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Haloarenes undergo nucleophilic and electrophilic substitution reactions. 

a) Write two examples for ambident nucleophiles.

b) Write one example for the nucleophilic substitution reaction of chlorobenzene.

c) Write any two examples of electrophilic substitution reaction of chlorobenzene.

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a) Cyanide ion (CN) and nitrite ion (NO2).

b) Chlorobenzene when heated with aquous sodium hydroxide solution at a temperature of 623 K and a pressure of 300 atmosphere gets converted to phenol by a nucleophilic substitution reaction.

c) Nitration – When chloroform is treated with the nitrating mixture (a mixture of conc, HNO3 and cone. H2SO4), a mixture of 1-Chloro-2-nitrobenzene (minor product) and 1-Chloro-4-nitrobenzene (major product) is obtained.

Friedel-Crafts alkylation – When chloroform is treated with methyl chloride in presence of anhydrous AICI a mixture of 1 – Chloro – 2 – methylbenzene (minor product) and 1-Chloro-4- methylbenzene (major product) are obtained.

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