(a) Interpretation: An orbital symmetry analysis for showing the suprafacial [ 1 , 5 ] carbon migrations that should occur with retention of configuration in the migrating group is to be stated. Concept introduction: The pericyclic reactions in which one sigma bond is converted to another sigma bond within the uncatalyzed intramolecular reaction are known as sigmatropic reactions. In this rearrangement, the shifting of one substituent from one region of a π − system to another region takes place simultaneously.

Question

Show how to construct themolecular orbitals of a conjugatedcyclic system similar to benzene andcyclobutadiene

Answer 1

Question

Chapter 28, Problem 28.18P

Interpretation Introduction

(a)

Interpretation:

An orbital symmetry analysis for showing the suprafacial [1,5] carbon migrations that should occur with retention of configuration in the migrating group is to be stated.

Concept introduction:

The pericyclic reactions in which one sigma bond is converted to another sigma bond within the uncatalyzed intramolecular reaction are known as sigmatropic reactions. In this rearrangement, the shifting of one substituent from one region of a π− system to another region takes place simultaneously.

Interpretation Introduction

(b)

Interpretation:

The type of sigmatropic reactions that is involved in the given reactions is to be stated. Whether the stereochemistry of the first step is according to the predictions of orbital symmetry or not is to be stated.

Concept introduction:

The pericyclic reactions in which one sigma bond is converted to another sigma bond within the uncatalyzed intramolecular reaction are known as sigmatropic reactions. In this rearrangement, the shifting of one substituent from one region of a π− system to another region takes place simultaneously.

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Show how to construct themolecular orbitals of a conjugatedcyclic system similar to benzene andcyclobutadiene

Predict the electronic configurations of (a) the benzeneanion, (b) the benzene cation. Estimate the π-bond energy in each case.

The Diels–Alder reaction between butadiene and dimethyl maleate yields a ring structure, as shown in the product. Complete the structure by drawing any missing bonds and indicating the stereochemistry of the new stereocenters.

Answer 2

Question

Chapter 28, Problem 28.18P

Interpretation Introduction

(a)

Interpretation:

An orbital symmetry analysis for showing the suprafacial [1,5] carbon migrations that should occur with retention of configuration in the migrating group is to be stated.

Concept introduction:

The pericyclic reactions in which one sigma bond is converted to another sigma bond within the uncatalyzed intramolecular reaction are known as sigmatropic reactions. In this rearrangement, the shifting of one substituent from one region of a π− system to another region takes place simultaneously.

Interpretation Introduction

(b)

Interpretation:

The type of sigmatropic reactions that is involved in the given reactions is to be stated. Whether the stereochemistry of the first step is according to the predictions of orbital symmetry or not is to be stated.

Concept introduction:

The pericyclic reactions in which one sigma bond is converted to another sigma bond within the uncatalyzed intramolecular reaction are known as sigmatropic reactions. In this rearrangement, the shifting of one substituent from one region of a π− system to another region takes place simultaneously.

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Answer 3

Question

Chapter 28, Problem 28.18P

Interpretation Introduction

(a)

Interpretation:

An orbital symmetry analysis for showing the suprafacial [1,5] carbon migrations that should occur with retention of configuration in the migrating group is to be stated.

Concept introduction:

The pericyclic reactions in which one sigma bond is converted to another sigma bond within the uncatalyzed intramolecular reaction are known as sigmatropic reactions. In this rearrangement, the shifting of one substituent from one region of a π− system to another region takes place simultaneously.

Interpretation Introduction

(b)

Interpretation:

The type of sigmatropic reactions that is involved in the given reactions is to be stated. Whether the stereochemistry of the first step is according to the predictions of orbital symmetry or not is to be stated.

Concept introduction:

The pericyclic reactions in which one sigma bond is converted to another sigma bond within the uncatalyzed intramolecular reaction are known as sigmatropic reactions. In this rearrangement, the shifting of one substituent from one region of a π− system to another region takes place simultaneously.

