What are enols and enolates?

Question

2245 views around the world

You can reuse this answer
Creative Commons License

Answer 1 · 2016-05-22T20:52:54

An enol is a tautomer of a carbonyl compound; the enolate is its anion.

Ketones typically undergo tautomerism to give an enol:

$H_3C-C(=O)CH_3 rightleftharpoons H_2C=C(-OH)CH_3$

The enol may be deprotonated to give an enolate:

$H_2C=C(-OH)CH_3 +" Base"rarr H_2C=C(-O^-)CH_3 + "Base"H^+$

This is the enolate form; this is conceived to be in equilibrium with the carbanion:

$H_2C=C(-O^-)CH_3 rightleftharpoons H_2^(-)C-C(=O)CH_3$

Enolates and carbanions are habitually used in organic chemistry to form $C-C$ bonds.