Organic Chemistry As a Second Language: First Semester Topics
Organic Chemistry As a Second Language: First Semester Topics
4th Edition
ISBN: 9781119110668
Author: David R. Klein
Publisher: WILEY
Question
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Chapter 12.6, Problem 12.33P

(a)

Interpretation Introduction

Interpretation:

Mechanism for the tautomerization process that occurs under acidic conditions has to be drawn.

Concept Introduction:

Keto-enol tautomerization occurs when a hydroxyl group is present next to a double bond in presence of acid or base.  Due to this the ketone will have few amount of enol also.  The quantity of ketone and enol is determined only by equilibrium.

Organic Chemistry As a Second Language: First Semester Topics, Chapter 12.6, Problem 12.33P , additional homework tip  1

Acid catalyzed tautomerization:

Compounds that are ketone can undergo keto-enol tautomerization in presence of acid.  Tautomers are not same as resonance structures.  The chemical properties of tautomers will be different.  A general mechanism of keto-enol tautomerization that occur in acidic condition can be given as,

Organic Chemistry As a Second Language: First Semester Topics, Chapter 12.6, Problem 12.33P , additional homework tip  2

First step is the formation of carbocation.  Second step is the formation of double bond between oxygen and carbon atom.  The water acts as a base and abstracts a proton to form the final keto compound.

(b)

Interpretation Introduction

Interpretation:

Mechanism for the tautomerization process that occurs under basic conditions has to be drawn.

Concept Introduction:

Keto-enol tautomerization occurs when a hydroxyl group is present next to a double bond in presence of acid or base.  Due to this the ketone will have few amount of enol also.  The quantity of ketone and enol is determined only by equilibrium.

Organic Chemistry As a Second Language: First Semester Topics, Chapter 12.6, Problem 12.33P , additional homework tip  3

Base catalyzed tautomerization:

Compounds that are ketone can undergo keto-enol tautomerization in presence of acid.  Tautomers are not same as resonance structures.  The chemical properties of tautomers will be different.  A general mechanism of keto-enol tautomerization that occur in basic condition can be given as,

Organic Chemistry As a Second Language: First Semester Topics, Chapter 12.6, Problem 12.33P , additional homework tip  4

First step is the removal of proton.  Second step is the formation of double bond between oxygen and carbon atom.  The water acts as an acid and donates a proton to form the final keto compound.

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