Raffles Institution (Junior College)

H2 Chemistry 2010/11
Tutorial 13 Arenes
Prepared by: Mr Tham Zi Sheng

REMINDER: Please study before you attempt the questions.

Self-Check Questions
1

Give the structural formula of each compound given below.

(i) 1-iodo-3-nitrobenzene
(ii) 3-amino-5-hydroxybenzaldehyde
(iii) 1,3-dichloro-2,5-diethylbenzene

Suggest suitable reagents and conditions to carry out the conversions given below.
(i) benzene
1-chloro-2-ethylbenzene
(ii) phenol
2-hydroxybenzene-1,5-dicarboxylic acid

Describe two simple chemical tests which would enable you to distinguish between
ethylbenzene, phenylethene and benzoic acid. State clearly how each compound behaves in
each test and write balanced equations for the reactions involved.

Discussion Questions
1

Modified from J90/III/9

(a) Saccharin is an artificial sweetening agent used in some soft drinks and is manufactured
from methylbenzene by the following series of reactions.
ClSO3H
I

CH3

CH3

CH3

SO2Cl

SO2NH2

S
O

III

N
H

COOH

II

SO2NH2

(i) What types of reaction do steps I, II and III illustrate?

(ii) Suggest reagents for step II.
(b) When methylbenzene is nitrated by a mixture of concentrated nitric acid and concentrated
sulfuric acid, the product consists largely of two isomers of formula C7H7NO2.
(i) Draw the structural formulae of the two isomers.
(ii) Briefly outline the mechanism of this reaction.

Compound A, which has molecular formula, C8H8, burns with a smoky flame. A instantly
decolourises bromine dissolved in tetrachloromethane. When A is refluxed with acidified
potassium manganate(VII), a white crystalline precipitate, B, with molecular formula, C7H6O2,
is obtained. A also undergoes hydrogenation in the presence of a platinum catalyst to form
compound C, with molecular formula, C8H10. C has no apparent reaction with bromine in the
dark. However, dense white fumes, D, appear if a small amount of iron powder is added.
Identify the compounds A to D, giving their structural formulae, and explain your reasoning.

Modified from N97/I/6

Methylbenzene can be used an additive in unleaded petrol. Some chemical transformations of
methylbenzene are given below.

COOH

I
CH3

II

IV
C7H5O2Br

CH2Br

III

CH3
Br
A
(a) Suggest reagents and conditions for each of the reactions I, II and III, and describe the
type of reaction undergone in each case.
(b) There are two other positional isomers of A. Draw their structural formulae, and suggest
which one is more likely to be formed along with A in reaction III.
(c) Reactions IV and V yield different isomers with the molecular formula, C7H6O2Br. Give the
structural formulae of the isomers and explain why reactions IV and V produce different
isomers.
Challenging Question
1

(a) A student tried to synthesise 2-methylphenylamine by reacting phenylamine with

chloromethane in the presence of aluminium chloride. However, the reaction yielded a
different product, X.
Suggest the structural formula of X and explain why the reaction yielded X instead of
2-methylphenylamine.
(b) When benzene reacts with 1-bromopropane in the presence of iron(III) bromide, the
product formed is (methylethyl)benzene. Outline the mechanism of this reaction.