forces
are greater in bromine than they are in chlorine
B bromine instantaneous dipole-induced dipole forces
are greater in chlorine than they are in bromine
C chlorine instantaneous dipole-induced dipole forces
are greater in bromine than they are in chlorine
D chlorine instantaneous dipole-induced dipole forces
are greater in chlorine than they are in bromine

19 Water and ammonia take part in a reaction that produces the ammonium ion.

Which statement about this reaction is correct?

A Neither the ammonia molecule nor the ammonium ion has a dipole moment.

B The bond angle changes from 109.5° in the ammonia molecule to 107° in the ammonium ion.
C The reaction is a redox reaction.
D The water is acting as an acid.

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20 Limonene is found in lemon and orange oils.

limonene

What will be the major product when limonene is reacted with an excess of dry hydrogen
chloride?

A B C D

Cl Cl
Cl Cl

Cl
Cl

21 The compound rotundone is responsible for the peppery smell of pepper and is also found in
some red wines.

rotundone

How many hydrogen atoms are in one molecule of rotundone?

A 15 B 19 C 22 D 24

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22 The reaction CH3CH2CH2CH2Br + OH– → CH3CH2CH2CH2OH + Br– proceeds via an SN2


mechanism.

The reaction (CH3)3CBr + OH– → (CH3)3COH + Br– proceeds via an SN1 mechanism.

Which statement about these two reactions is correct?

A Both reactions involve homolytic bond fission.


B Both reactions involve hydroxide ions acting as electron pair donors.
C Both reactions involve the formation of a positively-charged intermediate.
D Both reactions occur in a single step.

23 The equation shows a reaction that occurs between carbon monoxide and nitrogen monoxide in a
catalytic converter.

2CO(g) + 2NO(g) → 2CO2(g) + N2(g)

Which statement is correct?

A The catalyst used is finely divided iron.


B The reaction prevents greenhouse gas emissions into the atmosphere.
C The reaction reduces the possibility of the formation of photochemical smog.
D The reaction results in increased ozone depletion.

24 Which statement about stereoisomers is correct?

A Cis-trans isomers are mirror images of each other.


B Optical isomers must contain a double bond that restricts rotation.
C Stereoisomers have the same structural formula as each other.
D Stereoisomers must contain a chiral centre.

25 Which compound can be oxidised by acidified potassium manganate(VII) to give


3-methylpentan-2-one?

A B C D
OH O OH
OH
OH

© UCLES 2016 9701/12/O/N/16


11

26 Ethane-1,2-diol, HOCH2CH2OH, reacts with an excess of ethanoic acid, CH3CO2H, in the


presence of an acid catalyst. A compound is formed with the molecular formula C6H10O4.

What is the structure of this compound?

A CH3OCOCH2CH2CO2CH3
B CH3CO2CH2CH2CO2CH3
C CH3CO2CH2CH2OCOCH3
D HOCH2CH2COCH2OCOCH3

27 Compound X is heated with a mild oxidising agent. One of the products of the reaction will react
with hydrogen cyanide, forming 2-hydroxybutanenitrile.

What is compound X?

A butan-1-ol
B butan-2-ol
C propan-1-ol
D propan-2-ol

28 Which row correctly describes the reactivity of aldehydes and ketones?

with NaBH4 with H+ / Cr2O72–(aq)

A both react both react


B both react only aldehydes react
C only ketones react both react
D only ketones react only aldehydes react

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12

29 How many of the compounds shown will react with aqueous sodium hydroxide to form the sodium
salt of a carboxylic acid?

H 3C O H O

C CH2 CH3 C CH2 CH3

O O

O O

H C H3 C CH C

O CH2 CH2 CH3 CH3 O H

A 1 B 2 C 3 D 4

30 Some vegetable oils contain ‘trans fats’ that are associated with undesirable increases in the
amount of cholesterol in the blood. In these oils the word ‘trans’ describes, in the usual way, the
arrangement of groups at a C=C double bond.

In the diagrams below, R1 and R2 are different unbranched hydrocarbon chains.

Which diagram correctly shows an optically active ‘trans fat’?

A B

H R1CO2CH2 H R1CO2CH2

CH3(CH2)6C C(CH2)7CO2CH CH3(CH2)6C C(CH2)7CO2CH

H R1CO2CH2 H R2CO2CH2

C D

H H R1CO2CH2 H H R1CO2CH2

CH3(CH2)6C C(CH2)7CO2CH CH3(CH2)6C C(CH2)7CO2CH

R1CO2CH2 R2CO2CH2

© UCLES 2016 9701/12/O/N/16


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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

31 Photochromic lenses in spectacles darken in sunlight because silver crystals are produced by the
reaction shown.

Ag+ + Cl – → Ag + Cl

Which statements are correct for this reaction?

1 Both silver and chlorine atoms have an oxidation number of zero.


2 The oxidation number of chlorine increases.
3 Electrons are transferred from Cl – ions to Ag+ ions.

32 A cathedral in New Zealand has been constructed from cardboard. Cardboard contains polymer
molecules. Part of one such polymer molecule is shown below.

CH2OH H OH
O O
H H OH H H

OH H H H H
O O
H OH CH2OH

Which statements about this polymer are correct?

1 The polymer molecules can form hydrogen bonds with each other.
2 The polymer can form intermolecular forces with water molecules.
3 The polymer will not burn easily because it is a secondary alcohol.

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14

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

33 X is an element that has

● its outer electrons in the 4th principal quantum shell,


● a higher 1st ionisation energy than calcium.

What could be the identity of X?

1 bromine
2 krypton
3 xenon

34 Methanol, CH3OH, can be produced industrially by reacting CO with H2.

CO(g) + 2H2(g) CH3OH(g) ∆H = –91 kJ mol–1

The process can be carried out at 4 × 103 kPa and 1150 K.

Which statements about this reaction are correct?

1 Increasing the temperature will increase the rate of reaction because more effective
collisions will occur.
2 Lowering the temperature will reduce the rate of reaction because the forward reaction is
exothermic.
3 Increasing the pressure will reduce the rate of reaction because there are a larger number of
moles on the left-hand side of the equation.

35 Equal masses of barium carbonate and magnesium carbonate powders are mixed together. The
mixture is then heated using a Bunsen burner flame until there is no further change. A gas is
given off.

Which statements are correct?

1 The residue left after heating reacts with aqueous hydrochloric acid to produce carbon
dioxide.
2 The percentage decrease in mass after heating is 26% (to 2 significant figures).
3 The gas given off during heating relights a glowing splint.

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15

36 Oxides of both sulfur and nitrogen are present in the atmosphere.

Which statements are correct?

1 Oxides of both sulfur and nitrogen can be formed in internal combustion engines.
2 Oxides of both sulfur and nitrogen can be produced by direct combination of the elements.
3 Oxides of both sulfur and nitrogen are involved in the formation of acid rain.

37 A species of termite produces a chemical defence secretion which contains the molecule shown.

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

To help determine the structure of this compound, it is treated with hot, concentrated, acidified
manganate(VII) ions.

Which compounds are produced in this reaction?

1 CO2
2 CH3COCH3
3 CH3CO2H

38 1-bromopropane reacts with NaOH in different ways depending on the solvent used.

Which statements about this reaction are correct?

solvent used main organic product

1 ethanol propene
2 water propan-1-ol
3 ethanol propane-1-2-diol

© UCLES 2016 9701/12/O/N/16 [Turn over


16

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

39 The compound shown is produced when sugar burns.

H 3C C CHO

Which reagents would give a positive result with this compound?

1 alkaline aqueous iodine


2 2,4-dinitrophenylhydrazine
3 Fehling’s solution

40 Which statements about the formation of a carboxylic acid are correct?

1 A carboxylic acid can be produced by hydrolysis of a nitrile.


2 A carboxylic acid can be produced by oxidation of a primary alcohol.
3 A carboxylic acid can be produced by reduction of an aldehyde.

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.

To avoid the issue of disclosure of answer-related information to candidates, all copyright acknowledgements are reproduced online in the Cambridge
International Examinations Copyright Acknowledgements Booklet. This is produced for each series of examinations and is freely available to download at
www.cie.org.uk after the live examination series.

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 2016 9701/12/O/N/16


Page 2 Mark Scheme Syllabus Paper
Cambridge International AS/A Level – October/November 2016 9701 12

Question Question
Key Key
Number Number
1 D 21 C
2 C 22 B
3 B 23 C
4 D 24 C
5 D 25 D

6 A 26 C
7 D 27 C
8 C 28 B
9 B 29 D
10 A 30 B

11 A 31 A
12 D 32 B
13 A 33 B
14 D 34 D
15 C 35 B

16 A 36 A
17 C 37 B
18 C 38 B
19 D 39 A
20 C 40 B

© UCLES 2016
2

Section A

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

Use of the Data Booklet may be appropriate for some questions.

1 The diagram represents, for a given temperature, the Boltzmann distribution of the kinetic
energies of the molecules in a mixture of two gases that react together. The activation energy for
the reaction, Ea , is marked.

proportion of
molecules
with a
given energy
0
0 Ea molecular
energy

The dotted curves below show the Boltzmann distribution for the same reaction at a higher
temperature. On these diagrams, H represents the activation energy at the higher temperature.

Which diagram is correct?

A B

proportion of proportion of
molecules molecules
with a with a
given energy given energy
0 0
0 Ea molecular 0 Ea molecular
energy H energy
H
C D

proportion of proportion of
molecules molecules
with a with a
given energy given energy
0 0
0 Ea molecular 0 Ea molecular
energy energy
H H

© UCLES 2016 9701/13/O/N/16


3

2 In the ideal gas equation, pV = nRT, what are the units of n and T ?

n T

A no units °C
B no units K
C mol °C
D mol K

3 The reaction between acidified dichromate(VI) ions, Cr2O72–, and aqueous Fe2+ ions results in the
dichromate(VI) ions being reduced to Cr3+ ions.

What is the correct equation for this reaction?

A Cr2O72– + Fe2+ + 14H+ → 2Cr3+ + Fe3+ + 7H2O

B Cr2O72– + 2Fe2+ + 14H+ → 2Cr3+ + 2Fe3+ + 7H2O

C Cr2O72– + 3Fe2+ + 14H+ → 2Cr3+ + 3Fe3+ + 7H2O

D Cr2O72– + 6Fe2+ + 14H+ → 2Cr3+ + 6Fe3+ + 7H2O

4 Sodium azide, NaN3 is an explosive used to inflate airbags in cars when they crash. It consists of
positive sodium ions and negative azide ions.

What are the numbers of electrons in the sodium ion and the azide ion?

sodium ion azide ion

A 10 20
B 10 22
C 12 20
D 12 22

5 The 68Ge isotope is medically useful because it undergoes a natural radioactive process to give
an isotope of a different element, 68X, which can be used to detect tumours. This transformation
of 68Ge occurs when an electron enters the nucleus and changes a proton into a neutron.

Which statement about the composition of an atom of 68X is correct?

A It has 4 electrons in its outer p orbitals.


B It has 13 electrons in its outer shell.
C It has 37 neutrons.
D Its proton number is 32.

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4

6 Histamine is produced in the body to help fight infection. Its shape allows it to fit into receptors
which expand blood vessels.

H H H N C

xN N
yC C C
z H
C
H H H
H
histamine

What are the bond angles x, y and z in histamine, from the smallest to the largest?

smallest largest
bond angle bond angle

A x y z
B y x z
C y z x
D z y x

7 The approximate percentage composition of the atmospheres on four different planets is given in
the table below.

Which mixture of gases has the greatest density?

major gases /
planet % by number of molecules
H2 He CH4

A Jupiter 89.8 10.2 0.0


B Neptune 80.0 19.0 1.0
C Saturn 96.3 3.3 0.4
D Uranus 82.5 15.2 2.3

8 An important reaction in the manufacture of nitric acid is the catalytic oxidation of ammonia.

4NH3(g) + 5O2(g) 4NO(g) + 6H2O(g)

For every mole of O2 that reacts in this way, 181.8 kJ of energy are released.

A factory makes 2.50 × 105 mol of NO every day.

How much energy, in kJ, is released every day?

A 3.64 × 107 B 4.55 × 107 C 5.68 × 107 D 2.27 × 108

© UCLES 2016 9701/13/O/N/16


5

9 Sodium chromate(VI), Na2CrO4, is manufactured by heating chromite, FeCr2O4, with sodium


carbonate in an oxidising atmosphere. Chromite contains Cr2O42– ions.

2FeCr2O4 + 4Na2CO3 + 3 21 O2 → 4Na2CrO4 + Fe2O3 + 4CO2

What happens in this reaction?

A Chromium and iron are the only elements oxidised.


B Chromium, iron and carbon are oxidised.
C Only chromium is oxidised.
D Only iron is oxidised.

10 The table shows the partial pressures in an equilibrium mixture formed by the Haber process.

substance partial pressure / kPa

nitrogen 7000 3H2(g) + N2(g) 2NH3(g)


hydrogen 8000
ammonia 4000

What is the numerical value of the equilibrium constant, Kp, for this reaction?

A 4.46 × 10–9

B 4.76 × 10–5

C 7.14 × 10–5

D 2.24 × 108

11 An autocatalytic reaction is a reaction in which one of the products catalyses the reaction.

Which curve would be obtained if the rate of an autocatalytic reaction is plotted against time?

A B C D

rate rate rate rate

0 0 0 0
0 time 0 time 0 time 0 time

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12 1.15 g of a metallic element needs 300 cm3 of oxygen for complete reaction, at 298 K and 1 atm
pressure, to form an oxide which contains O2– ions.

