Mark the reaction that does not yield aniline from the given options:
Hydrolysis of phenyl isocyanide with an acidic solution
Degradation of benzamide with bromine in alkaline solution
Reduction of nitrobenzene with in ethanol
Treatment of potassium salt of phthalimide with chlorobenzene followed by hydrolysis in an aqueous NaOH solution
Gabriel phthalimide synthesis is used for the preparation of primary aliphatic amines. It cannot be used for the preparation of primary aromatic amines (like aniline) because aryl halides (such as chlorobenzene) do not undergo nucleophilic substitution with the anion formed by phthalimide due to the resonance stabilization and partial double bond character of the C-Cl bond.
Other reactions:
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