(a) Interpretation: The formation of both the isomeric products from the starting material by a sigmatropic rearrangement involving a C − H bond is to be shown. Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

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Answer 1

Question

Chapter 25, Problem 45P

Interpretation Introduction

(a)

Interpretation: The formation of both the isomeric products from the starting material by a sigmatropic rearrangement involving a C−H bond is to be shown.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

Interpretation Introduction

(b)

Interpretation: The reasons as to why 2−methylcyclopenta−1,3−diene is not formed directly from 5−methylcyclopenta−1,3−diene by a [1,3] rearrangement.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

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Students have asked these similar questions

(a) What product is formed when triene N undergoes thermal electrocyclic ring closure? (b)What product is formed when triene N undergoes photochemical ring closure? (c) Label each process as conrotatory or disrotatory.

2) The Diels-Alder reaction, developed by German chemists Otto Diels and Kurt Alder (who received the Nobel Prize in 1950 for their discovery), has great synthetic importance due to the possibility of forming an unsaturated six-membered cycle without involving intermediates ionic. About the reaction, answer: (a) Indicate the reagents necessary for the synthesis of the following compounds, indicating who is the diene and who is the dienophile.

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.

Answer 2

Question

Chapter 25, Problem 45P

Interpretation Introduction

(a)

Interpretation: The formation of both the isomeric products from the starting material by a sigmatropic rearrangement involving a C−H bond is to be shown.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

Interpretation Introduction

(b)

Interpretation: The reasons as to why 2−methylcyclopenta−1,3−diene is not formed directly from 5−methylcyclopenta−1,3−diene by a [1,3] rearrangement.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

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Answer 3

Question

Chapter 25, Problem 45P

Interpretation Introduction

(a)

Interpretation: The formation of both the isomeric products from the starting material by a sigmatropic rearrangement involving a C−H bond is to be shown.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

Interpretation Introduction

(b)

Interpretation: The reasons as to why 2−methylcyclopenta−1,3−diene is not formed directly from 5−methylcyclopenta−1,3−diene by a [1,3] rearrangement.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

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Answer 4

Question

Chapter 25, Problem 45P

Interpretation Introduction

(a)

Interpretation: The formation of both the isomeric products from the starting material by a sigmatropic rearrangement involving a C−H bond is to be shown.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

Interpretation Introduction

(b)

Interpretation: The reasons as to why 2−methylcyclopenta−1,3−diene is not formed directly from 5−methylcyclopenta−1,3−diene by a [1,3] rearrangement.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

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Answer 5

Chapter 25, Problem 45P

Interpretation Introduction

(a)

Interpretation: The formation of both the isomeric products from the starting material by a sigmatropic rearrangement involving a C−H bond is to be shown.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

Interpretation Introduction

(b)

Interpretation: The reasons as to why 2−methylcyclopenta−1,3−diene is not formed directly from 5−methylcyclopenta−1,3−diene by a [1,3] rearrangement.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

Answer 6

Chapter 25, Problem 45P

Interpretation Introduction

(a)

Interpretation: The formation of both the isomeric products from the starting material by a sigmatropic rearrangement involving a C−H bond is to be shown.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

Answer 7

Chapter 25, Problem 45P

Interpretation Introduction

(a)

Interpretation: The formation of both the isomeric products from the starting material by a sigmatropic rearrangement involving a C−H bond is to be shown.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

Answer 8

Interpretation Introduction

(b)

Interpretation: The reasons as to why 2−methylcyclopenta−1,3−diene is not formed directly from 5−methylcyclopenta−1,3−diene by a [1,3] rearrangement.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

Answer 9

Interpretation Introduction

(b)

Interpretation: The reasons as to why 2−methylcyclopenta−1,3−diene is not formed directly from 5−methylcyclopenta−1,3−diene by a [1,3] rearrangement.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 25.1 - Prob. 1P Ch. 25.2 - Problem 27.2 For each molecular orbital in Figure...Ch. 25.2 - Problem 27.3 (a) Using Figure 27.2 as a guide,...Ch. 25.3 - Prob. 4P Ch. 25.3 - Prob. 5P Ch. 25.3 - Prob. 6P Ch. 25.3 - Prob. 7P Ch. 25.3 - Prob. 8P Ch. 25.3 - Prob. 9P Ch. 25.3 - Problem 27.11 What product would be formed by the...

Solution Summary: The author explains the formation of both the isomeric products from the starting material by a sigmatropic rearrangement involving C- H bond.

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Chapter 25 Solutions