The keto ester shown is treated with an excess of lithium aluminium hydride in dry ether, followed by aqueous work-up. Which structure is the product?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: C

Methyl 4-oxopentanoate has a ketone and an ester. Lithium aluminium hydride is strong enough to reduce both: the ketone gives a secondary alcohol and the ester gives a primary alcohol (the methoxy group is lost as methanol). The product is pentane-1,4-diol.

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