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 chlorobenzene followed by hydrolysis with aqueous $\mathrm{NaOH}$ solution
D) hydrolysis of phenylisocyanide with acidic solution.
Answer: potassium salt of phthalimide treated with chlorobenzene 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.
