Master Organic Chemistry Reaction Guide

Addition of NaBH4 to ketones to give secondary alcohols

Description:  Addition of sodium borohydride (NaBH4) to ketones gives secondary alcohols (after addition of acid) Content available for Reactionguide members only. Not a member? Get access for about 30 cents / day!

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5 thoughts on “Addition of NaBH4 to ketones to give secondary alcohols

    1. It can; you might find this to be somewhat textbook dependent. In practice, it can go either way. To get addition to occur exclusively on the carbonyl carbon, sometimes cerium trichloride is used. Google “Luche reduction”

    1. The hydride in NaH behaves like a strong base rather than a nucleophile. Since hydride is so small, it’s not polarizable and therefore not nucleophilic. BH4- is nucleophilic.

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