1

Organic Chemistry A-2

ARENES

ARENES
1. Methylbenzene can react with chlorine in two ways, depending on
the conditions of the reaction.
(ii) bromobenzene,

(iii) nitrobenzene.
(a) State the condition needed for
(i) reaction I,

[4]

..............................................................................................................
(ii) reaction II.

(b) The nitration of benzene is a two-step reaction that can be

represented as follows.

..........................................................................................................[2]
(b) One of the two compounds A and B reacts with NaOH(aq), but
the other is inert. (i) Which one (A or B) does not react? Give a
reason for your answer.
..............................................................................................................
..............................................................................................................
(ii) Write an equation for the reaction with NaOH(aq) that does occur.

[2]
[Total: 4]
s02/q6

2. Chloroacetophenone (compound D, below) was formerly the most

widely used tear gas, under the codename CN. It was used in warfare
and in riot control. It can be synthesized from ethylbenzene, A, by the
following route.

(i) Identify the cation A+.

...............................................................................................
(ii) Draw the structure of the intermediate B in the box.
[2]
(c) The position of substitution during the electrophilic substitution of
arenes is determined by the nature of the group already attached to
the ring. Electron-withdrawing groups such as CO2H or NO2 direct
the incoming group to the 3-position.

On the other hand, electron-donating groups such as CH3 or NH2

direct the incoming group to the 2- or 4- positions.
(a) Suggest reagents and conditions for step I.
..........................................................................................................[1]
(b) Suggest reagents and conditions for converting ethylbenzene into
compound E, an isomer of B.
Use this information to suggest a likely structure for the organic
product of each of the following reactions.

..........................................................................................................[1]
(c) Draw the structure of the product obtained by heating
ethylbenzene with KMnO4.

[1]
s03/q4

3. (a) State the reagents and conditions needed to convert benzene

into
(i) chlorobenzene,

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Organic Chemistry A-2
ARENES
..........................................................................................................[2]
[Total: 11]
s05/q6

6- Benzocaine is an important local anaesthetic used in skin creams

for sprains and other muscular pains. It can be made by the following
route.

Benzocaine
(a) Suggest reagents and conditions for each of the above four
reactions.
I ............................................................................................................
[2]
[Total: 8]

II .......................................................................................................[3]
(b) Draw steps to show the mechanism of reaction I.

s04/q5

4- The antipyretic (fever-reducing) drug antifebrin can be made from

benzene and ethanoic acid by the following route.

[2]
s06/q5

7- The following scheme shows some reactions of methylbenzene.

(a) (i) What type of reaction is reaction I?

..............................................................................................................
(ii) Suggest the reagents and conditions for reaction I.
..............................................................................................................
(iii) Complete the following scheme showing the mechanism of
reaction I, by drawing appropriate formulae in the three boxes.

(a) Suggest reagents and conditions for reactions I to IV.

I ............................................................................................................
[6]
(b) (i) What type of reaction is reaction II?

II............................................................................................................

..............................................................................................................
(ii) Suggest the reagents and conditions for reaction II.

III ..........................................................................................................

..............................................................................................................
[2]
(c) Suggest the reagents and conditions for reaction III.
..........................................................................................................[1]
(d) (i) Apart from the benzene ring, name the functional group in
antifebrin.

IV .........................................................................................................
[4]
(b) What type of reaction is each of the following?
reaction I
..............................................................................................................
reaction III
..........................................................................................................[2]

..............................................................................................................
(ii) What reagents and conditions are needed to hydrolyse
antifebrin?

s07/q5

8- Both ethene and benzene react with bromine, but the mechanisms
and the types of products of the two reactions are different.

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3
Organic Chemistry A-2
ARENES
If Y is an electron-withdrawing group, the next substitution will be in
position 3. If Y is an electron-releasing group, the next substitution will
be mostly in position 4.

(a) State the type of reaction undergone in each of reactions I and

II.
reaction I
..............................................................................................................
reaction II

The following table lists some electron-withdrawing and electronreleasing substituents.

electron-withdrawing groups
electron-releasing groups
NO2
CH3
COCH3
CH2Br
CO2H
NH2

..........................................................................................................[2]
Use the above information to draw relevant structural formulae in the
boxes in the schemes below.

