The following sigmatropic reaction is to be classified and the curved-arrow notation is to be given, the stereochemistry is that expected for a thermal concerted reaction is to be shown.(This reaction, discovered by Prof. J. A. Berson at Yale University, was the first example of this type of pericyclic reaction.) Concept introduction: Sigmatropic reaction can be described as the migration of allylic sigma bond at one end of the π-electron system to the other end of the π-electron system as an uncatalyzed intramolecular reaction. In some cases, Lewis acid catalysts can also be applied. Though, the position of π-bond is changed in Sigmatropic reaction, the total number of π-bonds remain unchanged. The sigma bond can be cleaved at the middle or at the end of the π-system. The formation of sigma bond at 3, 3-position of a 1, 5-diene is called as cope rearrangement.

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Chapter 28, Problem 28.39AP

Interpretation Introduction

Interpretation:

The following sigmatropic reaction is to be classified and the curved-arrow notation is to be given, the stereochemistry is that expected for a thermal concerted reaction is to be shown.(This reaction, discovered by Prof. J. A. Berson at Yale University, was the first example of this type of pericyclic reaction.)

Concept introduction:

Sigmatropic reaction can be described as the migration of allylic sigma bond at one end of the π-electron system to the other end of the π-electron system as an uncatalyzed intramolecular reaction. In some cases, Lewis acid catalysts can also be applied. Though, the position of π-bond is changed in Sigmatropic reaction, the total number of π-bonds remain unchanged. The sigma bond can be cleaved at the middle or at the end of the π-system. The formation of sigma bond at 3, 3-position of a 1, 5-diene is called as cope rearrangement.

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Q1: For each molecule, assign each stereocenter as R or S. Circle the meso compounds. Label each compound as chiral or achiral. + CI OH woཡི།༠w Br H مه D CI ပ။ Br H, Br Br H₂N OMe R IN Ill N S H CI Br CI CI D OH H 1/111

Draw the two products of the reaction. H₂C. CH₂ H :0: CH3 CH₂ +1

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Answer 2

Question

Chapter 28, Problem 28.39AP

Interpretation Introduction

Interpretation:

The following sigmatropic reaction is to be classified and the curved-arrow notation is to be given, the stereochemistry is that expected for a thermal concerted reaction is to be shown.(This reaction, discovered by Prof. J. A. Berson at Yale University, was the first example of this type of pericyclic reaction.)

Concept introduction:

Sigmatropic reaction can be described as the migration of allylic sigma bond at one end of the π-electron system to the other end of the π-electron system as an uncatalyzed intramolecular reaction. In some cases, Lewis acid catalysts can also be applied. Though, the position of π-bond is changed in Sigmatropic reaction, the total number of π-bonds remain unchanged. The sigma bond can be cleaved at the middle or at the end of the π-system. The formation of sigma bond at 3, 3-position of a 1, 5-diene is called as cope rearrangement.

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Answer 3

Question

Chapter 28, Problem 28.39AP

Interpretation Introduction

Interpretation:

The following sigmatropic reaction is to be classified and the curved-arrow notation is to be given, the stereochemistry is that expected for a thermal concerted reaction is to be shown.(This reaction, discovered by Prof. J. A. Berson at Yale University, was the first example of this type of pericyclic reaction.)

Concept introduction:

Sigmatropic reaction can be described as the migration of allylic sigma bond at one end of the π-electron system to the other end of the π-electron system as an uncatalyzed intramolecular reaction. In some cases, Lewis acid catalysts can also be applied. Though, the position of π-bond is changed in Sigmatropic reaction, the total number of π-bonds remain unchanged. The sigma bond can be cleaved at the middle or at the end of the π-system. The formation of sigma bond at 3, 3-position of a 1, 5-diene is called as cope rearrangement.

