The halide shown is treated with sodium cyanide in DMSO. Which structure is the major product?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: D

The halide is 1-bromobutane, an unhindered primary halide, and cyanide is a good nucleophile that is only weakly basic. In a polar aprotic solvent SN2 attack at carbon gives pentanenitrile, not but-1-ene (E2) or the isocyanide.

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