The formation of an acetal from a ketone or aldehyde requires acidic conditions to generate a water leaving group. At very acidic pH, however, the rate of imine formation slows down whereas the rate of acetal formation does not. This pH dependence of imine formation is to be explained. Concept introduction: Under mild acidic conditions, ammonia and amines add reversibly to carbonyl groups. At very low pH, the N atom from ammonia or amine gets protonated. A protonated N has no lone pair of electrons, and hence, it would not act as a nucleophile.

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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 18, Problem 18.60P

Interpretation Introduction

Interpretation:

The formation of an acetal from a ketone or aldehyde requires acidic conditions to generate a water leaving group. At very acidic pH, however, the rate of imine formation slows down whereas the rate of acetal formation does not. This pH dependence of imine formation is to be explained.

Concept introduction:

Under mild acidic conditions, ammonia and amines add reversibly to carbonyl groups. At very low pH, the N atom from ammonia or amine gets protonated. A protonated N has no lone pair of electrons, and hence, it would not act as a nucleophile.

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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 18, Problem 18.60P

Interpretation Introduction

Interpretation:

The formation of an acetal from a ketone or aldehyde requires acidic conditions to generate a water leaving group. At very acidic pH, however, the rate of imine formation slows down whereas the rate of acetal formation does not. This pH dependence of imine formation is to be explained.

Concept introduction:

Under mild acidic conditions, ammonia and amines add reversibly to carbonyl groups. At very low pH, the N atom from ammonia or amine gets protonated. A protonated N has no lone pair of electrons, and hence, it would not act as a nucleophile.

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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 18, Problem 18.60P

Interpretation Introduction

Interpretation:

The formation of an acetal from a ketone or aldehyde requires acidic conditions to generate a water leaving group. At very acidic pH, however, the rate of imine formation slows down whereas the rate of acetal formation does not. This pH dependence of imine formation is to be explained.

Concept introduction:

Under mild acidic conditions, ammonia and amines add reversibly to carbonyl groups. At very low pH, the N atom from ammonia or amine gets protonated. A protonated N has no lone pair of electrons, and hence, it would not act as a nucleophile.

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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 18, Problem 18.60P

Interpretation Introduction