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Question:

Method by which aniline cannot be prepared is: reduction of nitrobenzene with H2/Pd in ethanol; potassium salt of phthalimide treated with chlorobenzene followed by hydrolysis with aqueous NaOH solution; hydrolysis of phenylisocyanide with acidic solution; degradation of benzamide with bromine in alkaline solution.

reduction of nitrobenzene withH2/Pdin ethanol

potassium salt of phthalimide treated with chlorobenzene followed by hydrolysis with aqueous NaOH solution

degradation of benzamide with bromine in alkaline solution

hydrolysis of phenylisocyanide with acidic solution

Solution:

Method by which aniline cannot be prepared is the method (B) potassium salt of phthalimide treated with chlorobenzene followed by hydrolysis with aqueous NaOH solution. This is because aryl halides do not undergo nucleophilic substitution with potassium phthalimide under ordinary conditions.