Why is the Gabriel phthalimide synthesis strictly unsuitable for the preparation of primary aromatic — Amines Chemistry Question

💡 Solution & Explanation

In the Gabriel synthesis, the nucleophilic phthalimide anion must attack an alkyl halide via an $S_N2$ mechanism. Aryl halides (like chlorobenzene) do not undergo facile nucleophilic substitution because the $C-X$ bond acquires partial double bond character due to resonance, and back-side $S_N2$ attack is sterically blocked by the electron-rich benzene ring.