(a) Interpretation: The reason as to why the equilibrium favors the α , β -unsaturated ketone over its β , γ -unsaturated isomer is to be stated. Concept introduction: In organic chemistry , the class of functional group which is derived from conjugated diene by replacing one double bond with a carbonyl group. The dienone compound is in conjugation to each other. The conversion of dienone to phenol is known as dienone-phenol rearrangement.

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Answer 1

Question

Chapter 22, Problem 22.73AP

Interpretation Introduction

(a)

Interpretation:

The reason as to why the equilibrium favors the α,β-unsaturated ketone over its β,γ-unsaturated isomer is to be stated.

Concept introduction:

In organic chemistry, the class of functional group which is derived from conjugated diene by replacing one double bond with a carbonyl group. The dienone compound is in conjugation to each other. The conversion of dienone to phenol is known as dienone-phenol rearrangement.

Interpretation Introduction

(b)

Interpretation:

The mechanism of the given reaction in an aqueous NaOH solution is to be stated.

Concept introduction:

In organic chemistry, the class of functional group which is derived from conjugated diene by replacing one double bond with a carbonyl group. The dienone compound is in conjugation to each other. The conversion of dienone to phenol is known as dienone-phenol rearrangement.

Interpretation Introduction

(c)

Interpretation:

The mechanism of the given reaction in a dilute aqueous H2SO4 solution is to be stated.

Concept introduction:

In organic chemistry, the class of functional group which is derived from conjugated diene by replacing one double bond with a carbonyl group. The dienone compound is in conjugation to each other. The conversion of dienone to phenol is known as dienone-phenol rearrangement.

Interpretation Introduction

(d)

Interpretation:

Whether the equilibrium reaction constant for the analogous reaction of 4−methyl−3−cyclohexenone is greater or smaller is to be stated.

Concept introduction:

In organic chemistry, the class of functional group which is derived from conjugated diene by replacing one double bond with a carbonyl group. The dienone compound is in conjugation to each other. The conversion of dienone to phenol is known as dienone-phenol rearrangement.

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Indicate the products of the reaction of 2-(3-aminopropyl)cyclohexan-1-one with H2SO4. Draw the structures of the compounds.

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Question 4 For the molecule shown below, (7 marks): A) Sketch the Newman projection for the view looking along the bond from the perspective of the arrow. B) Then, draw the Newman projection for each 60° rotation along the bond until it returns to the starting point. C) Clearly indicate which Newman projection is the one we see in the structure shown below, and clearly indicate which Newman projection is the highest in energy and which is the lowest in energy. H H Me 'H Me Me

Answer 2

Question

Chapter 22, Problem 22.73AP

Interpretation Introduction

(a)

Interpretation:

The reason as to why the equilibrium favors the α,β-unsaturated ketone over its β,γ-unsaturated isomer is to be stated.

Concept introduction:

In organic chemistry, the class of functional group which is derived from conjugated diene by replacing one double bond with a carbonyl group. The dienone compound is in conjugation to each other. The conversion of dienone to phenol is known as dienone-phenol rearrangement.

Interpretation Introduction

(b)

Interpretation:

The mechanism of the given reaction in an aqueous NaOH solution is to be stated.

Concept introduction:

In organic chemistry, the class of functional group which is derived from conjugated diene by replacing one double bond with a carbonyl group. The dienone compound is in conjugation to each other. The conversion of dienone to phenol is known as dienone-phenol rearrangement.

Interpretation Introduction

(c)

Interpretation:

The mechanism of the given reaction in a dilute aqueous H2SO4 solution is to be stated.

Concept introduction:

In organic chemistry, the class of functional group which is derived from conjugated diene by replacing one double bond with a carbonyl group. The dienone compound is in conjugation to each other. The conversion of dienone to phenol is known as dienone-phenol rearrangement.

Interpretation Introduction

(d)

Interpretation:

Whether the equilibrium reaction constant for the analogous reaction of 4−methyl−3−cyclohexenone is greater or smaller is to be stated.

Concept introduction:

In organic chemistry, the class of functional group which is derived from conjugated diene by replacing one double bond with a carbonyl group. The dienone compound is in conjugation to each other. The conversion of dienone to phenol is known as dienone-phenol rearrangement.

