(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

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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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Five isomeric alkenes. A through each undergo catalytic hydrogenation to give 2-methylpentane The IR spectra of these five alkenes have the key absorptions (in cm Compound Compound A –912. (§), 994 (5), 1643 (%), 3077 (1) Compound B 833 (3), 1667 (W), 3050 (weak shoulder on C-Habsorption) Compound C Compound D) –714 (5), 1665 (w), 3010 (m) 885 (3), 1650 (m), 3086 (m) 967 (5), no aharption 1600 to 1700, 3040 (m) Compound K Match each compound to the data presented. Compound A Compound B Compound C Compound D Compound

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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