What could be the identity of this metallic element?

A calcium
B magnesium
C potassium
D sodium

13 The diagram shows the melting points of eight elements with consecutive atomic numbers.

Which element could be sodium?

D
melting
point / K
C
A

B
atomic number

14 The properties of chlorine, bromine and their compounds are compared.

Which property is smaller for chlorine than for bromine?

A bond strength of the hydrogen-halide bond


B first ionisation energy
C solubility of the silver halide in NH3(aq)
D strength of the van der Waals’ forces between molecules of the element

© UCLES 2016 9701/13/O/N/16


7

15 At 550 °C nitrogen dioxide reacts with unburnt hydrocarbon fragments such as CH3• in the
catalytic converter of a motor vehicle.

4CH3• + 7NO2 → 3 21 N2 + 4CO2 + 6H2O

The following table lists types of energy change for this reaction and possible reasons for them.

Which row gives the energy change for this reaction and the reason for it?

energy change reason why the reaction is endothermic


of reaction or exothermic

A endothermic chemical energy is converted to heat energy


B endothermic the N≡N bond energy is very high
C exothermic CO2 and H2O have large negative values
D exothermic double bonds are broken in NO2

16 Magnesium nitrate, Mg(NO3)2, will decompose when heated to give a white solid and a mixture of
gases. One of the gases released is an oxide of nitrogen, X.

7.4 g of anhydrous magnesium nitrate is heated until no further reaction takes place.

What mass of X is produced?

A 1.5 g B 2.3 g C 3.0 g D 4.6 g

17 Compound T is a white crystalline solid.

When a sample of T was mixed with aqueous sodium hydroxide and heated, a pungent smelling
gas was produced which turned damp red litmus paper blue. This same gas produced dense
white smoke with hydrogen chloride gas.

Further testing of a solution of T with barium chloride solution produced a dense white precipitate
which did not dissolve when dilute hydrochloric acid was added to the mixture.

What is the identity of compound T?

A ammonium carbonate
B ammonium sulfate
C sodium carbonate
D sodium sulfate

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18 Which row of the table gives correct comparisons between the solubilities of calcium and barium
hydroxide and the thermal stabilities of calcium and barium carbonate?

solubility thermal stability


calcium hydroxide barium hydroxide calcium carbonate barium carbonate

A higher lower higher lower


B higher lower lower higher
C lower higher higher lower
D lower higher lower higher

19 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) Y –(aq) Z –(aq)

X2(aq) no reaction no reaction no reaction


Y2(aq) X2 formed no reaction Z2 formed
Z2(aq) X2 formed no reaction no reaction

Which row of the following table contains the ions X –, Y – and Z – in order of their decreasing
strength as reducing agents?

strongest weakest

A X– Y– Z–
B X– Z– Y–
C Y– Z– X–
D Z– X– Y–

© UCLES 2016 9701/13/O/N/16


9

20 In 1865 Kekulé suggested a ring structure for benzene, C6H6, in which a hydrogen atom is
attached to each carbon atom.

H C H
C C

C C
H C H

Kekulé structure

In this structure all of the bonds remain in the places shown. Assuming this is the structure of
benzene, how many isomers of dichlorobenzene, C6H4Cl 2, would exist?

A 3 B 4 C 5 D 6

21 The diagram shows the structure of vitamin A.

H 3C CH3 CH3 CH3

OH

CH3
vitamin A

How many chiral centres are present in one vitamin A molecule?

A 0 B 1 C 2 D 3

22 PVC is difficult to dispose of. Two possible methods are burying it in landfill sites and disposal by
combustion.

Which row of the table is correct?

rate of biodegradation gases produced when


of PVC in landfill sites PVC combusts

A fast CO2, H2O, HCl


B fast CO2, H2O, Cl 2
C slow CO2, H2O, Cl 2
D slow CO2, H2O, HCl

© UCLES 2016 9701/13/O/N/16 [Turn over


10

23 Part of the structure of a fungicide, strobilurin, is shown. R and R' are inert groups.

O OCH3

R'
R

strobilurin

In this reaction, strobilurin is warmed with aqueous sulfuric acid producing compound X.
Compound X is then treated with hydrogen in the presence of a nickel catalyst producing
compound Y.

What could be the structure of compound Y?

A B

O OH HO OCH3

R' R'
R R

C D

OH O OH
OH OH
R' R'
R R
OH

24 Chloroethane can be used to make sodium propanoate.

chloroethane → Q → sodium propanoate

The intermediate, Q, is hydrolysed with boiling aqueous sodium hydroxide to give sodium
propanoate.

Which reagent would produce the intermediate, Q, from chloroethane?

A concentrated ammonia solution


B dilute sulfuric acid
C hydrogen cyanide in water
D potassium cyanide in ethanol

© UCLES 2016 9701/13/O/N/16


11

25 X, Y and Z are three isomeric alcohols.

X CH3CH2CH2CH2CH2OH
Y CH3CH2CH(OH)CH2CH3
Z (CH3)2C(OH)CH2CH3

Two or more of these alcohols react with mild oxidising agents.

One of these alcohols, when dehydrated, will give a pair of cis-trans isomers with molecular
formula C5H10.

Which row is correct?

reacts with mild gives cis-trans


oxidising reagents isomers

A X, Y and Z Y only
B X, Y and Z Z only
C X and Y only Y only
D X and Y only Z only

26 Propanone reacts with an aqueous mixture of HCN and NaCN by a nucleophilic addition
mechanism.

The first stage of the mechanism involves attack by cyanide ions.

Which diagram correctly represents this?

A B

CH3 CH3
– δ+ δ– – δ+ δ–
N C C O N C C O

CH3 CH3

C D

CH3 CH3
– δ+ δ– – δ+ δ–
C N C O N C C O

CH3 CH3

© UCLES 2016 9701/13/O/N/16 [Turn over


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27 P, Q and R are carbonyl compounds.

CH2 CH2 CH2


O C C O O C C O O C C O

H 3C H H H H3 C CH3
P Q R

Fehling’s solution can be used to help identify these compounds.

Which compounds form a red-brown precipitate on warming with Fehling’s solution?

A P, Q and R B P and Q only C P only D Q only

28 Which reaction would not give ethanoic acid?

A heating ethanenitrile under reflux with dilute sodium hydroxide


B heating ethanenitrile under reflux with dilute sulfuric acid

C heating ethanal under reflux with acidified sodium dichromate(VI)

D heating ethanol under reflux with acidified sodium dichromate(VI)

29 Which formula represents an ester that will form propanoic acid on hydrolysis with dilute sulfuric
acid?

A B C D

O O O O

O O O O

© UCLES 2016 9701/13/O/N/16


13

30 A solvent, X, used in printing inks has a molecular formula C6H10O4. It may be made by reacting
ethane-1,2-diol with ethanoic acid in the presence of an acid catalyst.

H H

HO C C OH

H H

ethane-1,2-diol

What is the structure of solvent X?

A B

H H O O H H O

HO C C O C C O C C O C

H H CH3 H 3C H H CH3

C D

O H H O O H H O

C C C C C C C O C

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

© UCLES 2016 9701/13/O/N/16 [Turn over


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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

31 A sample of boron contains aluminium as the only impurity. A mass spectrum of the mixture
shows three lines corresponding to three ions, X+, Y+ and Z+.

ion X+ Y+ Z+

m/e 10 11 27
percentage 15.52 74.48 10.00
abundance

Which statements are correct?

1 There are more electrons in Z+ than in X+.


2 The Ar of boron in the sample is 10.83 to four significant figures.
3 There are more protons in Y+ than in X+.

32 Which elements can form π bonds in their compounds?

1 carbon
2 oxygen
3 nitrogen

33 For which enthalpy changes is the value of ∆H always negative?

1 combustion
2 hydration
3 solution

© UCLES 2016 9701/13/O/N/16


15

34 In the manufacture of sulfuric acid, the following exothermic reaction occurs.

2SO2(g) + O2(g) 2SO3(g)

Which changes will move the position of the equilibrium to the right?

1 increasing the pressure


2 increasing the temperature
3 using twice as much catalyst

35 Water is added to anhydrous aluminium chloride to make a 0.1 mol dm–3 solution.

Which observations are correct?

1 The reaction is endothermic.


2 The solution is acidic.
3 The solution contains the ion [Al (H2O)6]3+.

36 Catalytic converters are used to modify exhaust emissions from motor vehicles.

Which reactions occur in catalytic converters?

1 C8H18 + 12 21 O2 → 8CO2 + 9H2O

2 2NO + 2CO → N2 + 2CO2

3 NO + SO3 → NO2 + SO2

37 Which compounds would produce a carboxylic acid and a ketone when treated with hot,
concentrated, acidified KMnO4?

1 2 3

38 Bromoethane reacts with NaOH in different ways depending on the solvent used.

Which statements about these reactions are correct?

solvent used main organic product

1 water ethane-1,2-diol
2 ethanol ethene
3 water ethanol

© UCLES 2016 9701/13/O/N/16 [Turn over


16

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

39 Several structural isomers of C3H6O3 are listed below.

HOCH2COCH2OH
HOCH2CH(OH)CHO
HOCH2CH2CO2H
CH3CH(OH)CO2H

Which statements about these structural isomers are correct?

1 One mole of each reacts with two moles of sodium.


2 Only one of the isomers contains a tertiary alcohol group.
3 They all contain a primary alcohol group.

40 When onions are peeled in air, the reaction shown is thought to occur.

2CH3CH2C + 2H2O + 2[O] → H2SO4 + H2S + 2CH3CH2CHO

S O

Which tests would give a positive reaction with the organic product?

1 warming with Tollens’ reagent

2 warming with acidified potassium manganate(VII)


3 warming with alkaline aqueous iodine

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.

To avoid the issue of disclosure of answer-related information to candidates, all copyright acknowledgements are reproduced online in the Cambridge
International Examinations Copyright Acknowledgements Booklet. This is produced for each series of examinations and is freely available to download at
www.cie.org.uk after the live examination series.

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 2016 9701/13/O/N/16


Page 2 Mark Scheme Syllabus Paper
Cambridge International AS/A Level – October/November 2016 9701 13

Question Question
Key Key
Number Number
1 C 21 A
2 D 22 D
3 D 23 A
4 B 24 D
5 C 25 C

6 A 26 D
7 D 27 B
8 C 28 A
9 A 29 A
10 A 30 B

11 C 31 B
12 D 32 A
13 C 33 B
14 D 34 D
15 C 35 C

16 D 36 B
17 B 37 A
18 D 38 C
19 B 39 D
20 B 40 B

© UCLES 2016
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 diagram shows a Boltzmann distribution of molecular energies for a gaseous mixture. The
distribution has a peak, labelled P on the diagram.

activation
number of energy
molecules

0
0
molecular energy

What happens when an effective catalyst is added to the mixture?

A The height of the peak decreases and the activation energy moves to the right.
B The height of the peak decreases and the activation energy moves to the left.
C The height of the peak remains the same and the activation energy moves to the right.
D The height of the peak remains the same and the activation energy moves to the left.

2 Which quantity gives the best indication of the relative strengths of the hydrogen bonds between
the molecules in liquid hydrogen halides?

A bond dissociation energies


B enthalpy changes of formation
C enthalpy changes of solution
D enthalpy changes of vaporisation

3 Use of the Data Booklet is relevant to this question.

1.00 g of carbon is combusted in a limited supply of pure oxygen. 0.50 g of the carbon combusts
to form CO2 and 0.50 g of the carbon combusts to form CO.

The resultant mixture of CO2 and CO is passed through excess NaOH(aq) and the remaining gas
is then dried and collected.

What is the volume of the remaining gas? (All gas volumes are measured at 25 °C and
1 atmosphere pressure.)

A 1 dm3 B 1.5 dm3 C 2 dm3 D 3 dm3

© UCLES 2015 9701/11/M/J/15


3

4 In oxygen difluoride, OF2, fluorine has an oxidation number of –1. OF2 will react with sulfur
dioxide according to the following equation.

OF2 + SO2 → SO3 + F2

What is oxidised and what is reduced in this reaction?

oxygen
fluorine sulfur
in OF2

A oxidised oxidised reduced


B oxidised reduced oxidised
C reduced oxidised reduced
D reduced reduced oxidised

5 Use of the Data Booklet is relevant to this question.

The gas laws can be summarised in the ideal gas equation below.

pV = nRT

0.96 g of oxygen gas is contained in a glass vessel of volume 7.0 × 10–3 m3 at a temperature of
30 °C.

Assume the gas behaves as an ideal gas.

What is the pressure in the vessel?

A 1.1 kPa B 2.1 kPa C 10.8 kPa D 21.6 kPa

6 One mole of phosphorus(V) chloride, PCl 5, is heated to 600 K in a sealed flask of volume 1 dm3.
Equilibrium is established and measurements are taken.

PCl 5(g) PCl 3(g) + Cl 2(g)

The experiment is repeated with one mole of phosphorus(V) chloride heated to 600 K in a sealed
flask of volume 2 dm3.

How will the measurements vary?

A The equilibrium concentrations of PCl 3(g) and Cl 2(g) are higher in the second experiment.
B The equilibrium concentration of PCl 5(g) is lower in the second experiment.
C The equilibrium concentrations of all three gases are the same in both experiments.
D The value of the equilibrium constant is higher in the second experiment.

© UCLES 2015 9701/11/M/J/15 [Turn over


4

7 The standard enthalpy changes of combustion of glucose and ethanol are given as –2820 and
–1368 kJ mol–1 respectively.

Glucose, C6H12O6, can be converted into ethanol.

