To predict the major product in the given set of reactions and propose a mechanism for the same. Concept introduction: Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then undergoes E2 elimination when treated with pyridine to form α , β − unsaturated ketone and α , β − unsaturated aldehyde respectively depending upon the starting material taken.

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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 22.2, Problem 9CC

(a)

Interpretation Introduction

Interpretation:

To predict the major product in the given set of reactions and propose a mechanism for the same.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then undergoes E2 elimination when treated with pyridine to form α,β− unsaturated ketone and α,β− unsaturated aldehyde respectively depending upon the starting material taken.

(b)

Interpretation Introduction

Interpretation:

To predict the major product in the given set of reactions and propose a mechanism for the same.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then undergoes E2 elimination when treated with pyridine to form α,β− unsaturated ketone and α,β− unsaturated aldehyde respectively depending upon the starting material taken.

(c)

Interpretation Introduction

Interpretation:

To predict the major product in the given set of reactions and propose a mechanism for the same.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then undergoes E2 elimination when treated with pyridine to form α,β− unsaturated ketone and α,β− unsaturated aldehyde respectively depending upon the starting material taken.

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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 22.2, Problem 9CC

(a)

Interpretation Introduction

Interpretation:

To predict the major product in the given set of reactions and propose a mechanism for the same.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then undergoes E2 elimination when treated with pyridine to form α,β− unsaturated ketone and α,β− unsaturated aldehyde respectively depending upon the starting material taken.

(b)

Interpretation Introduction

Interpretation:

To predict the major product in the given set of reactions and propose a mechanism for the same.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then undergoes E2 elimination when treated with pyridine to form α,β− unsaturated ketone and α,β− unsaturated aldehyde respectively depending upon the starting material taken.

(c)

Interpretation Introduction

Interpretation:

To predict the major product in the given set of reactions and propose a mechanism for the same.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then undergoes E2 elimination when treated with pyridine to form α,β− unsaturated ketone and α,β− unsaturated aldehyde respectively depending upon the starting material taken.

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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 22.2, Problem 9CC

(a)

Interpretation Introduction

Interpretation:

To predict the major product in the given set of reactions and propose a mechanism for the same.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then undergoes E2 elimination when treated with pyridine to form α,β− unsaturated ketone and α,β− unsaturated aldehyde respectively depending upon the starting material taken.

(b)

Interpretation Introduction

Interpretation:

To predict the major product in the given set of reactions and propose a mechanism for the same.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then undergoes E2 elimination when treated with pyridine to form α,β− unsaturated ketone and α,β− unsaturated aldehyde respectively depending upon the starting material taken.

(c)

Interpretation Introduction

Interpretation:

To predict the major product in the given set of reactions and propose a mechanism for the same.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then undergoes E2 elimination when treated with pyridine to form α,β− unsaturated ketone and α,β− unsaturated aldehyde respectively depending upon the starting material taken.

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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 22.2, Problem 9CC

(a)

Interpretation Introduction

Interpretation:

To predict the major product in the given set of reactions and propose a mechanism for the same.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then undergoes E2 elimination when treated with pyridine to form α,β− unsaturated ketone and α,β− unsaturated aldehyde respectively depending upon the starting material taken.

(b)

Interpretation Introduction

Interpretation:

To predict the major product in the given set of reactions and propose a mechanism for the same.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then undergoes E2 elimination when treated with pyridine to form α,β− unsaturated ketone and α,β− unsaturated aldehyde respectively depending upon the starting material taken.

(c)

Interpretation Introduction

Interpretation:

To predict the major product in the given set of reactions and propose a mechanism for the same.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then undergoes E2 elimination when treated with pyridine to form α,β− unsaturated ketone and α,β− unsaturated aldehyde respectively depending upon the starting material taken.

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Answer 5

Chapter 22.2, Problem 9CC

(a)

Interpretation Introduction

Interpretation:

To predict the major product in the given set of reactions and propose a mechanism for the same.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then undergoes E2 elimination when treated with pyridine to form α,β− unsaturated ketone and α,β− unsaturated aldehyde respectively depending upon the starting material taken.

(b)

Interpretation Introduction

Interpretation:

To predict the major product in the given set of reactions and propose a mechanism for the same.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then undergoes E2 elimination when treated with pyridine to form α,β− unsaturated ketone and α,β− unsaturated aldehyde respectively depending upon the starting material taken.

(c)

Interpretation Introduction

Interpretation:

To predict the major product in the given set of reactions and propose a mechanism for the same.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then undergoes E2 elimination when treated with pyridine to form α,β− unsaturated ketone and α,β− unsaturated aldehyde respectively depending upon the starting material taken.

Answer 6

Chapter 22.2, Problem 9CC

(a)

Interpretation Introduction

Interpretation:

To predict the major product in the given set of reactions and propose a mechanism for the same.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then undergoes E2 elimination when treated with pyridine to form α,β− unsaturated ketone and α,β− unsaturated aldehyde respectively depending upon the starting material taken.

Answer 7

Chapter 22.2, Problem 9CC

(a)

Interpretation Introduction

Interpretation:

To predict the major product in the given set of reactions and propose a mechanism for the same.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then undergoes E2 elimination when treated with pyridine to form α,β− unsaturated ketone and α,β− unsaturated aldehyde respectively depending upon the starting material taken.

Answer 8

(b)

Interpretation Introduction

Interpretation:

To predict the major product in the given set of reactions and propose a mechanism for the same.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then undergoes E2 elimination when treated with pyridine to form α,β− unsaturated ketone and α,β− unsaturated aldehyde respectively depending upon the starting material taken.

Answer 9

(b)

Interpretation Introduction

Interpretation:

To predict the major product in the given set of reactions and propose a mechanism for the same.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then undergoes E2 elimination when treated with pyridine to form α,β− unsaturated ketone and α,β− unsaturated aldehyde respectively depending upon the starting material taken.

Answer 10

(c)

Interpretation Introduction

Interpretation:

To predict the major product in the given set of reactions and propose a mechanism for the same.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then undergoes E2 elimination when treated with pyridine to form α,β− unsaturated ketone and α,β− unsaturated aldehyde respectively depending upon the starting material taken.

Answer 11

(c)

Interpretation Introduction

Interpretation:

To predict the major product in the given set of reactions and propose a mechanism for the same.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then undergoes E2 elimination when treated with pyridine to form α,β− unsaturated ketone and α,β− unsaturated aldehyde respectively depending upon the starting material taken.

Answer 12

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Answer 13

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Answer 14

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Answer 15

Ch. 22.1 - Prob. 1CC Ch. 22.1 - Prob. 2CC Ch. 22.1 - Prob. 3CC Ch. 22.1 - Prob. 1LTS Ch. 22.1 - Prob. 4PTS Ch. 22.1 - Prob. 5ATS Ch. 22.1 - Prob. 6CC Ch. 22.1 - Prob. 7CC Ch. 22.1 - Prob. 8CC Ch. 22.2 - Prob. 9CC

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Chapter 22 Solutions