(a) Interpretation: The detailed mechanism for the reaction of the given compound with HCl is to be drawn. The major product of the reaction is to be predicted. Concept introduction: In an addition of a Bronsted acid across a double bond, the proton can bond to one of the two possible carbon atoms. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate. If alkene is symmetrical, then it results in only one product. If an alkene is unsymmetrical, then two constitutional isomers can be produced. The major product is the one in which a more stable carbocation intermediate is produced. Tertiary carbocation is the most stable, followed by secondary and then primary. Methyl carbocations are least stable.

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Answer 1

Question

Chapter 11, Problem 11.4P

Interpretation Introduction

(a)

Interpretation:

The detailed mechanism for the reaction of the given compound with HCl is to be drawn. The major product of the reaction is to be predicted.

Concept introduction:

In an addition of a Bronsted acid across a double bond, the proton can bond to one of the two possible carbon atoms. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate. If alkene is symmetrical, then it results in only one product. If an alkene is unsymmetrical, then two constitutional isomers can be produced. The major product is the one in which a more stable carbocation intermediate is produced. Tertiary carbocation is the most stable, followed by secondary and then primary. Methyl carbocations are least stable.

Interpretation Introduction

(b)

Interpretation:

The detailed mechanism for the reaction of the given compound with HCl is to be drawn. The major product of the reaction is to be predicted.

Concept introduction:

In an addition of a Bronsted acid across a double bond, the proton can bond to one of the two possible carbon atoms. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate. If alkene is symmetrical, then it results in only one product. If an alkene is unsymmetrical, then two constitutional isomers can be produced. The major product is the one in which a more stable carbocation intermediate is produced. Tertiary carbocation is the most stable, followed by secondary and then primary. Methyl carbocations are least stable.

Interpretation Introduction

(c)

Interpretation:

The detailed mechanism for the reaction of the given compound with HCl is to be drawn. The major product of the reaction is to be predicted.

Concept introduction:

In an addition of a Bronsted acid across a double bond, the proton can bond to one of the two possible carbon atoms. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate. If alkene is symmetrical, then it results in only one product. If an alkene is unsymmetrical, then two constitutional isomers can be produced. The major product is the one in which a more stable carbocation intermediate is produced. Tertiary carbocation is the most stable, followed by secondary and then primary. Methyl carbocations are least stable.

Interpretation Introduction

(d)

Interpretation:

The detailed mechanism for the reaction of the given compound with HCl is to be drawn. The major product of the reaction is to be predicted.

Concept introduction:

In an addition of a Bronsted acid across a double bond, the proton can bond to one of the two possible carbon atoms. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate. If alkene is symmetrical, then it results in only one product. If an alkene is unsymmetrical, then two constitutional isomers can be produced. The major product is the one in which a more stable carbocation intermediate is produced. Tertiary carbocation is the most stable, followed by secondary and then primary. Methyl carbocations are least stable.

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Answer 2

Question

Chapter 11, Problem 11.4P

Interpretation Introduction

(a)

Interpretation:

The detailed mechanism for the reaction of the given compound with HCl is to be drawn. The major product of the reaction is to be predicted.

Concept introduction:

In an addition of a Bronsted acid across a double bond, the proton can bond to one of the two possible carbon atoms. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate. If alkene is symmetrical, then it results in only one product. If an alkene is unsymmetrical, then two constitutional isomers can be produced. The major product is the one in which a more stable carbocation intermediate is produced. Tertiary carbocation is the most stable, followed by secondary and then primary. Methyl carbocations are least stable.

Interpretation Introduction

(b)

Interpretation:

The detailed mechanism for the reaction of the given compound with HCl is to be drawn. The major product of the reaction is to be predicted.

Concept introduction:

In an addition of a Bronsted acid across a double bond, the proton can bond to one of the two possible carbon atoms. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate. If alkene is symmetrical, then it results in only one product. If an alkene is unsymmetrical, then two constitutional isomers can be produced. The major product is the one in which a more stable carbocation intermediate is produced. Tertiary carbocation is the most stable, followed by secondary and then primary. Methyl carbocations are least stable.

Interpretation Introduction

(c)

Interpretation:

The detailed mechanism for the reaction of the given compound with HCl is to be drawn. The major product of the reaction is to be predicted.

