The product for the given reaction has to be shown and the major product has to be indicated. Concept introduction: Autoxidation involves reaction of a C − H bond, (usually allylic one) with oxygen under radical initiation condition. The product is a hydroperoxide. Mechanism involves a radical chain process in which resonance-delocalized allylic radical intermediates reacts with molecular oxygen to give peroxy radical that continues the radical chain. Major product is more substituted double bond.

Question

Select the stronger base from each pair of compounds. (a) H₂CNH₂ or EtzN (b) CI or NH2 NH2 (c) .Q or EtzN (d) or (e) N or (f) H or H

Answer 1

Question

Chapter 8, Problem 8.31P

(a)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be shown and the major product has to be indicated.

Concept introduction:

Autoxidation involves reaction of a C−H bond, (usually allylic one) with oxygen under radical initiation condition. The product is a hydroperoxide.

Mechanism involves a radical chain process in which resonance-delocalized allylic radical intermediates reacts with molecular oxygen to give peroxy radical that continues the radical chain.

Major product is more substituted double bond.

(b)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be shown and the major product has to be indicated.

Concept introduction:

Autoxidation involves reaction of a C−H bond, (usually allylic one) with oxygen under radical initiation condition. The product is a hydroperoxide.

Mechanism involves a radical chain process in which resonance-delocalized allylic radical intermediates reacts with molecular oxygen to give peroxy radical that continues the radical chain.

Major product is more substituted double bond.

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Select the stronger base from each pair of compounds. (a) H₂CNH₂ or EtzN (b) CI or NH2 NH2 (c) .Q or EtzN (d) or (e) N or (f) H or H

4. Provide a clear arrow-pushing mechanism for each of the following reactions. Do not skip proton transfers, do not combine steps, and make sure your arrows are clear enough to be interpreted without ambiguity. a. 2. 1. LDA 3. H3O+ HO

b. H3C CH3 H3O+ ✓ H OH

Answer 2

Question

Chapter 8, Problem 8.31P

(a)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be shown and the major product has to be indicated.

Concept introduction:

Autoxidation involves reaction of a C−H bond, (usually allylic one) with oxygen under radical initiation condition. The product is a hydroperoxide.

Mechanism involves a radical chain process in which resonance-delocalized allylic radical intermediates reacts with molecular oxygen to give peroxy radical that continues the radical chain.

Major product is more substituted double bond.

(b)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be shown and the major product has to be indicated.

Concept introduction:

Autoxidation involves reaction of a C−H bond, (usually allylic one) with oxygen under radical initiation condition. The product is a hydroperoxide.

Mechanism involves a radical chain process in which resonance-delocalized allylic radical intermediates reacts with molecular oxygen to give peroxy radical that continues the radical chain.

Major product is more substituted double bond.

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Answer 3

Question

Chapter 8, Problem 8.31P

(a)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be shown and the major product has to be indicated.

Concept introduction:

Autoxidation involves reaction of a C−H bond, (usually allylic one) with oxygen under radical initiation condition. The product is a hydroperoxide.

Mechanism involves a radical chain process in which resonance-delocalized allylic radical intermediates reacts with molecular oxygen to give peroxy radical that continues the radical chain.

Major product is more substituted double bond.

(b)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be shown and the major product has to be indicated.

Concept introduction:

Autoxidation involves reaction of a C−H bond, (usually allylic one) with oxygen under radical initiation condition. The product is a hydroperoxide.

Mechanism involves a radical chain process in which resonance-delocalized allylic radical intermediates reacts with molecular oxygen to give peroxy radical that continues the radical chain.

Major product is more substituted double bond.

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Answer 4

Question

Chapter 8, Problem 8.31P

(a)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be shown and the major product has to be indicated.

Concept introduction:

Autoxidation involves reaction of a C−H bond, (usually allylic one) with oxygen under radical initiation condition. The product is a hydroperoxide.

