Paddington Academy

A LEVEL CHEMISTRY
TOPIC 18 – AROMATIC CHEMISTRY

TEST

Answer all questions

Max 50 marks

Name ……………………………………………………………..

Mark ……../50 ……....% Grade ………

1.

Page 1
 Paddington Academy
2. The hydrocarbons benzene and cyclohexene are both unsaturated compounds.
Benzene normally undergoes substitution reactions, but cyclohexene normally
undergoes addition reactions.

(a) The molecule cyclohexatriene does not exist and is described as hypothetical.
Use the following data to state and explain the stability of benzene compared with
the hypothetical cyclohexatriene.

......................................................................................................................

......................................................................................................................

......................................................................................................................

......................................................................................................................

......................................................................................................................

......................................................................................................................

......................................................................................................................

......................................................................................................................
(4)

Page 2
 Paddington Academy

(b) Benzene can be converted into amine U by the two-step synthesis shown below.

The mechanism of Reaction 1 involves attack by an electrophile.

Give the reagents used to produce the electrophile needed in Reaction 1.

Write an equation showing the formation of this electrophile.

Outline a mechanism for the reaction of this electrophile with benzene.

......................................................................................................................

......................................................................................................................

......................................................................................................................

......................................................................................................................

......................................................................................................................

......................................................................................................................

......................................................................................................................

......................................................................................................................
(6)

Page 3
 Paddington Academy

(c) Cyclohexene can be converted into amine W by the two-step synthesis shown
below.

Suggest an identity for compound V.

For Reaction 3, give the reagent used and name the mechanism.

For Reaction 4, give the reagent and condition used and name the mechanism.

Equations and mechanisms with curly arrows are not required.

......................................................................................................................

......................................................................................................................

......................................................................................................................

......................................................................................................................

......................................................................................................................

......................................................................................................................

......................................................................................................................
(6)

(d) Explain why amine U is a weaker base than amine W.

......................................................................................................................

......................................................................................................................

......................................................................................................................

......................................................................................................................

......................................................................................................................
(3)
(Total 19 marks)

Page 4
 Paddington Academy

Page 5
 Paddington Academy

2. Give a reagent that could be used in a test-tube reaction to distinguish between benzene
and cyclohexene.
Describe what you would see when the reagent is added to each compound and the test
tube is shaken.

........................................................................................................................

........................................................................................................................

........................................................................................................................

........................................................................................................................

........................................................................................................................

........................................................................................................................

........................................................................................................................
(3)
(Total 3 marks)

3. An equation for the formation of phenylethanone is shown below. In this reaction a

(i) Give the formula of the reactive intermediate.

.............................................................................................................

(ii) Outline a mechanism for the reaction of this intermediate with benzene to form
phenylethanone.

(4)

Page 6
 Paddington Academy
(Total 4 marks)

4. (a) Outline a mechanism for the formation of ethylamine from bromoethane. State why
the ethylamine formed is contaminated with other amines. Suggest how the reaction
conditions could be modified to minimise this contamination.

........................................................................................................................

........................................................................................................................

........................................................................................................................

........................................................................................................................

........................................................................................................................

........................................................................................................................

........................................................................................................................
(6)

(b) Suggest one reason why phenylamine cannot be prepared from bromobenzene in a
similar way. Outline a synthesis of phenylamine from benzene. In your answer you
should give reagents and conditions for each step, but equations and mechanisms
are not required.

........................................................................................................................

........................................................................................................................

........................................................................................................................

........................................................................................................................

........................................................................................................................

........................................................................................................................

........................................................................................................................
(5)
(Total 11 marks)

Page 7
 Paddington Academy

5. Kevlar is a polymer used in protective clothing.

One of the monomers used in the synthesis of Kevlar is

An industrial synthesis of this monomer uses the following two-stage process

Stage 1

X
Stage 2

(a) Suggest why the reaction of ammonia with X in Stage 1 might be considered
unexpected.

...............................................................................................................

...............................................................................................................

...............................................................................................................

...............................................................................................................
(2)

(b) Suggest a combination of reagents for the reaction in Stage 2.

...............................................................................................................
(1)

Page 8
 Paddington Academy

(c) Compound X can be produced by nitration of chlorobenzene.

Give the combination of reagents for this nitration of chlorobenzene.

Reagents ...............................................................................................

...............................................................................................................

Equation(s) ............................................................................................

...............................................................................................................
(3)

(d) Name and outline a mechanism for the formation of X from chlorobenzene and
the reactive intermediate in part (iii).

Name of mechanism ......................................................................................

Mechanism

(4)
(Total 10 marks)

Page 9
 Paddington Academy

6. Which one of the following does not contain any delocalised electrons?

A poly(propene)

B benzene

C graphite

D sodium
(Total 1 mark)

7. The relative molecular mass (Mr) of benzene-1,4-dicarboxylic acid is

A 164

B 166

C 168

C 170
(Total 1 mark)

8. Ethanoyl chloride reacts with methylbenzene forming compound X according to the

If the experimental yield is 40.0%, the mass in grams of X (Mr = 134.0) formed from 18.4 g
of methylbenzene (Mr = 92.0) is

A 26.8

B 16.1

C 10.7

D 7.4
(Total 1 mark)

Page 10