With the help of Robinson annulation the given compound is to be synthesized. Concept introduction: Condensation reaction takes place when methyl vinyl ketone or substituted methyl vinyl ketone derivative reacts with a ketone. The product formed is cyclohexanone ring. Robinson annulation occurs through Michael addition to methyl vinyl ketone followed by aldol condensation and dehydration.

Question

Propose a two reaction sequence to convert each of the following substrates into the indicated products.

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 22, Problem 22.67SP

(a)

Interpretation Introduction

Interpretation:

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

Concept introduction:

Condensation reaction takes place when methyl vinyl ketone or substituted methyl vinyl ketone derivative reacts with a ketone. The product formed is cyclohexanone ring. Robinson annulation occurs through Michael addition to methyl vinyl ketone followed by aldol condensation and dehydration.

(b)

Interpretation Introduction

Interpretation:

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

Concept introduction:

Condensation reaction takes place when methyl vinyl ketone or substituted methyl vinyl ketone derivative reacts with a ketone. The product formed is cyclohexanone ring. Robinson annulation occurs through Michael addition to methyl vinyl ketone followed by aldol condensation and dehydration.

(c)

Interpretation Introduction

Interpretation:

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

Concept introduction:

Condensation reaction takes place when methyl vinyl ketone or substituted methyl vinyl ketone derivative reacts with a ketone. The product formed is cyclohexanone ring. Robinson annulation occurs through Michael addition to methyl vinyl ketone followed by aldol condensation and dehydration.

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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 22, Problem 22.67SP

(a)

Interpretation Introduction

Interpretation:

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

Concept introduction:

Condensation reaction takes place when methyl vinyl ketone or substituted methyl vinyl ketone derivative reacts with a ketone. The product formed is cyclohexanone ring. Robinson annulation occurs through Michael addition to methyl vinyl ketone followed by aldol condensation and dehydration.

(b)

Interpretation Introduction

Interpretation:

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

Concept introduction:

Condensation reaction takes place when methyl vinyl ketone or substituted methyl vinyl ketone derivative reacts with a ketone. The product formed is cyclohexanone ring. Robinson annulation occurs through Michael addition to methyl vinyl ketone followed by aldol condensation and dehydration.

(c)

Interpretation Introduction

Interpretation:

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

Concept introduction:

Condensation reaction takes place when methyl vinyl ketone or substituted methyl vinyl ketone derivative reacts with a ketone. The product formed is cyclohexanone ring. Robinson annulation occurs through Michael addition to methyl vinyl ketone followed by aldol condensation and dehydration.

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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, Problem 22.67SP

(a)

Interpretation Introduction

Interpretation:

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

Concept introduction:

Condensation reaction takes place when methyl vinyl ketone or substituted methyl vinyl ketone derivative reacts with a ketone. The product formed is cyclohexanone ring. Robinson annulation occurs through Michael addition to methyl vinyl ketone followed by aldol condensation and dehydration.

(b)

Interpretation Introduction

Interpretation:

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

Concept introduction:

Condensation reaction takes place when methyl vinyl ketone or substituted methyl vinyl ketone derivative reacts with a ketone. The product formed is cyclohexanone ring. Robinson annulation occurs through Michael addition to methyl vinyl ketone followed by aldol condensation and dehydration.

(c)

Interpretation Introduction

Interpretation:

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

Concept introduction:

Condensation reaction takes place when methyl vinyl ketone or substituted methyl vinyl ketone derivative reacts with a ketone. The product formed is cyclohexanone ring. Robinson annulation occurs through Michael addition to methyl vinyl ketone followed by aldol condensation and dehydration.

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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, Problem 22.67SP

(a)

Interpretation Introduction

Interpretation:

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

Concept introduction:

Condensation reaction takes place when methyl vinyl ketone or substituted methyl vinyl ketone derivative reacts with a ketone. The product formed is cyclohexanone ring. Robinson annulation occurs through Michael addition to methyl vinyl ketone followed by aldol condensation and dehydration.

