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Why cannot aromatic primary amines be prepared by Gabriel phthalimide synthesis?

Why cannot aromatic primary amines be prepared by Gabriel phthalimide synthesis?

Grade:11

2 Answers

Gaurav
askIITians Faculty 164 Points
9 years ago
Hello Student
Gabrielphthalimidesynthesis is used for the preparation of aliphatic primary amines. It involvesnucleophilicsubstitution (SN2) of alkyl halides by the anion formed by the phthalimide.
But aryl halides do not undergo nucleophilic substitution with the anion formed by the phthalimide.
Anjali parashar
13 Points
7 years ago
One of the step of Gabriel`s synthesis involves nucleophilic substitution of alkyl halide in which halo group is replaced by phthalimide ion . Aryl halide do not undergo nucleophilic substitution under ordinary conditions because of resonance stabilisation and partial double bond character of aryl halogen bond. Therefore, they don`t react with potassium phthalimide to form N-phenyl phthalimide. Consequently , aniline and other aromatic amines cannot be prepared by Gabriel`s phthalimide synthesis

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