Cyanohydrin formation

Click the structures and reaction arrows in sequence to view the 3D models and animations respectively

View the stereochemical properties of these reactions

Cyanohydrin formation can occur via the attack of cyanide to both aldehydes and ketones, usually in the presence of acid which protonates the resulting alkoxide to give the hydroxy group. Cyanide contains sp hybridised C and N atoms, and its HOMO is an sp orbital on carbon. The reaction is a typical nucleophilic addition reaction to a carbonyl group, with the electron pair from the HOMO of the cyanide (an sp orbital on carbon) moving into the C=O π* orbital, and the electrons from the C=O π orbital moving onto the oxygen atom.

M. North, Synlett, 1993, 1993, 807–820.


How useful was this page?

Click on a star to rate it!

Average rating / 5. Vote count:

No votes so far! Be the first to rate this page.

As you found this page useful...

Follow us on social media!

We are sorry that this page was not useful for you!

Let us improve this page!

Tell us how we can improve this page (in your own language if you prefer)? If you would like a response, please include your email address e.g. [email protected]

Provided by the