(b) In each of reactions I and II, the intermediate is a brominecontaining cation. In eachof the following boxes, draw the intermediate
and use curly arrows to show how it is converted into the product.

product

Reaction I

s08/q6

(b) Phenylamine can be made from benzene by the following two

reactions.
intermediate

intermediate

(i) Suggest reagents and conditions for

reaction III,
..............................................................................................................
reaction IV.
..............................................................................................................
(ii) State the type of reaction for
reaction III,

[4]
(c) Why do ethene and benzene differ in their reaction with bromine?

..............................................................................................................
reaction IV.

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

..............................................................................................................
[5]

product

Reaction II

s09/q6

..........................................................................................................[1]
[Total: 7]
s08/q5

9-The substituted benzene

compound

10- Benzene can be converted into nitrobenzene by a nitration

reaction.

can be further substituted.

If Y is an electron-withdrawing group, the next substitution will be in
position 3. If Y is an electron-releasing group, the next substitution will
be mostly in position 4.

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4
Organic Chemistry A-2
ARENES
(a) State the reagents and conditions necessary to carry out this
reaction.

[2]
[Total: 10]
w02/q5

..............................................................................................................
..........................................................................................................[2]
(b) What type of reaction mechanism is this?

11- This question is concerned with organochlorine compounds.

(a) State the conditions needed to produce the two compounds A and
B.

..........................................................................................................[1]
(c) The reaction proceeds via two steps:

(i) conditions for reaction I

(i) Draw the structure of the intermediate Y in the box.
(ii) Identify the cation
X+..................................................................................................
(iii) Identify the cation

..............................................................................................................
(ii) conditions for reaction II
..........................................................................................................[2]
(b) State the reagent needed to carry out the following reaction.

Z+..................................................................................................
(iv) Write an equation to show how X+ is produced from the reagents.
..........................................................................................................[5]

reagent for reaction III:

................................................................................................. [1]
w04/q5

(d) Some aromatic poly-nitro compounds are used in perfumes as

artificial musks. An example is Baur musk.
12- Ethylbenzene is an important starting material for making
polystyrene (poly(phenylethene)).

(i) Draw the structural formula of the hydrocarbon that could be

nitrated in order toproduce Baur musk.
(a) (i) State the conditions needed to carry out reaction I in the
laboratory.
..............................................................................................................
(ii) State the reagent and conditions needed for reaction II.
(ii) Suggest the structural formula of the compound formed by
reacting Baur musk with an excess of tin and concentrated
hydrochloric acid.

..............................................................................................................
(iii) Draw the structure of the repeat unit of polystyrene.

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5
Organic Chemistry A-2
ARENES
(iv) There are several polymers that consist of phenylethene copolymerised with other monomers. The following formula shows part of
the chain of one such co-polymer.

[3]
[Total: 12]
w06/q4

13- The nitration of benzene occurs in the following steps.

Deduce the structural formula of the other monomer.

(a) What reagents and conditions are needed for this reaction?
..........................................................................................................[2]
(b) Write an equation showing how the electrophile NO2+ is formed
from the reagents.
..........................................................................................................[1]
[5]
(b) Compound B undergoes the following series of reactions.
(c) The nitration of methylbenzene produces mainly 2nitromethylbenzene, whereas the nitration of benzoic acid produces
mainly 3-nitrobenzoic acid.
(i) Suggest reagents and conditions for reaction III.
..............................................................................................................
(ii) What would you see when reaction IV was carried out?
..............................................................................................................
(iii) Draw structures for C and D in the boxes above.
[4]

(c) Ethylbenzene can react with chlorine under a different set of

conditions to give compound E, an isomer of compound B. Compound
E undergoes the following reaction.

Use this information to suggest suitable intermediates G and H in the

following two 2-stage syntheses of chlorobenzoic acids, and suggest
suitable reagents for reactions I to IV.

reagents:
reaction I .................................... reaction II ........................................
reaction III .............................. reaction IV .......................................
[4]
[Total: 7]
w07/q7

(i) Draw a structure for E in the box above.

(ii) Describe the conditions used for reaction V.
..............................................................................................................
(iii) State the reagents used for reaction VI.
..............................................................................................................

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6
Organic Chemistry A-2
ARENES

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