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Discussion

When chlorobenzene is treated with Cl2 in the presence of anhydrous FeCl3 catalyst gives a mixture of 1,2-dichlorobenzene and 1,4-dichlorobenzene. This reaction is an example of

  • A.Nucleophilic substitution reaction
  • B.Electrophilic substitution reaction
  • C.Free radical substitution reaction
  • D.Nucleophilic addition reaction
  • E.Electrophilic addition reaction

Answer: B

It is an electrophilic substitution reaction.

The Lewis acid FeCl3 polarises Cl2 to generate the electrophile Cl+, which attacks the benzene ring. A hydrogen of the ring is replaced, so the aromatic ring is kept. The chlorine already on the ring is ortho-para directing, giving 1,2- and 1,4-dichlorobenzene.

Nucleophilic substitution would replace the existing chlorine, free-radical substitution occurs in the side chain under light, and an addition reaction would destroy the aromatic system.

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