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 27
Science in context a nickel catalyst; alternatively
sodium and ethanol are used to
After reading the Science in Context passage about reduce the butanenitrile.
William Perkin, ask learners to work in small
ii 1-bromopropane
groups to carry out the three tasks. Discussion
of the role of serendipity in scientific discovery iii nitriles and amides (nitro-alkanes
should bring out the chance element but also the also acceptable)
astute responses of the pioneering scientists who b i 2-aminophenol, C6H4(OH)NH2
then recognise the potential importance of their OH
stroke of luck.
NH2
Research on the internet should reveal some cases
of serendipitous discoveries in chemistry. For
example, saccharin used as an artificial sweetener
discovered by Constantine Fahlberg (there is ii reduction
a link with William Perkin here as both were 3 a i P
 henylamine, because of the
experimenting with coal tar when their discoveries greater electron density around
were made); Teflon discovered by Roy Plunkett; the benzene ring, because the
Super Glue discovered by Harry Coover; Vaseline lone pair of the nitrogen atom
discovered by Robert Chesebrough. Ask each is delocalised into the π bonding
group to give one of their examples, and a brief electron system.
explanation of what happened in that particular
ii X
discovery, rotating around the class until there are NH2 + 3X+ X NH2+ 3H+
no new suggestions. (in excess)
X
The structure that all the dyes have in ­common is
b i The benzenediazonium ion will
the –N=N– group. This is called an ‘azo’ group;
decompose, giving off nitrogen
hence the name ‘azo dyes’.
gas, above 10 °C. The nitrous
acid used as a reactant also
Self-assessment questions decomposes above 10 °C.
1 a i pentylamine ii NaNO2 + HCl → HNO2 + NaCl
ii dipropylamine iii Step 1
iii ethylammonium chloride  NH2 + HNO2 + HCl
+
N
–
NCl + 2H2O

b Diethylamine is a stronger base than benzenediazonium

chloride
ethylamine because it has two ethyl
groups each releasing electrons to its Step 2
N atom, making the lone pair more +
N N + N(CH3)2
readily available to bond with an H+
ion than it is in ethylamine, which only
has one electron-donating ethyl group.
2 a i T
 he vapour of butanenitrile and
N N N(CH3)2 + H +
hydrogen gas are passed over 

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

 CAMBRIDGE INTERNATIONAL AS & A LEVEL CHEMISTRY: COURSEBOOK

4 a i A b CH3 CH(CH3)2
ii They have relatively high melting
H2N C COOH + H2N C COOH
points for organic compounds
of their molecular mass because H H
of the strong electrostatic forces of
attraction between the oppositely
charged parts of the zwitterions
formed.
b i H
CH3 H CH(CH3)2
O
H2N C C N C COOH + H2O
H C H
H O H
H2N C COOH
6 a i CH3CH2COCl + NH3 →
H
CH3CH2CONH2 + HCl
ii H
O ii C2H5COCl + C2H5NH2 →
C2H5CONHC2H5 + HCl
H C H
b i C3H7CONH2 + H2O →
+
H3N C COO – C3H7COOH + NH3
(note that NH3 will react with
H
excess HCl to give NH +4 Cl – )
iii H
O ii C3H7CONHC2H5 + NaOH →
C3H7COONa + C2H5NH2
H C H
+ 7 a H2N CH COO–
H3N C COOH
H
H
H 2N CH COO–
iv H
O CH2

H C H

H2N C COO– H 2N CH COO–

CHCH3
H
CH3
v The isoelectric point of serine
is the pH value at which there is b i start
no overall charge on an aqueous
solution of serine. + –
5 a H H H
H Gly Val Phe
H C C C H
H C H ii The molecules are separated
H H
according to size, with the smallest
H2N C COOH H2N C COOH
(glycine) moving furthest, and the
H H largest (phenylalanine) moving the
shortest distance. Each of the ions
alanine valine
will have a −1 charge at pH 10,
so the size of the ions is the only
factor involved in their separation.
c The amino acid would remain in
position / not move.

