What functional group transformation is achieved during the reduction of an ester with lithium aluminum hydride (LiAlH4) followed by aqueous workup?
Answer and explanation
Correct answer: A. Reduction to two primary alcohol molecules
- Step 1: LiAlH4 is a powerful reducing agent that delivers hydride ions to the carbonyl carbon of esters. Step 2. The ester carbonyl is reduced to an alkoxide that protonates to a primary alcohol, and the leaving alkoxy group also protonates to form an alcohol. Answer: Reduction to two primary alcohol molecules. Why not the others: DIBAL-H at -78 °C gives aldehydes; LiAlH4 completely reduces esters to primary alcohols.
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