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

Please draw the structure in the box that is consistent with all the spectral data and alphabetically label all of the equivalent protons in the structure (Ha, Hb, Hc....) in order to assign all the proton NMR peaks. The integrations are computer generated and approximate the number of equivalent protons. Molecular formula: C13H1802 14 13 12 11 10 11 (ppm) Structure with assigned H peaks 2.08 3.13

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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Please draw the structure in the box that is consistent with all the spectral data and alphabetically label all of the equivalent protons in the structure (Ha, Hb, Hc....) in order to assign all the proton NMR peaks. The integrations are computer generated and approximate the number of equivalent protons. Molecular formula: C13H1802 14 13 12 11 10 11 (ppm) Structure with assigned H peaks 2.08 3.13

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Firefly luciferin exhibits three rings. Identify which of the rings are aromatic. Identify which lone pairs are involved in establishing aromaticity. The lone pairs are labeled A-D below.

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.

Expert Solution & Answer

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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.

Expert Solution & Answer

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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.

Expert Solution & Answer

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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 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