(a) Interpretation: The complete, detailed mechanism for the given reaction is to be drawn, and the major product is to be predicted. Concept introduction: The electrophilic addition of a Bronsted acid to the carbon-carbon double bond of alkenes is susceptible to carbocation rearrangements due to the stability of the carbocation. The carbocation rearrangement occurs via either 1, 2 hydride shift or 1, 2 methyl shift, depending on the stability of carbocation formed. The stability order for carbocations is secondary benzylic > tertiary > secondary benzylic > secondary allylic > secondary > primary > methyl etc.

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Answer 1

Question

Chapter 11, Problem 11.7P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

The electrophilic addition of a Bronsted acid to the carbon-carbon double bond of alkenes is susceptible to carbocation rearrangements due to the stability of the carbocation. The carbocation rearrangement occurs via either 1, 2 hydride shift or 1, 2 methyl shift, depending on the stability of carbocation formed. The stability order for carbocations is secondary benzylic > tertiary > secondary benzylic > secondary allylic > secondary > primary > methyl etc.

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

The electrophilic addition of a Bronsted acid to the carbon-carbon double bond of alkenes is susceptible to carbocation rearrangements due to the stability of the carbocation. The carbocation rearrangement occurs via either 1, 2 hydride shift or 1, 2 methyl shift, depending on the stability of carbocation formed. The stability order for carbocations is secondary benzylic > tertiary > secondary benzylic > secondary allylic > secondary > primary > methyl etc.

Interpretation Introduction

(c)

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

The electrophilic addition of a Bronsted acid to the carbon-carbon double bond of alkenes is susceptible to carbocation rearrangements due to the stability of the carbocation. The carbocation rearrangement occurs via either 1, 2 hydride shift or 1, 2 methyl shift, depending on the stability of carbocation formed. The stability order for carbocations is secondary benzylic > tertiary > secondary benzylic > secondary allylic > secondary > primary > methyl etc.

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Answer 2

Question

Chapter 11, Problem 11.7P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

The electrophilic addition of a Bronsted acid to the carbon-carbon double bond of alkenes is susceptible to carbocation rearrangements due to the stability of the carbocation. The carbocation rearrangement occurs via either 1, 2 hydride shift or 1, 2 methyl shift, depending on the stability of carbocation formed. The stability order for carbocations is secondary benzylic > tertiary > secondary benzylic > secondary allylic > secondary > primary > methyl etc.

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

The electrophilic addition of a Bronsted acid to the carbon-carbon double bond of alkenes is susceptible to carbocation rearrangements due to the stability of the carbocation. The carbocation rearrangement occurs via either 1, 2 hydride shift or 1, 2 methyl shift, depending on the stability of carbocation formed. The stability order for carbocations is secondary benzylic > tertiary > secondary benzylic > secondary allylic > secondary > primary > methyl etc.

Interpretation Introduction

(c)

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

The electrophilic addition of a Bronsted acid to the carbon-carbon double bond of alkenes is susceptible to carbocation rearrangements due to the stability of the carbocation. The carbocation rearrangement occurs via either 1, 2 hydride shift or 1, 2 methyl shift, depending on the stability of carbocation formed. The stability order for carbocations is secondary benzylic > tertiary > secondary benzylic > secondary allylic > secondary > primary > methyl etc.

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Answer 3

Question

Chapter 11, Problem 11.7P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

The electrophilic addition of a Bronsted acid to the carbon-carbon double bond of alkenes is susceptible to carbocation rearrangements due to the stability of the carbocation. The carbocation rearrangement occurs via either 1, 2 hydride shift or 1, 2 methyl shift, depending on the stability of carbocation formed. The stability order for carbocations is secondary benzylic > tertiary > secondary benzylic > secondary allylic > secondary > primary > methyl etc.

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

The electrophilic addition of a Bronsted acid to the carbon-carbon double bond of alkenes is susceptible to carbocation rearrangements due to the stability of the carbocation. The carbocation rearrangement occurs via either 1, 2 hydride shift or 1, 2 methyl shift, depending on the stability of carbocation formed. The stability order for carbocations is secondary benzylic > tertiary > secondary benzylic > secondary allylic > secondary > primary > methyl etc.

Interpretation Introduction

(c)

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

The electrophilic addition of a Bronsted acid to the carbon-carbon double bond of alkenes is susceptible to carbocation rearrangements due to the stability of the carbocation. The carbocation rearrangement occurs via either 1, 2 hydride shift or 1, 2 methyl shift, depending on the stability of carbocation formed. The stability order for carbocations is secondary benzylic > tertiary > secondary benzylic > secondary allylic > secondary > primary > methyl etc.

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Answer 4

Question

Chapter 11, Problem 11.7P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

The electrophilic addition of a Bronsted acid to the carbon-carbon double bond of alkenes is susceptible to carbocation rearrangements due to the stability of the carbocation. The carbocation rearrangement occurs via either 1, 2 hydride shift or 1, 2 methyl shift, depending on the stability of carbocation formed. The stability order for carbocations is secondary benzylic > tertiary > secondary benzylic > secondary allylic > secondary > primary > methyl etc.

