a) Interpretation: How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation is to be shown. Concept introduction: The steps involved in the reaction are i) Reaction of the cyclic ketone with pyrrolidine ii) Michael addition of enamine to cyclohexanone iii) A proton transfer iv) Hydrolysis of the enamine to eliminate the amine v) Abstraction of a proton from the diketone vi) Internal aldol reaction to form the second ring vii) Protonation and dehydration. To give: How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation.

Question

Predict the products of aldol,Claisen, and Michael condensations,and draw mechanisms to show howthey are formed. Show how thesecondensations are useful in synthesis

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 65AP

Interpretation Introduction

a)

Interpretation:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation is to be shown.

Concept introduction:

The steps involved in the reaction are i) Reaction of the cyclic ketone with pyrrolidine ii) Michael addition of enamine to cyclohexanone iii) A proton transfer iv) Hydrolysis of the enamine to eliminate the amine v) Abstraction of a proton from the diketone vi) Internal aldol reaction to form the second ring vii) Protonation and dehydration.

To give:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation.

Interpretation Introduction

b)

Interpretation:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation is to be shown.

Concept introduction:

The steps involved in the reaction are i) Reaction of the cyclic ketone with pyrrolidine ii) Michael addition of enamine to cyclohexanone iii) A proton transfer iv) Hydrolysis of the enamine to eliminate the amine v) Abstraction of a proton from the diketone vi) Internal aldol reaction to form the second ring vii) Protonation and dehydration.

To give:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation.

Interpretation Introduction

c)

Interpretation:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation is to be shown.

Concept introduction:

The steps involved in the reaction are i) Reaction of the cyclic ketone with pyrrolidine ii) Michael addition of enamine to cyclohexanone iii) A proton transfer iv) Hydrolysis of the enamine to eliminate the amine v) Abstraction of a proton from the diketone vi) Internal aldol reaction to form the second ring vii) Protonation and dehydration.

To give:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation.

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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 23.SE, Problem 65AP

Interpretation Introduction

a)

Interpretation:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation is to be shown.

Concept introduction:

The steps involved in the reaction are i) Reaction of the cyclic ketone with pyrrolidine ii) Michael addition of enamine to cyclohexanone iii) A proton transfer iv) Hydrolysis of the enamine to eliminate the amine v) Abstraction of a proton from the diketone vi) Internal aldol reaction to form the second ring vii) Protonation and dehydration.

To give:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation.

Interpretation Introduction

b)

Interpretation:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation is to be shown.

Concept introduction:

The steps involved in the reaction are i) Reaction of the cyclic ketone with pyrrolidine ii) Michael addition of enamine to cyclohexanone iii) A proton transfer iv) Hydrolysis of the enamine to eliminate the amine v) Abstraction of a proton from the diketone vi) Internal aldol reaction to form the second ring vii) Protonation and dehydration.

To give:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation.

Interpretation Introduction

c)

Interpretation:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation is to be shown.

Concept introduction:

The steps involved in the reaction are i) Reaction of the cyclic ketone with pyrrolidine ii) Michael addition of enamine to cyclohexanone iii) A proton transfer iv) Hydrolysis of the enamine to eliminate the amine v) Abstraction of a proton from the diketone vi) Internal aldol reaction to form the second ring vii) Protonation and dehydration.

To give:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation.

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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 23.SE, Problem 65AP

Interpretation Introduction

a)

Interpretation:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation is to be shown.

Concept introduction:

The steps involved in the reaction are i) Reaction of the cyclic ketone with pyrrolidine ii) Michael addition of enamine to cyclohexanone iii) A proton transfer iv) Hydrolysis of the enamine to eliminate the amine v) Abstraction of a proton from the diketone vi) Internal aldol reaction to form the second ring vii) Protonation and dehydration.

To give:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation.

Interpretation Introduction

b)

Interpretation:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation is to be shown.

Concept introduction:

The steps involved in the reaction are i) Reaction of the cyclic ketone with pyrrolidine ii) Michael addition of enamine to cyclohexanone iii) A proton transfer iv) Hydrolysis of the enamine to eliminate the amine v) Abstraction of a proton from the diketone vi) Internal aldol reaction to form the second ring vii) Protonation and dehydration.

