Question

Identify the product 'C' in the following reaction.
Aniline $\underset{\text{Pyridine}}{\overset{(C{H}_{3}CO{)}_{2}O}{\to }}A\underset{C{H}_{3}COOH}{\overset{B{r}_2}{\to }}B\stackrel{H^{+}orO{H}^{-}}{\to }C$

• A. Acetanilide
• B. p-Bromoacetanilide
• C. p - Bromoaniline
• D. o - Bromoaniline

Answer 1

Answer: (C)

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'.