Mechanism involves a radical chain process in which resonance-delocalized allylic radical intermediates reacts with molecular oxygen to give peroxy radical that continues the radical chain.

Major product is more substituted double bond.

(b)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be shown and the major product has to be indicated.

Concept introduction:

Autoxidation involves reaction of a C−H bond, (usually allylic one) with oxygen under radical initiation condition. The product is a hydroperoxide.

Mechanism involves a radical chain process in which resonance-delocalized allylic radical intermediates reacts with molecular oxygen to give peroxy radical that continues the radical chain.

Major product is more substituted double bond.

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Answer 5

Chapter 8, Problem 8.31P

(a)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be shown and the major product has to be indicated.

Concept introduction:

Autoxidation involves reaction of a C−H bond, (usually allylic one) with oxygen under radical initiation condition. The product is a hydroperoxide.

Mechanism involves a radical chain process in which resonance-delocalized allylic radical intermediates reacts with molecular oxygen to give peroxy radical that continues the radical chain.

Major product is more substituted double bond.

(b)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be shown and the major product has to be indicated.

Concept introduction:

Autoxidation involves reaction of a C−H bond, (usually allylic one) with oxygen under radical initiation condition. The product is a hydroperoxide.

Mechanism involves a radical chain process in which resonance-delocalized allylic radical intermediates reacts with molecular oxygen to give peroxy radical that continues the radical chain.

Major product is more substituted double bond.

Answer 6

Chapter 8, Problem 8.31P

(a)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be shown and the major product has to be indicated.

Concept introduction:

Autoxidation involves reaction of a C−H bond, (usually allylic one) with oxygen under radical initiation condition. The product is a hydroperoxide.

Mechanism involves a radical chain process in which resonance-delocalized allylic radical intermediates reacts with molecular oxygen to give peroxy radical that continues the radical chain.

Major product is more substituted double bond.

Answer 7

Chapter 8, Problem 8.31P

(a)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be shown and the major product has to be indicated.

Concept introduction:

Autoxidation involves reaction of a C−H bond, (usually allylic one) with oxygen under radical initiation condition. The product is a hydroperoxide.

Mechanism involves a radical chain process in which resonance-delocalized allylic radical intermediates reacts with molecular oxygen to give peroxy radical that continues the radical chain.

Major product is more substituted double bond.

Answer 8

(b)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be shown and the major product has to be indicated.

Concept introduction:

Autoxidation involves reaction of a C−H bond, (usually allylic one) with oxygen under radical initiation condition. The product is a hydroperoxide.

Mechanism involves a radical chain process in which resonance-delocalized allylic radical intermediates reacts with molecular oxygen to give peroxy radical that continues the radical chain.

Major product is more substituted double bond.

Answer 9

(b)

Interpretation Introduction

Interpretation:

The product for the given reaction has to be shown and the major product has to be indicated.

Concept introduction:

Autoxidation involves reaction of a C−H bond, (usually allylic one) with oxygen under radical initiation condition. The product is a hydroperoxide.

Mechanism involves a radical chain process in which resonance-delocalized allylic radical intermediates reacts with molecular oxygen to give peroxy radical that continues the radical chain.

Major product is more substituted double bond.

Answer 10

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Answer 21

Ch. 8.2 - Prob. 8.1P Ch. 8.4 - Name and draw structural formulas for all...Ch. 8.4 - Using the table of bond dissociation enthalpies in...Ch. 8.5 - Prob. 8.4P Ch. 8.6 - Given the solution to Example 8.5, predict the...Ch. 8.7 - Prob. 8.6P Ch. 8.7 - Linoleic acid is shown below. What makes this...Ch. 8.7 - Prob. BQ Ch. 8.7 - Prob. CQ Ch. 8.7 - The strength of the HO bond in vitamin E is weaker...

Solution Summary: The author explains that autoxidation involves reaction of a C-H bond with oxygen under radical initiation condition.

Chapter 8 Solutions