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

The electrophilic addition of a Bronsted acid to the carbon-carbon double bond of alkenes is susceptible to carbocation rearrangements due to the stability of the carbocation. The carbocation rearrangement occurs via either 1, 2 hydride shift or 1, 2 methyl shift, depending on the stability of carbocation formed. The stability order for carbocations is secondary benzylic > tertiary > secondary benzylic > secondary allylic > secondary > primary > methyl etc.

Interpretation Introduction

(c)

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

The electrophilic addition of a Bronsted acid to the carbon-carbon double bond of alkenes is susceptible to carbocation rearrangements due to the stability of the carbocation. The carbocation rearrangement occurs via either 1, 2 hydride shift or 1, 2 methyl shift, depending on the stability of carbocation formed. The stability order for carbocations is secondary benzylic > tertiary > secondary benzylic > secondary allylic > secondary > primary > methyl etc.

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Answer 5

Chapter 11, Problem 11.7P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

The electrophilic addition of a Bronsted acid to the carbon-carbon double bond of alkenes is susceptible to carbocation rearrangements due to the stability of the carbocation. The carbocation rearrangement occurs via either 1, 2 hydride shift or 1, 2 methyl shift, depending on the stability of carbocation formed. The stability order for carbocations is secondary benzylic > tertiary > secondary benzylic > secondary allylic > secondary > primary > methyl etc.

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

The electrophilic addition of a Bronsted acid to the carbon-carbon double bond of alkenes is susceptible to carbocation rearrangements due to the stability of the carbocation. The carbocation rearrangement occurs via either 1, 2 hydride shift or 1, 2 methyl shift, depending on the stability of carbocation formed. The stability order for carbocations is secondary benzylic > tertiary > secondary benzylic > secondary allylic > secondary > primary > methyl etc.

Interpretation Introduction

(c)

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

The electrophilic addition of a Bronsted acid to the carbon-carbon double bond of alkenes is susceptible to carbocation rearrangements due to the stability of the carbocation. The carbocation rearrangement occurs via either 1, 2 hydride shift or 1, 2 methyl shift, depending on the stability of carbocation formed. The stability order for carbocations is secondary benzylic > tertiary > secondary benzylic > secondary allylic > secondary > primary > methyl etc.

Answer 6

Chapter 11, Problem 11.7P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

The electrophilic addition of a Bronsted acid to the carbon-carbon double bond of alkenes is susceptible to carbocation rearrangements due to the stability of the carbocation. The carbocation rearrangement occurs via either 1, 2 hydride shift or 1, 2 methyl shift, depending on the stability of carbocation formed. The stability order for carbocations is secondary benzylic > tertiary > secondary benzylic > secondary allylic > secondary > primary > methyl etc.

Answer 7

Chapter 11, Problem 11.7P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

The electrophilic addition of a Bronsted acid to the carbon-carbon double bond of alkenes is susceptible to carbocation rearrangements due to the stability of the carbocation. The carbocation rearrangement occurs via either 1, 2 hydride shift or 1, 2 methyl shift, depending on the stability of carbocation formed. The stability order for carbocations is secondary benzylic > tertiary > secondary benzylic > secondary allylic > secondary > primary > methyl etc.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

The electrophilic addition of a Bronsted acid to the carbon-carbon double bond of alkenes is susceptible to carbocation rearrangements due to the stability of the carbocation. The carbocation rearrangement occurs via either 1, 2 hydride shift or 1, 2 methyl shift, depending on the stability of carbocation formed. The stability order for carbocations is secondary benzylic > tertiary > secondary benzylic > secondary allylic > secondary > primary > methyl etc.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

The electrophilic addition of a Bronsted acid to the carbon-carbon double bond of alkenes is susceptible to carbocation rearrangements due to the stability of the carbocation. The carbocation rearrangement occurs via either 1, 2 hydride shift or 1, 2 methyl shift, depending on the stability of carbocation formed. The stability order for carbocations is secondary benzylic > tertiary > secondary benzylic > secondary allylic > secondary > primary > methyl etc.

Answer 10

Interpretation Introduction

(c)

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

The electrophilic addition of a Bronsted acid to the carbon-carbon double bond of alkenes is susceptible to carbocation rearrangements due to the stability of the carbocation. The carbocation rearrangement occurs via either 1, 2 hydride shift or 1, 2 methyl shift, depending on the stability of carbocation formed. The stability order for carbocations is secondary benzylic > tertiary > secondary benzylic > secondary allylic > secondary > primary > methyl etc.

Answer 11

Interpretation Introduction

(c)

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

The electrophilic addition of a Bronsted acid to the carbon-carbon double bond of alkenes is susceptible to carbocation rearrangements due to the stability of the carbocation. The carbocation rearrangement occurs via either 1, 2 hydride shift or 1, 2 methyl shift, depending on the stability of carbocation formed. The stability order for carbocations is secondary benzylic > tertiary > secondary benzylic > secondary allylic > secondary > primary > methyl etc.

Answer 12

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Answer 13

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Answer 14

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Answer 15

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 electrophilic addition of a Bronsted acid to the carbon-carbon double bond of alkenes is susceptible to carbocation rearrangements due to their stability.

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Chapter 11 Solutions