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

Q: What is the correct answer for CBSE12?

The correct answer is C. Gabriel phthalimide synthesis involves the nucleophilic substitution of an alkyl halide by the phthalimide anion. Aromatic primary amines cannot be prepared by this method because aryl halides do not readily undergo nucleophilic substitution with the anion formed by phthalimide due to the partial double bond character of the C-X bond and resonance stabilization of the aryl halide.

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

The correct answer is C. Gabriel phthalimide synthesis involves the nucleophilic substitution of an alkyl halide by the phthalimide anion. Aromatic primary amines cannot be prepared by this method because aryl halides do not readily undergo nucleophilic substitution with the anion formed by phthalimide due to the partial double bond character of the C-X bond and resonance stabilization of the aryl halide.

Q: What are the options for this CBSE12 question?

A. Aryl halides are too reactive. · B. Phthalimide does not react with aromatic compounds. · C. Aryl halides do not undergo nucleophilic substitution with the anion formed by phthalimide. · D. Aromatic amines are unstable under the reaction conditions.

Question

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

FirstInTest · Accepted Answer

Gabriel phthalimide synthesis involves the nucleophilic substitution of an alkyl halide by the phthalimide anion. Aromatic primary amines cannot be prepared by this method because aryl halides do not readily undergo nucleophilic substitution with the anion formed by phthalimide due to the partial double bond character of the C-X bond and resonance stabilization of the aryl halide.

Answer

Aryl halides are too reactive.

Answer

Phthalimide does not react with aromatic compounds.

Answer

Aryl halides do not undergo nucleophilic substitution with the anion formed by phthalimide.

Answer

Aromatic amines are unstable under the reaction conditions.

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