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

A $C X_{6} H X_{5} NH X_{2}$
B $(CH X_{3}) X_{2} CHCH X_{2} NH X_{2}$
C $C X_{6} H X_{5} CH X_{2} NH X_{2}$
D $CH X_{3} CH X_{2} NH X_{2}$

Answer: A

Gabriel synthesis needs an SN2 attack of the phthalimide anion on an alkyl halide, so only primary aliphatic amines are obtained. Aryl halides do not undergo this substitution, so aniline cannot be made this way. The other three come from primary alkyl halides.

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