The ketone shown is treated first with sodium cyanide and acid, and the product is then reduced with an excess of lithium aluminium hydride, followed by work-up. Which structure is the final product?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: C

Acetophenone adds HCN to give the cyanohydrin 2-hydroxy-2-phenylpropanenitrile. Lithium aluminium hydride reduces the nitrile to CH2NH2 and leaves the tertiary OH, giving the beta-amino alcohol 1-amino-2-phenylpropan-2-ol.

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