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.

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 18.11P

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

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

For each reaction below, decide if the first stable organic product that forms in solution will create a new CC bond, and check the appropriate box. Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below. Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions - just focus on the first stable product you expect to form in solution. ? NH2 MgBr Will the first product that forms in this reaction create a new CC bond? ○ Yes ○ No MgBr ? Will the first product that forms in this reaction create a new CC bond? O Yes O No Click and drag to start drawing a structure. :☐ G x c olo Ar HE

Predicting As the lead product manager at OrganometALEKS Industries, you are trying to decide if the following reaction will make a molecule with a new C - C bond as its major product: H₂N O H 1. ? 2. H3O+ If this reaction will work, draw the major organic product or products you would expect in the drawing area below. If there's more than one major product, you can draw them in any arrangement you like. Be sure you use wedge and dash bonds if necessary, for example to distinguish between major products with different stereochemistry. 0 If the major products of this reaction won't have a new CC bond, just check the box under the drawing area and leave it blank. فا Explanation Check Click and drag to start drawing a structure.

Highlight the chirality (or stereogenic) center(s) in the given compound. A compound may have one or more stereogenic centers. OH OH OH OH OH OH

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 18.11P

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

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 18.11P

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

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 18.11P

Interpretation Introduction