a) Interpretation: The major products formed during the addition of one equivalent of HCl to hexa-2, 4-diene along with the mechanism of their formation is to be shown. Concept introduction: Conjugated dienes undergo electrophilic addition reactions through the formation of an allyl carbocation. The allyl cation is resonance stabilized and the attack of chloride ion on each of these forms leads to the formation of a mixture of 1, 2- and 1, 4-addition products. To show: The major product formed during the addition of one equivalent of HCl to hexa-2, 4-diene along with the mechanism of their formation.

Question

20.44 The Diels-Alder reaction is not limited to making six-membered rings with only car- bon atoms. Predict the products of the following reactions that produce rings with atoms other than carbon in them. OCCH OCCH H (b) CH C(CH₂)s COOCH མ་ནས་བ (c) N=C H -0.X- (e) H C=N COOCHS + CH2=CHCH₂ →→

Answer 1

Question

Chapter 14.SE, Problem 20MP

Interpretation Introduction

a)

Interpretation:

The major products formed during the addition of one equivalent of HCl to hexa-2, 4-diene along with the mechanism of their formation is to be shown.

Concept introduction:

Conjugated dienes undergo electrophilic addition reactions through the formation of an allyl carbocation. The allyl cation is resonance stabilized and the attack of chloride ion on each of these forms leads to the formation of a mixture of 1, 2- and 1, 4-addition products.

To show:

The major product formed during the addition of one equivalent of HCl to hexa-2, 4-diene along with the mechanism of their formation.

Interpretation Introduction

b)

Interpretation:

The major products formed during the addition of one equivalent of HX to 3-methylpenta-1, 3-diene along with the mechanism of their formation is to be shown.

Concept introduction:

Conjugated dienes undergo electrophilic addition reactions through the formation of an allyl carbocation. The allyl cation is resonance stabilized and the attack of chloride ion on each of these forms leads to the formation of a mixture of 1, 2- and 1, 4-addition products.

To show:

The major products formed during the addition of one equivalent of HBr to 3-methylpenta-1, 3-diene along with the mechanism of their formation.

Interpretation Introduction

c)

Interpretation:

The major product formed during the addition of one equivalent of HCl to 1, 2-dimethylenecyclobutane, along with the mechanism of their formation is to be shown.

Concept introduction:

Conjugated dienes undergo electrophilic addition reactions through the formation of an allyl carbocation. The allyl cation is resonance stabilized and the attack of chloride ion on each of these forms leads to the formation of a mixture of 1, 2- and 1, 4-addition products.

To show:

The major product formed during the addition of one equivalent of HCl to 1, 2-dimethylenecyclobutane along with the mechanism of their formation.

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20.44 The Diels-Alder reaction is not limited to making six-membered rings with only car- bon atoms. Predict the products of the following reactions that produce rings with atoms other than carbon in them. OCCH OCCH H (b) CH C(CH₂)s COOCH མ་ནས་བ (c) N=C H -0.X- (e) H C=N COOCHS + CH2=CHCH₂ →→

Given the attached data, provide the drawing for the corresponding structure.

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Answer 2

Question

Chapter 14.SE, Problem 20MP

Interpretation Introduction

a)

Interpretation:

The major products formed during the addition of one equivalent of HCl to hexa-2, 4-diene along with the mechanism of their formation is to be shown.

Concept introduction:

Conjugated dienes undergo electrophilic addition reactions through the formation of an allyl carbocation. The allyl cation is resonance stabilized and the attack of chloride ion on each of these forms leads to the formation of a mixture of 1, 2- and 1, 4-addition products.

To show:

The major product formed during the addition of one equivalent of HCl to hexa-2, 4-diene along with the mechanism of their formation.

Interpretation Introduction

b)

Interpretation:

The major products formed during the addition of one equivalent of HX to 3-methylpenta-1, 3-diene along with the mechanism of their formation is to be shown.

Concept introduction:

Conjugated dienes undergo electrophilic addition reactions through the formation of an allyl carbocation. The allyl cation is resonance stabilized and the attack of chloride ion on each of these forms leads to the formation of a mixture of 1, 2- and 1, 4-addition products.

To show:

The major products formed during the addition of one equivalent of HBr to 3-methylpenta-1, 3-diene along with the mechanism of their formation.

Interpretation Introduction

c)

Interpretation:

The major product formed during the addition of one equivalent of HCl to 1, 2-dimethylenecyclobutane, along with the mechanism of their formation is to be shown.

Concept introduction:

Conjugated dienes undergo electrophilic addition reactions through the formation of an allyl carbocation. The allyl cation is resonance stabilized and the attack of chloride ion on each of these forms leads to the formation of a mixture of 1, 2- and 1, 4-addition products.

To show:

The major product formed during the addition of one equivalent of HCl to 1, 2-dimethylenecyclobutane along with the mechanism of their formation.

