The rate determining step of the given reaction has to be predicted. Concept Introduction: Reactions of conjugated dienes: An electrophilic addition reaction to a conjugated diene forms both 1,2-addition and 1,4-addition products because the resonance contributors of the allylic cation give cation carbon and the chances for the nucleophile to attack at the electrophilic centre will occur. Kinetic and thermodynamic products: Kinetic product: The more rapidly formed product is called the kinetic product. The reactions that produce the kinetic product as the major product are said to be kinetically controlled. The kinetic product predominates when the reaction is irreversible. Thermodynamic product: The more stable product is called the thermodynamic product. The reactions that produce the thermodynamic product as the major product are said to be thermodynamically controlled. The thermodynamic product predominates when the reaction is reversible. 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 8.13, Problem 35P

a)

Interpretation Introduction

Interpretation:

The rate determining step of the given reaction has to be predicted.

Concept Introduction:

Reactions of conjugated dienes:

An electrophilic addition reaction to a conjugated diene forms both 1,2-addition and 1,4-addition products because the resonance contributors of the allylic cation give cation carbon and the chances for the nucleophile to attack at the electrophilic centre will occur.

Kinetic and thermodynamic products:

Kinetic product: The more rapidly formed product is called the kinetic product. The reactions that produce the kinetic product as the major product are said to be kinetically controlled. The kinetic product predominates when the reaction is irreversible.

Thermodynamic product: The more stable product is called the thermodynamic product. The reactions that produce the thermodynamic product as the major product are said to be thermodynamically controlled. The thermodynamic product predominates when the reaction is reversible.

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 product determining step of the given reaction has to be predicted.

Concept Introduction:

Reactions of conjugated dienes:

An electrophilic addition reaction to a conjugated diene forms both 1,2-addition and 1,4-addition products because the resonance contributors of the allylic cation give cation carbon and the chances for the nucleophile to attack at the electrophilic centre will occur.

Kinetic and thermodynamic products:

Kinetic product: The more rapidly formed product is called the kinetic product. The reactions that produce the kinetic product as the major product are said to be kinetically controlled. The kinetic product predominates when the reaction is irreversible.

Thermodynamic product: The more stable product is called the thermodynamic product. The reactions that produce the thermodynamic product as the major product are said to be thermodynamically controlled. The thermodynamic product predominates when the reaction is reversible.

Rule: The stabilities of carbocation are,

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

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Students have asked these similar questions

a.What carbon radical is formed by homolysis of the C–Ha bond in propylbenzene? Draw all reasonable resonance structures for this radical. b.What carbon radical is formed by homolysis of the C–Hb bond in propylbenzene? Draw all reasonable resonance structures for this radical. c. The bond dissociation energy of one of the C–H bonds is considerably less than the bond dissociation energy of the other. Which C–H bond is weaker? Offer an explanation.

8. Which factors affect the reaction rate in Diels-Alder reactions? O A. Electron donating group on the diene and electron withdrawing group on dienophile. O B. Electron donating group on both the diene and the dienophile. OC. Electron withdrawing group on both the diene and the dienophile. OD. Addition of catalyst.

27. Which is the expected product for the reaction of propyne with excess HBr?. A. 1-bromopropane B. 2-bromopane C. 2,2-dibromopropane D. 1,1-dibromopropane 28. The following compounds undergo electrophilic aromatic substitution EXCEPT I. A. I and II B. III and IV C. II and III D. III II. III. IV.

Answer 2

Question

Chapter 8.13, Problem 35P

a)

Interpretation Introduction

Interpretation:

The rate determining step of the given reaction has to be predicted.

Concept Introduction:

Reactions of conjugated dienes:

An electrophilic addition reaction to a conjugated diene forms both 1,2-addition and 1,4-addition products because the resonance contributors of the allylic cation give cation carbon and the chances for the nucleophile to attack at the electrophilic centre will occur.

Kinetic and thermodynamic products:

Kinetic product: The more rapidly formed product is called the kinetic product. The reactions that produce the kinetic product as the major product are said to be kinetically controlled. The kinetic product predominates when the reaction is irreversible.

Thermodynamic product: The more stable product is called the thermodynamic product. The reactions that produce the thermodynamic product as the major product are said to be thermodynamically controlled. The thermodynamic product predominates when the reaction is reversible.

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 product determining step of the given reaction has to be predicted.

