CAMBRIDGE INTERNATIONAL AS & A LEVEL CHEMISTRY: COURSEBOOK

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Coursebook answers
Chapter 27
Self-assessment questions
1 a i pentylamine b i  he benzenediazonium ion will
T
ii dipropylamine decompose, giving off nitrogen
gas, above 10 °C. The nitrous
iii ethylammonium chloride acid used as a reactant also
b Diethylamine is a stronger base than decomposes above 10 °C.
ethylamine because it has two ethyl ii NaNO2 + HCl → HNO2 + NaCl
groups each releasing electrons to its
N atom, making the lone pair more iii Step 1
readily available to bond with an H+  NH2 + HNO2 + HCl
+
N
–
NCl + 2H2O
ion than it is in ethylamine, which only
benzenediazonium
has one electron-donating ethyl group. chloride

2 a i  he vapour of butanenitrile and

T Step 2
hydrogen gas are passed over +
a nickel catalyst; alternatively N N + N(CH3)2
sodium and ethanol are used to
reduce the butanenitrile.
ii 1-bromopropane
N N N(CH3)2 + H +
iii  itriles and amides (nitro-alkanes
n 
also acceptable)
4 a i A
b i 2-aminophenol, C6H4(OH)NH2
ii  hey have relatively high melting
T
OH
points for organic compounds
NH2 of their molecular mass because
of the strong electrostatic forces of
attraction between the oppositely
ii reduction charged parts of the zwitterions
formed.
3 a i  henylamine, because of the
P
greater electron density around b i H
O
the benzene ring, because the
lone pair of the nitrogen atom H C H
is delocalised into the π bonding
electron system. H2N C COOH

ii X
H
NH2 + 3X+ X NH2+ 3H+
(in excess) ii H
X
O

H C H
+
H3N C COO–

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

 CAMBRIDGE INTERNATIONAL AS & A LEVEL CHEMISTRY: COURSEBOOK

iii H 7 a H 2N CH COO–
O
H
H C H H 2N CH COO–
+
H3N C COOH CH2

H
iv H
H 2N CH COO–
O
CHCH3
H C H
CH3
H2N C COO–
b i start
H
+ –
v  he isoelectric point of serine
T
is the pH value at which there is
no overall charge on an aqueous Gly Val Phe
solution of serine.
ii  he molecules are separated
T
5 a H H H
according to size, with the
H
H C C C H
smallest (glycine) moving furthest,
and the largest (phenylalanine)
H C H
H H moving the shortest distance.
H2N C COOH H2N C COOH Each of the ions will have a −1
charge at pH 10, so the size of the
H H ions is the only factor involved in
alanine valine their separation.
c The amino acid would remain in
b CH3 CH(CH3)2 position / not move.
H2N C COOH + H2N C COOH

H H

CH3 H CH(CH3)2

H2N C C N C COOH + H2O

H O H

6 a i CH3CH2COCl + NH3 →
CH3CH2CONH2 + HCl
ii C2H5COCl + C2H5NH2 →
C2H5CONHC2H5 + HCl
b i C3H7CONH2 + H2O →
C3H7COOH + NH3
(note that NH3 will react with
excess HCl to give NH +4 Cl – )
ii C3H7CONHC2H5 + NaOH →
C3H7COONa + C2H5NH2

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