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Answer 4

Question

Chapter 28, Problem 28.39AP

Interpretation Introduction

Interpretation:

The following sigmatropic reaction is to be classified and the curved-arrow notation is to be given, the stereochemistry is that expected for a thermal concerted reaction is to be shown.(This reaction, discovered by Prof. J. A. Berson at Yale University, was the first example of this type of pericyclic reaction.)

Concept introduction:

Sigmatropic reaction can be described as the migration of allylic sigma bond at one end of the π-electron system to the other end of the π-electron system as an uncatalyzed intramolecular reaction. In some cases, Lewis acid catalysts can also be applied. Though, the position of π-bond is changed in Sigmatropic reaction, the total number of π-bonds remain unchanged. The sigma bond can be cleaved at the middle or at the end of the π-system. The formation of sigma bond at 3, 3-position of a 1, 5-diene is called as cope rearrangement.

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Answer 5

Chapter 28, Problem 28.39AP

Interpretation Introduction

Interpretation:

The following sigmatropic reaction is to be classified and the curved-arrow notation is to be given, the stereochemistry is that expected for a thermal concerted reaction is to be shown.(This reaction, discovered by Prof. J. A. Berson at Yale University, was the first example of this type of pericyclic reaction.)

Concept introduction:

Sigmatropic reaction can be described as the migration of allylic sigma bond at one end of the π-electron system to the other end of the π-electron system as an uncatalyzed intramolecular reaction. In some cases, Lewis acid catalysts can also be applied. Though, the position of π-bond is changed in Sigmatropic reaction, the total number of π-bonds remain unchanged. The sigma bond can be cleaved at the middle or at the end of the π-system. The formation of sigma bond at 3, 3-position of a 1, 5-diene is called as cope rearrangement.

Answer 6

Chapter 28, Problem 28.39AP

Interpretation Introduction

Interpretation:

The following sigmatropic reaction is to be classified and the curved-arrow notation is to be given, the stereochemistry is that expected for a thermal concerted reaction is to be shown.(This reaction, discovered by Prof. J. A. Berson at Yale University, was the first example of this type of pericyclic reaction.)

Concept introduction:

Sigmatropic reaction can be described as the migration of allylic sigma bond at one end of the π-electron system to the other end of the π-electron system as an uncatalyzed intramolecular reaction. In some cases, Lewis acid catalysts can also be applied. Though, the position of π-bond is changed in Sigmatropic reaction, the total number of π-bonds remain unchanged. The sigma bond can be cleaved at the middle or at the end of the π-system. The formation of sigma bond at 3, 3-position of a 1, 5-diene is called as cope rearrangement.

Answer 7

Chapter 28, Problem 28.39AP

Interpretation Introduction

Interpretation:

The following sigmatropic reaction is to be classified and the curved-arrow notation is to be given, the stereochemistry is that expected for a thermal concerted reaction is to be shown.(This reaction, discovered by Prof. J. A. Berson at Yale University, was the first example of this type of pericyclic reaction.)

Concept introduction:

Sigmatropic reaction can be described as the migration of allylic sigma bond at one end of the π-electron system to the other end of the π-electron system as an uncatalyzed intramolecular reaction. In some cases, Lewis acid catalysts can also be applied. Though, the position of π-bond is changed in Sigmatropic reaction, the total number of π-bonds remain unchanged. The sigma bond can be cleaved at the middle or at the end of the π-system. The formation of sigma bond at 3, 3-position of a 1, 5-diene is called as cope rearrangement.

Answer 8

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Answer 11

Ch. 28 - Prob. 28.1P Ch. 28 - Prob. 28.2P Ch. 28 - Prob. 28.3P Ch. 28 - Prob. 28.4P Ch. 28 - Prob. 28.5P Ch. 28 - Prob. 28.6P Ch. 28 - Prob. 28.7P Ch. 28 - Prob. 28.8P Ch. 28 - Prob. 28.9P Ch. 28 - Prob. 28.10P

Solution Summary: The author explains how the sigmatropic reaction is explained using curved-arrowed mechanism.

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Chapter 28 Solutions