Concept Introduction:

Reactions of conjugated dienes:

An electrophilic addition reaction to a conjugated diene forms both 1,2-addition and 1,4-addition products because the resonance contributors of the allylic cation give cation carbon and the chances for the nucleophile to attack at the electrophilic centre will occur.

Kinetic and thermodynamic products:

Kinetic product: The more rapidly formed product is called the kinetic product. The reactions that produce the kinetic product as the major product are said to be kinetically controlled. The kinetic product predominates when the reaction is irreversible.

Thermodynamic product: The more stable product is called the thermodynamic product. The reactions that produce the thermodynamic product as the major product are said to be thermodynamically controlled. The thermodynamic product predominates when the reaction is reversible.

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 8.13, Problem 35P

a)

Interpretation Introduction

Interpretation:

The rate determining step of the given reaction has to be predicted.

Concept Introduction:

Reactions of conjugated dienes:

An electrophilic addition reaction to a conjugated diene forms both 1,2-addition and 1,4-addition products because the resonance contributors of the allylic cation give cation carbon and the chances for the nucleophile to attack at the electrophilic centre will occur.

Kinetic and thermodynamic products:

Kinetic product: The more rapidly formed product is called the kinetic product. The reactions that produce the kinetic product as the major product are said to be kinetically controlled. The kinetic product predominates when the reaction is irreversible.

Thermodynamic product: The more stable product is called the thermodynamic product. The reactions that produce the thermodynamic product as the major product are said to be thermodynamically controlled. The thermodynamic product predominates when the reaction is reversible.

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 product determining step of the given reaction has to be predicted.

Concept Introduction:

Reactions of conjugated dienes:

An electrophilic addition reaction to a conjugated diene forms both 1,2-addition and 1,4-addition products because the resonance contributors of the allylic cation give cation carbon and the chances for the nucleophile to attack at the electrophilic centre will occur.

Kinetic and thermodynamic products:

Kinetic product: The more rapidly formed product is called the kinetic product. The reactions that produce the kinetic product as the major product are said to be kinetically controlled. The kinetic product predominates when the reaction is irreversible.

Thermodynamic product: The more stable product is called the thermodynamic product. The reactions that produce the thermodynamic product as the major product are said to be thermodynamically controlled. The thermodynamic product predominates when the reaction is reversible.

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 4

Question

Chapter 8.13, Problem 35P

a)

Interpretation Introduction

Interpretation:

The rate determining step of the given reaction has to be predicted.

Concept Introduction:

Reactions of conjugated dienes:

An electrophilic addition reaction to a conjugated diene forms both 1,2-addition and 1,4-addition products because the resonance contributors of the allylic cation give cation carbon and the chances for the nucleophile to attack at the electrophilic centre will occur.

Kinetic and thermodynamic products:

Kinetic product: The more rapidly formed product is called the kinetic product. The reactions that produce the kinetic product as the major product are said to be kinetically controlled. The kinetic product predominates when the reaction is irreversible.

Thermodynamic product: The more stable product is called the thermodynamic product. The reactions that produce the thermodynamic product as the major product are said to be thermodynamically controlled. The thermodynamic product predominates when the reaction is reversible.

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 product determining step of the given reaction has to be predicted.

Concept Introduction:

Reactions of conjugated dienes:

An electrophilic addition reaction to a conjugated diene forms both 1,2-addition and 1,4-addition products because the resonance contributors of the allylic cation give cation carbon and the chances for the nucleophile to attack at the electrophilic centre will occur.

Kinetic and thermodynamic products:

Kinetic product: The more rapidly formed product is called the kinetic product. The reactions that produce the kinetic product as the major product are said to be kinetically controlled. The kinetic product predominates when the reaction is irreversible.

Thermodynamic product: The more stable product is called the thermodynamic product. The reactions that produce the thermodynamic product as the major product are said to be thermodynamically controlled. The thermodynamic product predominates when the reaction is reversible.

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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See solution

Answer 5

Chapter 8.13, Problem 35P

a)

Interpretation Introduction

Interpretation:

The rate determining step of the given reaction has to be predicted.

Concept Introduction:

Reactions of conjugated dienes:

An electrophilic addition reaction to a conjugated diene forms both 1,2-addition and 1,4-addition products because the resonance contributors of the allylic cation give cation carbon and the chances for the nucleophile to attack at the electrophilic centre will occur.

Kinetic and thermodynamic products:

Kinetic product: The more rapidly formed product is called the kinetic product. The reactions that produce the kinetic product as the major product are said to be kinetically controlled. The kinetic product predominates when the reaction is irreversible.

