The bromide shown is heated with sodium acetate in DMF, where substitution occurs by SN2 and elimination is negligible. Which structure is the main product?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: A

(S)-2-Bromopentane undergoes backside attack by acetate oxygen, giving the ester of the opposite spatial arrangement, (R)-pentan-2-yl acetate. The retained ester would need two inversions or an SN1 path, the alkene is elimination, and the alcohol would need hydrolysis.

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