(a) Interpretation: The following pericyclic reaction is to be classified. (More than one classification is possible.) 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.

Question

Want to see the full answer?

Answer 1

Question

Chapter 28, Problem 28.32AP

Interpretation Introduction

(a)

Interpretation:

The following pericyclic reaction is to be classified. (More than one classification is possible.)

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.

Interpretation Introduction

(b)

Interpretation:

Suppose the migrating methyl group in part (a) were labeled with the hydrogen isotopes deuterium (D) and tritium (T) so that it is a -CHDT group with the S configuration. The configuration of this group in the product is to be stated.

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

21.38 Arrange the molecules in each set in order of increasing acidity (from least acidic to most acidic). OH OH SH NH2 8 NH3 OH (b) OH OH OH (c) & & & CH3 NO2 21.39 Explain the trends in the acidity of phenol and the monofluoro derivatives of phenol. OH OH OH OH PK 10.0 PK 8.81 PK 9.28 PK 9.81

identify which spectrum is for acetaminophen and which is for phenacetin

The Concept of Aromaticity 21.15 State the number of 2p orbital electrons in each molecule or ion. (a) (b) (e) (f) (c) (d) (h) (i) DA (k) 21.16 Which of the molecules and ions given in Problem 21.15 are aromatic according to the Hückel criteria? Which, if planar, would be antiaromatic? 21.17 Which of the following structures are considered aromatic according to the Hückel criteria? ---0-0 (a) (b) (c) (d) (e) (h) H -H .8.0- 21.18 Which of the molecules and ions from Problem 21.17 have electrons donated by a heteroatom?

Answer 2

Question

Chapter 28, Problem 28.32AP

Interpretation Introduction

(a)

Interpretation:

The following pericyclic reaction is to be classified. (More than one classification is possible.)

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.

Interpretation Introduction

(b)

Interpretation:

Suppose the migrating methyl group in part (a) were labeled with the hydrogen isotopes deuterium (D) and tritium (T) so that it is a -CHDT group with the S configuration. The configuration of this group in the product is to be stated.

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 3

Question

Chapter 28, Problem 28.32AP

Interpretation Introduction

(a)

Interpretation:

The following pericyclic reaction is to be classified. (More than one classification is possible.)

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.

Interpretation Introduction

(b)

Interpretation:

Suppose the migrating methyl group in part (a) were labeled with the hydrogen isotopes deuterium (D) and tritium (T) so that it is a -CHDT group with the S configuration. The configuration of this group in the product is to be stated.

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 4

Question

Chapter 28, Problem 28.32AP

Interpretation Introduction

(a)

Interpretation:

The following pericyclic reaction is to be classified. (More than one classification is possible.)

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.

Interpretation Introduction

(b)

Interpretation:

Suppose the migrating methyl group in part (a) were labeled with the hydrogen isotopes deuterium (D) and tritium (T) so that it is a -CHDT group with the S configuration. The configuration of this group in the product is to be stated.

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 5

Chapter 28, Problem 28.32AP

Interpretation Introduction

(a)

Interpretation:

The following pericyclic reaction is to be classified. (More than one classification is possible.)

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.

Interpretation Introduction

(b)

Interpretation:

Suppose the migrating methyl group in part (a) were labeled with the hydrogen isotopes deuterium (D) and tritium (T) so that it is a -CHDT group with the S configuration. The configuration of this group in the product is to be stated.

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.

Answer 6

Chapter 28, Problem 28.32AP

Interpretation Introduction

(a)

Interpretation:

The following pericyclic reaction is to be classified. (More than one classification is possible.)

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 28.32AP

Interpretation Introduction

(a)

Interpretation:

The following pericyclic reaction is to be classified. (More than one classification is possible.)

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

Interpretation Introduction

(b)

Interpretation:

Suppose the migrating methyl group in part (a) were labeled with the hydrogen isotopes deuterium (D) and tritium (T) so that it is a -CHDT group with the S configuration. The configuration of this group in the product is to be stated.

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.

Answer 9

Interpretation Introduction

(b)

Interpretation:

Suppose the migrating methyl group in part (a) were labeled with the hydrogen isotopes deuterium (D) and tritium (T) so that it is a -CHDT group with the S configuration. The configuration of this group in the product is to be stated.

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.

Answer 10

Expert Solution & Answer

Answer 11

Expert Solution & Answer

Answer 12

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 13

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 that the pericyclic reaction can be classified as an uncatalyzed intramolecular reaction.

Concept explainers

Want to see the full answer?

Chapter 28 Solutions