C6H12O6(s) → 2C2H5OH(l) + 2CO2(g)

What is the standard enthalpy change for this reaction?

A –1452 kJ mol–1
B –84 kJ mol–1
C +84 kJ mol–1
D +1452 kJ mol–1

8 In which reaction is the underlined substance acting as a base?

A HNO3 + H2SO4 → H2NO3+ + HSO4–

B HSiO3– + HCN → CN– + H2O + SiO2

C HNO2 + HCO3– → H2O + CO2 + NO2–

D C6H5O– + CH2Cl CO2H → C6H5OH + CH2Cl CO2–

9 One molecule of haemoglobin, Hb, can bind with four molecules of oxygen according to the
following equation.

Hb(aq) + 4O2(aq) Hb(O2)4(aq)

When the equilibrium concentration of O2 is 7.6 × 10–6 mol dm–3, the equilibrium concentrations of
Hb and Hb(O2)4 are equal.

What is the value of Kc for this equilibrium?

A 3.0 × 1020 B 1.3 × 105 C 7.6 × 10–6 D 3.3 × 10–21

10 The double bond between the two carbon atoms in an ethene molecule consists of one σ bond
and one π bond.

Which orbitals overlap to form each of these bonds?

σ bond π bond

A sp2–sp2 p–p
B sp2–sp2 sp2–sp2
C sp3–sp3 p–p
D sp3–sp3 sp2–sp2

© UCLES 2015 9701/11/M/J/15


5

11 The diagram shows a reaction pathway for an endothermic reaction.

Which arrow represents the activation energy for the forward reaction?

enthalpy B
/ kJ mol–1 A D

0
0
extent of reaction

12 In the industrial electrolysis of brine to manufacture chlorine, the diaphragm used is a porous
screen which allows the flow of electrolytes but keeps other chemicals separate.

Which substance needs to be kept separate from the chlorine by the diaphragm?

A hydrogen
B sodium chloride
C sodium hydroxide
D water

13 The three minerals below are obtained from mines around the world. Each one behaves as a
mixture of two carbonate compounds. They can be used as fire retardants because they
decompose in the heat, producing CO2. This gas smothers the fire.

barytocite BaCa(CO3)2
dolomite CaMg(CO3)2
huntite Mg3Ca(CO3)4

What is the order of effectiveness as fire retardant, from best to worst?

best worst

A dolomite barytocite huntite


B dolomite huntite barytocite
C huntite barytocite dolomite
D huntite dolomite barytocite

© UCLES 2015 9701/11/M/J/15 [Turn over


6

14 Which observations are made when a sample of silicon chloride, SiCl 4, is added to a beaker of
water?

A No visible changes are observed.


B Steamy fumes and a white precipitate are both observed.
C The appearance of a white precipitate is the only observation.
D The appearance of steamy fumes is the only observation.

15 Use of the Data Booklet is relevant to this question.

Which diagram correctly shows the atomic radii of the elements Mg, Al, Si and P plotted against
their melting points?

A B

Al Mg

Mg P
atomic atomic
radius radius Si
Al
Si
P

melting point melting point

C D

Mg Mg

atomic Al atomic Al
radius radius
Si Si
P P

melting point melting point

© UCLES 2015 9701/11/M/J/15


7

16 Chlorine is widely used in water treatment plants.

Which reaction takes place when chlorine dissolves in water?

A Cl 2 + H2O → HCl + HCl O

B 2Cl 2 + 2H2O → 3HCl + HCl O2

C 3Cl 2 + 3H2O → 5HCl + HCl O3

D 4Cl 2 + 4H2O → 7HCl + HCl O4

17 Astatine, At, is below iodine in Group VII of the Periodic Table.

Which statement is most likely to be correct?

A AgAt(s) reacts with excess dilute aqueous ammonia to form a solution of a soluble complex.
B Astatine and KCl (aq) react to form KAt(aq) and chlorine.
C KAt(aq) and dilute sulfuric acid react to form white fumes of HAt(g).
D NaAt(s) and concentrated sulfuric acid react to form astatine.

18 Mohr’s salt is a pale green crystalline solid which is soluble in water. It contains two cations, one
of which is Fe2+, and one anion which is SO42–.

The identity of the second cation was determined by heating Mohr’s salt with aqueous sodium
hydroxide. A colourless gas was evolved which readily dissolved in water giving an alkaline
solution.

A green precipitate was also formed.

What are the identities of the gas and the precipitate?

gas precipitate

A NH3 Fe(OH)2
B NH3 Na2SO4
C SO2 Fe(OH)2
D SO2 Na2SO4

19 Use of the Data Booklet is relevant to this question.

Which mass of solid residue will 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

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8

20 Which reagent will give a different observation with compounds P and Q?

HOCH2CH(OH)CHO HOCH2COCH2OH
P Q

A Br2(aq)
B hot acidified KMnO4
C silver nitrate in ammonia solution
D warm acidified K2Cr2O7

21 The cyclic compound M is heated with dilute hydrochloric acid.

O
NH

O
compound M

What are the products of the reaction?

A HOCH2CO2H and H2NCH2CO2H


B HO2CCH2OH and HO2CCH2NH3+
C H2NCOCH2OH and HOCH2CHO
D HOCH2CONH3+ and HOCH2CHO

22 Cottonseed oil contains large amounts of polyunsaturated carboxylic acids. When this oil is used
to make margarine, the C=C double bonds in the unsaturated carboxylic acids are hydrogenated.

What reagents and conditions would be suitable to bring about this hydrogenation reaction?

A H2 gas, nickel catalyst, 400 °C


B LiAl H4 in dry ether
C NaBH4, aqueous solution

D steam, concentrated H2SO4, 300 °C and 60 atm pressure

23 Which intermediate ion forms in the greatest amount during the addition of HBr to propene?

A CH3CH+CH3
B CH3CH2CH2+
C CH3CH–CH2Br
D CH3CHBrCH2–

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9

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

N CH2CH2CH3
H

coniine

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 1,1-dibromo-2-propylcyclopentane
B 1,2-dibromo-2-propylcyclopentane
C 1,4-dibromooctane
D 1,5-dibromooctane

25 2-bromopropane reacts with a hot concentrated solution of sodium hydroxide in ethanol.

Which substance is the major product of this reaction?

A propan-1-ol
B propan-2-ol
C 2-hydroxypropene
D propene

26 The presence of a halogen in an organic compound may be detected by warming the organic
compound with aqueous silver nitrate.

Which compound would be the quickest to produce a precipitate?

A B C D
Cl F F Cl

Cl Cl F Br

Cl F I F

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10

27 Which reagent will give a different observation with compounds W and X?

CH2OH CH3 OH

W X

A hot SOCl 2
B hot acidified K2Cr2O7
C NaOH(aq)
D warm Fehling’s reagent

28 In 1869 Ladenburg suggested a structure for benzene, C6H6, in which one hydrogen atom is
attached to each carbon atom.

CH
HC CH

CH
HC CH

Ladenburg structure

A compound C6H4Cl 2 could be formed with the same carbon skeleton as the Ladenburg structure.

How many structural isomers would this compound have?

A 3 B 4 C 5 D 6

© UCLES 2015 9701/11/M/J/15


11

29 The citrus flavour of lemons is due to the compound limonene, present in both the peel and the
juice.

limonene

What is the mole ratio of carbon dioxide to water produced when limonene is completely burnt in
oxygen?

number of moles number of moles


carbon dioxide water

A 4 3
B 5 4
C 5 8
D 9 7

30 What is the organic product when ethanamide, CH3CONH2, is boiled with excess aqueous
sodium hydroxide?

A CH3CN
B CH3CO2–NH4+
C CH3CONH–Na+
D CH3CO2–Na+

© UCLES 2015 9701/11/M/J/15 [Turn over


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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

31 Use of the Data Booklet is relevant to this question.

The 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 It has 13 more neutrons than protons.


2 It has 43 protons.
3 It has 99 nucleons.

32 Urea is a product of animal metabolism. It can also be used as a fertiliser.

x N
H
O C
H
N

H
urea

The diagram shows angle x in this molecule.

Which statements about the structure of urea are correct?

1 Angle x is approximately 120°.

2 The molecule has two π bonds.


3 The molecule has only three lone pairs of electrons.

© UCLES 2015 9701/11/M/J/15


13

33 Aluminium is extracted from aluminium oxide by electrolysis.

Which statements are correct?

1 Aluminium oxide has an extremely high melting point.


2 Bauxite is added to the aluminium oxide to lower its melting point.
3 Oxygen produced at the graphite cathode reacts with the graphite to produce CO2.

34 Why does raising the pressure of a fixed mass of gaseous reactants at a constant temperature
cause an increase in the rate of reaction?

1 More collisions occur per second when the pressure is increased.


2 More molecules have energy greater than the activation energy at the higher pressure.
3 Raising the pressure lowers the activation energy.

35 Which statements about the industrial manufacture of sulfuric acid are correct?

1 Sulfur is burned to form sulfur dioxide.


2 The stage that forms sulfur trioxide involves a V2O5 catalyst.
3 The stage that forms sulfur trioxide is non-reversible.

36 X is a Group II metal. It forms a sulfate which is more soluble than barium sulfate. It forms a
hydroxide which is more soluble than calcium hydroxide.

What could be the identity of X?

1 strontium
2 magnesium
3 beryllium

37 The diagram shows the structure of an alkene molecule.

CH3 CH3
CH3 C C H
C C H H
H CH3

Which statements about this molecule are correct?

1 All the carbon atoms are in the same plane.


2 It has geometrical isomers.
3 It is optically active.

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14

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

38 An organic compound, X, will react with calcium metal to produce a salt with the empirical formula
CaC4H4O4.

What could be the identity of X?

1 ethanoic acid
2 butanedioic acid
3 2-methylpropanedioic acid

39 Which compounds will react with HBr to give the compound R?

Br

1 2 3
OH

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15

40 5-hydroxypentanoic acid is readily converted into the cyclic compound L.

O
L

Which statements about this reaction are correct?

1 Acidified sodium dichromate(VI) is used as a reagent.


2 A water molecule is produced in the reaction.
3 The reaction is catalysed by concentrated H2SO4.

© UCLES 2015 9701/11/M/J/15


Page 2 Mark Scheme Syllabus Paper
Cambridge International AS/A Level – May/June 2015 9701 11

Question Question
Key Key
Number Number
1 D 21 B
2 D 22 A
3 A 23 A
4 B 24 D
5 C 25 D

6 B 26 C
7 B 27 B
8 C 28 A
9 A 29 B
10 A 30 D

11 B 31 A
12 C 32 D
13 D 33 D
14 B 34 D
15 C 35 B

16 A 36 D
17 D 37 C
18 A 38 C
19 C 39 A
20 C 40 C

© Cambridge International Examinations 2015


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 which option do all three particles have the same electronic configuration and the same
number of neutrons?
15
A N3– 16
O2– 19 –
F
18
B O2– 19 –
F 20
Ne
19 – 20 23
C F Ne Na+
22 23 24
D Ne Na Mg2+

2 The shell of a chicken’s egg makes up 5% of the mass of an average egg. An average egg has a
mass of 50 g.

Assume the egg shell is pure calcium carbonate.

How many complete chicken’s egg shells would be needed to neutralise 50 cm3 of 2.0 mol dm–3
ethanoic acid?

A 1 B 2 C 3 D 4

3 Phosphorus forms a compound with hydrogen called phosphine, PH3. This compound can react
with a hydrogen ion, H+.

Which type of interaction occurs between PH3 and H+?

A dative covalent bond


B dipole-dipole forces
C hydrogen bond
D ionic bond

4 Which solid has a simple molecular lattice?

A calcium fluoride
B nickel

C silicon(IV) oxide
D sulfur

© UCLES 2015 9701/12/M/J/15


3

5 Use of the Data Booklet is relevant to this question.

The gas laws can be summarised in the ideal gas equation below.

pV = nRT

The volume of a sample of methane is measured at a temperature of 60 °C and a pressure of


103 kPa. The volume measured is 5.37 × 10–3 m3.

Assume the gas behaves as an ideal gas.

What is the mass of the sample of methane, given to two significant figures?

A 0.00018 g B 0.0032 g C 0.18 g D 3.2 g

6 Metaldehyde, (CH3CHO)4, is used as a solid fuel for camping stoves. The equation for the
complete combustion of metaldehyde is shown.

(CH3CHO)4(s) + 10 O2(g) → 8CO2(g) + 8H2O(l)

= standard enthalpy change of combustion.

Which expression will give a correct value for the enthalpy change of formation of metaldehyde?

A metaldehyde – (8 carbon + 8 hydrogen)


B metaldehyde – (8 carbon + 16 hydrogen)
C (8 carbon + 8 hydrogen) – metaldehyde
D (8 carbon + 16 hydrogen) – metaldehyde

7 In industry, copper metal is purified by electrolysis.

Which changes occur to the masses of the electrodes and to the colour of the electrolyte during
this process?

mass of mass of colour of


anode cathode electrolyte

A decrease increase little or no change occurs


B decrease increase pale blue to blue
C increase decrease little or no change occurs
D increase decrease blue to pale blue

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4

8 Nitrogen dioxide, NO2, exists in equilibrium with dinitrogen tetroxide, N2O4.

2NO2(g) N2O4(g) ∆H = –57 kJ mol–1

Which conditions give the greatest percentage of N2O4(g) at equilibrium?

pressure temperature

A high high
B high low
C low high
D low low

9 When a sample of HI is warmed to a particular temperature the equilibrium below is established.

2HI(g) H2(g) + I2(g)

At this temperature, it is found that the partial pressure of HI(g) is 28 times the partial pressure of
H2(g).

