The addition of HBr to buta-1, 3-diene results in 1, 2-addition at cold temperatures and 1, 4-addition at warm temperatures. If the 1, 2-adduct is first formed at cold temperatures and then warmed up, the 1, 4-adduct is formed, as shown. A mechanism for this isomerization reaction is to be drawn. Concept introduction: At high temperatures, electrophilic addition to a conjugated diene takes place under thermodynamic control, so the major product is the one that is lowest in energy. The 1, 4-adduct must be a thermodynamic product, and the 1, 2-adduct must be a kinetic product.

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Answer 1

Question

Chapter 11, Problem 11.46P

Interpretation Introduction

Interpretation:

The addition of HBr to buta-1, 3-diene results in 1, 2-addition at cold temperatures and 1, 4-addition at warm temperatures. If the 1, 2-adduct is first formed at cold temperatures and then warmed up, the 1, 4-adduct is formed, as shown. A mechanism for this isomerization reaction is to be drawn.

Concept introduction:

At high temperatures, electrophilic addition to a conjugated diene takes place under thermodynamic control, so the major product is the one that is lowest in energy. The 1, 4-adduct must be a thermodynamic product, and the 1, 2-adduct must be a kinetic product.

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Answer 2

Question

Chapter 11, Problem 11.46P

Interpretation Introduction

Interpretation:

The addition of HBr to buta-1, 3-diene results in 1, 2-addition at cold temperatures and 1, 4-addition at warm temperatures. If the 1, 2-adduct is first formed at cold temperatures and then warmed up, the 1, 4-adduct is formed, as shown. A mechanism for this isomerization reaction is to be drawn.

Concept introduction:

At high temperatures, electrophilic addition to a conjugated diene takes place under thermodynamic control, so the major product is the one that is lowest in energy. The 1, 4-adduct must be a thermodynamic product, and the 1, 2-adduct must be a kinetic product.

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Answer 3

Question

Chapter 11, Problem 11.46P

Interpretation Introduction

Interpretation:

The addition of HBr to buta-1, 3-diene results in 1, 2-addition at cold temperatures and 1, 4-addition at warm temperatures. If the 1, 2-adduct is first formed at cold temperatures and then warmed up, the 1, 4-adduct is formed, as shown. A mechanism for this isomerization reaction is to be drawn.

Concept introduction:

At high temperatures, electrophilic addition to a conjugated diene takes place under thermodynamic control, so the major product is the one that is lowest in energy. The 1, 4-adduct must be a thermodynamic product, and the 1, 2-adduct must be a kinetic product.

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Answer 4

Question

Chapter 11, Problem 11.46P

Interpretation Introduction

Interpretation:

The addition of HBr to buta-1, 3-diene results in 1, 2-addition at cold temperatures and 1, 4-addition at warm temperatures. If the 1, 2-adduct is first formed at cold temperatures and then warmed up, the 1, 4-adduct is formed, as shown. A mechanism for this isomerization reaction is to be drawn.

Concept introduction:

At high temperatures, electrophilic addition to a conjugated diene takes place under thermodynamic control, so the major product is the one that is lowest in energy. The 1, 4-adduct must be a thermodynamic product, and the 1, 2-adduct must be a kinetic product.

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Answer 5

Chapter 11, Problem 11.46P

Interpretation Introduction

Interpretation:

The addition of HBr to buta-1, 3-diene results in 1, 2-addition at cold temperatures and 1, 4-addition at warm temperatures. If the 1, 2-adduct is first formed at cold temperatures and then warmed up, the 1, 4-adduct is formed, as shown. A mechanism for this isomerization reaction is to be drawn.

Concept introduction:

At high temperatures, electrophilic addition to a conjugated diene takes place under thermodynamic control, so the major product is the one that is lowest in energy. The 1, 4-adduct must be a thermodynamic product, and the 1, 2-adduct must be a kinetic product.

Answer 6

Chapter 11, Problem 11.46P

Interpretation Introduction

Interpretation:

The addition of HBr to buta-1, 3-diene results in 1, 2-addition at cold temperatures and 1, 4-addition at warm temperatures. If the 1, 2-adduct is first formed at cold temperatures and then warmed up, the 1, 4-adduct is formed, as shown. A mechanism for this isomerization reaction is to be drawn.

Concept introduction:

At high temperatures, electrophilic addition to a conjugated diene takes place under thermodynamic control, so the major product is the one that is lowest in energy. The 1, 4-adduct must be a thermodynamic product, and the 1, 2-adduct must be a kinetic product.

Answer 7

Chapter 11, Problem 11.46P

Interpretation Introduction

Interpretation:

The addition of HBr to buta-1, 3-diene results in 1, 2-addition at cold temperatures and 1, 4-addition at warm temperatures. If the 1, 2-adduct is first formed at cold temperatures and then warmed up, the 1, 4-adduct is formed, as shown. A mechanism for this isomerization reaction is to be drawn.

Concept introduction:

At high temperatures, electrophilic addition to a conjugated diene takes place under thermodynamic control, so the major product is the one that is lowest in energy. The 1, 4-adduct must be a thermodynamic product, and the 1, 2-adduct must be a kinetic product.

Answer 8

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Answer 9

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Answer 10

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Answer 11

Ch. 11 - Prob. 11.1P Ch. 11 - Prob. 11.2P Ch. 11 - Prob. 11.3P Ch. 11 - Prob. 11.4P Ch. 11 - Prob. 11.5P Ch. 11 - Prob. 11.6P Ch. 11 - Prob. 11.7P Ch. 11 - Prob. 11.8P Ch. 11 - Prob. 11.9P Ch. 11 - Prob. 11.10P

Solution Summary: The author explains the mechanism for the given isomerization reaction. The 1, 2- and 1, 4-adducts are produced from the same carbocation intermediate.

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