A mechanism for the base catalyzed isomerisation of the minor product formed in the intramolecular aldo cyclization of 2, 5-heptanedione into the major product upon treatment with aqueous NaOH is to be proposed. Concept introduction: The steps involved in the conversion required are i) Attack of the hydroxide ion on α, β-unsaturated ketone . ii) A proton transfer iii) Ring opening iv) Protonation to yield a diketon vi) Deprotonation of α-carbon of the diketone vii) Intramolecular aldol condensation viii) Protonation and dehydration. To give: A mechanism for the base catalyzed isomerisation of the minor product formed in the intramolecular aldo cyclization of 2, 5-heptanedione into the major product upon treatment with aqueous NaOH is to be proposed.

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 ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 23.SE, Problem 53AP

Interpretation Introduction

Interpretation:

A mechanism for the base catalyzed isomerisation of the minor product formed in the intramolecular aldo cyclization of 2, 5-heptanedione into the major product upon treatment with aqueous NaOH is to be proposed.

Concept introduction:

The steps involved in the conversion required are i) Attack of the hydroxide ion on α, β-unsaturated ketone. ii) A proton transfer iii) Ring opening iv) Protonation to yield a diketon vi) Deprotonation of α-carbon of the diketone vii) Intramolecular aldol condensation viii) Protonation and dehydration.

To give:

A mechanism for the base catalyzed isomerisation of the minor product formed in the intramolecular aldo cyclization of 2, 5-heptanedione into the major product upon treatment with aqueous NaOH is to be proposed.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

The intramolecular aldol reaction of 6-oxoheptanal [CH3CO(CH2)4CHO] can yield threecyclic D,E-unsaturated ketones. Give the threeproducts and suggest a mechanism for formingone of the products.

The base-promoted rearrangement of an a-haloketone to a carboxylic acid, known as the Favorskii rearrangement, is illustrated by the conversion of 2-chlorocyclohexanone to cyclopentanecarboxylic acid. Jo Han Sow La NaOH, THF O Nat H3O+ OH NaOH, THF The mechanism involves the following 5 steps: -ō cyclopropanone intermediate 1. Abstraction of a proton to form enolate anion 1; 2. Formation of a cyclopropanone intermediate 2 with expulsion of chloride ion; 3. Addition of hydroxide ion to form tetrahedral intermediate 3; 4. Collapse of the tetrahedral intermediate and breakage of the three-membered ring to form carbanion intermediate 4; 5. Proton transfer to form the rearranged carboxylic acid. For the following reaction, draw the reaction out on paper, and then draw the structure of cyclopropanone intermediate 2 in the window. 1. NaOH, THF 2. H3O* OH

When propionaldehyde is warmed with sodium hydroxide, one of the products is2-methylpent-2-enal. Propose a mechanism for this reaction.

Answer 2

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 23.SE, Problem 53AP

Interpretation Introduction

Interpretation:

A mechanism for the base catalyzed isomerisation of the minor product formed in the intramolecular aldo cyclization of 2, 5-heptanedione into the major product upon treatment with aqueous NaOH is to be proposed.

Concept introduction:

The steps involved in the conversion required are i) Attack of the hydroxide ion on α, β-unsaturated ketone. ii) A proton transfer iii) Ring opening iv) Protonation to yield a diketon vi) Deprotonation of α-carbon of the diketone vii) Intramolecular aldol condensation viii) Protonation and dehydration.

To give:

A mechanism for the base catalyzed isomerisation of the minor product formed in the intramolecular aldo cyclization of 2, 5-heptanedione into the major product upon treatment with aqueous NaOH is to be proposed.

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 ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 23.SE, Problem 53AP

Interpretation Introduction

Interpretation:

A mechanism for the base catalyzed isomerisation of the minor product formed in the intramolecular aldo cyclization of 2, 5-heptanedione into the major product upon treatment with aqueous NaOH is to be proposed.

Concept introduction:

The steps involved in the conversion required are i) Attack of the hydroxide ion on α, β-unsaturated ketone. ii) A proton transfer iii) Ring opening iv) Protonation to yield a diketon vi) Deprotonation of α-carbon of the diketone vii) Intramolecular aldol condensation viii) Protonation and dehydration.

To give:

A mechanism for the base catalyzed isomerisation of the minor product formed in the intramolecular aldo cyclization of 2, 5-heptanedione into the major product upon treatment with aqueous NaOH is to be proposed.

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 ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 23.SE, Problem 53AP

Interpretation Introduction