Q19 of 102 Page 310

How the following conversions can be carried out?

Aniline to phenylisocyanide

Aniline on reaction with trichloride alkyl group and KOH forms isophenylcyanide. It is electrophillic addition reaction in which an electron deficient group attaches to benzene ring at ortho or para.


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19

How the following conversions can be carried out?

Benzene to diphenyl

 19

How the following conversions can be carried out?

tert-Butyl bromide to isobutyl bromide

 20

The treatment of alkyl chlorides with aqueous KOH leads to the formation of alcohols but in the presence of alcoholic KOH, alkenes are major products. Explain.

 21

Primary alkyl halide C4H9Br (a) reacted with alcoholic KOH to give compound (b). Compound (b) is reacted with HBr to give (c) which is an isomer of (a). When (a) is reacted with sodium metal it gives compound (d), C8H18 which is different from the compound formed when n-butyl bromide is reacted with sodium. Give the structural formula of (a) and write the equations for all the reactions.