What is the value of Kp at this temperature?

A 1.28 × 10–3 B 0.035 C 28 D 784

10 Photochromic glass, used for sunglasses, darkens when exposed to bright light and becomes
more transparent again when the light is less bright. The darkness of the glass is related to the
concentration of silver atoms.

The following reactions are involved.

reaction 1 Ag+ + Cl – Ag + Cl

reaction 2 Cu+ + Cl → Cu2+ + Cl –

reaction 3 Cu2+ + Ag → Cu+ + Ag+

Which statement about these reactions is correct?

A Cu+ and Cu2+ ions act as catalysts.


B Cu+ ions act as an oxidising agent in reaction 2.
C Reaction 3 increases the darkness of the glass.
D Silver atoms are reduced in reaction 3.

© UCLES 2015 9701/12/M/J/15


5

11 The Boltzmann distribution below shows the distribution of molecular energies in a sample of a
gas at a given temperature.

number of
molecules

0
0 molecular energy

Which statement correctly describes the change in such a distribution if the temperature is
increased?

A Fewer molecules possess the most probable energy value and this value shifts to the left.
B Fewer molecules possess the most probable energy value and this value shifts to the right.
C More molecules possess the most probable energy value and this value shifts to the left.
D The area under the curve of the distribution increases.

12 Use of the Data Booklet is relevant to this question.

When 3.00 g of an anhydrous nitrate of a Group II metal is decomposed, 1.53 g of gas is


produced.

What is the nitrate compound?

A beryllium nitrate
B calcium nitrate
C magnesium nitrate
D strontium nitrate

13 What happens when a piece of magnesium ribbon is placed in cold water?

A A vigorous effervescence occurs.


B Bubbles of gas form slowly on the magnesium.
C The magnesium floats on the surface of the water and reacts quickly.
D The magnesium glows and a white solid is produced.

14 Compound X releases carbon dioxide gas and forms a white solid, Y, when it is heated. Neither X
nor Y are soluble in water. Compound Y is used as a refractory kiln lining.

What is compound X?

A CaCO3 B CaO C MgCO3 D MgO

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6

15 Use of the Data Booklet is relevant to this question.

Which diagram correctly shows the electronegativity of the elements Na, Mg, Al and Si plotted
against their first ionisation energies?

A B

Si Si

Al Al
electronegativity electronegativity
Mg Mg

Na Na

first ionisation energy first ionisation energy

C D

Na Na

Al Mg
electronegativity electronegativity
Mg Al

Si Si

first ionisation energy first ionisation energy

© UCLES 2015 9701/12/M/J/15


7

16 The diagram shows a diaphragm cell used for the electrolysis of brine. Brine is concentrated
aqueous sodium chloride.

brine

P Q

R S
exit pipe

_
anode + diaphragm cathode

A solution of sodium chlorate(I), commonly used as bleach, can be made by mixing which two
substances?

A P and R B P and S C Q and R D Q and S

17 Which statement about the ammonium ion, NH4+, is correct?

A All bond angles are 107°.


B Ammonium ions are formed when ammonia behaves as an acid.
C Ammonium ions are unreactive when heated with NaOH(aq).
D The bonds are all the same length.

18 Carbon monoxide, CO, nitrogen dioxide, NO2, and sulfur dioxide, SO2, are all atmospheric
pollutants.

Which reaction concerning these compounds occurs in the atmosphere?

A CO is spontaneously oxidised to CO2


B NO2 is reduced to NO by CO
C NO2 is reduced to NO by SO2
D SO2 is oxidised to SO3 by CO2

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8

19 Chlorate(V) ions, Cl O3–, are produced in the redox reaction between chlorine and hot aqueous
sodium hydroxide. Oxidation numbers can be used to help balance the equation for this reaction.

What will be the values of coefficients v, x and y in the balanced equation?

vCl 2(g) + wOH–(aq) → xCl –(aq) + yCl O3–(aq) + zH2O(l)

v x y

A 2 3 1
B 3 4 2
C 3 5 1
D 7 12 2

20 Which alcohol will react with an acidified solution of potassium dichromate(VI) to produce a
ketone containing six carbon atoms?

A 2,2-dimethylbutan-1-ol
B 2-methylpentan-3-ol
C 3,3-dimethylpentan-2-ol
D 3-methylpentan-3-ol

21 What is the major product formed when compound Q is warmed with excess HBr?

OH
OH

A B

Br Br OH
OH Br
Br

C D

Br Br Br
Br Br
Br

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9

22 Four students, W, X, Y and Z, made the following statements about alkanes and alkenes.

W ‘Bromine reacts with alkanes by electrophilic substitution.’


X ‘Bromine reacts with alkenes by a free-radical addition mechanism.’

Y ‘Alkenes can be oxidised by acidified manganate(VII) ions.’


Z ‘Alkenes are formed from alkanes by cracking.’

Which two students are correct?

A W and X B W and Z C X and Y D Y and Z

23 Butanedioic acid may be synthesised in two steps from 1,2-dibromoethane.

step 1 step 2
BrCH2CH2Br X HO2CCH2CH2CO2H

Which reagents could be used for this synthesis?

step 1 step 2

A HCN(g) HCl (aq)


B HCO2Na(aq) HCl (aq)
C KCN(alcoholic) H2SO4(aq)
D NaOH(aq) K2Cr2O7 / H2SO4(aq)

24 Which reaction would not give propene?

A adding excess hot concentrated sulfuric acid to propan-1-ol


B adding warm aqueous sodium hydroxide to 2-bromopropane
C adding warm ethanolic sodium hydroxide to 1-bromopropane
D passing propan-2-ol vapour over heated aluminium oxide

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10

25 Terpinen-4-ol is one of the active ingredients in tea tree oil.

HO

terpinen-4-ol

What is the molecular formula of terpinen-4-ol?

A C7H11O B C10H16O C C10H17O D C10H18O

26 Use of the Data Booklet is relevant to this question.

2.40 g of propan-2-ol were mixed with excess acidified potassium dichromate(VI). The reaction
mixture was then boiled under reflux for twenty minutes. The organic product was then collected
by distillation. The yield of product was 75.0%.

What mass of product was collected?

A 1.74 g B 1.80 g C 2.22 g D 2.32 g

27 The diagram shows the structure of compound X.

O O

What is the product of the reaction between compound X and an excess of NaBH4?

A B C D
OH OH OH OH O O O OH

© UCLES 2015 9701/12/M/J/15


11

28 Lactic acid occurs naturally, for example in sour milk.

H O O

H C C C

H H O H

lactic acid

What is a property of lactic acid?

A It decolourises aqueous bromine rapidly.


B It is insoluble in water.
C It reduces Fehling’s reagent.
D Two molecules react with each other in the presence of a strong acid.

29 Citric acid is found in lemon juice.

HO2CCH2C(OH)(CO2H)CH2CO2H
citric acid

What is the volume of 0.4 mol dm–3 sodium hydroxide solution required to neutralise a solution
containing 0.005 mol of citric acid?

A 12.5 cm3 B 25.0 cm3 C 37.5 cm3 D 50.0 cm3

© UCLES 2015 9701/12/M/J/15 [Turn over


12

30 The drug Sirolimus is used to treat patients after kidney transplants.

OH
H 3C
O CH3
N O
H H H
O O O
O
H 3C
O H 3C
HO
OH
H 3C
H
CH3 O
O O

H3C H 3C
CH3

CH3

Sirolimus

On reaction with hot aqueous sodium hydroxide, Sirolimus produces an equimolar mixture of two
organic products.

What is the structural formula of the product with the lower relative molecular mass?

A B C D

N N CO2Na N N CO2Na
H H CO2Na CO2Na

© UCLES 2015 9701/12/M/J/15


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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

31 Use of the Data Booklet is relevant to this question.

Which statements about the phosphide ion, 31P3–, and the chloride ion, 35Cl –, are correct?

1 They have the same number of electrons.


2 They have the same number of neutrons.
3 They have the same number of protons.

32 Why does aluminium chloride, Al2Cl6, sublime at the relatively low temperature of 180 °C?

1 The intermolecular forces between the Al 2Cl 6 molecules are weak.


2 The co-ordinate bonds between aluminium and chlorine are weak.
3 The covalent bonds between aluminium and chlorine are weak.

33 Which statements are correct for all exothermic reactions?

1 ∆H for the reaction is negative.


2 On a reaction pathway diagram the products are shown lower than the reactants.
3 The reaction will happen spontaneously.

© UCLES 2015 9701/12/M/J/15 [Turn over


14

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

34 Which of these reactions are redox reactions?

1 6NO(g) + 4NH3(g) → 5N2(g) + 6H2O(g)

2 2SO2(g) + O2(g) → 2SO3(g)

3 SO3(g) + H2O(g) → H2SO4(g)

35 When added to water, which oxides will cause a change in the pH of the water?

1 SiO2
2 CaO
3 SO2

36 Halogenated hydrocarbons have many uses.

What have halogenated hydrocarbons been used for?

1 solvents
2 refrigerants
3 monomers in polymer manufacture

37 In which structures do the four carbon atoms labelled C lie in the same plane?

1 2 3

C
C
C
C C C
C C
C C
C C

© UCLES 2015 9701/12/M/J/15


15

38 Which statements about 2-methylbutan-1-ol are correct?

1 It can give HCl (g) on reaction with PCl 5.


2 It can be oxidised to give an aldehyde.
3 It exists in two optically active forms.

39 Propanone and hydrogen cyanide react together by this mechanism.

H 3C H3C O– H 3C OH
C O C H CN C + CN–

H 3C H3C CN H 3C CN
CN–

Which statements about this mechanism are correct?

1 CN– is an electrophile.
2 It is an addition reaction.
3 Heterolytic bond breaking is involved.

40 Monopotassium citrate is used as an emulsifying agent in powdered milk and in powdered soups.
It may be represented by the formula shown.

CH2CO2H

HO C CO2– K+

CH2CO2H

monopotassium citrate

Which statements about monopotassium citrate are correct?

1 It does not have a chiral carbon atom.


2 It can act as a dibasic acid.
3 It reacts with NaHCO3 to give CO2.

© UCLES 2015 9701/12/M/J/15


Page 2 Mark Scheme Syllabus Paper
Cambridge International AS/A Level – May/June 2015 9701 12

Question Question
Key Key
Number Number
1 B 21 C
2 B 22 D
3 A 23 C
4 D 24 B
5 D 25 D

6 C 26 A
7 A 27 A
8 B 28 D
9 A 29 C
10 A 30 B

11 B 31 D
12 D 32 D
13 B 33 B
14 C 34 B
15 B 35 C

16 B 36 A
17 D 37 B
18 C 38 A
19 C 39 C
20 B 40 A

© Cambridge International Examinations 2015


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 diagram shows the 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 Ea1 Ea2

molecular energy

Ea is used to represent the activation energy for the reaction between the gases. Of the two
values shown, one is the activation energy for a catalysed reaction, the other for an uncatalysed
reaction.

Which statement about Ea1 is correct?

A Ea1 corresponds to a catalysed reaction with fewer effective collisions than the uncatalysed
reaction.
B Ea1 corresponds to an uncatalysed reaction with fewer effective collisions than the catalysed
reaction.
C Ea1 corresponds to a catalysed reaction with a greater number of effective collisions than the
uncatalysed reaction.
D Ea1 corresponds to an uncatalysed reaction with a greater number of effective collisions than
the catalysed reaction.

2 Which diagram shows the correct graph of pV against n for an ideal gas at constant temperature?

A B C D

pV pV pV pV

0 0 0 0
0 n 0 n 0 n 0 n

© UCLES 2015 9701/13/M/J/15


3

3 A student performed an experiment to measure the enthalpy change of combustion of ethane.

He used the following values for the standard enthalpy changes of combustion of carbon and
hydrogen.

carbon = –394 kJ mol–1


hydrogen = –286 kJ mol–1

He calculated the enthalpy change of formation of ethane to be –140 kJ mol–1.

What was his experimental value for the standard enthalpy change of combustion of ethane?

A –2364 kJ mol–1
B –1506 kJ mol–1
C –1112 kJ mol–1
D –540 kJ mol–1

4 Which pair has species with different shapes?

A BeCl 2 and CO2


B CH4 and NH4+
C NH3 and BF3
D SCl 2 and H2O

5 In which reaction does an element have the largest change in oxidation number?

A Cr2O72– + 6Fe2+ + 14H+ → 2Cr3+ + 6Fe3+ + 7H2O

B 3OCl – → Cl O3– + 2Cl –

C 5Fe2+ + MnO4– + 8H+ → 5Fe3+ + Mn2+ + 4H2O

D PbO2 + Sn2+ + 4H+ → Sn4+ + Pb2+ + 2H2O

6 Which statement can be explained by intermolecular hydrogen bonding?

A Ethanol has a higher boiling point than propane.


B Hydrogen chloride has a higher boiling point than silane, SiH4.
C Hydrogen iodide forms an acidic solution when dissolved in water.
D Propanone has a higher boiling point than propane.

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4

7 Carbon monoxide and methanol can react together to form ethanoic acid.

CO(g) + CH3OH(l) CH3CO2H(l)

Standard enthalpy changes of combustion are given in the table.

standard enthalpy change


compound
of combustion,

CO –283.0 kJ mol–1
CH3OH –726.0 kJ mol–1
CH3CO2H –874.1 kJ mol–1

What is the value for for the reaction between carbon monoxide and methanol?

