PYQ NEET- Organic Compounds Containing Nitrogen L-1

Question: Method by which aniline cannot be prepared is#

A) degradation of benzamide with bromine in alkaline solution

B) reduction of nitrobenzene with $\mathrm{H}_2 / \mathrm{Pd}$ in ethanol

C) potassium salt of phthalimide treated with benzene followed by hydrolysis with aqueous $\mathrm{NaOH}$ solution

D) hydrolysis of phenylisocyanide with acidic solution.

potassium salt of phthalimide treated with benzoyl chloride followed by hydrolysis with aqueous $\mathrm{NaOH}$ solution#

Sol:#

Aniline cannot be prepared by this method because aryl halides do not undergo nucleophilic substitution reaction with potassium phthalimide under mild conditions.