The type of stereoisomers formed by the given reaction has to be predicted. Concept Introduction: Effect of delocalized electrons on the product of the reaction: The presence of delocalizes electrons while electrophilic addition or substitution the cation intermediate formed is shifted to stable carbocation form at higher rate, and that leads to the product. Rule: The stabilities of carbocation are, Benzyl cation = allyl cation = 3 ∘ carbocation > 2 ∘ carbocation > 1 ∘ carbocation > methyl cation > vinyl cation

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Answer 1

Question

Chapter 8.12, Problem 30P

(a)

Interpretation Introduction

Interpretation:

The type of stereoisomers formed by the given reaction has to be predicted.

Concept Introduction:

Effect of delocalized electrons on the product of the reaction:

The presence of delocalizes electrons while electrophilic addition or substitution the cation intermediate formed is shifted to stable carbocation form at higher rate, and that leads to the product.

Rule: The stabilities of carbocation are,

Benzyl cation = allyl cation = 3∘carbocation > 2∘ carbocation > 1∘ carbocation > methyl cation > vinyl cation

b)

Interpretation Introduction

Interpretation:

The type of stereoisomers formed by the given reaction has to be predicted.

Concept Introduction:

Effect of delocalized electrons on the product of the reaction:

The presence of delocalizes electrons while electrophilic addition or substitution the cation intermediate formed is shifted to stable carbocation form at higher rate, and that leads to the product.

Rule: The stabilities of carbocation are,

Benzyl cation = allyl cation = 3∘carbocation > 2∘ carbocation > 1∘ carbocation > methyl cation > vinyl cation

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1. Consider the Diels-Alder cycloaddition reaction below. D heat H D = deuterium = 2H Draw the major regioisomer (or in other words, constitutional isomer) expected to form. Draw appropriate resonance structures and explain why only one constitutional isomer is expected to form. Discuss if this can be drawn with both groups on the dieneophile being endo or one has to be endo and the other has to be exo.

Answer 2

Question

Chapter 8.12, Problem 30P

(a)

Interpretation Introduction

Interpretation:

The type of stereoisomers formed by the given reaction has to be predicted.

Concept Introduction:

Effect of delocalized electrons on the product of the reaction:

The presence of delocalizes electrons while electrophilic addition or substitution the cation intermediate formed is shifted to stable carbocation form at higher rate, and that leads to the product.

Rule: The stabilities of carbocation are,

Benzyl cation = allyl cation = 3∘carbocation > 2∘ carbocation > 1∘ carbocation > methyl cation > vinyl cation

b)

Interpretation Introduction

Interpretation:

The type of stereoisomers formed by the given reaction has to be predicted.

Concept Introduction:

Effect of delocalized electrons on the product of the reaction:

The presence of delocalizes electrons while electrophilic addition or substitution the cation intermediate formed is shifted to stable carbocation form at higher rate, and that leads to the product.

Rule: The stabilities of carbocation are,

Benzyl cation = allyl cation = 3∘carbocation > 2∘ carbocation > 1∘ carbocation > methyl cation > vinyl cation

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Answer 3

Question

Chapter 8.12, Problem 30P

(a)

Interpretation Introduction

Interpretation:

The type of stereoisomers formed by the given reaction has to be predicted.

Concept Introduction:

Effect of delocalized electrons on the product of the reaction:

The presence of delocalizes electrons while electrophilic addition or substitution the cation intermediate formed is shifted to stable carbocation form at higher rate, and that leads to the product.

Rule: The stabilities of carbocation are,

Benzyl cation = allyl cation = 3∘carbocation > 2∘ carbocation > 1∘ carbocation > methyl cation > vinyl cation

b)

Interpretation Introduction

Interpretation:

The type of stereoisomers formed by the given reaction has to be predicted.

Concept Introduction:

Effect of delocalized electrons on the product of the reaction:

The presence of delocalizes electrons while electrophilic addition or substitution the cation intermediate formed is shifted to stable carbocation form at higher rate, and that leads to the product.

Rule: The stabilities of carbocation are,

Benzyl cation = allyl cation = 3∘carbocation > 2∘ carbocation > 1∘ carbocation > methyl cation > vinyl cation

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Answer 4

Question

Chapter 8.12, Problem 30P

(a)

Interpretation Introduction

Interpretation:

The type of stereoisomers formed by the given reaction has to be predicted.

Concept Introduction:

Effect of delocalized electrons on the product of the reaction:

The presence of delocalizes electrons while electrophilic addition or substitution the cation intermediate formed is shifted to stable carbocation form at higher rate, and that leads to the product.

