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Aldehyde Reactions: Formation of Alcohol from Aldehyde, Ketone using NaBH4

Primary and secondary alcohols can be formed from aldehydes and ketones (respectively) using sodium borohydride (NaBH4):

Aldehyde Reactions: Formation of Alcohol from Aldehyde, Ketone using NaBH4 image1.png

This is a straightforward reaction. Visually, change the double bond to a single bond, add a H atom to the O, and the reaction is complete. If studying for a test or the MCATs, this reaction is the same as LiAlH4 and represents one of two ways to reduce aldehydes/ketones:

LiAlH4/NaBH4 ExampleAldehyde Reactions: Formation of Alcohol from Aldehyde, Ketone using NaBH4 image3.png

The reaction mechanism is depicted below:

Aldehyde Reactions: Formation of Alcohol from Aldehyde, Ketone using NaBH4 image2.png

In the first step, the hydrogen-boron bond breaks forming a hydride ion, which attacks the carbon atom that is part of the aldehyde/ketone functional group. This breaks the double bond between carbon and oxygen, sending the electrons to the oxygen atom.

In the second step, the newly acquired lone pair electrons on the oxygen atom attack a nearby MeOH (methanol) molecule, stripping away its proton, finishing the reaction.

The reagents used for this reaction are NaBH4and usually some sort of acid workup (H+, H3O+, H2SO4), or combined with another alcohol (MeOH, EtOH).