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Sodium Borohydraride reduction of a Ketone; Hydrobenzoin from Benzil

Accepted Answer

Sodium borohydride (NaBH4) is a common reducing agent used to reduce ketones to secondary alcohols. In the case of benzil reduction, NaBH4 will convert the two ketone groups in benzil to two hydroxyl groups, yielding hydrobenzoin. The reaction proceeds via a nucleophilic attack of the hydride ion (H-) from NaBH4 on the carbonyl carbon of the ketone, followed by protonation of the resulting alkoxide intermediate. This reaction is typically carried out in a protic solvent like methanol or ethanol.


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