The cyclic ketone shown is treated with sodium cyanide and acid, and the resulting product is then heated with aqueous acid. Which structure is the final product?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: D

Cyclopentanone adds HCN to give the cyanohydrin, 1-hydroxycyclopentanecarbonitrile. Hot aqueous acid hydrolyses the nitrile to a carboxylic acid without removing the tertiary OH, giving 1-hydroxycyclopentanecarboxylic acid.

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