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Answer 4

Question

Chapter 28, Problem 28.18P

Interpretation Introduction

(a)

Interpretation:

An orbital symmetry analysis for showing the suprafacial [1,5] carbon migrations that should occur with retention of configuration in the migrating group is to be stated.

Concept introduction:

The pericyclic reactions in which one sigma bond is converted to another sigma bond within the uncatalyzed intramolecular reaction are known as sigmatropic reactions. In this rearrangement, the shifting of one substituent from one region of a π− system to another region takes place simultaneously.

Interpretation Introduction

(b)

Interpretation:

The type of sigmatropic reactions that is involved in the given reactions is to be stated. Whether the stereochemistry of the first step is according to the predictions of orbital symmetry or not is to be stated.

Concept introduction:

The pericyclic reactions in which one sigma bond is converted to another sigma bond within the uncatalyzed intramolecular reaction are known as sigmatropic reactions. In this rearrangement, the shifting of one substituent from one region of a π− system to another region takes place simultaneously.

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Answer 5

Chapter 28, Problem 28.18P

Interpretation Introduction

(a)

Interpretation:

An orbital symmetry analysis for showing the suprafacial [1,5] carbon migrations that should occur with retention of configuration in the migrating group is to be stated.

Concept introduction:

The pericyclic reactions in which one sigma bond is converted to another sigma bond within the uncatalyzed intramolecular reaction are known as sigmatropic reactions. In this rearrangement, the shifting of one substituent from one region of a π− system to another region takes place simultaneously.

Interpretation Introduction

(b)

Interpretation:

The type of sigmatropic reactions that is involved in the given reactions is to be stated. Whether the stereochemistry of the first step is according to the predictions of orbital symmetry or not is to be stated.

Concept introduction:

The pericyclic reactions in which one sigma bond is converted to another sigma bond within the uncatalyzed intramolecular reaction are known as sigmatropic reactions. In this rearrangement, the shifting of one substituent from one region of a π− system to another region takes place simultaneously.

Answer 6

Chapter 28, Problem 28.18P

Interpretation Introduction

(a)

Interpretation:

An orbital symmetry analysis for showing the suprafacial [1,5] carbon migrations that should occur with retention of configuration in the migrating group is to be stated.

Concept introduction:

The pericyclic reactions in which one sigma bond is converted to another sigma bond within the uncatalyzed intramolecular reaction are known as sigmatropic reactions. In this rearrangement, the shifting of one substituent from one region of a π− system to another region takes place simultaneously.

Answer 7

Chapter 28, Problem 28.18P

Interpretation Introduction

(a)

Interpretation:

An orbital symmetry analysis for showing the suprafacial [1,5] carbon migrations that should occur with retention of configuration in the migrating group is to be stated.

Concept introduction:

The pericyclic reactions in which one sigma bond is converted to another sigma bond within the uncatalyzed intramolecular reaction are known as sigmatropic reactions. In this rearrangement, the shifting of one substituent from one region of a π− system to another region takes place simultaneously.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The type of sigmatropic reactions that is involved in the given reactions is to be stated. Whether the stereochemistry of the first step is according to the predictions of orbital symmetry or not is to be stated.

Concept introduction:

The pericyclic reactions in which one sigma bond is converted to another sigma bond within the uncatalyzed intramolecular reaction are known as sigmatropic reactions. In this rearrangement, the shifting of one substituent from one region of a π− system to another region takes place simultaneously.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The type of sigmatropic reactions that is involved in the given reactions is to be stated. Whether the stereochemistry of the first step is according to the predictions of orbital symmetry or not is to be stated.

Concept introduction:

The pericyclic reactions in which one sigma bond is converted to another sigma bond within the uncatalyzed intramolecular reaction are known as sigmatropic reactions. In this rearrangement, the shifting of one substituent from one region of a π− system to another region takes place simultaneously.

Answer 10

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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 pericyclic reactions are known as sigmatropic reactions. The HOMO and LUMO of the migrating carbon cation involve in the bonding interaction which is suprafacial

Chapter 28 Solutions