The complete and detailed mechanism for the hydrolysis reaction in Equation 18-20 is to be drawn. Concept introduction: Under strongly acidic conditions, the nitrogen atom of an amine is protonated. This step is followed by the nucleophilic addition of water at the imine carbon. The added water molecule loses a proton to another molecule of water to produce a hemiaminal (an amine and a hydroxyl group on the same carbon). Another proton transfer converts the amine group to a quaternary ammonium group. The heterolysis of this group produces a resonance stabilized carbocation with a hydroxyl group on the same carbon. Extraction of the hydrogen from the OH converts this to the final product, an aldehyde or a ketone . The overall reaction is one of hydrolysis, effectively a reversal of the formation of an imine from a carbonyl compound.

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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 18, Problem 18.11P

Interpretation Introduction

Interpretation:

The complete and detailed mechanism for the hydrolysis reaction in Equation 18-20 is to be drawn.

Concept introduction:

Under strongly acidic conditions, the nitrogen atom of an amine is protonated. This step is followed by the nucleophilic addition of water at the imine carbon. The added water molecule loses a proton to another molecule of water to produce a hemiaminal (an amine and a hydroxyl group on the same carbon). Another proton transfer converts the amine group to a quaternary ammonium group. The heterolysis of this group produces a resonance stabilized carbocation with a hydroxyl group on the same carbon. Extraction of the hydrogen from the OH converts this to the final product, an aldehyde or a ketone.

The overall reaction is one of hydrolysis, effectively a reversal of the formation of an imine from a carbonyl compound.

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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 18.11P

Interpretation Introduction

Interpretation:

The complete and detailed mechanism for the hydrolysis reaction in Equation 18-20 is to be drawn.

Concept introduction:

Under strongly acidic conditions, the nitrogen atom of an amine is protonated. This step is followed by the nucleophilic addition of water at the imine carbon. The added water molecule loses a proton to another molecule of water to produce a hemiaminal (an amine and a hydroxyl group on the same carbon). Another proton transfer converts the amine group to a quaternary ammonium group. The heterolysis of this group produces a resonance stabilized carbocation with a hydroxyl group on the same carbon. Extraction of the hydrogen from the OH converts this to the final product, an aldehyde or a ketone.

The overall reaction is one of hydrolysis, effectively a reversal of the formation of an imine from a carbonyl compound.

Expert Solution & Answer

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Check out a sample textbook solution

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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 18, Problem 18.11P

Interpretation Introduction

Interpretation:

The complete and detailed mechanism for the hydrolysis reaction in Equation 18-20 is to be drawn.

Concept introduction:

Under strongly acidic conditions, the nitrogen atom of an amine is protonated. This step is followed by the nucleophilic addition of water at the imine carbon. The added water molecule loses a proton to another molecule of water to produce a hemiaminal (an amine and a hydroxyl group on the same carbon). Another proton transfer converts the amine group to a quaternary ammonium group. The heterolysis of this group produces a resonance stabilized carbocation with a hydroxyl group on the same carbon. Extraction of the hydrogen from the OH converts this to the final product, an aldehyde or a ketone.

The overall reaction is one of hydrolysis, effectively a reversal of the formation of an imine from a carbonyl compound.

Expert Solution & Answer

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Check out a sample textbook solution

See solution

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 18, Problem 18.11P

Interpretation Introduction