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Question
Why cannot aniline be prepared by Gabriel phthalimide synthesis?
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Solution
- Gabriel phthalimide synthesis is used for the preparation of aliphatic primary amines.
- It involves the nucleophilic substitution 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.
Hence, aniline cannot be prepared by Gabriel phthalimide synthesis.
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