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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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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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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Answer 4

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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