(a) Interpretation: A reaction free-energy diagram for acid-catalyzed enol formation using the mechanism in Eq.22.17b is to be sketched. Concept Introduction: Conversion of ketone group into enol group is known as enolization reaction. Keto to enol conversion can be done by two types either using a base or using an acid. In the acid catalyzed enolization, conjugate acid of carbonyl compound is formed.

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Answer 1

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 22, Problem 22.12P

Interpretation Introduction

(a)

Interpretation:

A reaction free-energy diagram for acid-catalyzed enol formation using the mechanism in Eq.22.17b is to be sketched.

Concept Introduction:

Conversion of ketone group into enol group is known as enolization reaction. Keto to enol conversion can be done by two types either using a base or using an acid. In the acid catalyzed enolization, conjugate acid of carbonyl compound is formed.

Interpretation Introduction

(b)

Interpretation:

A reaction free-energy diagram for the acid catalyzed halogenation of aldehyde or ketone is to be drawn.

Concept Introduction:

Halogenation reaction of aldehyde or ketone is done either in acidic or in basic aqueous medium. The halogenation takes place at the α position of aldehyde or ketone. In the halogenation reaction of ketone, first keto group gets converted into enol. Then, halogen gets added to the enol structure to form intermediate which after elimination of HX forms haloketone.

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(a) Explain the mechanism of a nucleophilic attack on the carbonyl group of an aldehyde or a ketone.(b) An organic compound (A) (molecular formula CgH16Q2) was hydrolysed with dilute sulphuric acid to give a carboxylic acid (B) and an alcohol (C). Oxidation of (C) with chromic acid also produced (B). On dehydration (C) gives but-1-ene. Write the equations for the reactions involved.

(b) Suggest a reasonable biosynthesis for the naturally occurring alkaloid coniine (isolated from hemlock), starting from octanoic acid. Coniine

Provide the reagents and solvents (where appropriate) needed to bring about the following transformations. (a) CI (b)

Answer 2

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 22, Problem 22.12P

Interpretation Introduction

(a)

Interpretation:

A reaction free-energy diagram for acid-catalyzed enol formation using the mechanism in Eq.22.17b is to be sketched.

Concept Introduction:

Conversion of ketone group into enol group is known as enolization reaction. Keto to enol conversion can be done by two types either using a base or using an acid. In the acid catalyzed enolization, conjugate acid of carbonyl compound is formed.

Interpretation Introduction

(b)

Interpretation:

A reaction free-energy diagram for the acid catalyzed halogenation of aldehyde or ketone is to be drawn.

Concept Introduction:

Halogenation reaction of aldehyde or ketone is done either in acidic or in basic aqueous medium. The halogenation takes place at the α position of aldehyde or ketone. In the halogenation reaction of ketone, first keto group gets converted into enol. Then, halogen gets added to the enol structure to form intermediate which after elimination of HX forms haloketone.

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Answer 3

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 22, Problem 22.12P

Interpretation Introduction

(a)

Interpretation:

A reaction free-energy diagram for acid-catalyzed enol formation using the mechanism in Eq.22.17b is to be sketched.

Concept Introduction:

Conversion of ketone group into enol group is known as enolization reaction. Keto to enol conversion can be done by two types either using a base or using an acid. In the acid catalyzed enolization, conjugate acid of carbonyl compound is formed.

Interpretation Introduction

(b)

Interpretation:

A reaction free-energy diagram for the acid catalyzed halogenation of aldehyde or ketone is to be drawn.

Concept Introduction:

Halogenation reaction of aldehyde or ketone is done either in acidic or in basic aqueous medium. The halogenation takes place at the α position of aldehyde or ketone. In the halogenation reaction of ketone, first keto group gets converted into enol. Then, halogen gets added to the enol structure to form intermediate which after elimination of HX forms haloketone.

