JEE Main Chemistry question

In the preparation of chlorobenzene from aniline, the most suitable reagent is

(A)Chlorine in the presence of ultraviolet light
(B)Chlorine in the presence of
(C)Nitrous acid followed by heating with Correct
(D)HCl and

Answer: (C)

Solution

Direct chlorination of aniline (routes A, B) is unsuitable because the strongly activating group makes the ring highly reactive and prone to overhalogenation/oxidation side-reactions, and option (D) (HCl with alone, without diazotisation) does not generate the required intermediate. The standard,

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Question ID VK-148085