Which of the following amines cannot be prepa | vedclass

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(A) Gabriel phthalimide synthesis is used for the preparation of primary aliphatic amines. In this reaction,potassium phthalimide reacts with an alkyl

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$Ph-NH_2$

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(A) Gabriel phthalimide synthesis is used for the preparation of primary aliphatic amines. In this reaction,potassium phthalimide reacts with an alkyl halide via an $S_N2$ mechanism. Aryl halides do not undergo nucleophilic substitution reactions with the phthalimide anion under these conditions because the carbon-halogen bond in aryl halides has partial double bond character and the electron-rich ring repels the nucleophile. Therefore,aromatic amines like aniline $(Ph-NH_2)$ cannot be prepared by this method.

Which of the following amines cannot be prepared by Gabriel phthalimide synthesis?

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