Question

Convert aniline to:
(I) p-bromoaniline
(II) phenol

Hint:

The bromination of aniline typically occurs at the para position due to the electron-donating nature of the amino group.

Answer 1

(I) To convert aniline to p-bromoaniline, we perform bromination in the presence of a strong electrophile (Br₂) in a non-polar solvent like CS₂. The bromine atom will predominantly enter the para position relative to the -NH₂ group, as the amino group is an electron-donating group.
(II) To convert aniline to phenol, we perform diazotization of aniline, followed by hydrolysis. The steps are: 1. React aniline with nitrous acid (HNO₂) to form the diazonium salt.
2. Treat the diazonium salt with water (H₂O), resulting in the displacement of the diazonium group and formation of phenol.