A –1883.1 kJ mol–1
B –134.9 kJ mol–1
C +134.9 kJ mol–1
D +1883.1 kJ mol–1

© UCLES 2015 9701/13/M/J/15


5

8 The following reaction was carried out.

HCO2CH3(aq) + NaOH(aq) → HCO2Na(aq) + CH3OH(aq)

The concentration of methanol, [CH3OH(aq)], was measured with time, t.

Which graph shows the relationship between [CH3OH(aq)] and t ?

A B

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

0 0
0 t 0 t

C D

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

0 0
0 t 0 t

9 Brine is concentrated aqueous sodium chloride. Brine is electrolysed in a diaphragm cell.

What is the purpose of the diaphragm?

A to prevent Cl 2 reacting with H2


B to prevent HCl reacting with Na
C to prevent NaOH reacting with Cl 2
D to prevent NaOH reacting with HCl

© UCLES 2015 9701/13/M/J/15 [Turn over


6

10 Use of the Data Booklet is relevant to this question.

1.00 g of a metallic element reacts completely with 300 cm3 of oxygen at 298 K and 1 atm
pressure to form an oxide which contains O2– ions.

The volume of one mole of gas at this temperature and pressure is 24.0 dm3.

What could be the identity of the metal?

A calcium
B magnesium
C potassium
D sodium

11 Use of the Data Booklet is relevant to this question.

The gas laws can be summarised in the ideal gas equation below.

pV = nRT

When an evacuated tube of volume 400 cm3 is filled with gas at 300 K and 101 kPa, the mass of
the tube increases by 0.65 g.

Assume the gas behaves as an ideal gas.

What could be the identity of the gas?

A argon
B helium
C krypton
D neon

12 Which oxide will produce the solution with the highest pH when it is mixed with water?

A Al 2O3 B CO2 C Na2O D SO2

13 Barium is a more reactive metal than aluminium.

Which method could be suitable for the extraction of barium?

A electrolysing aqueous barium chloride


B electrolysing molten barium chloride
C reducing barium oxide with aluminium
D reducing barium oxide with carbon

© UCLES 2015 9701/13/M/J/15


7

14 The compound (CH3)3NAl Cl 3 has a simple molecular structure.

Which statement about (CH3)3NAl Cl 3 is correct?

A (CH3)3NAl Cl 3 molecules attract each other by hydrogen bonds.


B The Al atom has an incomplete valance shell of electrons.
C The bonds around the Al atom are planar.
D The molecules contain coordinate and covalent bonding

15 The labels had become detached from four bottles in the laboratory. A student realised that the
contents of one of them could easily be identified, because on addition of water it would not give
fumes of hydrogen chloride.

Which did not give the HCl fumes?

A Al 2Cl 6 B MgCl 2 C PCl 5 D SiCl 4

16 Transition elements and their compounds are widely used as catalysts.

What is the identity and what is the oxidation number of the element present in the catalyst used
in the Contact process?

element oxidation number

A iron 0
B iron +3
C vanadium 0
D vanadium +5

17 This question refers to isolated gaseous species.

The species F–, Ne and Na+ are isoelectronic. This means they have the same number of
electrons.

In which order do their radii increase?

smallest largest

A Na+ F– Ne
B F– Ne Na+
C Na+ Ne F–
D Ne F– Na+

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8

18 Due to their similar ionic radii, the reactions of lithium and magnesium and their corresponding
compounds are very similar.

Which statement about the reactions of lithium or its compounds can be predicted from this
statement?

A Lithium burns very slowly in oxygen.


B Lithium carbonate decomposes on heating in a blue Bunsen burner flame, forming lithium
oxide and carbon dioxide.
C Lithium nitrate decomposes on heating, forming lithium nitrite, LiNO2, and oxygen.
D Lithium reacts very violently with cold water, liberating hydrogen.

19 Two separate tests were carried out on an aqueous solution of a salt which contains only two
ions.

In each test, the resulting mixtures were filtered and the filtrate solution was collected.

reagent result filtrate collected

test 1 aqueous silver nitrate


yellow precipitate forms solution P
acidified with dilute nitric acid

test 2 dilute sulfuric acid white precipitate forms solution Q

Which ions are present in the filtrates?

solution P solution Q

A Ba2+(aq) Cl –(aq)
B Ba2+(aq) I–(aq)
C Mg2+(aq) Cl –(aq)
D Mg2+(aq) I–(aq)

20 An organic compound Z

● is oxidised by hot acidified potassium manganate(VII),


● reacts with sodium to give hydrogen.

What could be compound Z?

A (CH3)3COH
B CH3CH2CH2CHO
C CH3CH2CH(OH)CH3
D CH3CH2COCH3

© UCLES 2015 9701/13/M/J/15


9

21 The diagram shows a molecule that has σ bonds and π bonds.

CH2 CH CH2 C O CH2 CH CH2

How many σ bonds are present in this molecule?

A 15 B 17 C 18 D 21

22 The Finkelstein reaction occurs when NaI in propanone reacts with a chloroalkane or
bromoalkane. The halogen is directly replaced by I and the reaction only works for primary
halogenoalkanes.

Which halogenoalkane would produce compound X?

compound X

A (CH3)2CHCH(CH3)CH2CH2Br
B (CH3)2CHCH(CH3)CH2Br
C (CH3)2CHCH2CH2CH(CH3)Cl
D (CH3)2CHCH2CH(CH3)CH2Cl

23 An ester P with a fruity odour has the following structural formula.

CH3C

OCH2CH2CH(CH3)2

Which compounds are produced when P is hydrolysed using hydrochloric acid?

A CH3COCl and (CH3)2CHCH2CH2OH


B CH3CHO and (CH3)2CHCH2CH2OH
C CH3CO2H and (CH3)2CHCH2CH2CHO
D CH3CO2H and (CH3)2CHCH2CH2OH

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10

24 The naturally-occurring molecule civetone is found in a gland of the African civet cat and has
been used in perfumery.

CH2 CH2
CH2
H 2C CH2 CH2
C O
H 2C
CH CH2

HC CH2
CH2 H2C

H 2C CH2
CH2

civetone

Which reagent will not react with civetone?

A 2,4-dinitrophenylhydrazine reagent
B Fehling’s reagent
C hydrogen bromide

D sodium tetrahydridoborate(III), NaBH4

25 Compound X, C5H12O, is oxidised by acidified sodium dichromate(VI) to compound Y.

Compound Y reacts with butan-2-ol in the presence of a little concentrated sulfuric acid to give
liquid Z.

What could be the formula of Z?

A CH3(CH2)3CO2CH(CH3)CH2CH3
B CH3(CH2)3CO2(CH2)3CH3
C CH3(CH2)2CO2CH(CH3)CH2CH3
D (CH3)2CHCH2CO2C(CH3)3

© UCLES 2015 9701/13/M/J/15


11

26 Alkane X has molecular formula C4H10.

X reacts with Cl 2(g) in the presence of sunlight to produce only two different monochloroalkanes,
C4H9Cl. Both of these monochloroalkanes produce the same alkene Y, and no other organic
products, when they are treated with hot ethanolic KOH.

What is produced when Y is treated with hot concentrated acidified KMnO4?

A CO2 and CH3CH2CO2H


B CO2 and CH3COCH3
C HCO2H and CH3COCH3
D CH3CO2H only

27 The compound aspartame is widely used as a sweetener in ‘diet’ soft drinks.

CH3

O O
O
HO C 6H 5
NH

O NH2

aspartame

Aspartame is chiral. (There are no chiral carbon atoms in C6H5.)

How many chiral carbon atoms are present in a molecule of aspartame?

A 1 B 2 C 3 D 4

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28 A tertiary bromoalkane, indicated here by C–Br , reacts with aqueous NaOH. The mechanism
has the reaction pathway below.

Y
energy C–Br + OH–

C–OH + Br –

extent of reaction

Which point in the diagram is correctly identified?

A X is C+


B X is HO C Br

C Y is C+


D Y is HO C Br

29 Four drops of 1-chlorobutane, 1-bromobutane and 1-iodobutane were put separately into three
test-tubes containing 1.0 cm3 of aqueous silver nitrate at 60 °C.

In each case, a hydrolysis reaction occurred. R represents the butane chain C4H9 and X the
halogen atom.

H2O(l) + R–X(l) + Ag+(aq) → R–OH(aq) + AgX(s) + H+(aq)

The rate of formation of cloudiness in the test-tubes was in the order RCl < RBr < RI.

Why is this?

A The bond energy of R–X decreases from RCl to RI.

B The first ionisation energy of the halogen decreases from Cl to I.

C The solubility of AgX(s) decreases from AgCl to AgI.

D The R–X bond polarity decreases from RCl to RI.

© UCLES 2015 9701/13/M/J/15


13

30 Malic acid occurs in apples.

OH

H C CH2CO2H

CO2H

malic acid

Under suitable conditions, which substance will react with only one of the –OH groups in the
malic acid molecule?

A Cr2O72– / H+(aq)
B Na(s)
C NaOH(aq)
D PCl 5(s)

© UCLES 2015 9701/13/M/J/15 [Turn over


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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

31 The technetium-99 isotope, 99Tc, is radioactive and has been found in lobsters and seaweed near
to nuclear fuel reprocessing plants.

Which statements about an atom of 99Tc are correct?


1 It has 13 fewer protons than neutrons.
2 It forms 99Tc2+ which has 45 electrons.
3 It has 56 nucleons.

32 Nitrogen exists in air as covalently bonded diatomic molecules, N2.

Which features are present in one N2 molecule?

1 three π bonds
2 three shared pairs of electrons
3 two lone pairs of electrons

33 When dilute acid is added to an aqueous solution containing nitrite ions, NO2–, a mixture of gases
is produced.

2H+(aq) + 2NO2–(aq) → H2O(l) + NO(g) + NO2(g)

Which statements correctly describe the process?

1 Some nitrogen atoms are oxidised and some nitrogen atoms are reduced.
2 The H+(aq) ion is oxidised by NO2–(aq).
3 The H+(aq) ion acts as a catalyst.

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15

34 Which physical properties are due to hydrogen bonding between water molecules?

1 Water has a higher boiling point than H2S.


2 Ice floats on water.

3 The H−O−H bond angle in water is approximately 104°.

35 Under atmospheric conditions, in which transformations is sulfur dioxide involved as either a


reagent or a catalyst?

1 NO2 to NO
2 NO to NO2
3 CO to CO2

36 The element astatine, At, is below iodine in Group VII of the Periodic Table.

Which statements concerning At can be predicted to be correct?

1 At2 reacts with hydrogen more slowly than I2 does.

2 At – ions react with I2(aq) to form At2 molecules.


3 At2 is a dark coloured solid at room temperature.

37 The diagram shows a molecule of a compound used as a flame retardant.

Br
Br

Br

Br Br
Br

Which statements about this structure are correct?

1 Each brominated C atom is chiral.


2 The molecular formula is C12H20Br6.

3 The C–C–C bond angles are all 120°.

© UCLES 2015 9701/13/M/J/15 [Turn over


16

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

38 Which changes in bonding occur during the reaction of propanal and hydrogen cyanide?

1 A carbon-hydrogen bond is broken.


2 An oxygen-hydrogen bond is formed.
3 A carbon-carbon bond is formed.

39 Which pairs of reagents will react together in a redox reaction?

1 CH3CHO + Fehling’s reagent


2 C2H4 + Br2(aq)
3 CH4 + Cl 2(g)

40 Which types of reaction are undergone by CH2BrCHCH2?

1 hydrolysis
2 free radical substitution
3 nucleophilic addition

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.

To avoid the issue of disclosure of answer-related information to candidates, all copyright acknowledgements are reproduced online in the Cambridge
International Examinations Copyright Acknowledgements Booklet. This is produced for each series of examinations and is freely available to download at
www.cie.org.uk after the live examination series.

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 2015 9701/13/M/J/15


Page 2 Mark Scheme Syllabus Paper
Cambridge International AS/A Level – May/June 2015 9701 13

Question Question
Key Key
Number Number
1 C 21 C
2 D 22 D
3 B 23 D
4 C 24 B
5 C 25 A

6 A 26 B
7 B 27 B
8 A 28 C
9 C 29 A
10 A 30 A

11 A 31 D
12 C 32 C
13 B 33 D
14 D 34 B
15 B 35 D

16 D 36 A
17 C 37 D
18 B 38 A
19 B 39 A
20 C 40 B

© Cambridge International Examinations 2015


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 table gives the successive ionisation energies for an element X.

1st 2nd 3rd 4th 5th 6th

ionisation energy / kJ mol–1 950 1800 2700 4800 6000 12 300

What could be the formula of a chloride of X?

A XCl B XCl 2 C XCl 3 D XCl 4

2 Which set of conditions gives the highest yield of ammonia at equilibrium?

N2(g) + 3H2(g) 2NH3(g) ∆H o = –92 kJ mol–1

catalyst pressure temperature

A absent high low


B absent low high
C present high high
D present low low

3 Use of the Data Booklet is relevant to this question.

The compound S2O7 is hydrolysed by water to produce sulfuric acid and oxygen only.

Which volume of oxygen, measured at room temperature and pressure, is evolved when 0.352 g
of S2O7 is hydrolysed?

A 12 cm3 B 24 cm3 C 48 cm3 D 96 cm3

4 Nitrogen, N2, and carbon monoxide, CO, both have Mr = 28.

The boiling point of N2 is 77 K.

The boiling point of CO is 82 K.

