a) Interpretation: The major product obtainable from addition of HBr to methylidenecyclohexane is to be predicted. Concept introduction: The first step in the addition of HBr with alkenes is the formation of a stable carbocation by the attack of the π electrons of the double bond on the positively polarized hydrogen of HBr eliminating a bromide ion. In the second step the carbocation reacts with the bromide ion to yield the product. To predict: The major product obtainable from addition of HBr to methylidenecyclohexane.

Question

Please draw the structure in the box that is consistent with all the spectral data and alphabetically label all of the equivalent protons in the structure (Ha, Hb, Hc....) in order to assign all the proton NMR peaks. The integrations are computer generated and approximate the number of equivalent protons. Molecular formula: C13H1802 14 13 12 11 10 11 (ppm) Structure with assigned H peaks 2.08 3.13

Answer 1

Question

Chapter 7.SE, Problem 58AP

Interpretation Introduction

a)

Interpretation:

The major product obtainable from addition of HBr to methylidenecyclohexane is to be predicted.

Concept introduction:

The first step in the addition of HBr with alkenes is the formation of a stable carbocation by the attack of the π electrons of the double bond on the positively polarized hydrogen of HBr eliminating a bromide ion. In the second step the carbocation reacts with the bromide ion to yield the product.

To predict:

The major product obtainable from addition of HBr to methylidenecyclohexane.

Interpretation Introduction

b)

Interpretation:

The major product obtainable from addition of HBr to the octahydronaphthalene is to be predicted.

Concept introduction:

The first step in the addition of HBr with alkenes is the formation of a stable carbocation by the attack of the π electrons of the double bond on the positively polarized hydrogen of HBr eliminating a bromide ion. In the second step the carbocation reacts with the bromide ion to yield the product.

To predict:

The major product obtainable from addition of HBr to octahydronaphthalene.

Interpretation Introduction

c)

Interpretation:

The major product obtainable from addition of HBr to 4-methyl-2-pentene is to be predicted.

Concept introduction:

In electrophilic addition reactions, the first step is the attack of the π electrons of the double bond on the hydrogen of another reactant to yield a carbocation. One of the carbon in C=C gets attached to hydrogen while the other acquires a positive charge. In the second step, the carbocation formed can rearrange to give another more stable carbocation either by a hydride shift (shift of hydrogen atom with its electron pair) or by an alkyl shift (shift of an alkyl group with its electron pair) between neighboring carbons. In the last step the carbocation produced reacts with a negatively charged ion or eliminates a proton to give the product.

To give:

The major product obtainable from addition of HBr to 4-methyl-2-pentene.

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Answer 2

Question

Chapter 7.SE, Problem 58AP

Interpretation Introduction

a)

Interpretation:

The major product obtainable from addition of HBr to methylidenecyclohexane is to be predicted.

Concept introduction:

The first step in the addition of HBr with alkenes is the formation of a stable carbocation by the attack of the π electrons of the double bond on the positively polarized hydrogen of HBr eliminating a bromide ion. In the second step the carbocation reacts with the bromide ion to yield the product.

To predict:

The major product obtainable from addition of HBr to methylidenecyclohexane.

Interpretation Introduction

b)

Interpretation:

The major product obtainable from addition of HBr to the octahydronaphthalene is to be predicted.

Concept introduction:

The first step in the addition of HBr with alkenes is the formation of a stable carbocation by the attack of the π electrons of the double bond on the positively polarized hydrogen of HBr eliminating a bromide ion. In the second step the carbocation reacts with the bromide ion to yield the product.

To predict:

The major product obtainable from addition of HBr to octahydronaphthalene.

Interpretation Introduction

c)

Interpretation:

The major product obtainable from addition of HBr to 4-methyl-2-pentene is to be predicted.

Concept introduction:

In electrophilic addition reactions, the first step is the attack of the π electrons of the double bond on the hydrogen of another reactant to yield a carbocation. One of the carbon in C=C gets attached to hydrogen while the other acquires a positive charge. In the second step, the carbocation formed can rearrange to give another more stable carbocation either by a hydride shift (shift of hydrogen atom with its electron pair) or by an alkyl shift (shift of an alkyl group with its electron pair) between neighboring carbons. In the last step the carbocation produced reacts with a negatively charged ion or eliminates a proton to give the product.

To give:

The major product obtainable from addition of HBr to 4-methyl-2-pentene.

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Answer 3

Question

Chapter 7.SE, Problem 58AP

Interpretation Introduction

a)

Interpretation:

The major product obtainable from addition of HBr to methylidenecyclohexane is to be predicted.

