Which reducing agent reduces esters to alcohols?

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Multiple Choice

Which reducing agent reduces esters to alcohols?

To push an ester all the way to a primary alcohol you need a strong hydride donor that can break the ester C–O bond and deliver hydride twice, once to form an aldehyde intermediate and again to give the alcohol after workup. Lithium aluminium hydride provides several hydride equivalents and is powerful enough to reduce esters to alcohols. Sodium borohydride is a milder reductant and typically reduces aldehydes and ketones but not esters under normal conditions, so it won’t efficiently convert esters to alcohols. PCC is an oxidizing agent, not a reducing one, so it won’t perform this transformation. Hydrogenation over Pd/C can reduce many groups, but esters generally aren’t reduced to alcohols reliably by simple catalytic hydrogenation; stronger reducing conditions like LiAlH4 are the standard route.

To push an ester all the way to a primary alcohol you need a strong hydride donor that can break the ester C–O bond and deliver hydride twice, once to form an aldehyde intermediate and again to give the alcohol after workup. Lithium aluminium hydride provides several hydride equivalents and is powerful enough to reduce esters to alcohols.

Sodium borohydride is a milder reductant and typically reduces aldehydes and ketones but not esters under normal conditions, so it won’t efficiently convert esters to alcohols. PCC is an oxidizing agent, not a reducing one, so it won’t perform this transformation. Hydrogenation over Pd/C can reduce many groups, but esters generally aren’t reduced to alcohols reliably by simple catalytic hydrogenation; stronger reducing conditions like LiAlH4 are the standard route.

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