JEE Main Chemistry question

Electrolytic reduction of nitrobenzene in a weakly acidic medium gives

(A)Aniline
(B)*p*-Aminophenol (via acid-catalysed rearrangement of the intermediate phenylhydroxylamine)Correct
(C)Unreacted nitrobenzene
(D)*N*-Phenylhydroxylamine (the intermediate under neutral, non-rearranging conditions)

Answer: (B)

Solution

Nitrobenzene is first reduced to *N*-phenylhydroxylamine; under weakly acidic conditions this intermediate undergoes an acid-catalysed [3,3]-type

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Question ID VK-140432