Thermodynamic product: The more stable product is called the thermodynamic product. The reactions that produce the thermodynamic product as the major product are said to be thermodynamically controlled. The thermodynamic product predominates when the reaction is reversible.

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 product determining step of the given reaction has to be predicted.

Concept Introduction:

Reactions of conjugated dienes:

An electrophilic addition reaction to a conjugated diene forms both 1,2-addition and 1,4-addition products because the resonance contributors of the allylic cation give cation carbon and the chances for the nucleophile to attack at the electrophilic centre will occur.

Kinetic and thermodynamic products:

Kinetic product: The more rapidly formed product is called the kinetic product. The reactions that produce the kinetic product as the major product are said to be kinetically controlled. The kinetic product predominates when the reaction is irreversible.

Thermodynamic product: The more stable product is called the thermodynamic product. The reactions that produce the thermodynamic product as the major product are said to be thermodynamically controlled. The thermodynamic product predominates when the reaction is reversible.

Rule: The stabilities of carbocation are,

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

Answer 6

Chapter 8.13, Problem 35P

a)

Interpretation Introduction

Interpretation:

The rate determining step of the given reaction has to be predicted.

Concept Introduction:

Reactions of conjugated dienes:

An electrophilic addition reaction to a conjugated diene forms both 1,2-addition and 1,4-addition products because the resonance contributors of the allylic cation give cation carbon and the chances for the nucleophile to attack at the electrophilic centre will occur.

Kinetic and thermodynamic products:

Kinetic product: The more rapidly formed product is called the kinetic product. The reactions that produce the kinetic product as the major product are said to be kinetically controlled. The kinetic product predominates when the reaction is irreversible.

Thermodynamic product: The more stable product is called the thermodynamic product. The reactions that produce the thermodynamic product as the major product are said to be thermodynamically controlled. The thermodynamic product predominates when the reaction is reversible.

Rule: The stabilities of carbocation are,

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

Answer 7

Chapter 8.13, Problem 35P

a)

Interpretation Introduction

Interpretation:

The rate determining step of the given reaction has to be predicted.

Concept Introduction:

Reactions of conjugated dienes:

An electrophilic addition reaction to a conjugated diene forms both 1,2-addition and 1,4-addition products because the resonance contributors of the allylic cation give cation carbon and the chances for the nucleophile to attack at the electrophilic centre will occur.

Kinetic and thermodynamic products:

Kinetic product: The more rapidly formed product is called the kinetic product. The reactions that produce the kinetic product as the major product are said to be kinetically controlled. The kinetic product predominates when the reaction is irreversible.

Thermodynamic product: The more stable product is called the thermodynamic product. The reactions that produce the thermodynamic product as the major product are said to be thermodynamically controlled. The thermodynamic product predominates when the reaction is reversible.

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 product determining step of the given reaction has to be predicted.

Concept Introduction:

Reactions of conjugated dienes:

An electrophilic addition reaction to a conjugated diene forms both 1,2-addition and 1,4-addition products because the resonance contributors of the allylic cation give cation carbon and the chances for the nucleophile to attack at the electrophilic centre will occur.

Kinetic and thermodynamic products:

Kinetic product: The more rapidly formed product is called the kinetic product. The reactions that produce the kinetic product as the major product are said to be kinetically controlled. The kinetic product predominates when the reaction is irreversible.

Thermodynamic product: The more stable product is called the thermodynamic product. The reactions that produce the thermodynamic product as the major product are said to be thermodynamically controlled. The thermodynamic product predominates when the reaction is reversible.

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 product determining step of the given reaction has to be predicted.

Concept Introduction:

Reactions of conjugated dienes:

An electrophilic addition reaction to a conjugated diene forms both 1,2-addition and 1,4-addition products because the resonance contributors of the allylic cation give cation carbon and the chances for the nucleophile to attack at the electrophilic centre will occur.

Kinetic and thermodynamic products:

Kinetic product: The more rapidly formed product is called the kinetic product. The reactions that produce the kinetic product as the major product are said to be kinetically controlled. The kinetic product predominates when the reaction is irreversible.

Thermodynamic product: The more stable product is called the thermodynamic product. The reactions that produce the thermodynamic product as the major product are said to be thermodynamically controlled. The thermodynamic product predominates when the reaction is reversible.

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 rate determining step of the given reaction has to be predicted.

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