The compound shown is treated with excess LiAlH4 in dry ether, followed by aqueous work-up. Which structure is the organic product?

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The compound shown is treated with excess $LiAlH X_{4}$ in dry ether, followed by aqueous work-up. Which structure is the organic product?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: C

The compound is methyl benzoate.

LiAlH X_{4}

reduces an ester fully to the primary alcohol (and releases methanol), so benzyl alcohol is formed. The aldehyde is only an intermediate that is reduced faster than the ester, and the acid is an oxidation level that is not produced.

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The compound shown is treated with excess LiAlHX4​ in dry ether, followed by aqueous work-up. Which structure is the organic product?

Answer: C

More questions on Hydride reductions of drawn compounds (LiAlH4 / NaBH4 / DIBAL-H)

The compound shown is treated with excess $LiAlH X_{4}$ in dry ether, followed by aqueous work-up. Which structure is the organic product?