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Q. Identify the product 'C' in the following reaction.
Aniline $\xrightarrow[\text{Pyridine}]{(CH_3 CO)_2 O} A\xrightarrow[CH_3COOH] {Br_2} B \xrightarrow{H^{+} or \, OH^{-}} C $

MHT CETMHT CET 2018Amines

Solution:

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In the given reaction sequence, aniline gets deactivated by treating it with acetic anhydride in presence of pyridine and then subjected to bromination. Obtained $o/ p$ - nitroacetanilide upon hydrolysis gives $o / p$ -bromoaniline. The major product formed is $p$ -bromoaniline and thus the most suitable option is 'C'.