The Gabriel phthalimide synthesis is a highly specialized reaction. Why is this method strictly unsuitable for the laboratory synthesis of primary aromatic amines such as aniline?

Question

Prashant Kotian · Accepted Answer

Correct answer: C. The critical second step of the Gabriel synthesis requires the phthalimide anion to nucleophilically attack an alkyl halide via an mechanism. Aryl halides possess profound partial double bond character at the bond due to resonance, rendering them highly inert to standard nucleophilic substitution, effectively stopping the synthesis.

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