Method by which aniline cannot be prepared is

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(C) Aniline cannot be prepared by the reaction of potassium phthalimide with chlorobenzene because chlorobenzene does not undergo nucleophilic substit

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

Vedclass · Answer

(C) Aniline cannot be prepared by the reaction of potassium phthalimide with chlorobenzene because chlorobenzene does not undergo nucleophilic substitution reaction under mild conditions. This is because the $C-Cl$ bond in chlorobenzene acquires partial double bond character due to resonance,making it resistant to nucleophilic attack by the phthalimide anion. Therefore,the Gabriel phthalimide synthesis is not suitable for the preparation of aromatic primary amines using aryl halides.

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