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 21.2, Problem 8CC

(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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What spectral features allow you to differentiate the product from the starting material? Use four separate paragraphs for each set of comparisons. You should have one paragraph each devoted to MS, HNMR, CNMR and IR. 2) For MS, the differing masses of molecular ions are a popular starting point. Including a unique fragmentation is important, too. 3) For HNMR, CNMR and IR state the peaks that are different and what makes them different (usually the presence or absence of certain groups). See if you can find two differences (in each set of IR, HNMR and CNMR spectra) due to the presence or absence of a functional group. Include peak locations. Alternatively, you can state a shift of a peak due to a change near a given functional group. Including peak locations for shifted peaks, as well as what these peaks are due to. Ideally, your focus should be on not just identifying the differences but explaining them in terms of functional group changes.

Question 6 What is the major product of the following Diels-Alder reaction? ? Aldy by day of A. H о B. C. D. E. OB OD Oc OE OA

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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 21.2, Problem 8CC

(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 21.2, Problem 8CC

(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 21.2, Problem 8CC

(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 21.2, Problem 8CC

(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 21.2, Problem 8CC

(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 21.2, Problem 8CC

(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. 21.1 - Prob. 1CC Ch. 21.1 - Prob. 2CC Ch. 21.1 - Prob. 3CC Ch. 21.1 - Prob. 1LTS Ch. 21.1 - Prob. 4PTS Ch. 21.1 - APPLY the skill As with aldehydes and ketones, the...Ch. 21.1 - Draw the enolate ion that is formed when each of...Ch. 21.1 - Prob. 7CC Ch. 21.2 - Prob. 8CC Ch. 21.2 - Prob. 9CC

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