Concept introduction:

The first step in the addition of HBr with alkenes is the formation of a stable carbocation by the attack of the π electrons of the double bond on the positively polarized hydrogen of HBr eliminating a bromide ion. In the second step the carbocation reacts with the bromide ion to yield the product.

To predict:

The major product obtainable from addition of HBr to methylidenecyclohexane.

Interpretation Introduction

b)

Interpretation:

The major product obtainable from addition of HBr to the octahydronaphthalene is to be predicted.

Concept introduction:

The first step in the addition of HBr with alkenes is the formation of a stable carbocation by the attack of the π electrons of the double bond on the positively polarized hydrogen of HBr eliminating a bromide ion. In the second step the carbocation reacts with the bromide ion to yield the product.

To predict:

The major product obtainable from addition of HBr to octahydronaphthalene.

Interpretation Introduction

c)

Interpretation:

The major product obtainable from addition of HBr to 4-methyl-2-pentene is to be predicted.

Concept introduction:

In electrophilic addition reactions, the first step is the attack of the π electrons of the double bond on the hydrogen of another reactant to yield a carbocation. One of the carbon in C=C gets attached to hydrogen while the other acquires a positive charge. In the second step, the carbocation formed can rearrange to give another more stable carbocation either by a hydride shift (shift of hydrogen atom with its electron pair) or by an alkyl shift (shift of an alkyl group with its electron pair) between neighboring carbons. In the last step the carbocation produced reacts with a negatively charged ion or eliminates a proton to give the product.

To give:

The major product obtainable from addition of HBr to 4-methyl-2-pentene.

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Answer 4

Question

Chapter 7.SE, Problem 58AP

Interpretation Introduction

a)

Interpretation:

The major product obtainable from addition of HBr to methylidenecyclohexane is to be predicted.

Concept introduction:

The first step in the addition of HBr with alkenes is the formation of a stable carbocation by the attack of the π electrons of the double bond on the positively polarized hydrogen of HBr eliminating a bromide ion. In the second step the carbocation reacts with the bromide ion to yield the product.

To predict:

The major product obtainable from addition of HBr to methylidenecyclohexane.

Interpretation Introduction

b)

Interpretation:

The major product obtainable from addition of HBr to the octahydronaphthalene is to be predicted.

Concept introduction:

The first step in the addition of HBr with alkenes is the formation of a stable carbocation by the attack of the π electrons of the double bond on the positively polarized hydrogen of HBr eliminating a bromide ion. In the second step the carbocation reacts with the bromide ion to yield the product.

To predict:

The major product obtainable from addition of HBr to octahydronaphthalene.

Interpretation Introduction

c)

Interpretation:

The major product obtainable from addition of HBr to 4-methyl-2-pentene is to be predicted.

Concept introduction:

In electrophilic addition reactions, the first step is the attack of the π electrons of the double bond on the hydrogen of another reactant to yield a carbocation. One of the carbon in C=C gets attached to hydrogen while the other acquires a positive charge. In the second step, the carbocation formed can rearrange to give another more stable carbocation either by a hydride shift (shift of hydrogen atom with its electron pair) or by an alkyl shift (shift of an alkyl group with its electron pair) between neighboring carbons. In the last step the carbocation produced reacts with a negatively charged ion or eliminates a proton to give the product.

To give:

The major product obtainable from addition of HBr to 4-methyl-2-pentene.

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Answer 5

Chapter 7.SE, Problem 58AP

Interpretation Introduction

a)

Interpretation:

The major product obtainable from addition of HBr to methylidenecyclohexane is to be predicted.

Concept introduction:

The first step in the addition of HBr with alkenes is the formation of a stable carbocation by the attack of the π electrons of the double bond on the positively polarized hydrogen of HBr eliminating a bromide ion. In the second step the carbocation reacts with the bromide ion to yield the product.

To predict:

The major product obtainable from addition of HBr to methylidenecyclohexane.

Interpretation Introduction

b)

Interpretation:

The major product obtainable from addition of HBr to the octahydronaphthalene is to be predicted.

Concept introduction:

The first step in the addition of HBr with alkenes is the formation of a stable carbocation by the attack of the π electrons of the double bond on the positively polarized hydrogen of HBr eliminating a bromide ion. In the second step the carbocation reacts with the bromide ion to yield the product.

To predict:

The major product obtainable from addition of HBr to octahydronaphthalene.

Interpretation Introduction

c)

Interpretation:

The major product obtainable from addition of HBr to 4-methyl-2-pentene is to be predicted.

