(a) Interpretation: The allowed and reasonable sigmatropic reaction can account for the given reaction 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 1

Question

Chapter 28, Problem 28.19P

Interpretation Introduction

(a)

Interpretation:

The allowed and reasonable sigmatropic reaction can account for the given reaction 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 expected product from a similar reaction of 2,3−dimethyl−1,3−cyclopentadiene 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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Students have asked these similar questions

Draw an approximate reaction-energy diagram showing the curves for the two possible pathways for ionic addition of HBr to 1-methylcyclohexene. (a) Formation of the major product, 1-bromo-1-methylcyclohexane, and (b) formation of the minor product, 1-bromo-2-methylcyclohexane. Point out how these curves show that 1-bromo-1-methylcyclohexane should be formed faster

A student adds NBS to a solution of 1-methylcyclohexene and irradiates the mixture with a sunlamp until all the NBS has reacted. After a careful distillation, the product mixture contains two major products of formula C7H11Br. (a) Draw the resonance forms of the three possible allylic free radical intermediates.

When treated with NaOH, the bromide below gives an alkene by the E2 mechanism, by elimination of the H atom indicated by the arrow: (a) Draw the Newman projection from which elimination takes place. (b) Draw the mechanism. (c) Draw the product with the proper stereochemistry. (d) Assign the proper stereochemical descriptor to the product. (e) Give the rate equation

Answer 2

Question

Chapter 28, Problem 28.19P

Interpretation Introduction

(a)

Interpretation:

The allowed and reasonable sigmatropic reaction can account for the given reaction 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 expected product from a similar reaction of 2,3−dimethyl−1,3−cyclopentadiene 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 28.19P

Interpretation Introduction

(a)

Interpretation:

The allowed and reasonable sigmatropic reaction can account for the given reaction 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 expected product from a similar reaction of 2,3−dimethyl−1,3−cyclopentadiene 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 28.19P

Interpretation Introduction

(a)

Interpretation:

The allowed and reasonable sigmatropic reaction can account for the given reaction 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 expected product from a similar reaction of 2,3−dimethyl−1,3−cyclopentadiene 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 28.19P

Interpretation Introduction

(a)

Interpretation:

The allowed and reasonable sigmatropic reaction can account for the given reaction 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 expected product from a similar reaction of 2,3−dimethyl−1,3−cyclopentadiene 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 28.19P

Interpretation Introduction

(a)

Interpretation:

The allowed and reasonable sigmatropic reaction can account for the given reaction 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 28.19P

Interpretation Introduction

(a)

Interpretation:

The allowed and reasonable sigmatropic reaction can account for the given reaction 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 expected product from a similar reaction of 2,3−dimethyl−1,3−cyclopentadiene 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 expected product from a similar reaction of 2,3−dimethyl−1,3−cyclopentadiene 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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Answer 11

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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 allowed and reasonable sigmatropic reaction can account for the given reaction.

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Chapter 28 Solutions