Essential Organic Chemistry, Global Edition
Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 13.2, Problem 7P
Interpretation Introduction

Interpretation:

The two enol tautomer of the given compound has to be drawn and more stable structure has to be identified.

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).

Tautomerism is the ability of a molecule to exist in more than one chemical form.

Tautomers are formed by the migration of a hydrogen atom, accompanied by the switching of a single and neighboring double bond.

The only difference in keto-enol tautomers is the location of hydrogen and double bond.

Essential Organic Chemistry, Global Edition, Chapter 13.2, Problem 7P

Enol tautomer is much less stable than the keto tautomer.

Enol tautomer is more stable when enol tautomer is aromatic or when the double bonds are conjugated.

Resonance: The delocalization of electrons which is characterized as several structural changes.

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Draw the keto- tautomer for the following enols
Draw enol tautomer(s) for each compound. Ignore stereoisomers.
Draw the keto tautomer of each enol.

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Essential Organic Chemistry, Global Edition

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