Concept introduction:

In electrophilic addition reactions, the first step is the attack of the π electrons of the double bond on the hydrogen of another reactant to yield a carbocation. One of the carbon in C=C gets attached to hydrogen while the other acquires a positive charge. In the second step, the carbocation formed can rearrange to give another more stable carbocation either by a hydride shift (shift of hydrogen atom with its electron pair) or by an alkyl shift (shift of an alkyl group with its electron pair) between neighboring carbons. In the last step the carbocation produced reacts with a negatively charged ion or eliminates a proton to give the product.

To give:

The major product obtainable from addition of HBr to 4-methyl-2-pentene.

Answer 6

Chapter 7.SE, Problem 58AP

Interpretation Introduction

a)

Interpretation:

The major product obtainable from addition of HBr to methylidenecyclohexane is to be predicted.

Concept introduction:

The first step in the addition of HBr with alkenes is the formation of a stable carbocation by the attack of the π electrons of the double bond on the positively polarized hydrogen of HBr eliminating a bromide ion. In the second step the carbocation reacts with the bromide ion to yield the product.

To predict:

The major product obtainable from addition of HBr to methylidenecyclohexane.

Answer 7

Chapter 7.SE, Problem 58AP

Interpretation Introduction

a)

Interpretation:

The major product obtainable from addition of HBr to methylidenecyclohexane is to be predicted.

Concept introduction:

The first step in the addition of HBr with alkenes is the formation of a stable carbocation by the attack of the π electrons of the double bond on the positively polarized hydrogen of HBr eliminating a bromide ion. In the second step the carbocation reacts with the bromide ion to yield the product.

To predict:

The major product obtainable from addition of HBr to methylidenecyclohexane.

Answer 8

Interpretation Introduction

b)

Interpretation:

The major product obtainable from addition of HBr to the octahydronaphthalene is to be predicted.

Concept introduction:

The first step in the addition of HBr with alkenes is the formation of a stable carbocation by the attack of the π electrons of the double bond on the positively polarized hydrogen of HBr eliminating a bromide ion. In the second step the carbocation reacts with the bromide ion to yield the product.

To predict:

The major product obtainable from addition of HBr to octahydronaphthalene.

Answer 9

Interpretation Introduction

b)

Interpretation:

The major product obtainable from addition of HBr to the octahydronaphthalene is to be predicted.

Concept introduction:

The first step in the addition of HBr with alkenes is the formation of a stable carbocation by the attack of the π electrons of the double bond on the positively polarized hydrogen of HBr eliminating a bromide ion. In the second step the carbocation reacts with the bromide ion to yield the product.

To predict:

The major product obtainable from addition of HBr to octahydronaphthalene.

Answer 10

Interpretation Introduction

c)

Interpretation:

The major product obtainable from addition of HBr to 4-methyl-2-pentene is to be predicted.

Concept introduction:

In electrophilic addition reactions, the first step is the attack of the π electrons of the double bond on the hydrogen of another reactant to yield a carbocation. One of the carbon in C=C gets attached to hydrogen while the other acquires a positive charge. In the second step, the carbocation formed can rearrange to give another more stable carbocation either by a hydride shift (shift of hydrogen atom with its electron pair) or by an alkyl shift (shift of an alkyl group with its electron pair) between neighboring carbons. In the last step the carbocation produced reacts with a negatively charged ion or eliminates a proton to give the product.

To give:

The major product obtainable from addition of HBr to 4-methyl-2-pentene.

Answer 11

Interpretation Introduction

c)

Interpretation:

The major product obtainable from addition of HBr to 4-methyl-2-pentene is to be predicted.

Concept introduction:

In electrophilic addition reactions, the first step is the attack of the π electrons of the double bond on the hydrogen of another reactant to yield a carbocation. One of the carbon in C=C gets attached to hydrogen while the other acquires a positive charge. In the second step, the carbocation formed can rearrange to give another more stable carbocation either by a hydride shift (shift of hydrogen atom with its electron pair) or by an alkyl shift (shift of an alkyl group with its electron pair) between neighboring carbons. In the last step the carbocation produced reacts with a negatively charged ion or eliminates a proton to give the product.

To give:

The major product obtainable from addition of HBr to 4-methyl-2-pentene.

Answer 12

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Ch. 7.2 - Calculate the degree of unsaturation in each of...Ch. 7.2 - Prob. 2P Ch. 7.2 - Diazepam, marketed as an antianxiety medication...Ch. 7.3 - Give IUPAC names for the following compounds:Ch. 7.3 - Prob. 5P Ch. 7.3 - Prob. 6P Ch. 7.3 - Prob. 7P Ch. 7.4 - Prob. 8P Ch. 7.4 - Prob. 9P Ch. 7.4 - Prob. 10P

Solution Summary: The author explains the major product obtainable from addition of HBr to methylidenecyclohexane.

Chapter 7 Solutions