What could be responsible for this difference in boiling points?

A CO molecules have a permanent dipole, the N2 molecules are not polar.

B N2 has σ and π bonding, CO has σ bonding only.


C N2 has a strong N≡N bond, CO has a C=O bond.
D The CO molecule has more electrons than the N2 molecule.

© UCLES 2015 9701/11/O/N/15


3

5 Some car paints contain small flakes of silica, SiO2.

In the structure of solid SiO2

● each silicon atom is bonded to x oxygen atoms,


● each oxygen atom is bonded to y silicon atoms,
● each bond is a z type bond.

What is the correct combination of x, y and z in these statements?

x y z

A 2 1 covalent
B 2 1 ionic
C 4 2 covalent
D 4 2 ionic

6 Solid sulfur consists of molecules made up of eight atoms covalently bonded together.

The bonding in sulfur dioxide is O=S=O.

enthalpy change of combustion of S8, S8(s)= –2376kJ mol–1


energy required to break 1 mole S8(s) into gaseous atoms = 2232 kJ mol–1
O=O bond enthalpy = 496 kJ mol–1

Using these data, what is the value of the S=O bond enthalpy?

A 239 kJ mol–1 B 257 kJ mol–1 C 319 kJ mol–1 D 536 kJ mol–1

7 Use of the Data Booklet is relevant for this question.

In an experiment, the burning of 1.45 g (0.025 mol) of propanone was used to heat 100 g of water.
The initial temperature of the water was 20.0 °C and the final temperature of the water was
78.0 °C.

Which experimental value for the enthalpy change of combustion for propanone can be
calculated from these results?

A –1304 kJ mol–1
B –970 kJ mol–1
C –352 kJ mol–1
D –24.2 kJ mol–1

© UCLES 2015 9701/11/O/N/15 [Turn over


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8 Which row correctly describes the electrodes that can be used in a diaphragm cell for the
production of chlorine, hydrogen and sodium hydroxide?

anode cathode

A steel graphite
B steel titanium
C titanium graphite
D titanium steel

9 Hexamine is a crystalline solid used as a fuel in portable stoves.

The diagram shows its skeletal structure.

N N
N

What is the empirical formula of hexamine?

A CH2N B C3H6N2 C C4H8N4 D C6H12N4

10 A mixture of nitrogen and hydrogen gases, at a temperature of 500 K, was put into an evacuated
vessel of volume 6.0 dm3. The vessel was then sealed.

N2(g) + 3H2(g) 2NH3(g)

The mixture was allowed to reach equilibrium. It was found that 7.2 mol of N2 and 12.0 mol of H2
were present in the equilibrium mixture. The value of the equilibrium constant, Kc, for this
equilibrium is 6.0 × 10–2 at 500 K.

What is the concentration of ammonia present in the equilibrium mixture at 500 K?

A 0.58 mol dm–3


B 0.76 mol dm–3
C 3.5 mol dm–3
D 27 mol dm–3

© UCLES 2015 9701/11/O/N/15


5

11 Ammonia is made by the Haber process. The reactants are nitrogen and hydrogen.

N2(g) + 3H2(g) 2NH3(g) ∆H –ve

What will increase the rate of the forward reaction?

A adding argon to the mixture but keeping the total volume constant
B decreasing the temperature
C increasing the total pressure by reducing the total volume at constant temperature
D removing ammonia as it is made but keeping the total volume of the mixture the same

12 X is a Group II metal. The carbonate of X decomposes when heated in a Bunsen flame to give
carbon dioxide and a white solid residue as the only products. This white solid residue is
sparingly soluble in water. Even when large amounts of the solid residue are added to water the
pH of the saturated solution is less than that of limewater.

What could be the identity of X?

A magnesium
B calcium
C strontium
D barium

13 Rat poison needs to be insoluble in rain water but soluble at the low pH of stomach contents.

What is a suitable barium compound to use for rat poison?

A barium carbonate
B barium chloride
C barium hydroxide
D barium sulfate

14 Use of the Data Booklet is relevant to this question.

Which of the elements sodium, magnesium, aluminium, silicon, phosphorus, sulfur and chlorine

• has a lower first ionisation energy than the preceding element in the Periodic Table,

• conducts electricity and

• has a lower atomic radius than the preceding element in the Periodic Table?

A aluminium
B magnesium
C phosphorus
D sulfur

© UCLES 2015 9701/11/O/N/15 [Turn over


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15 The melting points of the Period 3 elements sodium to aluminium are shown in the table.

element Na Mg Al
mp / K 371 923 932

Which factor explains the increase in melting points from sodium to aluminium?

A the changes in first ionisation energy from sodium to aluminium


B the increase in electronegativity from sodium to aluminium
C the increase in the Ar of the elements from sodium to aluminium
D the increase in the number of outer electrons in each atom from sodium to aluminium

16 X is the oxide of a Period 3 element. X reacts with water to give an acidic solution.

A solution is prepared by reacting 0.100 g of X with excess water. This solution was neutralised
by exactly 25.0 cm3 of 0.100 mol dm–3 sodium hydroxide solution.

What could be the identity of X?

A Al 2O3 B MgO C P4O10 D SO3

17 Which statement about bromine is correct?

A Bromine is insoluble in non-polar solvents.


B Bromine vapour is more dense than air.
C Bromine will not vaporise significantly under normal conditions.
D Gaseous bromine is purple.

18 The addition of aqueous silver nitrate to aqueous barium chloride produces a white precipitate
which dissolves in excess dilute aqueous ammonia to form a colourless solution.

The addition of excess dilute nitric acid to the colourless solution produces a white precipitate, Z.

What is Z?

A AgCl B BaCl 2 C Ba(NO3)2 D NH4NO3

© UCLES 2015 9701/11/O/N/15


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19 Element X forms a pollutant oxide Y. Y can be further oxidised to Z. Two students made the
following statements.

Student P ‘The molecule of Y contains lone pairs of electrons.’


Student Q ‘The oxidation number of X increases by 1 from Y to Z.’

X could be carbon or nitrogen or sulfur.

Which student(s) made a correct statement?

A P only
B Q only
C both P and Q
D neither P nor Q

20 How many isomeric esters have the molecular formula C4H8O2?

A 2 B 3 C 4 D 5

21 A new jet fuel has been produced that is a mixture of different structural isomers of compound Q.

Which skeletal formula represents a structural isomer of Q?

A B

C D

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22 Crude oil is a mixture of many hydrocarbons ranging in size from 1 to 40 carbon atoms per
molecule. The alkanes in crude oil can be separated because they have different boiling points.

The table below shows the boiling points of some alkanes.

boiling point
alkane Mr
/ °C

butane 0 58
pentane 36 72
hexane 69 86
2-methylbutane 28 72
dimethylpropane 10 72
2,3-dimethylbutane 58 86

What is the correct explanation for the difference in the boiling points of the three isomers with
Mr = 72?

A Boiling point is dependent upon the length of the carbon chain only.
B Increased branching on a carbon chain increases the boiling point.
C Increased branching reduces the strength of the intermolecular hydrogen bonding.
D Increased branching reduces the strength of the intermolecular van der Waals’ forces.

23 Compound Q contains three double bonds per molecule.

O O
Y
X
CH2 CH CH2 C CH2 C OH

Which bond, X or Y, will be ruptured by hot, concentrated acidified KMnO4 and how many lone
pairs of electrons are present in one molecule of Q?

bond ruptured by hot, number of


concentrated acidified KMnO4 lone pairs

A X 5
B X 6
C Y 5
D Y 6

© UCLES 2015 9701/11/O/N/15


9

24 Which compound undergoes an SN1 substitution reaction with NaOH(aq)?

A CH3CH2CH2Br

B (CH3)3CCH2I

CH3 Cl
C

D CH2=CHCl

25 If the starting material is iodoethane, which sequence of reactions will produce propanoic acid as
the main final product in good yield?

A add NaOH(aq), isolate the organic product, add acidified K2Cr2O7 and boil under reflux
B add NaOH(aq), isolate the organic product, add H2SO4(aq) and boil under reflux
C heat with HCN in ethanol, isolate the organic product, add H2SO4(aq) and boil under reflux
D heat with KCN in ethanol, isolate the organic product, add H2SO4(aq) and boil under reflux

26 Which compound cannot be oxidised by acidified potassium dichromate(VI) solution but does
react with sodium metal?

A (CH3)3COH
B CH3COCH2CH3
C CH3CH2CH2CH2OH
D CH3CH2CH(OH)CH3

27 Butan-2-ol can be made by reducing X with H2 / Ni.

Butan-2-ol can be dehydrated to form Y and Z which are structural isomers of each other.

Which row is correct?

cis-trans isomerism
X is
is shown by

A an aldehyde both Y and Z


B an aldehyde only one of Y and Z
C a ketone both Y and Z
D a ketone only one of Y and Z

© UCLES 2015 9701/11/O/N/15 [Turn over


10

28 Tollens’ reagent can be used to help identify compounds P, Q and R.

O O OH

H3C C CH3
C C
H 3C H H 3C CH3
H

P Q R

Which compound(s) form a silver precipitate on warming with Tollens’ reagent?

A P and Q B P only C Q only D R only

29 Sorbitol is a naturally-occurring compound with a sweet taste. It is often used as a substitute for
sucrose by the food industry.

H C OH

H C OH

H C OH

H C OH

H C OH

H C OH

sorbitol

How many chiral centres are present in sorbitol?

A 3 B 4 C 5 D 6

30 Which compound produces butan-2-ol and ethanoic acid on hydrolysis?

A CH3CO2CH(CH3)2
B CH3CO2CH(CH3)CH2CH3
C CH3CH(CH3)CO2CH2CH3
D CH3CH2CO2CH(CH3)CH2CH3

© UCLES 2015 9701/11/O/N/15


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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

31 Which statements about orbitals in a krypton atom are correct?

1 The 1s and 2s orbitals have the same energy as each other but different sizes.
2 The third energy level (n=3) has three subshells and nine orbitals.
3 The 3d subshell has five orbitals that have the same energy as each other in an isolated
atom.

32 The Group IV elements carbon, silicon and germanium can all exist in the giant molecular
structure which is also found in diamond. The bond lengths in these structures are given below.

element X C Si Ge
bond length X–X / nm 0.154 0.234 0.244

Why does the bond length increase down the group?

1 Orbital overlap decreases down the group.


2 Atomic radius increases down the group.
3 Nuclear charge increases down the group.

© UCLES 2015 9701/11/O/N/15 [Turn over


12

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

33 The salt NaCl O3 is used as a non-selective weedkiller.

On careful heating, this reaction occurs: 4NaCl O3 → NaCl + 3NaCl O4.

On strong heating this reaction occurs: NaCl O4 → NaCl + 2O2.

The overall reaction is 2NaCl O3 → 2NaCl + 3O2.

What do these equations show?

1 NaCl O3 can behave as an oxidising agent.


2 NaCl O3 can behave as a reducing agent.
3 The oxidation numbers of chlorine in the three compounds shown are +6, +8 and –1.

34 Which statements correctly describe an effect of a rise in temperature on a gas-phase reaction?

1 More particles now have energies greater than the activation energy.
2 The energy distribution profile changes with more particles having the most probable energy.
3 The activation energy of the reaction is decreased.

35 Which statements concerning the Group II elements magnesium, calcium and barium are
correct?

1 Their reactivity increases with increasing relative atomic mass.


2 The oxidation number exhibited in their stable compounds is +2.
3 On strong heating, their nitrates give off oxygen only.

36 Sulfur dioxide is used as a food preservative.

Which statements about sulfur dioxide, SO2, are correct?

1 SO2 behaves as an antioxidant.


2 Aqueous SO2 contains SO32– ions.
3 SO2 inhibits the growth of mould and yeasts.

© UCLES 2015 9701/11/O/N/15


13

37 An oxidising agent that can oxidise ethanal to ethanoic acid, or to ethanoate ions, will also oxidise
methanoic acid, HCO2H, to carbon dioxide and water.

Which reagents, on heating, will react differently with HCO2H and CH3CO2H?

1 Na2CO3(aq)
2 Fehling’s reagent
3 dilute acidified KMnO4

38 Each of the compounds below is treated separately with excess NaBH4. The product of each
reaction is then heated with excess concentrated H2SO4.

In each case, one or more products are formed with molecular formula C7H10.

Which compounds give only one final product with the molecular formula C7H10?

1 2 3

O
O

O O O

39 Which reactions result in the formation of propanoic acid?

1 CH3CH2CO2Na with dilute H2SO4(aq)


2 CH3CH=CHCH3 with hot, concentrated H+ / MnO4–(aq)
3 CH3CH2OH with H+ / Cr2O72–(aq)

40 The diagram shows the structure of propanamide.

H H O H

H C C C N

H H H

propanamide

Which statements about the hydrolysis of propanamide are correct?

1 Propanamide can be hydrolysed by heating under reflux with H2SO4(aq).


2 Propanamide can be hydrolysed by heating under reflux with NaOH(aq).
3 Propanamide can be hydrolysed by cold water.

© UCLES 2015 9701/11/O/N/15


Page 2 Mark Scheme Syllabus Paper
Cambridge International AS/A Level – October/November 2015 9701 11

Question Question
Key Key
Number Number
1 C 21 C
2 A 22 D
3 B 23 B
4 A 24 C
5 C 25 D

6 D 26 A
7 B 27 D
8 D 28 B
9 B 29 B
10 B 30 B

11 C 31 C
12 A 32 B
13 A 33 B
14 A 34 D
15 D 35 B

16 D 36 A
17 B 37 C
18 A 38 C
19 A 39 D
20 C 40 B

© Cambridge International Examinations 2015


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 type of bonding is never found in elements?

