Why are enols unstable?

Question

Delilah Anderson · Accepted Answer

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

More generally, one must take into account that any time an enol is present, it can undergo tautomerization, or conversion to what is known as the keto form. This keto form is characterized by the presence of a ketone rather than an alcohol and double bond, and it can be converted between the two forms in either an acidic or basic environment. To determine the mechanism involved, simply search for acid/base catalyzed tautomerization. Generally speaking, the keto form is more stable than the enol or enolate form; hence, one generally has an equilibrium that favors the keto form over the enol form, that is, conversion from enol to keto. I hope this was useful.

Jacob Anderson · Answer

undefined Enols are unstable due to the presence of a double bond between a carbon and an oxygen atom. This configuration leads to resonance structures, causing electron delocalization and instability. Additionally, the hydrogen attached to the oxygen atom in enols is acidic, making them prone to tautomerization into the more stable keto form.