Chapter 9.7, Problem 17ATS

Interpretation Introduction

Interpretation:

Tautomer form of warfarin having three carbonyl groups has to be drawn; a mechanism has to be shown for its formation.

Concept Introduction

Keto-Enol tautomerization: The enol and keto are said to be tautomer, are constitutional isomers that rapidly interconvert via the migration of a proton. The interconversion between an enol and a ketone is called keto-enol tautomerization. Tautomerization is an equilibrium process, that the equilibrium will establish specific concentrations for both the enol and the ketone. Once the equilibrium is reached, the concentrations of ketone and enol can be measured.

The tautomerization is catalyzed by even trace amounts of acid (or base).