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Answer 4

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 22, Problem 22.12P

Interpretation Introduction

(a)

Interpretation:

A reaction free-energy diagram for acid-catalyzed enol formation using the mechanism in Eq.22.17b is to be sketched.

Concept Introduction:

Conversion of ketone group into enol group is known as enolization reaction. Keto to enol conversion can be done by two types either using a base or using an acid. In the acid catalyzed enolization, conjugate acid of carbonyl compound is formed.

Interpretation Introduction

(b)

Interpretation:

A reaction free-energy diagram for the acid catalyzed halogenation of aldehyde or ketone is to be drawn.

Concept Introduction:

Halogenation reaction of aldehyde or ketone is done either in acidic or in basic aqueous medium. The halogenation takes place at the α position of aldehyde or ketone. In the halogenation reaction of ketone, first keto group gets converted into enol. Then, halogen gets added to the enol structure to form intermediate which after elimination of HX forms haloketone.

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Answer 5

Chapter 22, Problem 22.12P

Interpretation Introduction

(a)

Interpretation:

A reaction free-energy diagram for acid-catalyzed enol formation using the mechanism in Eq.22.17b is to be sketched.

Concept Introduction:

Conversion of ketone group into enol group is known as enolization reaction. Keto to enol conversion can be done by two types either using a base or using an acid. In the acid catalyzed enolization, conjugate acid of carbonyl compound is formed.

Interpretation Introduction

(b)

Interpretation:

A reaction free-energy diagram for the acid catalyzed halogenation of aldehyde or ketone is to be drawn.

Concept Introduction:

Halogenation reaction of aldehyde or ketone is done either in acidic or in basic aqueous medium. The halogenation takes place at the α position of aldehyde or ketone. In the halogenation reaction of ketone, first keto group gets converted into enol. Then, halogen gets added to the enol structure to form intermediate which after elimination of HX forms haloketone.

Answer 6

Chapter 22, Problem 22.12P

Interpretation Introduction

(a)

Interpretation:

A reaction free-energy diagram for acid-catalyzed enol formation using the mechanism in Eq.22.17b is to be sketched.

Concept Introduction:

Conversion of ketone group into enol group is known as enolization reaction. Keto to enol conversion can be done by two types either using a base or using an acid. In the acid catalyzed enolization, conjugate acid of carbonyl compound is formed.

Answer 7

Chapter 22, Problem 22.12P

Interpretation Introduction

(a)

Interpretation:

A reaction free-energy diagram for acid-catalyzed enol formation using the mechanism in Eq.22.17b is to be sketched.

Concept Introduction:

Conversion of ketone group into enol group is known as enolization reaction. Keto to enol conversion can be done by two types either using a base or using an acid. In the acid catalyzed enolization, conjugate acid of carbonyl compound is formed.

Answer 8

Interpretation Introduction

(b)

Interpretation:

A reaction free-energy diagram for the acid catalyzed halogenation of aldehyde or ketone is to be drawn.

Concept Introduction:

Halogenation reaction of aldehyde or ketone is done either in acidic or in basic aqueous medium. The halogenation takes place at the α position of aldehyde or ketone. In the halogenation reaction of ketone, first keto group gets converted into enol. Then, halogen gets added to the enol structure to form intermediate which after elimination of HX forms haloketone.

Answer 9

Interpretation Introduction

(b)

Interpretation:

A reaction free-energy diagram for the acid catalyzed halogenation of aldehyde or ketone is to be drawn.

Concept Introduction:

Halogenation reaction of aldehyde or ketone is done either in acidic or in basic aqueous medium. The halogenation takes place at the α position of aldehyde or ketone. In the halogenation reaction of ketone, first keto group gets converted into enol. Then, halogen gets added to the enol structure to form intermediate which after elimination of HX forms haloketone.

Answer 10

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Answer 11

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Answer 12

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Answer 13

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

Solution Summary: The author illustrates the reaction free-energy diagram for the acid catalyzed enol formation using Eq.22.17b.

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Chapter 22 Solutions