Notes

describe the chemistry of arenes as exemplified by the following
reactions of benzene and methylbenzene:
(i) substitution reactions with chlorine and with bromine
(ii) nitration
(iii) Friedel-Crafts alkylation and acylation
(iv) complete oxidation of the side-chain to give a benzoic acid
(v) hydrogenation of the benzene ring to form a cyclohexane ring
b) (i) describe the mechanism of electrophilic substitution in
arenes, as exemplified by the formation of nitrobenzene and
bromobenzene
(ii) suggest the mechanism of other electrophilic substitution
reactions, given data
(iii) describe the effect of the delocalisation of electrons in arenes in
such reactions
c) interpret the difference in reactivity between benzene and
chlorobenzene
d) predict whether halogenation will occur in the side-chain or in the
aromatic ring in arenes depending on reaction conditions
e) apply knowledge relating to position of substitution in the
electrophilic substitution of arenes (see the Data Booklet Table 9)

(vii) formation of esters by acylation with acyl chlorides using ethyl
ethanoate and phenyl benzoate as examples

a) recall the chemistry of phenol, as exemplified by the following
reactions:
(i) with bases
(ii) with sodium
(iii) with diazonium salts (see also Section 20.1)
(iv) nitration of, and bromination of, the aromatic ring
b) describe and explain the relative acidities of water, phenol and
ethanol