Question

How will you convert aniline to p-bromoaniline?

Hint:

- Direct bromination of aniline gives both ortho and para isomers. - Acetylation controls the reaction to favor p-bromoaniline.

Answer 1

Aniline is acetylated, then brominated, and finally hydrolyzed to obtain p-bromoaniline.
Step 1: Acetylation of Aniline \[ \text{Aniline} + (CH_3CO)_2O \rightarrow \text{Acetanilide} \] Step 2: Bromination of Acetanilide \[ \text{Acetanilide} + Br_2 + CH_3COOH \rightarrow \text{p-Bromoacetanilide} \] Step 3: Hydrolysis to p-Bromoaniline \[ \text{p-Bromoacetanilide} + OH^- \rightarrow \text{p-Bromoaniline} \]