A covalent
B ionic
C metallic
D van der Waals’ forces

2 Arsenic chloride, AsCl 3, reacts with sodium borohydride, NaBH4.

pAsCl 3 + qNaBH4 → rAsH3 + sNaCl + tBCl 3

What are the numbers p, q, r, s and t when this equation is balanced correctly?

p q r s t

A 2 3 2 3 1
B 3 3 3 3 2
C 4 3 4 3 3
D 4 4 4 4 3

3 Three substances have the physical properties shown in the table.

melting point boiling point conductivity conductivity conductivity


substance
/ °C / °C (solid) (liquid) (aqueous)

U 420 907 good good insoluble


V 993 1695 poor good good
W –70 58 poor poor hydrolyses, resulting
solution conducts well

What could be the identities of U, V and W?

U V W

A Na KCl SiCl 4
B Na NaF C2H5Br
C Zn KCl HCl
D Zn NaF SiCl 4

© UCLES 2015 9701/12/O/N/15


3

4 Flask X contains 5 dm3 of helium at 12 kPa pressure and flask Y contains 10 dm3 of neon at 6 kPa
pressure.

If the flasks are connected at constant temperature, what is the final pressure?

A 8 kPa B 9 kPa C 10 kPa D 11 kPa

5 Calcium forms an ionic compound with carbon, called calcium carbide. The oxidation number of
carbon in calcium carbide is –1.

Calcium carbide is readily hydrolysed by water giving two products only.

What could be the formulae of calcium carbide and the two products of hydrolysis?

calcium carbide products

A Ca2C CaO and C2H4


B Ca2C Ca(OH)2 and C2H2
C CaC2 CaO and C2H4
D CaC2 Ca(OH)2 and C2H2

6 Hess’ law may be used to determine enthalpy changes using average bond energies, as shown
in the diagram.

isolated gaseous atoms

U V

W
reactants products

U is the sum of the average bond energies of the reactants, and V is the sum of the average
bond energies of the products.

For the reaction shown below, which expression will give a value for W, the enthalpy change of
combustion of methane?

CH4 + 2O2 → CO2 + 2H2O

A U–V B U+V C 2(U – V) D V–U

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4

7 The process of electrolysis can be used to purify copper, and to extract aluminium from an
aluminium oxide / cryolite mixture.

What are the reactions at the anode in each of these processes?

purification of copper extraction of aluminium

A Cu2+ + 2e– → Cu 2O2– → O2 + 4e–


B Cu2+ + 2e– → Cu 4OH– → O2 + 2H2O + 4e–
C Cu → Cu2+ + 2e– 2O2– → O2 + 4e–
D Cu → Cu2+ + 2e– 4OH– → O2 + 2H2O + 4e–

8 Hydrogen can be obtained by reacting methane with steam.

CH4(g) + H2O(g) CO(g) + 3H2(g) ΔH o = +210 kJ mol–1

Which conditions of pressure and temperature will give the greatest equilibrium yield of hydrogen?

pressure temperature

A high high
B high low
C low high
D low low

9 Nitrogen monoxide reacts with oxygen in a reversible reaction according to the equation shown
below.

2NO(g) + O2(g) 2NO2(g)

The partial pressures of each of the components in an equilibrium mixture are shown in the table.

partial pressure NO / kPa partial pressure O2 / kPa partial pressure NO2 / kPa

10 30 20

What is the numerical value of the equilibrium constant, Kp, for this equilibrium?

A 6.67 × 10–2 B 1.33 × 10–1 C 7.50 D 15.0

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10 The decomposition reaction SF6(g) → SF4(g) + F2(g) can be described by the reaction
pathway diagram shown.

X SF4(g) + F2(g)
energy

SF6(g)

extent of reaction

What are the values of ΔH o and Ea for this reaction?

ΔH o Ea

A X X+Y
B X Y
C X–Y X
D Y–X X

11 Which row correctly describes what happens when the temperature of a chemical reaction is
decreased?

activation energy number of


(Ea) successful collisions

A decreases decreases
B decreases increases
C remains the same decreases
D remains the same increases

12 Which property decreases on descending Group II?

A radius of the cation, M2+


B reactivity of the element with water
C shielding of outermost electrons
D the ease of thermal decomposition of the carbonates, MCO3

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13 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

14 Which chloride of a Period 3 element dissolves in water to form a solution with a pH of 7?

A aluminium chloride

B phosphorus(V) chloride

C silicon(IV) chloride
D sodium chloride

15 Use of the Data Booklet is relevant to this question.

Which row correctly compares the electrical conductivity and first ionisation energy of magnesium
and aluminium?

higher electrical higher first


conductivity ionisation energy

A aluminium aluminium
B aluminium magnesium
C magnesium aluminium
D magnesium magnesium

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7

16 Use of the Data Booklet is relevant to this question.

Brine is concentrated aqueous sodium chloride.

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 yield of yield of sodium


chlorine / kg hydrogen / kg hydroxide / kg

A 35.5 1 40
B 35.5 2 40
C 71 1 40
D 71 2 80

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. Some
observations are recorded in the table.

sodium chloride sodium iodide

conc. H2SO4 colourless acidic gas formed purple vapour formed


conc. H3PO4 colourless acidic gas formed colourless acidic gas formed

Which deduction can be made from these observations?

A Concentrated phosphoric acid is a stronger oxidising agent than concentrated sulfuric acid.
B Concentrated phosphoric acid is a stronger oxidising agent than iodine.
C Concentrated sulfuric acid is a stronger oxidising agent than chlorine.
D Concentrated sulfuric acid is a stronger oxidising agent than iodine.

18 A white powder is a mixture of sodium chloride and sodium iodide. It is dissolved in water in a
test-tube. Excess aqueous silver nitrate is added to the test-tube. A precipitate, X, is observed.

Excess concentrated ammonia is then added to the test-tube containing X. After the test-tube has
been shaken, a precipitate, Y, is observed.

Which statement about X or Y is correct?

A X is a pure white colour.


B X is pure silver iodide.
C Y is pure silver chloride.
D Y is yellow.

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19 Use of the Data Booklet is relevant to this question.

4.70 g of an ammonium salt is heated with excess aqueous sodium hydroxide. The volume of
ammonia gas given off, measured at room temperature and pressure, is 1.41 dm3.

Which ammonium salt was used?

A ammonium bromide (Mr = 97.9)


B ammonium carbonate (Mr = 96)
C ammonium nitrate (Mr = 80)
D ammonium sulfate (Mr = 132.1)

20 Which ester is formed when the alcohol CH3CH2OH is reacted with CH3CH2CH2CO2H?

A butyl ethanoate
B ethyl butanoate
C ethyl propanoate
D propyl ethanoate

21 Which compound shows optical isomerism?

A 2-chloropropane
B 1,2-dichloropropane
C 1,3-dichloropropane
D 2,2-dichloropropane

22 Methanoic acid, HCO2H, has acidic properties similar to those of other carboxylic acids. In
addition it can be oxidised by the same oxidising agents that are capable of oxidising aldehydes.

Which pair consists of two compounds that will give the same observations with Fehling’s
reagent?

A HCO2H and CH3CO2H


B HCO2H and CH3CO2CH3
C HCO2H and CH3CH2COCH3
D HCO2H and CH3CH2CHO

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23 Compound Q can be made from propanone.

Which types of reaction will Q undergo?

A nucleophilic addition and electrophilic addition


B nucleophilic addition and nucleophilic substitution
C nucleophilic addition only
D nucleophilic substitution and electrophilic addition

24 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 CO2 D SO2

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25 Compound X has been investigated for use as an artificial sweetener.

OH

Cl O O

OH OH
O Cl

OH OH

The two C–Cl bonds can be hydrolysed by hot NaOH(aq). The C-O-C bonds cannot be
hydrolysed by hot NaOH(aq).

What are the numbers of specified types of –OH groups before and after hydrolysing the two
C–Cl bonds?

before
after hydrolysis
hydrolysis
secondary primary secondary tertiary

A 0 1 2 4
B 0 2 1 4
C 4 1 5 1
D 4 2 4 1

26 The compounds below are all produced by plants.

Each compound is warmed with acidified potassium dichromate(VI).

Which compound will give a different observation to the other three?

A B C D

OH

OH

OH OH

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11

27 What is the mechanism for the reaction of ethanal, CH3CHO, with hydrogen cyanide, HCN, in the
presence of a base?

O O– O

A CH3 C H CH3 C H CH3 C + H–

CN– CN CN


O O H C N OH

B CH3 C H CH3 C H CH3 C H + CN–

CN– CN CN

O H C N OH OH
+
C CH3 C H CH3 C H CH3 C H

CN– CN

D initiation HCN H• + •CN

O O•

propagation CH3C + • CN CH3C H

H CN

O• OH

CH3C H + H CN CH3C H + • CN

CN CN

O• OH

termination CH3C H + H• CH3C H

CN CN

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28 Menthol and menthone are both found in peppermint oil.

OH O

menthol menthone

Which statement about these compounds is correct?

A Both compounds can undergo mild oxidation.


B Both compounds will give an orange precipitate with 2,4-dinitrophenylhydrazine reagent.
C Menthol can be formed from menthone by reaction with NaBH4.
D Menthone gives a positive test when warmed with Tollens’ reagent.

29 What is the skeletal formula of 2-methylpentan-1-ol?

A B C D

OH OH
OH OH

30 The structure of aspartame, which is used as an artificial sweetener, is shown.

C 6H 5
O
1 2
O OCH3
N
H
OH NH2 O

aspartame

If aspartame is warmed in aqueous alkali, which of bonds 1 and 2 will be broken?

A both bond 1 and bond 2


B bond 1 only
C bond 2 only
D neither bond 1 nor bond 2

© UCLES 2015 9701/12/O/N/15


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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

31 The relative molecular mass, Mr, of a particular sample of chlorine is 72.0.

Which properties of the atoms in this sample will be the same for all of the atoms?

1 radius
2 nucleon number
3 isotopic mass

32 Which of the following influence the size of the ionisation energy of an atom?

1 the amount of shielding by the inner electrons


2 the charge on the nucleus
3 the distance between the outer electrons and the nucleus

33 Which equations can apply to an ideal gas?


[p = pressure, V = volume, M = molar mass, ρ = density, c = concentration, R = gas constant,
T = temperature]
ρRT
1 p= 2 pV = cRT 3 pV = MRT
M M

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14

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

34 Ammonia and chlorine react in the gas phase.

8NH3 + 3Cl 2 → N2 + 6NH4Cl

Which statements are correct?

1 Each nitrogen atom is oxidised.


2 Each chlorine atom is reduced.
3 Ammonia behaves as a base.

35 Which statements about calcium and strontium compounds are correct?

1 When calcium oxide and strontium oxide are added to water they both produce alkalis.
2 Calcium hydroxide is more soluble than strontium hydroxide.
3 Calcium sulfate is less soluble than strontium sulfate.

36 Which descriptions of the ammonium ion are correct?

1 It contains ten electrons.

2 It has a bond angle of 109.5°.


3 It has only three bonding pairs of electrons.

37 Compound Q is obtained by adding H2O across the double bond in compound P.

OH

P Q

Which statements about these two compounds are correct?

1 P shows cis-trans isomerism.


2 Q contains two chiral centres.
3 Q is a tertiary alcohol.

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15

38 X is an organic compound. X gives a precipitate with aqueous silver nitrate. Some or all of this
precipitate remains undissolved when excess dilute aqueous ammonia is added.

What could be the identity of X?

1 2-chlorobutane
2 2-bromobutane
3 iodomethane

39 Which compounds, on heating with excess concentrated sulfuric acid, produce only one product
with molecular formula C7H10?

1 2 3

OH
OH

OH

OH OH OH

40 Compound Z is heated with concentrated acidified potassium manganate(VII). This produces an


equimolar mixture of CO2 and CH3COCH2CH2CH(COCH3)CH2CO2H.

What could be the structural formula of Z?

1 2 3

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Page 2 Mark Scheme Syllabus Paper
Cambridge International AS/A Level – October/November 2015 9701 12

Question Question
Key Key
Number Number
1 B 21 B
2 C 22 D
3 D 23 A
4 A 24 A
5 D 25 C

6 A 26 D
7 C 27 B
8 C 28 C
9 B 29 A
10 C 30 A

11 C 31 D
12 D 32 A
13 B 33 D
14 D 34 C
15 B 35 D

16 A 36 B
17 D 37 C
18 D 38 C
19 C 39 B
20 B 40 A

© Cambridge International Examinations 2015


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 table gives the successive ionisation energies for an element X.

1st 2nd 3rd 4th 5th 6th

ionisation energy / kJ mol–1 950 1800 2700 4800 6000 12 300

What could be the formula of a chloride of X?

A XCl B XCl 2 C XCl 3 D XCl 4

2 Which set of conditions gives the highest yield of ammonia at equilibrium?

N2(g) + 3H2(g) 2NH3(g) ∆H o = –92 kJ mol–1

catalyst pressure temperature

A absent high low


B absent low high
C present high high
D present low low

3 Use of the Data Booklet is relevant to this question.

The compound S2O7 is hydrolysed by water to produce sulfuric acid and oxygen only.

Which volume of oxygen, measured at room temperature and pressure, is evolved when 0.352 g
of S2O7 is hydrolysed?

A 12 cm3 B 24 cm3 C 48 cm3 D 96 cm3

4 Nitrogen, N2, and carbon monoxide, CO, both have Mr = 28.

The boiling point of N2 is 77 K.

