CAMBRIDGE INTERNATIONAL AS & A LEVEL CHEMISTRY: COURSEBOOK

Exam-style questions and sample answers have been written by the authors. In examinations, the way marks are awarded
may be different.

Coursebook answers
Chapter 15
Exam-style questions
1 a 2-methylpentane: iii H
i C6H14 [1]
H C H
ii CH3CH(CH3)CH2CH2CH3 [1] H H H

iii H H H H H H C C C C H

H C C C C C H H H H
H C H
H H H H
H C H  H [1]

 H [1] iv

iv

 [1]  [1]
3-ethylpentane: b CnH2n+2 [1]
i C7H16 [1] c 2-methylpentane and
ii CH3CH2CH(CH2CH3)CH2CH3 [1] 2,3-dimethylbutane; [1]
iii H structural isomerism [1]
d Compounds with the same molecular
H C H formula [1]
but different structural formulae
H C H (or displayed formulae). [1]
H H H H
e 2,4-dimethylpentane [1]
H C C C C C H [Total: 18]
 H H H H H [1] 2 a No double bonds / only single bonds; [1]
iv compound of C and H only. [1]
b Non-polar nature / lack of polarity [1]
of C—H bond. [1]
 [1]
c i CH4 + 2O2 → CO2 + 2H2O [2]
2,3-dimethylbutane:
[1 mark for correct formulae;
i C6H14 [1] 1 mark for balancing]
ii CH3CH(CH3)CH(CH3)2 [1]

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 CAMBRIDGE INTERNATIONAL AS & A LEVEL CHEMISTRY: COURSEBOOK

1 5 a propene:
ii C2H6 + 3   O2 → 2CO2 + 3H2O
2
i C3H6 [1]
or
ii CH3CH═CH2 [1]
2C2H6 + 7O2 → 4CO2 + 6H2O [2]
iii H3C H
[1 mark for correct formulae;
1 mark for balancing] C C
[Total: 8]  H H [1]
3 a free-radical substitution [1] iv  [1]
b CH4 + Br2 → CH3Br + HBr [2]
cis-pent-2-ene:
[1 mark for correct formulae;
1 mark for balancing] i C5H10 [1]

c homolytic fission [1] ii CH3CH2CH═CHCH3 [1]

d UV/sunlight [1] iii H3C CH2 CH3

to break Br —Br bond [1] C C

e i Br2 → 2Br· [2]  H H [1]
[1 mark for correct formulae; iv
1 mark for showing free radical
 [1]
correctly]
trans-pent-2-ene:
ii Br· + CH4 → CH3· + HBr
i C5H10 [1]
or
ii CH3CH2CH═CHCH3 [1]
CH3· + Br2 → CH3Br + Br· [2]
iii H3C CH2 H
[1 mark for correct formulae;
1 mark for showing free radicals C C
correctly]
 H CH3 [1]
iii CH3· + Br· → CH3Br
or iv

CH3· + CH3· → C2H6 [2]  [1]

[1 mark for correct formulae; b CnH2n [1]

1 mark for showing free radicals c cis-pent-2-ene and trans-pent-2-ene [1]
correctly] d Because there is restricted rotation
[Total: 12] about the C═C double bond / due to
4 a Mr = 30.0 [1] the presence of a π (pi) bond which
would need to be broken. [1]
1.50
is 0.0500 mol [1] e H3C CH2 H H 3C H
30.0
b Mr = 64.5 [1] C C C C
1.29 H H H3C H
is 0.0200 mol [1]
64.5
but-1-ene methylpropene
c 0.0200  [1]
0.0500
H3C CH3 H3C H
= 40.0 % [1]
d 0.05 × 0.6 × 64.5 [1] C C C C

= 1.94 g [1] H H H CH3

[Total: 8] 
cis-but-2-ene trans-but-2-ene [8]
[1 mark for each structure; 1 mark for
each name]

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 CAMBRIDGE INTERNATIONAL AS & A LEVEL CHEMISTRY: COURSEBOOK

f HH
3C3C CH
CH22 CH
CH33 HH
3C3C CH
CH33 8 a Mr = 28.0 [1]
CC CC CC CC 2.80
2.80 g is mol = 0.100 mol [1]
28.0
HH
3C3C HH HH
3C
3C CH
CH
22 HH
b Mr = 99.0 [1]
trans-3-methylpent-2-ene
trans-3-methylpent-2-ene cis-3-methylpent-2-ene
cis-3-methylpent-2-ene 8.91
8.91 g is mol = 0.0900 mol [1]
99.0
[1 mark for each correct isomer;
1 mark for cis / trans labelled correctly] [3] c 0.0900  [1]
0.100
[Total: 27] = 90.0% [1]
6 a having one or more double bonds [1] d 80.0% of 0.100 mol is 0.0800 mol [1]
b As well as a σ bond [1] 0.0800 mol is 0.0800 × 99.0 g = 7.92 g [1]
there is a π bond caused by [Total: 8]
overlapping p orbitals. [1]
9 a i I t breaks the C═C bonds and
c planar; [1] oxidises the product molecules
all bond angles about 120° [1] to give a mixture of oxidation
d A functional group gives particular products (carboxylic acids,
chemical properties. [1] ketones and carbon dioxide). [2]

C═C double bond ii Chemists can identify the

[1]
oxidation products and deduce the
e Add bromine water; [1] position of the C═C bond in an
alkenes decolorise it. [1] alkene. [1]
[Total: 9] b but-1-ene (as there must be two
hydrogen atoms on one of the C═C
7 a electrophilic addition [1]
carbon atoms for CO2 to be produced,
b C2H4 + Br2 → C2H4Br2 [2] corresponding to CH2═CHCH2CH3)[1]
c heterolytic fission [1] c i H
d O
H H C C ethanoic acid
H H O H
C H C Br H
Br Br Br –
C δ+ δ– C and
+
H H H H H H
O
H H C C C propanoic acid
O H
 H H [3]
H C Br
ii C5H10 + 4[O] →
H C Br
CH3COOH + CH3CH2COOH  [1]
H [Total: 8]
for instantaneous dipole on bromine
molecule [1]
for curly arrow from double bond [1]
for bond breaking in bromine molecule[1]
for bond forming from bromide ion [1]
for structure of product [1]
e Br2 [1]
An electrophile is an electron-pair
acceptor.[1]
[Total: 11]

3 Cambridge International AS & A Level Chemistry © Cambridge University Press 2020