Which of the following foundational organic functional groups is definitively NOT reduced by the mild hydride donor sodium borohydride ( ) in an alcoholic solvent, but is instead readily and completel

Question

Which of the following foundational organic functional groups is definitively NOT reduced by the mild hydride donor sodium borohydride ( $NaBH_4$ ) in an alcoholic solvent, but is instead readily and completely reduced by lithium aluminum hydride ( $LiAlH_4$ )?

Prashant Kotian · Accepted Answer

Correct answer: C. Sodium borohydride ( ) is a notably mild and highly selective hydride donor. It successfully reduces highly electrophilic, unhindered carbonyls like aldehydes, ketones, and extremely reactive acid chlorides into their respective alcohols. However, it is fundamentally too weak to attack less electrophilic, resonance-stabilized carbonyls like esters, carboxylic acids, or amides. The much more powerful is required to aggressively reduce esters directly to primary alcohols.

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