The reagent shown is used in the Gabriel synthesis. Select all the amines that can NOT be prepared in a useful yield by this method.

AStructure A
BStructure B
CStructure C
DStructure D

Answer: B, C

The compound shown is phthalimide. The Gabriel route needs SN2 on a primary alkyl or benzylic halide, giving primary amines only. Butylamine (A) and benzylamine (D) are accessible. Tert-butylamine (B) would need a tertiary halide, which eliminates, and aniline (C) would need an aryl halide, which does not undergo SN2.

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