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Answer 3

Question

Chapter 14.SE, Problem 20MP

Interpretation Introduction

a)

Interpretation:

The major products formed during the addition of one equivalent of HCl to hexa-2, 4-diene along with the mechanism of their formation is to be shown.

Concept introduction:

Conjugated dienes undergo electrophilic addition reactions through the formation of an allyl carbocation. The allyl cation is resonance stabilized and the attack of chloride ion on each of these forms leads to the formation of a mixture of 1, 2- and 1, 4-addition products.

To show:

The major product formed during the addition of one equivalent of HCl to hexa-2, 4-diene along with the mechanism of their formation.

Interpretation Introduction

b)

Interpretation:

The major products formed during the addition of one equivalent of HX to 3-methylpenta-1, 3-diene along with the mechanism of their formation is to be shown.

Concept introduction:

Conjugated dienes undergo electrophilic addition reactions through the formation of an allyl carbocation. The allyl cation is resonance stabilized and the attack of chloride ion on each of these forms leads to the formation of a mixture of 1, 2- and 1, 4-addition products.

To show:

The major products formed during the addition of one equivalent of HBr to 3-methylpenta-1, 3-diene along with the mechanism of their formation.

Interpretation Introduction

c)

Interpretation:

The major product formed during the addition of one equivalent of HCl to 1, 2-dimethylenecyclobutane, along with the mechanism of their formation is to be shown.

Concept introduction:

Conjugated dienes undergo electrophilic addition reactions through the formation of an allyl carbocation. The allyl cation is resonance stabilized and the attack of chloride ion on each of these forms leads to the formation of a mixture of 1, 2- and 1, 4-addition products.

To show:

The major product formed during the addition of one equivalent of HCl to 1, 2-dimethylenecyclobutane along with the mechanism of their formation.

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Answer 4

Question

Chapter 14.SE, Problem 20MP

Interpretation Introduction

a)

Interpretation:

The major products formed during the addition of one equivalent of HCl to hexa-2, 4-diene along with the mechanism of their formation is to be shown.

Concept introduction:

Conjugated dienes undergo electrophilic addition reactions through the formation of an allyl carbocation. The allyl cation is resonance stabilized and the attack of chloride ion on each of these forms leads to the formation of a mixture of 1, 2- and 1, 4-addition products.

To show:

The major product formed during the addition of one equivalent of HCl to hexa-2, 4-diene along with the mechanism of their formation.

Interpretation Introduction

b)

Interpretation:

The major products formed during the addition of one equivalent of HX to 3-methylpenta-1, 3-diene along with the mechanism of their formation is to be shown.

Concept introduction:

Conjugated dienes undergo electrophilic addition reactions through the formation of an allyl carbocation. The allyl cation is resonance stabilized and the attack of chloride ion on each of these forms leads to the formation of a mixture of 1, 2- and 1, 4-addition products.

To show:

The major products formed during the addition of one equivalent of HBr to 3-methylpenta-1, 3-diene along with the mechanism of their formation.

Interpretation Introduction

c)

Interpretation:

The major product formed during the addition of one equivalent of HCl to 1, 2-dimethylenecyclobutane, along with the mechanism of their formation is to be shown.

Concept introduction:

Conjugated dienes undergo electrophilic addition reactions through the formation of an allyl carbocation. The allyl cation is resonance stabilized and the attack of chloride ion on each of these forms leads to the formation of a mixture of 1, 2- and 1, 4-addition products.

To show:

The major product formed during the addition of one equivalent of HCl to 1, 2-dimethylenecyclobutane along with the mechanism of their formation.

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Answer 5

Chapter 14.SE, Problem 20MP

Interpretation Introduction

a)

Interpretation:

The major products formed during the addition of one equivalent of HCl to hexa-2, 4-diene along with the mechanism of their formation is to be shown.

Concept introduction:

Conjugated dienes undergo electrophilic addition reactions through the formation of an allyl carbocation. The allyl cation is resonance stabilized and the attack of chloride ion on each of these forms leads to the formation of a mixture of 1, 2- and 1, 4-addition products.

To show:

The major product formed during the addition of one equivalent of HCl to hexa-2, 4-diene along with the mechanism of their formation.

Interpretation Introduction

b)

Interpretation:

The major products formed during the addition of one equivalent of HX to 3-methylpenta-1, 3-diene along with the mechanism of their formation is to be shown.

Concept introduction:

Conjugated dienes undergo electrophilic addition reactions through the formation of an allyl carbocation. The allyl cation is resonance stabilized and the attack of chloride ion on each of these forms leads to the formation of a mixture of 1, 2- and 1, 4-addition products.

To show:

The major products formed during the addition of one equivalent of HBr to 3-methylpenta-1, 3-diene along with the mechanism of their formation.

Interpretation Introduction

c)

Interpretation:

The major product formed during the addition of one equivalent of HCl to 1, 2-dimethylenecyclobutane, along with the mechanism of their formation is to be shown.

