Aniline is highly reactive and normally yields 2,4,6-tribromoaniline upon direct bromination. To syn — Aromatic Hydrocarbons Chemistry Question

💡 Solution & Explanation

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.