The complete, detailed mechanism for the given reaction is to be drawn, and using the mechanism, the products are to be predicted. Concept introduction: When aldehydes or ketones are treated with a strong base, they undergo an aldol addition, resulting in a β- hydroxy carbonyl compound. Under these conditions, an enolate anion acts as a nucleophile. In step one of this mechanism, HO − reversibly deprotonates the alpha carbon to yield an enolate anion. In step two, the newly formed enolate anion attacks a second molecule of the aldehyde that still has its proton. The immediate product is an alkoxide ion RO − , which is subsequently protonated in the third step to yield a β- hydroxy carbonyl compound. For this reaction to occur, the presence of α hydrogen is essential for at least one of the starting molecules.

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 18.21P

Interpretation Introduction

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn, and using the mechanism, the products are to be predicted.

Concept introduction:

When aldehydes or ketones are treated with a strong base, they undergo an aldol addition, resulting in a β- hydroxy carbonyl compound. Under these conditions, an enolate anion acts as a nucleophile. In step one of this mechanism, HO− reversibly deprotonates the alpha carbon to yield an enolate anion. In step two, the newly formed enolate anion attacks a second molecule of the aldehyde that still has its proton. The immediate product is an alkoxide ion RO−, which is subsequently protonated in the third step to yield a β- hydroxy carbonyl compound. For this reaction to occur, the presence of α hydrogen is essential for at least one of the starting molecules.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Which molecule is the most stable? Please explain.

Please see photo

Complete the equation...see image

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 18.21P

Interpretation Introduction

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn, and using the mechanism, the products are to be predicted.

Concept introduction:

When aldehydes or ketones are treated with a strong base, they undergo an aldol addition, resulting in a β- hydroxy carbonyl compound. Under these conditions, an enolate anion acts as a nucleophile. In step one of this mechanism, HO− reversibly deprotonates the alpha carbon to yield an enolate anion. In step two, the newly formed enolate anion attacks a second molecule of the aldehyde that still has its proton. The immediate product is an alkoxide ion RO−, which is subsequently protonated in the third step to yield a β- hydroxy carbonyl compound. For this reaction to occur, the presence of α hydrogen is essential for at least one of the starting molecules.

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 18.21P

Interpretation Introduction

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn, and using the mechanism, the products are to be predicted.

Concept introduction:

When aldehydes or ketones are treated with a strong base, they undergo an aldol addition, resulting in a β- hydroxy carbonyl compound. Under these conditions, an enolate anion acts as a nucleophile. In step one of this mechanism, HO− reversibly deprotonates the alpha carbon to yield an enolate anion. In step two, the newly formed enolate anion attacks a second molecule of the aldehyde that still has its proton. The immediate product is an alkoxide ion RO−, which is subsequently protonated in the third step to yield a β- hydroxy carbonyl compound. For this reaction to occur, the presence of α hydrogen is essential for at least one of the starting molecules.

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 18.21P

Interpretation Introduction