Rule: The stabilities of carbocation are,

Benzyl cation = allyl cation = 3∘carbocation > 2∘ carbocation > 1∘ carbocation > methyl cation > vinyl cation

b)

Interpretation Introduction

Interpretation:

The type of stereoisomers formed by the given reaction has to be predicted.

Concept Introduction:

Effect of delocalized electrons on the product of the reaction:

The presence of delocalizes electrons while electrophilic addition or substitution the cation intermediate formed is shifted to stable carbocation form at higher rate, and that leads to the product.

Rule: The stabilities of carbocation are,

Benzyl cation = allyl cation = 3∘carbocation > 2∘ carbocation > 1∘ carbocation > methyl cation > vinyl cation

Expert Solution & Answer

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Answer 5

Chapter 8.12, Problem 30P

(a)

Interpretation Introduction

Interpretation:

The type of stereoisomers formed by the given reaction has to be predicted.

Concept Introduction:

Effect of delocalized electrons on the product of the reaction:

The presence of delocalizes electrons while electrophilic addition or substitution the cation intermediate formed is shifted to stable carbocation form at higher rate, and that leads to the product.

Rule: The stabilities of carbocation are,

Benzyl cation = allyl cation = 3∘carbocation > 2∘ carbocation > 1∘ carbocation > methyl cation > vinyl cation

b)

Interpretation Introduction

Interpretation:

The type of stereoisomers formed by the given reaction has to be predicted.

Concept Introduction:

Effect of delocalized electrons on the product of the reaction:

The presence of delocalizes electrons while electrophilic addition or substitution the cation intermediate formed is shifted to stable carbocation form at higher rate, and that leads to the product.

Rule: The stabilities of carbocation are,

Benzyl cation = allyl cation = 3∘carbocation > 2∘ carbocation > 1∘ carbocation > methyl cation > vinyl cation

Answer 6

Chapter 8.12, Problem 30P

(a)

Interpretation Introduction

Interpretation:

The type of stereoisomers formed by the given reaction has to be predicted.

Concept Introduction:

Effect of delocalized electrons on the product of the reaction:

The presence of delocalizes electrons while electrophilic addition or substitution the cation intermediate formed is shifted to stable carbocation form at higher rate, and that leads to the product.

Rule: The stabilities of carbocation are,

Benzyl cation = allyl cation = 3∘carbocation > 2∘ carbocation > 1∘ carbocation > methyl cation > vinyl cation

Answer 7

Chapter 8.12, Problem 30P

(a)

Interpretation Introduction

Interpretation:

The type of stereoisomers formed by the given reaction has to be predicted.

Concept Introduction:

Effect of delocalized electrons on the product of the reaction:

The presence of delocalizes electrons while electrophilic addition or substitution the cation intermediate formed is shifted to stable carbocation form at higher rate, and that leads to the product.

Rule: The stabilities of carbocation are,

Benzyl cation = allyl cation = 3∘carbocation > 2∘ carbocation > 1∘ carbocation > methyl cation > vinyl cation

Answer 8

b)

Interpretation Introduction

Interpretation:

The type of stereoisomers formed by the given reaction has to be predicted.

Concept Introduction:

Effect of delocalized electrons on the product of the reaction:

The presence of delocalizes electrons while electrophilic addition or substitution the cation intermediate formed is shifted to stable carbocation form at higher rate, and that leads to the product.

Rule: The stabilities of carbocation are,

Benzyl cation = allyl cation = 3∘carbocation > 2∘ carbocation > 1∘ carbocation > methyl cation > vinyl cation

Answer 9

b)

Interpretation Introduction

Interpretation:

The type of stereoisomers formed by the given reaction has to be predicted.

Concept Introduction:

Effect of delocalized electrons on the product of the reaction:

The presence of delocalizes electrons while electrophilic addition or substitution the cation intermediate formed is shifted to stable carbocation form at higher rate, and that leads to the product.

Rule: The stabilities of carbocation are,

Benzyl cation = allyl cation = 3∘carbocation > 2∘ carbocation > 1∘ carbocation > methyl cation > vinyl cation

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 8.1 - Prob. 1P Ch. 8.1 - Prob. 2P Ch. 8.4 - Prob. 3P Ch. 8.5 - Prob. 4P Ch. 8.5 - Prob. 6P Ch. 8.6 - a. Predict the relative bond lengths of the three...Ch. 8.6 - Prob. 8P Ch. 8.6 - Prob. 9P Ch. 8.6 - Prob. 10P Ch. 8.7 - Prob. 11P

Solution Summary: The author explains that the type of stereoisomers formed by the given reaction has to be predicted.

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