Q.

Method by which aniline cannot be prepared is

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a

degradation of benzamide with bromine in alkaline solution

b

reduction of nitrobenzene with H2 / Pd in ethanol

c

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

d

hydrolysis of phenylisocyanide with acidic solution.

answer is C.

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Detailed Solution

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