The complete mechanism for this reaction is to be shown and the major product is to be predicted. Concept introduction: In acidic conditions, the carbonyl oxygen of an aldehyde or a ketone is protonated. This leads to keto-enol tautomerization. Any acidic α hydrogen present can then be extracted by a strong base. This generates a strong nucleophile that can be used for nucleophilic substitution on a halogen molecule in an S N 2 reaction. The result is α halogenation of the aldehyde/ketone. Unlike the α halogenation under basic conditions, the reaction stops at a single halogenation as the electronegativity of the halogen prevents the protonation of the carbonyl group necessary for the second keto-enol tautomerization.

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Answer 1

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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 10, Problem 10.13P

Interpretation Introduction

Interpretation:

The complete mechanism for this reaction is to be shown and the major product is to be predicted.

Concept introduction:

In acidic conditions, the carbonyl oxygen of an aldehyde or a ketone is protonated. This leads to keto-enol tautomerization. Any acidic α hydrogen present can then be extracted by a strong base. This generates a strong nucleophile that can be used for nucleophilic substitution on a halogen molecule in an SN2 reaction. The result is α halogenation of the aldehyde/ketone.

Unlike the α halogenation under basic conditions, the reaction stops at a single halogenation as the electronegativity of the halogen prevents the protonation of the carbonyl group necessary for the second keto-enol tautomerization.

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I have a question about this problem involving mechanisms and drawing curved arrows for acids and bases. I know we need to identify the nucleophile and electrophile, but are there different types of reactions? For instance, what about Grignard reagents and other types that I might not be familiar with? Can you help me with this? I want to identify the names of the mechanisms for problems 1-14, such as Gilman reagents and others. Are they all the same? Also, could you rewrite it so I can better understand? The handwriting is pretty cluttered. Additionally, I need to label the nucleophile and electrophile, but my main concern is whether those reactions differ, like the "Brønsted-Lowry acid-base mechanism, Lewis acid-base mechanism, acid-catalyzed mechanisms, acid-catalyzed reactions, base-catalyzed reactions, nucleophilic substitution mechanisms (SN1 and SN2), elimination reactions (E1 and E2), organometallic mechanisms, and so forth."

Answer 2

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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 10, Problem 10.13P

Interpretation Introduction

Interpretation:

The complete mechanism for this reaction is to be shown and the major product is to be predicted.

Concept introduction:

In acidic conditions, the carbonyl oxygen of an aldehyde or a ketone is protonated. This leads to keto-enol tautomerization. Any acidic α hydrogen present can then be extracted by a strong base. This generates a strong nucleophile that can be used for nucleophilic substitution on a halogen molecule in an SN2 reaction. The result is α halogenation of the aldehyde/ketone.

Unlike the α halogenation under basic conditions, the reaction stops at a single halogenation as the electronegativity of the halogen prevents the protonation of the carbonyl group necessary for the second keto-enol tautomerization.

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Answer 3

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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 10, Problem 10.13P

Interpretation Introduction

Interpretation:

The complete mechanism for this reaction is to be shown and the major product is to be predicted.

Concept introduction:

In acidic conditions, the carbonyl oxygen of an aldehyde or a ketone is protonated. This leads to keto-enol tautomerization. Any acidic α hydrogen present can then be extracted by a strong base. This generates a strong nucleophile that can be used for nucleophilic substitution on a halogen molecule in an SN2 reaction. The result is α halogenation of the aldehyde/ketone.

Unlike the α halogenation under basic conditions, the reaction stops at a single halogenation as the electronegativity of the halogen prevents the protonation of the carbonyl group necessary for the second keto-enol tautomerization.

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Check out a sample textbook solution

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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 10, Problem 10.13P

Interpretation Introduction