(b)

Interpretation Introduction

Interpretation:

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

Concept introduction:

Condensation reaction takes place when methyl vinyl ketone or substituted methyl vinyl ketone derivative reacts with a ketone. The product formed is cyclohexanone ring. Robinson annulation occurs through Michael addition to methyl vinyl ketone followed by aldol condensation and dehydration.

(c)

Interpretation Introduction

Interpretation:

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

Concept introduction:

Condensation reaction takes place when methyl vinyl ketone or substituted methyl vinyl ketone derivative reacts with a ketone. The product formed is cyclohexanone ring. Robinson annulation occurs through Michael addition to methyl vinyl ketone followed by aldol condensation and dehydration.

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Answer 5

Chapter 22, Problem 22.67SP

(a)

Interpretation Introduction

Interpretation:

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

Concept introduction:

Condensation reaction takes place when methyl vinyl ketone or substituted methyl vinyl ketone derivative reacts with a ketone. The product formed is cyclohexanone ring. Robinson annulation occurs through Michael addition to methyl vinyl ketone followed by aldol condensation and dehydration.

(b)

Interpretation Introduction

Interpretation:

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

Concept introduction:

Condensation reaction takes place when methyl vinyl ketone or substituted methyl vinyl ketone derivative reacts with a ketone. The product formed is cyclohexanone ring. Robinson annulation occurs through Michael addition to methyl vinyl ketone followed by aldol condensation and dehydration.

(c)

Interpretation Introduction

Interpretation:

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

Concept introduction:

Condensation reaction takes place when methyl vinyl ketone or substituted methyl vinyl ketone derivative reacts with a ketone. The product formed is cyclohexanone ring. Robinson annulation occurs through Michael addition to methyl vinyl ketone followed by aldol condensation and dehydration.

Answer 6

Chapter 22, Problem 22.67SP

(a)

Interpretation Introduction

Interpretation:

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

Concept introduction:

Condensation reaction takes place when methyl vinyl ketone or substituted methyl vinyl ketone derivative reacts with a ketone. The product formed is cyclohexanone ring. Robinson annulation occurs through Michael addition to methyl vinyl ketone followed by aldol condensation and dehydration.

Answer 7

Chapter 22, Problem 22.67SP

(a)

Interpretation Introduction

Interpretation:

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

Concept introduction:

Condensation reaction takes place when methyl vinyl ketone or substituted methyl vinyl ketone derivative reacts with a ketone. The product formed is cyclohexanone ring. Robinson annulation occurs through Michael addition to methyl vinyl ketone followed by aldol condensation and dehydration.

Answer 8

(b)

Interpretation Introduction

Interpretation:

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

Concept introduction:

Condensation reaction takes place when methyl vinyl ketone or substituted methyl vinyl ketone derivative reacts with a ketone. The product formed is cyclohexanone ring. Robinson annulation occurs through Michael addition to methyl vinyl ketone followed by aldol condensation and dehydration.

Answer 9

(b)

Interpretation Introduction

Interpretation:

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

Concept introduction:

Condensation reaction takes place when methyl vinyl ketone or substituted methyl vinyl ketone derivative reacts with a ketone. The product formed is cyclohexanone ring. Robinson annulation occurs through Michael addition to methyl vinyl ketone followed by aldol condensation and dehydration.

Answer 10

(c)

Interpretation Introduction

Interpretation:

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

Concept introduction:

Condensation reaction takes place when methyl vinyl ketone or substituted methyl vinyl ketone derivative reacts with a ketone. The product formed is cyclohexanone ring. Robinson annulation occurs through Michael addition to methyl vinyl ketone followed by aldol condensation and dehydration.

Answer 11

(c)

Interpretation Introduction

Interpretation:

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

Concept introduction:

Condensation reaction takes place when methyl vinyl ketone or substituted methyl vinyl ketone derivative reacts with a ketone. The product formed is cyclohexanone ring. Robinson annulation occurs through Michael addition to methyl vinyl ketone followed by aldol condensation and dehydration.

Answer 12

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Answer 23

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 explains that Robinson annulation is one of the useful reactions that lead to the formation of six-membered rings in polycyclic compounds.

Chapter 22 Solutions