Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 20, Problem 20.53P

(a)

Interpretation Introduction

Interpretation: The product formation in the given example of Cope rearrangement of 1,5-diene has to be shown.

Concept Introduction:

Cope-rearrangement:

It is a pericyclic reaction that involves the redistribution of six electrons through the formation of a cyclic transition state from which a 1,5-diene gets converted into its isomeric form.

Example with mechanism of cope-arrangement:

Organic Chemistry, Chapter 20, Problem 20.53P , additional homework tip  1

In this mechanism, two pi-bonds and one sigma bond of the reactant molecule has been rearranged and formed two new pi-bonds through a cyclic transition state.

Identification of cope-rearrangement in a1,5-diene:

In the cope-rearrangement, the flow of electrons takes place between six bonds that are bonded as C=C-C-C-C=C. Identification of such a bonding pattern in a 1,5-diene indicates the possibility of Cope rearrangement to occur as shown here:

Organic Chemistry, Chapter 20, Problem 20.53P , additional homework tip  2

The carbon atoms that are involving in the cope-rearrangement are shown in bold.

(b)

Interpretation Introduction

Interpretation: The product formation in the given example of Cope rearrangement of 1,5-diene has to be shown.

Concept Introduction:

Cope-rearrangement:

It is a pericyclic reaction that involves the redistribution of six electrons through the formation of a cyclic transition state from which a 1,5-diene gets converted into its isomeric form.

Example with mechanism of cope-arrangement:

Organic Chemistry, Chapter 20, Problem 20.53P , additional homework tip  3

In this mechanism, two pi-bonds and one sigma bond of the reactant molecule has been rearranged and formed two new pi-bonds through a cyclic transition state.

Identification of cope-rearrangement in a1,5-diene:

In the cope-rearrangement, the flow of electrons takes place between six bonds that are bonded as C=C-C-C-C=C. Identification of such a bonding pattern in a 1,5-diene indicates the possibility of Cope rearrangement to occur as shown here:

Organic Chemistry, Chapter 20, Problem 20.53P , additional homework tip  4

The carbon atoms that are involving in the cope-rearrangement are shown in bold.

(c)

Interpretation Introduction

Interpretation: The product formation in the given example of Cope rearrangement of 1,5-diene has to be shown.

Concept Introduction:

Cope-rearrangement:

It is a pericyclic reaction that involves the redistribution of six electrons through the formation of a cyclic transition state from which a 1,5-diene gets converted into its isomeric form.

Example with mechanism of cope-arrangement:

Organic Chemistry, Chapter 20, Problem 20.53P , additional homework tip  5

In this mechanism, two pi-bonds and one sigma bond of the reactant molecule has been rearranged and formed two new pi-bonds through a cyclic transition state.

Identification of cope-rearrangement in a1,5-diene:

In the cope-rearrangement, the flow of electrons takes place between six bonds that are bonded as C=C-C-C-C=C. Identification of such a bonding pattern in a 1,5-diene indicates the possibility of Cope rearrangement to occur as shown here:

Organic Chemistry, Chapter 20, Problem 20.53P , additional homework tip  6

The carbon atoms that are involving in the cope-rearrangement are shown in bold.

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Chapter 20 Solutions

Organic Chemistry

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