Why are enols unstable?

1 Answer
Feb 10, 2017

First, the free electrons on the oxygen can act as a base or nucleophile for chemical reactions.

Explanation:

More commonly, one must consider that any time you have an enol, it can undergo tautomerization, a conversion to what is called the keto form. The keto form has a ketone instead of the alcohol and double bond. The conversion between the two forms is possible in acid or base. Simply look for acid/base catalyzed tautomerization to find a mechanism. As a general rule, the keto form is more stable than the enol or enolate form. Therefore one generally has an equilibrium that favors the keto form over the enol form, which mean conversion from enol to keto.

Hope this helped!