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 14
Self-assessment questions
1 a i Find out the ratio of moles: ii H H H H H H H

C:H H C C C C C C C H
72 0.18
: H H H H H
12 1.0
= 0.06 : 0.18 H C HH C H

Simplest whole number ratio is: H C HH C H

1:3 H H
so empirical formula is CH3 iii H H H H H H H H
ii C2H6 H C C C C C C C C H
b C2H4O2 H H H H H
c i H H
H C HH C HH C H
C C
H H H
H H b i 3-ethyl-3-methylheptane
ii H H H ii
H C C C H

H H H
d i

ii octane = 3 a i H H H
CH3CH2CH2CH2CH2CH2CH2CH3
C C C H
octane = CH CH CH CH CH CH CH CH
2,2,4-trimethylpentane = =
3 2 2 2 2 2 2 3
2,2,4-trimethylpentane CH3C(CH3)2CH2CH(CH3)CH3
     CH
cyclohexaneC(CH3)2CH2CH(CH3)CH3
3 =
H H H

cyclohexane = CH2
ii H H H
CH2 CH2 H C C C H

CH2 CH2 H H H
CH2

2 a i H

H C H

H H H

H C C C C H

H H H H

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

 CAMBRIDGE INTERNATIONAL AS & A LEVEL CHEMISTRY: COURSEBOOK

iii H ii H O H

H C H H C C C H

H C H H H
propanone

H H H H
d H
H C C C C H
H O H
H H H H
H C C C H
b H Br Cl H H H
H H H
H C C C C C C H
propan-2-ol
H H Cl H H H

c C e H H H H H H H H H
H H
4 a i H H H C C C C C H H C C C C H

H C H H H H H H H H H
H C H pentane H C H
C C
C C H
H
H H H H methylbutane
H H H H H C H
H H
ii H H
H H H C C C H
C C H
H H
C C H
H C H C H
H C
H
H H
dimethylpropane
H H
iii H C C H
6 a i H H H
b i D
H C C H H C H
ii A = sp, B = sp2, C = sp3 H C
H C CH CH
5 a 1,2-dibromopropane, H H H C H
1,3-dibromopropane,
H
1,1-dibromopropane,
cis-but-2-ene trans-but-2-ene
2,2-dibromopropane
ii Br Cl Br
b Cl H H H Cl H

H C C C H H C C C H

H H H H H H
cis-1-bromo-2-chlorocylobutane trans-1-bromo-2-chlo
1-chloropropane 2-chloropropane
Br Cl Br Cl
c i H H
O
H C C C

H H H
cis-1-bromo-2-chlorocylobutane trans-1-bromo-2-chlorocylobutane
propanal

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

 CAMBRIDGE INTERNATIONAL AS & A LEVEL CHEMISTRY: COURSEBOOK

b H H

C C
F Cl Cl F
Br Br

c i B
ii Chiral centre in bold -
(CH3)2C═CHC*HClCH3
d methylcyclohexane has no chiral
centres, and 2-methylcyclohexanone
has one chiral centre. (Label the C
atom in the ring bonded to the methyl
group in 2-methylcyclohexanone).
e D, 8 chiral centres
7 a Cl2 → Cl· + Cl·
or Cl2 → 2Cl·
b H H

H C Cl H C+ + Cl–

H H

c OH −

d OH− has lone pairs of electrons on its

oxygen atom whereas H2 and H+ have
no available lone pairs of electrons.
e H+
f H+ can accept a pair of electrons,
whereas H2 and OH− cannot.
g Option B, because in this tertiary
carbocation there are three alkyl
groups, each tending to donate
electrons to the positively charged
carbon atom, reducing its charge
density and making the ion
energetically more stable than the
primary (option C) or secondary
(option A) carbocations.
8 a hydrolysis
b reduction
c elimination
d addition
e (free-radical) substitution

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