Concept introduction:

In an addition of a Bronsted acid across a double bond, the proton can bond to one of the two possible carbon atoms. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate. If alkene is symmetrical, then it results in only one product. If an alkene is unsymmetrical, then two constitutional isomers can be produced. The major product is the one in which a more stable carbocation intermediate is produced. Tertiary carbocation is the most stable, followed by secondary and then primary. Methyl carbocations are least stable.

Interpretation Introduction

(d)

Interpretation:

The detailed mechanism for the reaction of the given compound with HCl is to be drawn. The major product of the reaction is to be predicted.

Concept introduction:

In an addition of a Bronsted acid across a double bond, the proton can bond to one of the two possible carbon atoms. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate. If alkene is symmetrical, then it results in only one product. If an alkene is unsymmetrical, then two constitutional isomers can be produced. The major product is the one in which a more stable carbocation intermediate is produced. Tertiary carbocation is the most stable, followed by secondary and then primary. Methyl carbocations are least stable.

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Answer 3

Question

Chapter 11, Problem 11.4P

Interpretation Introduction

(a)

Interpretation:

The detailed mechanism for the reaction of the given compound with HCl is to be drawn. The major product of the reaction is to be predicted.

Concept introduction:

In an addition of a Bronsted acid across a double bond, the proton can bond to one of the two possible carbon atoms. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate. If alkene is symmetrical, then it results in only one product. If an alkene is unsymmetrical, then two constitutional isomers can be produced. The major product is the one in which a more stable carbocation intermediate is produced. Tertiary carbocation is the most stable, followed by secondary and then primary. Methyl carbocations are least stable.

Interpretation Introduction

(b)

Interpretation:

The detailed mechanism for the reaction of the given compound with HCl is to be drawn. The major product of the reaction is to be predicted.

Concept introduction:

In an addition of a Bronsted acid across a double bond, the proton can bond to one of the two possible carbon atoms. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate. If alkene is symmetrical, then it results in only one product. If an alkene is unsymmetrical, then two constitutional isomers can be produced. The major product is the one in which a more stable carbocation intermediate is produced. Tertiary carbocation is the most stable, followed by secondary and then primary. Methyl carbocations are least stable.

Interpretation Introduction

(c)

Interpretation:

The detailed mechanism for the reaction of the given compound with HCl is to be drawn. The major product of the reaction is to be predicted.

Concept introduction:

In an addition of a Bronsted acid across a double bond, the proton can bond to one of the two possible carbon atoms. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate. If alkene is symmetrical, then it results in only one product. If an alkene is unsymmetrical, then two constitutional isomers can be produced. The major product is the one in which a more stable carbocation intermediate is produced. Tertiary carbocation is the most stable, followed by secondary and then primary. Methyl carbocations are least stable.

Interpretation Introduction

(d)

Interpretation:

The detailed mechanism for the reaction of the given compound with HCl is to be drawn. The major product of the reaction is to be predicted.

Concept introduction:

In an addition of a Bronsted acid across a double bond, the proton can bond to one of the two possible carbon atoms. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate. If alkene is symmetrical, then it results in only one product. If an alkene is unsymmetrical, then two constitutional isomers can be produced. The major product is the one in which a more stable carbocation intermediate is produced. Tertiary carbocation is the most stable, followed by secondary and then primary. Methyl carbocations are least stable.

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Answer 4

Question

Chapter 11, Problem 11.4P

Interpretation Introduction

(a)

Interpretation:

The detailed mechanism for the reaction of the given compound with HCl is to be drawn. The major product of the reaction is to be predicted.

Concept introduction:

In an addition of a Bronsted acid across a double bond, the proton can bond to one of the two possible carbon atoms. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate. If alkene is symmetrical, then it results in only one product. If an alkene is unsymmetrical, then two constitutional isomers can be produced. The major product is the one in which a more stable carbocation intermediate is produced. Tertiary carbocation is the most stable, followed by secondary and then primary. Methyl carbocations are least stable.

Interpretation Introduction

(b)

Interpretation:

The detailed mechanism for the reaction of the given compound with HCl is to be drawn. The major product of the reaction is to be predicted.