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

 CAMBRIDGE INTERNATIONAL AS & A LEVEL CHEMISTRY: COURSEBOOK

Exam-style questions
1 a H H
H H
or
H C C N N C6H5N2+Cl− + C6H5OH →
H H C6H5N2C6H4OH + HCl
H H
[1]
ethylamine phenylamine  [2]
d dye[1]
[1 mark for each structure]
[Total: 6]
b e.g. C2H5NH2 + HCl → [1]
5 a i g lycine is aminoethanoic acid
C2H5NH3+Cl−  [1] (2-aminoethanoic acid) [1]
c lone pair on nitrogen [1] alanine is 2-aminopropanoic acid [1]
[Total: 5] ii
2 a reduction [1] OH OH
H2N H2N
b tin; [1]
O O
concentrated HCl(aq) [1]
glycine alanine [2]
c C6H5NO2 + 6[H] → [1]
C6H5NH2 + 2H2O  [1] [1 mark for each structure]

[Total: 5] b i H H

3 a sodium nitrite / sodium nitrate(III) / C C

HOOC NH2 H2N COOH
NaNO2[1]
CH3 H3C [2]
dilute HCl [1]
[1 mark for each structure]
b temperature below 10 °C [1]
ii It does not have a chiral carbon (a
c +
N N Cl – carbon with four different groups
/ atoms attached), so no optical
for C6H5− group [1] isomers;[1]
for N≡N[1] and it does not have a C═C
+ charge and Cl ion included
−
[1] double bond, so no geometrical
(cis / trans) isomers. [1]
d C6H5NH2 + NaNO2 + 2HCl →
C6H5N2+Cl− + NaCl + 2H2O [Total: 8]
or 6 a They can act as both an acid and as a
base / they can act as proton acceptors
C6H5NH2 + HNO2 + HCl → and proton donors. [1]
 C6H5N2+Cl− + 2H2O
b The —NH2 group has a lone pair of
correct reactants [1] electrons[1]
correct products [1] and therefore can accept a proton, i.e.
[Total: 8] act as a base. [1]
4 a temperature below 10 °C; [1] The —COOH group can ionise /
alkali / NaOH present [1] dissociate to give —COO− + H+[1]

b and therefore can act as an acid by

N donating a proton. [1]
N OH c i Glycine forms the zwitterion
+
H3NCH2COO−, i.e. it has two
for arene rings and phenol —OH[1] ions present. [1]
for —N═N—[1] ii They exist as ionic solids with
higher than expected melting /
c C6H5N2+Cl− + C6H5OH + NaOH→
decomposition points [1]
C6H5N2C6H4OH + NaCl + H2O

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

 CAMBRIDGE INTERNATIONAL AS & A LEVEL CHEMISTRY: COURSEBOOK

because of the electrostatic iv It works because ions move

attraction between oppositely
charged ions on neighbouring
zwitterions.[1]
They are soluble in water
because of the interactions
between the charged groups and
polar water molecules.
d O
H 2N CH2 C NH CH
at different rates towards the
oppositely charged electrode [1]
depending on the size / mass
[1] of ions [1]
and charge on the ions; [1]
larger ions will move more slowly; [1]
[1]
more highly charged ions will
O move more quickly. [1]
C [Total: 14]

CH3 OH

O O

H 2N CH C NH CH2 C


H 3C OH [4]
[2 marks for each structure]
[Total: 14]
7 a i CH3 O H O

H2N C C OH H2N C C OH

H H3C C C2H5

H
H O
H 2N C C

H OH [3]

[1 mark for each structure]

ii the second one in the diagram
above[1]
b i —CO—NH— / amide / peptide
bond / link [1]
ii Hydrolysis means splitting
of a bond / breaking down a
compound using water. [1]
H O O

N C NH2 + HO C
H OH
[2]
[1 mark for showing which bond
breaks, 1 mark for products]
iii electrophoresis[1]

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