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

Question

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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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.

Please don't answer if you've answered this already.

Propose an efficient synthesis for the following transformations using ONLY aldol, mciheal and other reactions related to enol/enolate.

Answer 2

Question

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

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

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 12

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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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