Aniline is highly reactive and normally yields 2,4,6-tribromoaniline upon direct bromination. To synthesize strictly p-bromoaniline, which sequence of reactions must be employed?

Question

Prashant Kotian · Accepted Answer

Correct answer: D. Acetylating aniline converts it to acetanilide. The cross-conjugation of the lone pair with the carbonyl reduces its activating power, preventing poly-substitution and allowing clean mono-substitution (mostly para). Hydrolysis then restores the amine.

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