Concept introduction:

Conjugated dienes undergo electrophilic addition reactions through the formation of an allyl carbocation. The allyl cation is resonance stabilized and the attack of chloride ion on each of these forms leads to the formation of a mixture of 1, 2- and 1, 4-addition products.

To show:

The major product formed during the addition of one equivalent of HCl to 1, 2-dimethylenecyclobutane along with the mechanism of their formation.

Answer 6

Chapter 14.SE, Problem 20MP

Interpretation Introduction

a)

Interpretation:

The major products formed during the addition of one equivalent of HCl to hexa-2, 4-diene along with the mechanism of their formation is to be shown.

Concept introduction:

Conjugated dienes undergo electrophilic addition reactions through the formation of an allyl carbocation. The allyl cation is resonance stabilized and the attack of chloride ion on each of these forms leads to the formation of a mixture of 1, 2- and 1, 4-addition products.

To show:

The major product formed during the addition of one equivalent of HCl to hexa-2, 4-diene along with the mechanism of their formation.

Answer 7

Chapter 14.SE, Problem 20MP

Interpretation Introduction

a)

Interpretation:

The major products formed during the addition of one equivalent of HCl to hexa-2, 4-diene along with the mechanism of their formation is to be shown.

Concept introduction:

Conjugated dienes undergo electrophilic addition reactions through the formation of an allyl carbocation. The allyl cation is resonance stabilized and the attack of chloride ion on each of these forms leads to the formation of a mixture of 1, 2- and 1, 4-addition products.

To show:

The major product formed during the addition of one equivalent of HCl to hexa-2, 4-diene along with the mechanism of their formation.

Answer 8

Interpretation Introduction

b)

Interpretation:

The major products formed during the addition of one equivalent of HX to 3-methylpenta-1, 3-diene along with the mechanism of their formation is to be shown.

Concept introduction:

Conjugated dienes undergo electrophilic addition reactions through the formation of an allyl carbocation. The allyl cation is resonance stabilized and the attack of chloride ion on each of these forms leads to the formation of a mixture of 1, 2- and 1, 4-addition products.

To show:

The major products formed during the addition of one equivalent of HBr to 3-methylpenta-1, 3-diene along with the mechanism of their formation.

Answer 9

Interpretation Introduction

b)

Interpretation:

The major products formed during the addition of one equivalent of HX to 3-methylpenta-1, 3-diene along with the mechanism of their formation is to be shown.

Concept introduction:

Conjugated dienes undergo electrophilic addition reactions through the formation of an allyl carbocation. The allyl cation is resonance stabilized and the attack of chloride ion on each of these forms leads to the formation of a mixture of 1, 2- and 1, 4-addition products.

To show:

The major products formed during the addition of one equivalent of HBr to 3-methylpenta-1, 3-diene along with the mechanism of their formation.

Answer 10

Interpretation Introduction

c)

Interpretation:

The major product formed during the addition of one equivalent of HCl to 1, 2-dimethylenecyclobutane, along with the mechanism of their formation is to be shown.

Concept introduction:

Conjugated dienes undergo electrophilic addition reactions through the formation of an allyl carbocation. The allyl cation is resonance stabilized and the attack of chloride ion on each of these forms leads to the formation of a mixture of 1, 2- and 1, 4-addition products.

To show:

The major product formed during the addition of one equivalent of HCl to 1, 2-dimethylenecyclobutane along with the mechanism of their formation.

Answer 11

Interpretation Introduction

c)

Interpretation:

The major product formed during the addition of one equivalent of HCl to 1, 2-dimethylenecyclobutane, along with the mechanism of their formation is to be shown.

Concept introduction:

Conjugated dienes undergo electrophilic addition reactions through the formation of an allyl carbocation. The allyl cation is resonance stabilized and the attack of chloride ion on each of these forms leads to the formation of a mixture of 1, 2- and 1, 4-addition products.

To show:

The major product formed during the addition of one equivalent of HCl to 1, 2-dimethylenecyclobutane along with the mechanism of their formation.

Answer 12

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Answer 13

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Answer 23

Ch. 14.1 - Prob. 1P Ch. 14.2 - Give the structures of both 1, 2 and 1, 4 adducts...Ch. 14.2 - Prob. 3P Ch. 14.2 - Give the structures of both 1, 2 and 1, 4 adducts...Ch. 14.3 - Prob. 5P Ch. 14.3 - Prob. 6P Ch. 14.5 - Predict the product of the following Dielsâ€“Alder...Ch. 14.5 - Prob. 8P Ch. 14.5 - Which of the following dienes have an s-cis...Ch. 14.5 - Predict the product of the following Dielsâ€“Alder...

Solution Summary: The author explains that the major products formed during the addition of one equivalent of HCl to hexa-2, 4-diene and the mechanism of their formation are to be shown.

Chapter 14 Solutions