Topic 18 Organic chemistry: arenes

18A Arenes: benzene

18A.1 Benzene: a molecule with two models

2 (a) Each C–H and C–C bond has two electrons in sigma bonds, and as there are
six of each, then 12 × 2 = 24 electrons are involved in sigma bonding.
(b) Each C atom supplies one electron to form the delocalised pi bond, so the
answer is 6 electrons in pi bonding.

18A.2 Some reactions of benzene

1

2 Phenylbutanone.

18A.3 Electrophilic substitution mechanisms

1 FeBr3  Br2  Br   FeBr4 

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2

18A.4 Phenol
1 The OH group is polar and can take part in hydrogen bonding. This means that phenol
molecules attract each other strongly, and so the melting temperature is above room
temperature. Its solubility in water is due to the formation of hydrogen bonds between
phenol molecules and water molecules.

Topic 18 Exam Practice

1 D
2 C
3 C
4 A
5 A
6 C

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7 (a) (i) C3H8 + Br2  C3H8Br2 (1).
C6H6 + Br2  C6H5Br + HBr (1).
(ii) Propene – nucleophilic addition (1).
Benzene – electrophilic substitution (1).
(b) (i) H2SO4 + HNO3  NO2+ + H2O + HSO4− (1)
HSO4− + H+  H2SO4

8 (a) (i) (3 × −120) = −360 kJ mol−1 (1)

(ii) The bonding in benzene is more stable than in the Kekulé structure by
152 kJ mol−1 (1). The double bond electrons are delocalised around
the ring (1). Benzene undergoes substitution reactions rather than
addition (1) in order to maintain its delocalised system of electrons (1).
(b) (i) Concentrated nitric acid (1), concentrated sulfuric acid (1).
(ii) Electrophile (1).
(iii) Br2 + FeBr3  FeBr4− + Br+ (1).

(iv)

(1).

Benzenesulfonic acid (1)

9 (a) H2SO4 + HNO3  NO2+ + H2O + HSO4− (1).

(b) Higher temperatures lead to the formation of dinitrobenzene, and possibly

trinitrobenzene (1).
At lower temperatures the reaction is too slow (1).
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10 (a) X-ray diffraction – all of the carbon to carbon bond lengths are the same (1).
In structure A the carbon to carbon bonds lengths would alternate between
‘short’ and ‘long’ (1).
(b) Enthalpy change of hydrogenation – the enthalpy change of hydrogenation of
benzene −208 kJ mol−1 (1). The enthalpy change for structure A would be
−360 kJ mol−1 (1).
(c) Reaction with bromine – benzene undergoes a substitution reaction with
bromine (1). Structure A would undergo an addition reaction with bromine (1).

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