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) 

This page is available to MOC Members only.
Sign up here for about 30 cents/ day!

 

 

Comments

Comment section

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

  1. Does nabh4 also give conjugated nucleophillic addition reaction with alpha beta unsaturated ketone?

    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.

Leave a Reply

Your email address will not be published.

This site uses Akismet to reduce spam. Learn how your comment data is processed.