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Answer 3

Question

Chapter 22, Problem 22.73AP

Interpretation Introduction

(a)

Interpretation:

The reason as to why the equilibrium favors the α,β-unsaturated ketone over its β,γ-unsaturated isomer is to be stated.

Concept introduction:

In organic chemistry, the class of functional group which is derived from conjugated diene by replacing one double bond with a carbonyl group. The dienone compound is in conjugation to each other. The conversion of dienone to phenol is known as dienone-phenol rearrangement.

Interpretation Introduction

(b)

Interpretation:

The mechanism of the given reaction in an aqueous NaOH solution is to be stated.

Concept introduction:

In organic chemistry, the class of functional group which is derived from conjugated diene by replacing one double bond with a carbonyl group. The dienone compound is in conjugation to each other. The conversion of dienone to phenol is known as dienone-phenol rearrangement.

Interpretation Introduction

(c)

Interpretation:

The mechanism of the given reaction in a dilute aqueous H2SO4 solution is to be stated.

Concept introduction:

In organic chemistry, the class of functional group which is derived from conjugated diene by replacing one double bond with a carbonyl group. The dienone compound is in conjugation to each other. The conversion of dienone to phenol is known as dienone-phenol rearrangement.

Interpretation Introduction

(d)

Interpretation:

Whether the equilibrium reaction constant for the analogous reaction of 4−methyl−3−cyclohexenone is greater or smaller is to be stated.

Concept introduction:

In organic chemistry, the class of functional group which is derived from conjugated diene by replacing one double bond with a carbonyl group. The dienone compound is in conjugation to each other. The conversion of dienone to phenol is known as dienone-phenol rearrangement.

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Answer 4

Question

Chapter 22, Problem 22.73AP

Interpretation Introduction

(a)

Interpretation:

The reason as to why the equilibrium favors the α,β-unsaturated ketone over its β,γ-unsaturated isomer is to be stated.

Concept introduction:

In organic chemistry, the class of functional group which is derived from conjugated diene by replacing one double bond with a carbonyl group. The dienone compound is in conjugation to each other. The conversion of dienone to phenol is known as dienone-phenol rearrangement.

Interpretation Introduction

(b)

Interpretation:

The mechanism of the given reaction in an aqueous NaOH solution is to be stated.

Concept introduction:

In organic chemistry, the class of functional group which is derived from conjugated diene by replacing one double bond with a carbonyl group. The dienone compound is in conjugation to each other. The conversion of dienone to phenol is known as dienone-phenol rearrangement.

Interpretation Introduction

(c)

Interpretation:

The mechanism of the given reaction in a dilute aqueous H2SO4 solution is to be stated.

Concept introduction:

In organic chemistry, the class of functional group which is derived from conjugated diene by replacing one double bond with a carbonyl group. The dienone compound is in conjugation to each other. The conversion of dienone to phenol is known as dienone-phenol rearrangement.

Interpretation Introduction

(d)

Interpretation:

Whether the equilibrium reaction constant for the analogous reaction of 4−methyl−3−cyclohexenone is greater or smaller is to be stated.

Concept introduction:

In organic chemistry, the class of functional group which is derived from conjugated diene by replacing one double bond with a carbonyl group. The dienone compound is in conjugation to each other. The conversion of dienone to phenol is known as dienone-phenol rearrangement.

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Answer 5

Chapter 22, Problem 22.73AP

Interpretation Introduction

(a)

Interpretation:

The reason as to why the equilibrium favors the α,β-unsaturated ketone over its β,γ-unsaturated isomer is to be stated.

Concept introduction:

In organic chemistry, the class of functional group which is derived from conjugated diene by replacing one double bond with a carbonyl group. The dienone compound is in conjugation to each other. The conversion of dienone to phenol is known as dienone-phenol rearrangement.

Interpretation Introduction

(b)

Interpretation:

The mechanism of the given reaction in an aqueous NaOH solution is to be stated.

Concept introduction:

In organic chemistry, the class of functional group which is derived from conjugated diene by replacing one double bond with a carbonyl group. The dienone compound is in conjugation to each other. The conversion of dienone to phenol is known as dienone-phenol rearrangement.

Interpretation Introduction

(c)

Interpretation:

The mechanism of the given reaction in a dilute aqueous H2SO4 solution is to be stated.

