Question

What are enols and enolates?

Answer 1

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

Explanation:

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.