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

Q7: For the following reactions, indicate the reaction conditions that would provide the indicated product in a high yield. Note the major reaction pathway that would take place (SN1, SN2, E1, or E2) Note: There may be other products that are not shown. There maybe more than one plausible pathway. Br H3C OH H3C CI ... H3C SCH2CH3 CI i SCH2CH3 ཨ་ Br System Sett

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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Q7: For the following reactions, indicate the reaction conditions that would provide the indicated product in a high yield. Note the major reaction pathway that would take place (SN1, SN2, E1, or E2) Note: There may be other products that are not shown. There maybe more than one plausible pathway. Br H3C OH H3C CI ... H3C SCH2CH3 CI i SCH2CH3 ཨ་ Br System Sett

Q2: Rank the compounds in each of the following groups in order of decreasing rate of solvolysis in aqueous acetone. OSO2CF3 OSO2CH3 OH a. b. CI Br

ох 4-tert-butyl oxy cyclohex-1-ene Incorrect, 1 attempt remaining The systematic name of this compound classifies the -OR group as a substituent of the hydrocarbon, which is considered the principal functional group. The ether substituent is named with the suffix 'oxy'. The general format for the systematic name of a hydrocarbon is: [prefix/substituent] + [parent] + [functional group suffix] Substituents are listed in alphabetical order. Molecules with a chiral center will indicate the absolute configuration at the beginning of its name with the R and S notation.

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