Tutorial Unit 5.4.

1: Arenes

1. a. Complete a table below which list part of a homologous series of

arenes.<41>

Name Molecular formula Structure formula

Benzene C6H6

Methylbenzene

b. Write a general molecular formula for the homologous series of arenes

shown in the table below.

c. Use your data booklet to compare the melting points and boiling points
of benzene and methylbenzene. Suggest reasons for the differences.

2. Would you expect the C=C bond in benzene to be more or less susceptible to
addition reaction than the C=C bond in alkenes? Explain your answer.<42>

3. Some of reactions of benzene and its result are shown in table below:<43>

a. Is the prediction you made in no. 1 verified by the observation on the

results table?

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 b. Why does benzene produce a sootier flame than either cyclohexane or
cyclohexene?

c. Which of the reactions appears to be a substitution reaction? Is there any

evidence of an addition reaction?

d. Which experiment could you use to distinguish between:

i. Benzene and cyclohexane

ii. Benzene and cyclohaxane

4. Write an equation for the substitution reaction of benzene with chlorine.

Name the products and state the conditions.<44a>

5. Write an equation for the addition reaction of benzene with chlorine. Name
the products and state the conditions.<44bi>

6. There are a number of geometric isomers of this addition product. Suggest a

reason.<44bii>

7. State a use for one of the geometric isomers.<44biii>

8. Write an equation for the reaction of benzene with fuming sulfuric acid. Name
the product and state the conditions.<45a>

9. Write an equation for the reaction of benzene with concentrated nitric acid
and concentrated sulfuric acid. Name the products and state the
conditions.<45b>

10.Suggest a reason for the fact that benzene, an unsaturated compound, does
not ready undergo addition reaqctions.<46>

11.Benzene can be nitrated using a mixture of concentrated nitric acid and

concentrated sulfuric acid.

a. Name the attacking species present in the mixture of acids and write a
balanced equation to represent its formation.<48a>

b. What is the mechanism for the nitration of benzene? State the type of
reaction taking place.<48b>

12.a. Complete the following equations and name the products.<50a>

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 b. What names are given to each of the reactions shown above?<50b>

c. Write mechanisms for reactions i) and ii) in part a.<50c>

13.Dry chlorine was passed slowly into about 20 cm3 of benzene contained in a
flask irradiated with an ultraviolet lamp. The entire apparatus was set up in a
fume cupboard and was covered completely with black paper.<51>

a. Give the structure formulae of the main products.

b. What was the function of the ultraviolet light?

c. Why was the apparatus covered with black paper?

d. Suggest a mechanism for the reaction.

e. Give two reasons for carrying out the experiment in a fume cupboard.

14.Explain briefly why phenol is more readily nitrated than benzene.<53>