Question

The method by which aniline cannot be prepared is

• A. Nitration of benzene followed by reduction with Sn and con HCI
• B. Degradation of benzamide with bromine in alkaline solution
• C. Reduction of nitrobenzene with $H_2 / Pd$ is ethanol
• D. Potassium salt of phthalimide treated with chlorgbenzene followed by the hydrolysis with aqueous NaOH solution

Answer 1

Answer: (D)

Potassium salt of phthalimide treated with chlorgbenzene followed by the hydrolysis with aqueous NaOH solution

Answer 2

Gabriel phthalimide synthesis not preferred for preparing aniline because amine formation involves
nucleophilic substitution of alkyl halides by the anion formed by phthalimide. But aryl halides do not
undergo nucleophilic substitution.