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

Question

Want to see the full answer?

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

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

When HBr adds to a conjugated diene, what is the product-determining step?

1. Free radicals are generated by subjecting a molecule such as chlorine or bromine gas to A. high temperature conditions. B. photolysis. C. ionizing conditions. D. choices A and B 2. Which of the following radical intermediates is the most stable? q •CF3 A. B. C. D. 3. In the reaction shown below the intermediate that is formed at the fastest rate is Cl₂ A. uv CH, CH₂CHCH₂CH₂CH₂ B. CH, CH.CCH₂CH₂CH, CH₂ C. CH.CHCHCH.CH, D. CH₂ CH₂CHCH₂CHCH

Which of the following statements about an SN2 reaction is true? A. There are two transition states. B. There is one energy maximum. C. The transition state can be isolated and studied. D. For a carbon electrophile in the transition state, the hybridization of an sp3 carbon remains unchanged. E. The reaction rate does not depend on the concentration of the electrophile.

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

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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

Want to see the full answer?

Check out a sample textbook solution

See solution

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

Want to see the full answer?

Check out a sample textbook solution

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

Expert Solution & Answer

Answer 11

Expert Solution & Answer

Answer 12

Want to see the full answer?

Check out a sample textbook solution

See solution

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.

Concept explainers

Want to see the full answer?

Chapter 8 Solutions