The boiling point of CO is 82 K.

What could be responsible for this difference in boiling points?

A CO molecules have a permanent dipole, the N2 molecules are not polar.

B N2 has σ and π bonding, CO has σ bonding only.


C N2 has a strong N≡N bond, CO has a C=O bond.
D The CO molecule has more electrons than the N2 molecule.

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5 Some car paints contain small flakes of silica, SiO2.

In the structure of solid SiO2

● each silicon atom is bonded to x oxygen atoms,


● each oxygen atom is bonded to y silicon atoms,
● each bond is a z type bond.

What is the correct combination of x, y and z in these statements?

x y z

A 2 1 covalent
B 2 1 ionic
C 4 2 covalent
D 4 2 ionic

6 Solid sulfur consists of molecules made up of eight atoms covalently bonded together.

The bonding in sulfur dioxide is O=S=O.

enthalpy change of combustion of S8, S8(s)= –2376kJ mol–1


energy required to break 1 mole S8(s) into gaseous atoms = 2232 kJ mol–1
O=O bond enthalpy = 496 kJ mol–1

Using these data, what is the value of the S=O bond enthalpy?

A 239 kJ mol–1 B 257 kJ mol–1 C 319 kJ mol–1 D 536 kJ mol–1

7 Use of the Data Booklet is relevant for this question.

In an experiment, the burning of 1.45 g (0.025 mol) of propanone was used to heat 100 g of water.
The initial temperature of the water was 20.0 °C and the final temperature of the water was
78.0 °C.

Which experimental value for the enthalpy change of combustion for propanone can be
calculated from these results?

A –1304 kJ mol–1
B –970 kJ mol–1
C –352 kJ mol–1
D –24.2 kJ mol–1

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8 Which row correctly describes the electrodes that can be used in a diaphragm cell for the
production of chlorine, hydrogen and sodium hydroxide?

anode cathode

A steel graphite
B steel titanium
C titanium graphite
D titanium steel

9 Hexamine is a crystalline solid used as a fuel in portable stoves.

The diagram shows its skeletal structure.

N N
N

What is the empirical formula of hexamine?

A CH2N B C3H6N2 C C4H8N4 D C6H12N4

10 A mixture of nitrogen and hydrogen gases, at a temperature of 500 K, was put into an evacuated
vessel of volume 6.0 dm3. The vessel was then sealed.

N2(g) + 3H2(g) 2NH3(g)

The mixture was allowed to reach equilibrium. It was found that 7.2 mol of N2 and 12.0 mol of H2
were present in the equilibrium mixture. The value of the equilibrium constant, Kc, for this
equilibrium is 6.0 × 10–2 at 500 K.

What is the concentration of ammonia present in the equilibrium mixture at 500 K?

A 0.58 mol dm–3


B 0.76 mol dm–3
C 3.5 mol dm–3
D 27 mol dm–3

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5

11 Ammonia is made by the Haber process. The reactants are nitrogen and hydrogen.

N2(g) + 3H2(g) 2NH3(g) ∆H –ve

What will increase the rate of the forward reaction?

A adding argon to the mixture but keeping the total volume constant
B decreasing the temperature
C increasing the total pressure by reducing the total volume at constant temperature
D removing ammonia as it is made but keeping the total volume of the mixture the same

12 X is a Group II metal. The carbonate of X decomposes when heated in a Bunsen flame to give
carbon dioxide and a white solid residue as the only products. This white solid residue is
sparingly soluble in water. Even when large amounts of the solid residue are added to water the
pH of the saturated solution is less than that of limewater.

What could be the identity of X?

A magnesium
B calcium
C strontium
D barium

13 Rat poison needs to be insoluble in rain water but soluble at the low pH of stomach contents.

What is a suitable barium compound to use for rat poison?

A barium carbonate
B barium chloride
C barium hydroxide
D barium sulfate

14 Use of the Data Booklet is relevant to this question.

Which of the elements sodium, magnesium, aluminium, silicon, phosphorus, sulfur and chlorine

• has a lower first ionisation energy than the preceding element in the Periodic Table,

• conducts electricity and

• has a lower atomic radius than the preceding element in the Periodic Table?

A aluminium
B magnesium
C phosphorus
D sulfur

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15 The melting points of the Period 3 elements sodium to aluminium are shown in the table.

element Na Mg Al
mp / K 371 923 932

Which factor explains the increase in melting points from sodium to aluminium?

A the changes in first ionisation energy from sodium to aluminium


B the increase in electronegativity from sodium to aluminium
C the increase in the Ar of the elements from sodium to aluminium
D the increase in the number of outer electrons in each atom from sodium to aluminium

16 X is the oxide of a Period 3 element. X reacts with water to give an acidic solution.

A solution is prepared by reacting 0.100 g of X with excess water. This solution was neutralised
by exactly 25.0 cm3 of 0.100 mol dm–3 sodium hydroxide solution.

What could be the identity of X?

A Al 2O3 B MgO C P4O10 D SO3

17 Which statement about bromine is correct?

A Bromine is insoluble in non-polar solvents.


B Bromine vapour is more dense than air.
C Bromine will not vaporise significantly under normal conditions.
D Gaseous bromine is purple.

18 The addition of aqueous silver nitrate to aqueous barium chloride produces a white precipitate
which dissolves in excess dilute aqueous ammonia to form a colourless solution.

The addition of excess dilute nitric acid to the colourless solution produces a white precipitate, Z.

What is Z?

A AgCl B BaCl 2 C Ba(NO3)2 D NH4NO3

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19 Element X forms a pollutant oxide Y. Y can be further oxidised to Z. Two students made the
following statements.

Student P ‘The molecule of Y contains lone pairs of electrons.’


Student Q ‘The oxidation number of X increases by 1 from Y to Z.’

X could be carbon or nitrogen or sulfur.

Which student(s) made a correct statement?

A P only
B Q only
C both P and Q
D neither P nor Q

20 How many isomeric esters have the molecular formula C4H8O2?

A 2 B 3 C 4 D 5

21 A new jet fuel has been produced that is a mixture of different structural isomers of compound Q.

Which skeletal formula represents a structural isomer of Q?

A B

C D

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22 Crude oil is a mixture of many hydrocarbons ranging in size from 1 to 40 carbon atoms per
molecule. The alkanes in crude oil can be separated because they have different boiling points.

The table below shows the boiling points of some alkanes.

boiling point
alkane Mr
/ °C

butane 0 58
pentane 36 72
hexane 69 86
2-methylbutane 28 72
dimethylpropane 10 72
2,3-dimethylbutane 58 86

What is the correct explanation for the difference in the boiling points of the three isomers with
Mr = 72?

A Boiling point is dependent upon the length of the carbon chain only.
B Increased branching on a carbon chain increases the boiling point.
C Increased branching reduces the strength of the intermolecular hydrogen bonding.
D Increased branching reduces the strength of the intermolecular van der Waals’ forces.

23 Compound Q contains three double bonds per molecule.

O O
Y
X
CH2 CH CH2 C CH2 C OH

Which bond, X or Y, will be ruptured by hot, concentrated acidified KMnO4 and how many lone
pairs of electrons are present in one molecule of Q?

bond ruptured by hot, number of


concentrated acidified KMnO4 lone pairs

A X 5
B X 6
C Y 5
D Y 6

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24 Which compound undergoes an SN1 substitution reaction with NaOH(aq)?

A CH3CH2CH2Br

B (CH3)3CCH2I

CH3 Cl
C

D CH2=CHCl

25 If the starting material is iodoethane, which sequence of reactions will produce propanoic acid as
the main final product in good yield?

A add NaOH(aq), isolate the organic product, add acidified K2Cr2O7 and boil under reflux
B add NaOH(aq), isolate the organic product, add H2SO4(aq) and boil under reflux
C heat with HCN in ethanol, isolate the organic product, add H2SO4(aq) and boil under reflux
D heat with KCN in ethanol, isolate the organic product, add H2SO4(aq) and boil under reflux

26 Which compound cannot be oxidised by acidified potassium dichromate(VI) solution but does
react with sodium metal?

A (CH3)3COH
B CH3COCH2CH3
C CH3CH2CH2CH2OH
D CH3CH2CH(OH)CH3

27 Butan-2-ol can be made by reducing X with H2 / Ni.

Butan-2-ol can be dehydrated to form Y and Z which are structural isomers of each other.

Which row is correct?

cis-trans isomerism
X is
is shown by

A an aldehyde both Y and Z


B an aldehyde only one of Y and Z
C a ketone both Y and Z
D a ketone only one of Y and Z

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28 Tollens’ reagent can be used to help identify compounds P, Q and R.

O O OH

H3C C CH3
C C
H 3C H H 3C CH3
H

P Q R

Which compound(s) form a silver precipitate on warming with Tollens’ reagent?

A P and Q B P only C Q only D R only

29 Sorbitol is a naturally-occurring compound with a sweet taste. It is often used as a substitute for
sucrose by the food industry.

H C OH

H C OH

H C OH

H C OH

H C OH

H C OH

sorbitol

How many chiral centres are present in sorbitol?

A 3 B 4 C 5 D 6

30 Which compound produces butan-2-ol and ethanoic acid on hydrolysis?

A CH3CO2CH(CH3)2
B CH3CO2CH(CH3)CH2CH3
C CH3CH(CH3)CO2CH2CH3
D CH3CH2CO2CH(CH3)CH2CH3

© UCLES 2015 9701/13/O/N/15


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 B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

31 Which statements about orbitals in a krypton atom are correct?

1 The 1s and 2s orbitals have the same energy as each other but different sizes.
2 The third energy level (n=3) has three subshells and nine orbitals.
3 The 3d subshell has five orbitals that have the same energy as each other in an isolated
atom.

32 The Group IV elements carbon, silicon and germanium can all exist in the giant molecular
structure which is also found in diamond. The bond lengths in these structures are given below.

element X C Si Ge
bond length X–X / nm 0.154 0.234 0.244

Why does the bond length increase down the group?

1 Orbital overlap decreases down the group.


2 Atomic radius increases down the group.
3 Nuclear charge increases down the group.

© UCLES 2015 9701/13/O/N/15 [Turn over


12

The responses A to D should be selected on the basis of

A B C D

1, 2 and 3 1 and 2 2 and 3 1 only


are only are only are is
correct correct correct correct

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

33 The salt NaCl O3 is used as a non-selective weedkiller.

On careful heating, this reaction occurs: 4NaCl O3 → NaCl + 3NaCl O4.

On strong heating this reaction occurs: NaCl O4 → NaCl + 2O2.

The overall reaction is 2NaCl O3 → 2NaCl + 3O2.

What do these equations show?

1 NaCl O3 can behave as an oxidising agent.


2 NaCl O3 can behave as a reducing agent.
3 The oxidation numbers of chlorine in the three compounds shown are +6, +8 and –1.

34 Which statements correctly describe an effect of a rise in temperature on a gas-phase reaction?

1 More particles now have energies greater than the activation energy.
2 The energy distribution profile changes with more particles having the most probable energy.
3 The activation energy of the reaction is decreased.

35 Which statements concerning the Group II elements magnesium, calcium and barium are
correct?

1 Their reactivity increases with increasing relative atomic mass.


2 The oxidation number exhibited in their stable compounds is +2.
3 On strong heating, their nitrates give off oxygen only.

36 Sulfur dioxide is used as a food preservative.

Which statements about sulfur dioxide, SO2, are correct?

1 SO2 behaves as an antioxidant.


2 Aqueous SO2 contains SO32– ions.
3 SO2 inhibits the growth of mould and yeasts.

© UCLES 2015 9701/13/O/N/15


13

37 An oxidising agent that can oxidise ethanal to ethanoic acid, or to ethanoate ions, will also oxidise
methanoic acid, HCO2H, to carbon dioxide and water.

Which reagents, on heating, will react differently with HCO2H and CH3CO2H?

1 Na2CO3(aq)
2 Fehling’s reagent
3 dilute acidified KMnO4

38 Each of the compounds below is treated separately with excess NaBH4. The product of each
reaction is then heated with excess concentrated H2SO4.

In each case, one or more products are formed with molecular formula C7H10.

Which compounds give only one final product with the molecular formula C7H10?

1 2 3

O
O

O O O

39 Which reactions result in the formation of propanoic acid?

1 CH3CH2CO2Na with dilute H2SO4(aq)


2 CH3CH=CHCH3 with hot, concentrated H+ / MnO4–(aq)
3 CH3CH2OH with H+ / Cr2O72–(aq)

40 The diagram shows the structure of propanamide.

H H O H

H C C C N

H H H

propanamide

Which statements about the hydrolysis of propanamide are correct?

1 Propanamide can be hydrolysed by heating under reflux with H2SO4(aq).


2 Propanamide can be hydrolysed by heating under reflux with NaOH(aq).
3 Propanamide can be hydrolysed by cold water.

© UCLES 2015 9701/13/O/N/15


Page 2 Mark Scheme Syllabus Paper
Cambridge International AS/A Level – October/November 2015 9701 13

Question Question
Key Key
Number Number
1 C 21 C
2 A 22 D
3 B 23 B
4 A 24 C
5 C 25 D

6 D 26 A
7 B 27 D
8 D 28 B
9 B 29 B
10 B 30 B

11 C 31 C
12 A 32 B
13 A 33 B
14 A 34 D
15 D 35 B

16 D 36 A
17 B 37 C
18 A 38 C
19 A 39 D
20 C 40 B

© Cambridge International Examinations 2015

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