Reaction of the week: Cyanohidrin Formation

Some notes on this reaction before we move on to the mechanism:

• ·         Useful to form new carbon/carbon bonds, as we see in the end product.
• ·         The cyanide anion forms from the HCN by easily ionizing in solution.
• ·         This reaction can be done with aldehydes or ketones. However, the reaction favors the addition product with aldehydes and methyl ketones. The longer your ketone chain is, the less the reaction product is favored.
• ·         In the last step (shown soon), the negatively charged oxygen can be protonated by water or other HCN molecules in solution.
• ·         Since a cyanohydrin is an addition product, the HCN is not a catalyst and is consumed in the reaction.

Let’s go through the mechanism! 

This post was made by Faith, @premedprobs01, a premed student in Colorado aspiring to become an MD working either in oncology or rural primary care internationally. Check out her original blog atwww.goodandfaithfulservice.wordpress.com