Concept introduction:

In organic chemistry, the class of functional group which is derived from conjugated diene by replacing one double bond with a carbonyl group. The dienone compound is in conjugation to each other. The conversion of dienone to phenol is known as dienone-phenol rearrangement.

Interpretation Introduction

(d)

Interpretation:

Whether the equilibrium reaction constant for the analogous reaction of 4−methyl−3−cyclohexenone is greater or smaller is to be stated.

Concept introduction:

In organic chemistry, the class of functional group which is derived from conjugated diene by replacing one double bond with a carbonyl group. The dienone compound is in conjugation to each other. The conversion of dienone to phenol is known as dienone-phenol rearrangement.

Answer 6

Chapter 22, Problem 22.73AP

Interpretation Introduction

(a)

Interpretation:

The reason as to why the equilibrium favors the α,β-unsaturated ketone over its β,γ-unsaturated isomer is to be stated.

Concept introduction:

In organic chemistry, the class of functional group which is derived from conjugated diene by replacing one double bond with a carbonyl group. The dienone compound is in conjugation to each other. The conversion of dienone to phenol is known as dienone-phenol rearrangement.

Answer 7

Chapter 22, Problem 22.73AP

Interpretation Introduction

(a)

Interpretation:

The reason as to why the equilibrium favors the α,β-unsaturated ketone over its β,γ-unsaturated isomer is to be stated.

Concept introduction:

In organic chemistry, the class of functional group which is derived from conjugated diene by replacing one double bond with a carbonyl group. The dienone compound is in conjugation to each other. The conversion of dienone to phenol is known as dienone-phenol rearrangement.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The mechanism of the given reaction in an aqueous NaOH solution is to be stated.

Concept introduction:

In organic chemistry, the class of functional group which is derived from conjugated diene by replacing one double bond with a carbonyl group. The dienone compound is in conjugation to each other. The conversion of dienone to phenol is known as dienone-phenol rearrangement.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The mechanism of the given reaction in an aqueous NaOH solution is to be stated.

Concept introduction:

In organic chemistry, the class of functional group which is derived from conjugated diene by replacing one double bond with a carbonyl group. The dienone compound is in conjugation to each other. The conversion of dienone to phenol is known as dienone-phenol rearrangement.

Answer 10

Interpretation Introduction

(c)

Interpretation:

The mechanism of the given reaction in a dilute aqueous H2SO4 solution is to be stated.

Concept introduction:

In organic chemistry, the class of functional group which is derived from conjugated diene by replacing one double bond with a carbonyl group. The dienone compound is in conjugation to each other. The conversion of dienone to phenol is known as dienone-phenol rearrangement.

Answer 11

Interpretation Introduction

(c)

Interpretation:

The mechanism of the given reaction in a dilute aqueous H2SO4 solution is to be stated.

Concept introduction:

In organic chemistry, the class of functional group which is derived from conjugated diene by replacing one double bond with a carbonyl group. The dienone compound is in conjugation to each other. The conversion of dienone to phenol is known as dienone-phenol rearrangement.

Answer 12

Interpretation Introduction

(d)

Interpretation:

Whether the equilibrium reaction constant for the analogous reaction of 4−methyl−3−cyclohexenone is greater or smaller is to be stated.

Concept introduction:

In organic chemistry, the class of functional group which is derived from conjugated diene by replacing one double bond with a carbonyl group. The dienone compound is in conjugation to each other. The conversion of dienone to phenol is known as dienone-phenol rearrangement.

Answer 13

Interpretation Introduction

(d)

Interpretation:

Whether the equilibrium reaction constant for the analogous reaction of 4−methyl−3−cyclohexenone is greater or smaller is to be stated.

Concept introduction:

In organic chemistry, the class of functional group which is derived from conjugated diene by replacing one double bond with a carbonyl group. The dienone compound is in conjugation to each other. The conversion of dienone to phenol is known as dienone-phenol rearrangement.

Answer 14

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Answer 15

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Answer 16

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Answer 17

Ch. 22 - Prob. 22.1P Ch. 22 - Prob. 22.2P Ch. 22 - Prob. 22.3P Ch. 22 - Prob. 22.4P Ch. 22 - Prob. 22.5P Ch. 22 - Prob. 22.6P Ch. 22 - Prob. 22.7P Ch. 22 - Prob. 22.8P Ch. 22 - Prob. 22.9P Ch. 22 - Prob. 22.10P

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Chapter 22 Solutions