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Chemistry · Glossary

What is Tautomerism?

Also known as: tautomers · keto--enol tautomerism · enol

Definition 25.1 University Chemistry — Year 2 · Chapter 25 — Enols, Enolates and the Aldol Reaction

Tautomers are isomers that interconvert by moving a hydrogen and a double bond. In keto–enol tautomerism, a carbonyl compound with a hydrogen on the carbon next to the carbonyl (the keto form) is in equilibrium with its enol, an alcohol carried by a C=C\ce{C=C} double bond.

Propanone and its enol, prop-1-en-2-ol. Acid (protonation of the carbonyl oxygen, then loss of an  hydrogen) or base (removal of an  hydrogen, then protonation of the oxygen) catalyses the interconversion; the equilibrium lies far on the side of the keto form.
Propanone and its enol, prop-1-en-2-ol. Acid (protonation of the carbonyl oxygen, then loss of an α\alpha hydrogen) or base (removal of an α\alpha hydrogen, then protonation of the oxygen) catalyses the interconversion; the equilibrium lies far on the side of the keto form.
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