The complete and detailed mechanism for the formation of the imine from the aldehyde in Equation 18-18 is to be drawn. Concept introduction: Aldehydes react with ammonia and 1 o or 2 o amines to form imines under mildly acidic conditions. Ammonia and amines are moderately strong nucleophiles and can add reversibly to the carbonyl carbon. Activation of the carbonyl group is not necessary. The oxygen becomes negatively charged as a result of the nucleophilic addition. The negatively charged oxygen then extracts two protons from two other molecules of ammonia or amine and is converted to the good leaving group − O + H 2 . The heterolysis of this group forms a resonance stabilized carbocation. The cation extracts a proton from another molecule of ammonia or amine to form the final product as a mixture of isomers.

Question

Want to see the full answer?

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 18, Problem 18.10P

Interpretation Introduction

Interpretation:

The complete and detailed mechanism for the formation of the imine from the aldehyde in Equation 18-18 is to be drawn.

Concept introduction:

Aldehydes react with ammonia and 1o or 2o amines to form imines under mildly acidic conditions. Ammonia and amines are moderately strong nucleophiles and can add reversibly to the carbonyl carbon. Activation of the carbonyl group is not necessary. The oxygen becomes negatively charged as a result of the nucleophilic addition. The negatively charged oxygen then extracts two protons from two other molecules of ammonia or amine and is converted to the good leaving group −O+H2. The heterolysis of this group forms a resonance stabilized carbocation. The cation extracts a proton from another molecule of ammonia or amine to form the final product as a mixture of isomers.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Rank the following compounds in order of decreasing boiling point. ннннн -С-С-Н . н-с- ННННН H ΗΤΗ НННН TTTĪ н-с-с-с-с-о-н НННН НН C' Н н-с-с-с-с-н НН || Ш НННН H-C-C-C-C-N-H ННННН IV

Rank the following compounds in order of decreasing dipole moment. |>||>||| ||>|||>| |>|||>|| |||>||>| O ||>>||| H F H F H c=c || H c=c F F III

choose the description that best describes the geometry for the following charged species ch3-

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 18, Problem 18.10P

Interpretation Introduction

Interpretation:

The complete and detailed mechanism for the formation of the imine from the aldehyde in Equation 18-18 is to be drawn.

Concept introduction:

Aldehydes react with ammonia and 1o or 2o amines to form imines under mildly acidic conditions. Ammonia and amines are moderately strong nucleophiles and can add reversibly to the carbonyl carbon. Activation of the carbonyl group is not necessary. The oxygen becomes negatively charged as a result of the nucleophilic addition. The negatively charged oxygen then extracts two protons from two other molecules of ammonia or amine and is converted to the good leaving group −O+H2. The heterolysis of this group forms a resonance stabilized carbocation. The cation extracts a proton from another molecule of ammonia or amine to form the final product as a mixture of isomers.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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 18.10P

Interpretation Introduction

Interpretation:

The complete and detailed mechanism for the formation of the imine from the aldehyde in Equation 18-18 is to be drawn.

Concept introduction:

Aldehydes react with ammonia and 1o or 2o amines to form imines under mildly acidic conditions. Ammonia and amines are moderately strong nucleophiles and can add reversibly to the carbonyl carbon. Activation of the carbonyl group is not necessary. The oxygen becomes negatively charged as a result of the nucleophilic addition. The negatively charged oxygen then extracts two protons from two other molecules of ammonia or amine and is converted to the good leaving group −O+H2. The heterolysis of this group forms a resonance stabilized carbocation. The cation extracts a proton from another molecule of ammonia or amine to form the final product as a mixture of isomers.

Expert Solution & Answer

Want to see the full answer?

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 18.10P

Interpretation Introduction