Essential Organic Chemistry, Global Edition
Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
Question
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Chapter 12.10, Problem 26P

(a)

Interpretation Introduction

Interpretation: The major product of the given reaction has to be identified.

Concept Introduction:

Major product in the reaction of α,β- unsaturated carbonyl compounds with weak bases:

α,β- Unsaturated carbonyl compounds on reaction with weak bases gives conjugate addition products as the major products as shown in the following general scheme:

General scheme:

  Essential Organic Chemistry, Global Edition, Chapter 12.10, Problem 26P , additional homework tip  1

It can be observed that the conjugate addition product has been formed by the addition of basic anion to the beta-carbon atom and that of hydrogen atom to the alpha-carbon carbon atom.

The examples for the weak bases are:

  HBrCH3SHCH3OHNH3

(b)

Interpretation Introduction

Interpretation: The major product of the given reaction has to be found.

Concept Introduction:

Major product in the reaction of α,β- unsaturated carbonyl compounds with strong bases:

α,β- Unsaturated carbonyl compounds on reaction with strong bases gives direct addition products as the major products as shown in the following general scheme:

General scheme:

Essential Organic Chemistry, Global Edition, Chapter 12.10, Problem 26P , additional homework tip  2

It can be observed that the direct addition product has been formed from the direct reaction of the strong base with the carbonyl functional group of the α,β- unsaturated carbonyl compounds.

The examples for the strong bases are:

CH3Mg2+BrGignardreagentNaBH4H-hydridedonor

(c)

Interpretation Introduction

Interpretation: The major product of the given reaction has to be found.

Concept Introduction:

Major product in the reaction of α,β- unsaturated carbonyl compounds with weak bases:

α,β- Unsaturated carbonyl compounds on reaction with weak bases gives conjugate addition products as the major products as shown in the following general scheme:

General scheme:

Essential Organic Chemistry, Global Edition, Chapter 12.10, Problem 26P , additional homework tip  3

It can be observed that the conjugate addition product has been formed by the addition of basic anion to the beta-carbon atom and that of hydrogen atom to the alpha-carbon carbon atom.

The examples for the weak bases are:

HBrCH3SHCH3OHNH3

(d)

Interpretation Introduction

Interpretation: The major product of the given reaction has to be found.

Concept Introduction:

Major product in the reaction of α,β- unsaturated carbonyl compounds with strong bases:

α,β- Unsaturated carbonyl compounds on reaction with strong bases gives direct addition products as the major products as shown in the following general scheme:

General scheme:

Essential Organic Chemistry, Global Edition, Chapter 12.10, Problem 26P , additional homework tip  4

It can be observed that the direct addition product has been formed from the direct reaction of the strong base with the carbonyl functional group of the α,β- unsaturated carbonyl compounds.

The examples for the strong bases are:

CH3Mg2+BrGignardreagentNaBH4H-hydridedonor

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