With the help of Robinson annulation the given compound has to be synthesized. Concept introduction: The Michael addition of a ketone and enolate to an α , β - unsaturated ketone gives δ - diketone as a final product. When the conjugate addition takes place under strongly acidic or basic conditions then δ - diketone undergoes a spontaneous intramolecular aldol condensation followed by dehydration to form a six membered ring compound commonly known as cyclohexenone. This synthesis is called as the Robinson annulation.

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Answer 1

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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 22.19, Problem 22.59P

(a)

Interpretation Introduction

Interpretation:

With the help of Robinson annulation the given compound has to be synthesized.

Concept introduction:

The Michael addition of a ketone and enolate to an α,β- unsaturated ketone gives δ- diketone as a final product. When the conjugate addition takes place under strongly acidic or basic conditions then δ- diketone undergoes a spontaneous intramolecular aldol condensation followed by dehydration to form a six membered ring compound commonly known as cyclohexenone. This synthesis is called as the Robinson annulation.

(b)

Interpretation Introduction

Interpretation:

With the help of Robinson annulation the given compound is to be synthesized.

Concept introduction:

The Michael addition of a ketone and enolate to an α,β- unsaturated ketone gives δ- diketone as a final product. When the conjugate addition takes place under strongly acidic or basic conditions then δ- diketone undergoes a spontaneous intramolecular aldol condensation followed by dehydration to form a six membered ring compound commonly known as cyclohexenone. This synthesis is called as the Robinson annulation.

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In this chapter, we will study three types of Condensation reactions: Michael, Aldol and Claisen. Match the right reaction with the statements below. ● This condensation reaction takes place between two esters. The electrophile in this reaction must be an a,B-unsaturated carbonyl compound. The B-hydroxy carbonyl products of this reaction are often dehydrated to form a,B- unsaturated carbonyl products.

The product below can be synthesized by a Robinson annulation, which is a Michael addition followed by an aldol condensation/elimination. Draw the starting materials you would use. Also draw the structure of the intermediate after the Michael addition is completed, but before the aldol reaction has started.

A different way of synthesising the product 4,4- diphenylbut-3-en-2-one is via an aldol condensation. What starting materials would you use and what reaction conditions would you employ? Draw the full reaction

Answer 2

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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 22.19, Problem 22.59P

(a)

Interpretation Introduction

Interpretation:

With the help of Robinson annulation the given compound has to be synthesized.

Concept introduction:

The Michael addition of a ketone and enolate to an α,β- unsaturated ketone gives δ- diketone as a final product. When the conjugate addition takes place under strongly acidic or basic conditions then δ- diketone undergoes a spontaneous intramolecular aldol condensation followed by dehydration to form a six membered ring compound commonly known as cyclohexenone. This synthesis is called as the Robinson annulation.

(b)

Interpretation Introduction

Interpretation:

With the help of Robinson annulation the given compound is to be synthesized.

Concept introduction:

The Michael addition of a ketone and enolate to an α,β- unsaturated ketone gives δ- diketone as a final product. When the conjugate addition takes place under strongly acidic or basic conditions then δ- diketone undergoes a spontaneous intramolecular aldol condensation followed by dehydration to form a six membered ring compound commonly known as cyclohexenone. This synthesis is called as the Robinson annulation.

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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 22.19, Problem 22.59P

(a)

Interpretation Introduction

Interpretation:

With the help of Robinson annulation the given compound has to be synthesized.

Concept introduction:

The Michael addition of a ketone and enolate to an α,β- unsaturated ketone gives δ- diketone as a final product. When the conjugate addition takes place under strongly acidic or basic conditions then δ- diketone undergoes a spontaneous intramolecular aldol condensation followed by dehydration to form a six membered ring compound commonly known as cyclohexenone. This synthesis is called as the Robinson annulation.

(b)

Interpretation Introduction

Interpretation:

With the help of Robinson annulation the given compound is to be synthesized.

Concept introduction:

The Michael addition of a ketone and enolate to an α,β- unsaturated ketone gives δ- diketone as a final product. When the conjugate addition takes place under strongly acidic or basic conditions then δ- diketone undergoes a spontaneous intramolecular aldol condensation followed by dehydration to form a six membered ring compound commonly known as cyclohexenone. This synthesis is called as the Robinson annulation.

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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 22.19, Problem 22.59P

(a)

Interpretation Introduction

Interpretation:

With the help of Robinson annulation the given compound has to be synthesized.

