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Why aromatic amines cannot be prepared b...

Why aromatic amines cannot be prepared by Gabriel phthalimide synthesis?

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In Gabriel phthalimide reaction, potassium phthalimide gives phthalimide anion which acts as nucleophile and attacks the electrophilic carbon of alkyl halide, say chloromethane, as shown ahead.

A similar reaction in aryl halides is not possible. This is due to much less reactivity of aryl halides in such reactions (nucleophilic substitution reactions). As such primary aromatic amines cannot be prepared by Gabriel phthalaimide synthesis.
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