Concept introduction:

In an addition of a Bronsted acid across a double bond, the proton can bond to one of the two possible carbon atoms. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate. If alkene is symmetrical, then it results in only one product. If an alkene is unsymmetrical, then two constitutional isomers can be produced. The major product is the one in which a more stable carbocation intermediate is produced. Tertiary carbocation is the most stable, followed by secondary and then primary. Methyl carbocations are least stable.

Interpretation Introduction

(c)

Interpretation:

The detailed mechanism for the reaction of the given compound with HCl is to be drawn. The major product of the reaction is to be predicted.

Concept introduction:

In an addition of a Bronsted acid across a double bond, the proton can bond to one of the two possible carbon atoms. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate. If alkene is symmetrical, then it results in only one product. If an alkene is unsymmetrical, then two constitutional isomers can be produced. The major product is the one in which a more stable carbocation intermediate is produced. Tertiary carbocation is the most stable, followed by secondary and then primary. Methyl carbocations are least stable.

Interpretation Introduction

(d)

Interpretation:

The detailed mechanism for the reaction of the given compound with HCl is to be drawn. The major product of the reaction is to be predicted.

Concept introduction:

In an addition of a Bronsted acid across a double bond, the proton can bond to one of the two possible carbon atoms. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate. If alkene is symmetrical, then it results in only one product. If an alkene is unsymmetrical, then two constitutional isomers can be produced. The major product is the one in which a more stable carbocation intermediate is produced. Tertiary carbocation is the most stable, followed by secondary and then primary. Methyl carbocations are least stable.

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Answer 5

Chapter 11, Problem 11.4P

Interpretation Introduction

(a)

Interpretation:

The detailed mechanism for the reaction of the given compound with HCl is to be drawn. The major product of the reaction is to be predicted.

Concept introduction:

In an addition of a Bronsted acid across a double bond, the proton can bond to one of the two possible carbon atoms. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate. If alkene is symmetrical, then it results in only one product. If an alkene is unsymmetrical, then two constitutional isomers can be produced. The major product is the one in which a more stable carbocation intermediate is produced. Tertiary carbocation is the most stable, followed by secondary and then primary. Methyl carbocations are least stable.

Interpretation Introduction

(b)

Interpretation:

The detailed mechanism for the reaction of the given compound with HCl is to be drawn. The major product of the reaction is to be predicted.

Concept introduction:

In an addition of a Bronsted acid across a double bond, the proton can bond to one of the two possible carbon atoms. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate. If alkene is symmetrical, then it results in only one product. If an alkene is unsymmetrical, then two constitutional isomers can be produced. The major product is the one in which a more stable carbocation intermediate is produced. Tertiary carbocation is the most stable, followed by secondary and then primary. Methyl carbocations are least stable.

Interpretation Introduction

(c)

Interpretation:

The detailed mechanism for the reaction of the given compound with HCl is to be drawn. The major product of the reaction is to be predicted.

Concept introduction:

In an addition of a Bronsted acid across a double bond, the proton can bond to one of the two possible carbon atoms. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate. If alkene is symmetrical, then it results in only one product. If an alkene is unsymmetrical, then two constitutional isomers can be produced. The major product is the one in which a more stable carbocation intermediate is produced. Tertiary carbocation is the most stable, followed by secondary and then primary. Methyl carbocations are least stable.

Interpretation Introduction

(d)

Interpretation:

The detailed mechanism for the reaction of the given compound with HCl is to be drawn. The major product of the reaction is to be predicted.

Concept introduction:

In an addition of a Bronsted acid across a double bond, the proton can bond to one of the two possible carbon atoms. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate. If alkene is symmetrical, then it results in only one product. If an alkene is unsymmetrical, then two constitutional isomers can be produced. The major product is the one in which a more stable carbocation intermediate is produced. Tertiary carbocation is the most stable, followed by secondary and then primary. Methyl carbocations are least stable.

Answer 6

Chapter 11, Problem 11.4P

Interpretation Introduction

(a)

Interpretation:

The detailed mechanism for the reaction of the given compound with HCl is to be drawn. The major product of the reaction is to be predicted.

Concept introduction:

In an addition of a Bronsted acid across a double bond, the proton can bond to one of the two possible carbon atoms. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate. If alkene is symmetrical, then it results in only one product. If an alkene is unsymmetrical, then two constitutional isomers can be produced. The major product is the one in which a more stable carbocation intermediate is produced. Tertiary carbocation is the most stable, followed by secondary and then primary. Methyl carbocations are least stable.