Concept introduction:

The Michael addition of a ketone and enolate to an α,β- unsaturated ketone gives δ- diketone as a final product. When the conjugate addition takes place under strongly acidic or basic conditions then δ- diketone undergoes a spontaneous intramolecular aldol condensation followed by dehydration to form a six membered ring compound commonly known as cyclohexenone. This synthesis is called as the Robinson annulation.

(b)

Interpretation Introduction

Interpretation:

With the help of Robinson annulation the given compound is to be synthesized.

Concept introduction:

The Michael addition of a ketone and enolate to an α,β- unsaturated ketone gives δ- diketone as a final product. When the conjugate addition takes place under strongly acidic or basic conditions then δ- diketone undergoes a spontaneous intramolecular aldol condensation followed by dehydration to form a six membered ring compound commonly known as cyclohexenone. This synthesis is called as the Robinson annulation.

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Answer 5

Chapter 22.19, Problem 22.59P

(a)

Interpretation Introduction

Interpretation:

With the help of Robinson annulation the given compound has to be synthesized.

Concept introduction:

The Michael addition of a ketone and enolate to an α,β- unsaturated ketone gives δ- diketone as a final product. When the conjugate addition takes place under strongly acidic or basic conditions then δ- diketone undergoes a spontaneous intramolecular aldol condensation followed by dehydration to form a six membered ring compound commonly known as cyclohexenone. This synthesis is called as the Robinson annulation.

(b)

Interpretation Introduction

Interpretation:

With the help of Robinson annulation the given compound is to be synthesized.

Concept introduction:

The Michael addition of a ketone and enolate to an α,β- unsaturated ketone gives δ- diketone as a final product. When the conjugate addition takes place under strongly acidic or basic conditions then δ- diketone undergoes a spontaneous intramolecular aldol condensation followed by dehydration to form a six membered ring compound commonly known as cyclohexenone. This synthesis is called as the Robinson annulation.

Answer 6

Chapter 22.19, Problem 22.59P

(a)

Interpretation Introduction

Interpretation:

With the help of Robinson annulation the given compound has to be synthesized.

Concept introduction:

The Michael addition of a ketone and enolate to an α,β- unsaturated ketone gives δ- diketone as a final product. When the conjugate addition takes place under strongly acidic or basic conditions then δ- diketone undergoes a spontaneous intramolecular aldol condensation followed by dehydration to form a six membered ring compound commonly known as cyclohexenone. This synthesis is called as the Robinson annulation.

Answer 7

Chapter 22.19, Problem 22.59P

(a)

Interpretation Introduction

Interpretation:

With the help of Robinson annulation the given compound has to be synthesized.

Concept introduction:

The Michael addition of a ketone and enolate to an α,β- unsaturated ketone gives δ- diketone as a final product. When the conjugate addition takes place under strongly acidic or basic conditions then δ- diketone undergoes a spontaneous intramolecular aldol condensation followed by dehydration to form a six membered ring compound commonly known as cyclohexenone. This synthesis is called as the Robinson annulation.

Answer 8

(b)

Interpretation Introduction

Interpretation:

With the help of Robinson annulation the given compound is to be synthesized.

Concept introduction:

The Michael addition of a ketone and enolate to an α,β- unsaturated ketone gives δ- diketone as a final product. When the conjugate addition takes place under strongly acidic or basic conditions then δ- diketone undergoes a spontaneous intramolecular aldol condensation followed by dehydration to form a six membered ring compound commonly known as cyclohexenone. This synthesis is called as the Robinson annulation.

Answer 9

(b)

Interpretation Introduction

Interpretation:

With the help of Robinson annulation the given compound is to be synthesized.

Concept introduction:

The Michael addition of a ketone and enolate to an α,β- unsaturated ketone gives δ- diketone as a final product. When the conjugate addition takes place under strongly acidic or basic conditions then δ- diketone undergoes a spontaneous intramolecular aldol condensation followed by dehydration to form a six membered ring compound commonly known as cyclohexenone. This synthesis is called as the Robinson annulation.

Answer 10

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Answer 13

Ch. 22.2A - Prob. 22.2P Ch. 22.4 - Without looking back, propose a mechanism for the...Ch. 22.4 - Prob. 22.8P Ch. 22.4 - Prob. 22.9P Ch. 22.5A - Prob. 22.10P Ch. 22.5A - Prob. 22.11P Ch. 22.5B - Prob. 22.12P Ch. 22.5B - Predict the products of the following reactions....Ch. 22.5B - Which compounds will give positive iodoform tests?...Ch. 22.5C - Propose a mechanism for the acid-catalyzed...

Solution Summary: The author describes Robinson annulation as a combination of Michael addition and aldol condensation reaction followed by dehydration.

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