A mechanism for the dehydration of diacetone alcohol to mesityl oxide in acidic medium is to be proposed. Concept introduction: When a basic or acidic mixture of an aldol product is heated, dehydration of alcohol functional group takes place. The product formed is a conjugated α , β − unsaturated aldehyde or ketone . An aldol condensation followed by dehydration leads to the formation of a new carbon-carbon double bond.

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Answer 1

Question

Chapter 22.8, Problem 22.22P

(a)

Interpretation Introduction

Interpretation:

A mechanism for the dehydration of diacetone alcohol to mesityl oxide in acidic medium is to be proposed.

Concept introduction:

When a basic or acidic mixture of an aldol product is heated, dehydration of alcohol functional group takes place. The product formed is a conjugated α,β− unsaturated aldehyde or ketone. An aldol condensation followed by dehydration leads to the formation of a new carbon-carbon double bond.

(b)

Interpretation Introduction

Interpretation:

A mechanism for the dehydration of diacetone alcohol to mesityl oxide in basic medium is to be proposed.

Concept introduction:

When a basic or acidic mixture of an aldol product is heated, dehydration of an alcohol functional group takes place. The product formed is a conjugated α,β− unsaturated aldehyde or ketone. An aldol condensation followed by dehydration leads to the formation of a new carbon-carbon double bond.

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Answer 2

Question

Chapter 22.8, Problem 22.22P

(a)

Interpretation Introduction

Interpretation:

A mechanism for the dehydration of diacetone alcohol to mesityl oxide in acidic medium is to be proposed.

Concept introduction:

When a basic or acidic mixture of an aldol product is heated, dehydration of alcohol functional group takes place. The product formed is a conjugated α,β− unsaturated aldehyde or ketone. An aldol condensation followed by dehydration leads to the formation of a new carbon-carbon double bond.

(b)

Interpretation Introduction

Interpretation:

A mechanism for the dehydration of diacetone alcohol to mesityl oxide in basic medium is to be proposed.

Concept introduction:

When a basic or acidic mixture of an aldol product is heated, dehydration of an alcohol functional group takes place. The product formed is a conjugated α,β− unsaturated aldehyde or ketone. An aldol condensation followed by dehydration leads to the formation of a new carbon-carbon double bond.

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Answer 3

Question

Chapter 22.8, Problem 22.22P

(a)

Interpretation Introduction

Interpretation:

A mechanism for the dehydration of diacetone alcohol to mesityl oxide in acidic medium is to be proposed.

Concept introduction:

When a basic or acidic mixture of an aldol product is heated, dehydration of alcohol functional group takes place. The product formed is a conjugated α,β− unsaturated aldehyde or ketone. An aldol condensation followed by dehydration leads to the formation of a new carbon-carbon double bond.

(b)

Interpretation Introduction

Interpretation:

A mechanism for the dehydration of diacetone alcohol to mesityl oxide in basic medium is to be proposed.

Concept introduction:

When a basic or acidic mixture of an aldol product is heated, dehydration of an alcohol functional group takes place. The product formed is a conjugated α,β− unsaturated aldehyde or ketone. An aldol condensation followed by dehydration leads to the formation of a new carbon-carbon double bond.

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Answer 4

Question

Chapter 22.8, Problem 22.22P

(a)

Interpretation Introduction

Interpretation:

A mechanism for the dehydration of diacetone alcohol to mesityl oxide in acidic medium is to be proposed.

Concept introduction:

When a basic or acidic mixture of an aldol product is heated, dehydration of alcohol functional group takes place. The product formed is a conjugated α,β− unsaturated aldehyde or ketone. An aldol condensation followed by dehydration leads to the formation of a new carbon-carbon double bond.

(b)

Interpretation Introduction

Interpretation:

A mechanism for the dehydration of diacetone alcohol to mesityl oxide in basic medium is to be proposed.

Concept introduction:

When a basic or acidic mixture of an aldol product is heated, dehydration of an alcohol functional group takes place. The product formed is a conjugated α,β− unsaturated aldehyde or ketone. An aldol condensation followed by dehydration leads to the formation of a new carbon-carbon double bond.

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Answer 5

Chapter 22.8, Problem 22.22P

(a)

Interpretation Introduction

Interpretation:

A mechanism for the dehydration of diacetone alcohol to mesityl oxide in acidic medium is to be proposed.

Concept introduction:

When a basic or acidic mixture of an aldol product is heated, dehydration of alcohol functional group takes place. The product formed is a conjugated α,β− unsaturated aldehyde or ketone. An aldol condensation followed by dehydration leads to the formation of a new carbon-carbon double bond.

(b)

Interpretation Introduction

Interpretation:

A mechanism for the dehydration of diacetone alcohol to mesityl oxide in basic medium is to be proposed.

Concept introduction:

When a basic or acidic mixture of an aldol product is heated, dehydration of an alcohol functional group takes place. The product formed is a conjugated α,β− unsaturated aldehyde or ketone. An aldol condensation followed by dehydration leads to the formation of a new carbon-carbon double bond.

Answer 6

Chapter 22.8, Problem 22.22P

(a)

Interpretation Introduction

Interpretation:

A mechanism for the dehydration of diacetone alcohol to mesityl oxide in acidic medium is to be proposed.

Concept introduction:

When a basic or acidic mixture of an aldol product is heated, dehydration of alcohol functional group takes place. The product formed is a conjugated α,β− unsaturated aldehyde or ketone. An aldol condensation followed by dehydration leads to the formation of a new carbon-carbon double bond.

Answer 7

Chapter 22.8, Problem 22.22P

(a)

Interpretation Introduction

Interpretation:

A mechanism for the dehydration of diacetone alcohol to mesityl oxide in acidic medium is to be proposed.

Concept introduction:

When a basic or acidic mixture of an aldol product is heated, dehydration of alcohol functional group takes place. The product formed is a conjugated α,β− unsaturated aldehyde or ketone. An aldol condensation followed by dehydration leads to the formation of a new carbon-carbon double bond.

Answer 8

(b)

Interpretation Introduction

Interpretation:

A mechanism for the dehydration of diacetone alcohol to mesityl oxide in basic medium is to be proposed.

Concept introduction:

When a basic or acidic mixture of an aldol product is heated, dehydration of an alcohol functional group takes place. The product formed is a conjugated α,β− unsaturated aldehyde or ketone. An aldol condensation followed by dehydration leads to the formation of a new carbon-carbon double bond.

Answer 9

(b)

Interpretation Introduction

Interpretation:

A mechanism for the dehydration of diacetone alcohol to mesityl oxide in basic medium is to be proposed.

Concept introduction:

When a basic or acidic mixture of an aldol product is heated, dehydration of an alcohol functional group takes place. The product formed is a conjugated α,β− unsaturated aldehyde or ketone. An aldol condensation followed by dehydration leads to the formation of a new carbon-carbon double bond.

Answer 10

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Answer 12

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Answer 13

Ch. 22.2A - Prob. 22.2P Ch. 22.4 - Without looking back, propose a mechanism for the...Ch. 22.4 - Prob. 22.8P Ch. 22.4 - Prob. 22.9P Ch. 22.5A - Prob. 22.10P Ch. 22.5A - Prob. 22.11P Ch. 22.5B - Prob. 22.12P Ch. 22.5B - Predict the products of the following reactions....Ch. 22.5B - Which compounds will give positive iodoform tests?...Ch. 22.5C - Propose a mechanism for the acid-catalyzed...

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Chapter 22 Solutions