Answer 7

Chapter 11, Problem 11.4P

Interpretation Introduction

(a)

Interpretation:

The detailed mechanism for the reaction of the given compound with HCl is to be drawn. The major product of the reaction is to be predicted.

Concept introduction:

In an addition of a Bronsted acid across a double bond, the proton can bond to one of the two possible carbon atoms. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate. If alkene is symmetrical, then it results in only one product. If an alkene is unsymmetrical, then two constitutional isomers can be produced. The major product is the one in which a more stable carbocation intermediate is produced. Tertiary carbocation is the most stable, followed by secondary and then primary. Methyl carbocations are least stable.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The detailed mechanism for the reaction of the given compound with HCl is to be drawn. The major product of the reaction is to be predicted.

Concept introduction:

In an addition of a Bronsted acid across a double bond, the proton can bond to one of the two possible carbon atoms. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate. If alkene is symmetrical, then it results in only one product. If an alkene is unsymmetrical, then two constitutional isomers can be produced. The major product is the one in which a more stable carbocation intermediate is produced. Tertiary carbocation is the most stable, followed by secondary and then primary. Methyl carbocations are least stable.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The detailed mechanism for the reaction of the given compound with HCl is to be drawn. The major product of the reaction is to be predicted.

Concept introduction:

In an addition of a Bronsted acid across a double bond, the proton can bond to one of the two possible carbon atoms. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate. If alkene is symmetrical, then it results in only one product. If an alkene is unsymmetrical, then two constitutional isomers can be produced. The major product is the one in which a more stable carbocation intermediate is produced. Tertiary carbocation is the most stable, followed by secondary and then primary. Methyl carbocations are least stable.

Answer 10

Interpretation Introduction

(c)

Interpretation:

The detailed mechanism for the reaction of the given compound with HCl is to be drawn. The major product of the reaction is to be predicted.

Concept introduction:

In an addition of a Bronsted acid across a double bond, the proton can bond to one of the two possible carbon atoms. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate. If alkene is symmetrical, then it results in only one product. If an alkene is unsymmetrical, then two constitutional isomers can be produced. The major product is the one in which a more stable carbocation intermediate is produced. Tertiary carbocation is the most stable, followed by secondary and then primary. Methyl carbocations are least stable.

Answer 11

Interpretation Introduction

(c)

Interpretation:

The detailed mechanism for the reaction of the given compound with HCl is to be drawn. The major product of the reaction is to be predicted.

Concept introduction:

In an addition of a Bronsted acid across a double bond, the proton can bond to one of the two possible carbon atoms. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate. If alkene is symmetrical, then it results in only one product. If an alkene is unsymmetrical, then two constitutional isomers can be produced. The major product is the one in which a more stable carbocation intermediate is produced. Tertiary carbocation is the most stable, followed by secondary and then primary. Methyl carbocations are least stable.

Answer 12

Interpretation Introduction

(d)

Interpretation:

The detailed mechanism for the reaction of the given compound with HCl is to be drawn. The major product of the reaction is to be predicted.

Concept introduction:

In an addition of a Bronsted acid across a double bond, the proton can bond to one of the two possible carbon atoms. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate. If alkene is symmetrical, then it results in only one product. If an alkene is unsymmetrical, then two constitutional isomers can be produced. The major product is the one in which a more stable carbocation intermediate is produced. Tertiary carbocation is the most stable, followed by secondary and then primary. Methyl carbocations are least stable.

Answer 13

Interpretation Introduction

(d)

Interpretation:

The detailed mechanism for the reaction of the given compound with HCl is to be drawn. The major product of the reaction is to be predicted.

Concept introduction:

In an addition of a Bronsted acid across a double bond, the proton can bond to one of the two possible carbon atoms. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate. If alkene is symmetrical, then it results in only one product. If an alkene is unsymmetrical, then two constitutional isomers can be produced. The major product is the one in which a more stable carbocation intermediate is produced. Tertiary carbocation is the most stable, followed by secondary and then primary. Methyl carbocations are least stable.

Answer 14

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Answer 15

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Answer 16

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Answer 17

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 an alkene and the major product of the reaction.

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