The major product of the given reaction is to be predicted. Concept introduction: Intramolecular reactions are the ones in which the electron-rich and electron-poor sites are present within the same molecule. When ketones or aldehydes are treated with a strong base, they yield β -hydroxycarbonyl compounds via an aldol addition. Under these basic conditions, an enolate anion acts as a nucleophile. An intramolecular reaction is favored when it forms a five or six-membered ring. Intramolecular reactions involving the attack of an aldehyde C=O are favored over ones involving the attack of a ketone C=O . The first step is the formation of an enolate ion. The HO − reversibly deprotonates the alpha carbon to yield an enolate anion. In step two, the newly formed enolate anion, which serves as a nucleophile, attacks the carbonyl carbon present within the same molecule. The product of this step is an alkoxide ion, which is subsequently protonated in step 3.

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 18.33P

Interpretation Introduction

Interpretation:

The major product of the given reaction is to be predicted.

Concept introduction:

Intramolecular reactions are the ones in which the electron-rich and electron-poor sites are present within the same molecule. When ketones or aldehydes are treated with a strong base, they yield β-hydroxycarbonyl compounds via an aldol addition. Under these basic conditions, an enolate anion acts as a nucleophile. An intramolecular reaction is favored when it forms a five or six-membered ring. Intramolecular reactions involving the attack of an aldehyde C=O are favored over ones involving the attack of a ketone C=O. The first step is the formation of an enolate ion. The HO− reversibly deprotonates the alpha carbon to yield an enolate anion. In step two, the newly formed enolate anion, which serves as a nucleophile, attacks the carbonyl carbon present within the same molecule. The product of this step is an alkoxide ion, which is subsequently protonated in step 3.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

please draw the complete, detailed mechanism and the product of this reaction.

Draw a complete, detailed mechanism for the reaction shown here.

Draw the complete, detailed mechanism for the following reaction.

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 18.33P

Interpretation Introduction

Interpretation:

The major product of the given reaction is to be predicted.

Concept introduction:

Intramolecular reactions are the ones in which the electron-rich and electron-poor sites are present within the same molecule. When ketones or aldehydes are treated with a strong base, they yield β-hydroxycarbonyl compounds via an aldol addition. Under these basic conditions, an enolate anion acts as a nucleophile. An intramolecular reaction is favored when it forms a five or six-membered ring. Intramolecular reactions involving the attack of an aldehyde C=O are favored over ones involving the attack of a ketone C=O. The first step is the formation of an enolate ion. The HO− reversibly deprotonates the alpha carbon to yield an enolate anion. In step two, the newly formed enolate anion, which serves as a nucleophile, attacks the carbonyl carbon present within the same molecule. The product of this step is an alkoxide ion, which is subsequently protonated in step 3.

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 18.33P

Interpretation Introduction

Interpretation:

The major product of the given reaction is to be predicted.

Concept introduction:

Intramolecular reactions are the ones in which the electron-rich and electron-poor sites are present within the same molecule. When ketones or aldehydes are treated with a strong base, they yield β-hydroxycarbonyl compounds via an aldol addition. Under these basic conditions, an enolate anion acts as a nucleophile. An intramolecular reaction is favored when it forms a five or six-membered ring. Intramolecular reactions involving the attack of an aldehyde C=O are favored over ones involving the attack of a ketone C=O. The first step is the formation of an enolate ion. The HO− reversibly deprotonates the alpha carbon to yield an enolate anion. In step two, the newly formed enolate anion, which serves as a nucleophile, attacks the carbonyl carbon present within the same molecule. The product of this step is an alkoxide ion, which is subsequently protonated in step 3.

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 18.33P

Interpretation Introduction