Identify the product 'C' in the following reaction.

Aniline $(C H_{3} C O)_{2} O ⟶ P y r i d i n e A B r_{2} ⟶ C H_{3} C O O H B H^{+} / O H^{-} ⟶ C$ .

Acetanilide

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p-Bromoacetanilide

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p-Bromoaniline

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o-Bromoaniline

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Solution

The correct option is C p-Bromoaniline

1) Amino group of aniline is acetylated with acetic anhydride / pyridine.

2) It is then brominated with bromine / acetic acid. As the -NHCOCH3 is ortho/para directing group (since lone pair on N activates the ring). Bromine enters in para position (para product is major).

3) The final step is acid hydrolysis in which $- N H C O C H_{3}$ group is hydrolysed to $- N H_{2}$ group.

So, the product C formed is p-bromoaniline.

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