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.

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 18.60P

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

14 Question (1 point) Disiamylborane adds to a triple bond to give an alkenylborane. Upon oxidation with OH, H2O2, the alkenylborane will form an enol that tautomerizes to an aldehyde. In the first box below, draw the mechanism arrows for the reaction of disiamylborane with the alkyne, and in the last box draw the structure of the aldehyde. 4th attempt Feedback i > 3rd attempt OH, H2O2 i See Periodic Table See Hint

answer with mechanisms and steps. handwritten please!

Hello I need some help with Smartwork. For drawing structure B, I know the correct answer is CH₃B₂, but when I try to type it in, it keeps giving me CH₄BH₃ instead. Do you know how I should write it properly? Should I use a bond or something else?

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 18.60P

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.

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 18.60P

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.

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 18.60P

Interpretation Introduction