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What is the principal product formed in the following reaction? CH3CH = CHCO2CH3 LiAlH4 →

1. CH3CH2CH2CO2CH3
2. CH3CH = CHCH2OH
3. CH3CH2CH2CH2OH
4. CH3CH2CH2CHO

Correct answer: CH3CH = CHCH2OH

Solution

LiAlH4 reduces the -CO2CH3 ester group to a primary alcohol but does not reduce the carbon-carbon double bond, giving CH3CH=CHCH2OH.

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