To give:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation.

Interpretation Introduction

c)

Interpretation:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation is to be shown.

Concept introduction:

The steps involved in the reaction are i) Reaction of the cyclic ketone with pyrrolidine ii) Michael addition of enamine to cyclohexanone iii) A proton transfer iv) Hydrolysis of the enamine to eliminate the amine v) Abstraction of a proton from the diketone vi) Internal aldol reaction to form the second ring vii) Protonation and dehydration.

To give:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation.

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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 23.SE, Problem 65AP

Interpretation Introduction

a)

Interpretation:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation is to be shown.

Concept introduction:

The steps involved in the reaction are i) Reaction of the cyclic ketone with pyrrolidine ii) Michael addition of enamine to cyclohexanone iii) A proton transfer iv) Hydrolysis of the enamine to eliminate the amine v) Abstraction of a proton from the diketone vi) Internal aldol reaction to form the second ring vii) Protonation and dehydration.

To give:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation.

Interpretation Introduction

b)

Interpretation:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation is to be shown.

Concept introduction:

The steps involved in the reaction are i) Reaction of the cyclic ketone with pyrrolidine ii) Michael addition of enamine to cyclohexanone iii) A proton transfer iv) Hydrolysis of the enamine to eliminate the amine v) Abstraction of a proton from the diketone vi) Internal aldol reaction to form the second ring vii) Protonation and dehydration.

To give:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation.

Interpretation Introduction

c)

Interpretation:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation is to be shown.

Concept introduction:

The steps involved in the reaction are i) Reaction of the cyclic ketone with pyrrolidine ii) Michael addition of enamine to cyclohexanone iii) A proton transfer iv) Hydrolysis of the enamine to eliminate the amine v) Abstraction of a proton from the diketone vi) Internal aldol reaction to form the second ring vii) Protonation and dehydration.

To give:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation.

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Answer 5

Chapter 23.SE, Problem 65AP

Interpretation Introduction

a)

Interpretation:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation is to be shown.

Concept introduction:

The steps involved in the reaction are i) Reaction of the cyclic ketone with pyrrolidine ii) Michael addition of enamine to cyclohexanone iii) A proton transfer iv) Hydrolysis of the enamine to eliminate the amine v) Abstraction of a proton from the diketone vi) Internal aldol reaction to form the second ring vii) Protonation and dehydration.

To give:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation.

Interpretation Introduction

b)

Interpretation:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation is to be shown.

Concept introduction:

The steps involved in the reaction are i) Reaction of the cyclic ketone with pyrrolidine ii) Michael addition of enamine to cyclohexanone iii) A proton transfer iv) Hydrolysis of the enamine to eliminate the amine v) Abstraction of a proton from the diketone vi) Internal aldol reaction to form the second ring vii) Protonation and dehydration.

To give:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation.

Interpretation Introduction

c)

Interpretation:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation is to be shown.

Concept introduction:

The steps involved in the reaction are i) Reaction of the cyclic ketone with pyrrolidine ii) Michael addition of enamine to cyclohexanone iii) A proton transfer iv) Hydrolysis of the enamine to eliminate the amine v) Abstraction of a proton from the diketone vi) Internal aldol reaction to form the second ring vii) Protonation and dehydration.

To give:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation.

Answer 6

Chapter 23.SE, Problem 65AP

Interpretation Introduction

a)

Interpretation:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation is to be shown.

Concept introduction:

The steps involved in the reaction are i) Reaction of the cyclic ketone with pyrrolidine ii) Michael addition of enamine to cyclohexanone iii) A proton transfer iv) Hydrolysis of the enamine to eliminate the amine v) Abstraction of a proton from the diketone vi) Internal aldol reaction to form the second ring vii) Protonation and dehydration.

To give:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation.

Answer 7

Chapter 23.SE, Problem 65AP

Interpretation Introduction

a)

Interpretation:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation is to be shown.

Concept introduction:

The steps involved in the reaction are i) Reaction of the cyclic ketone with pyrrolidine ii) Michael addition of enamine to cyclohexanone iii) A proton transfer iv) Hydrolysis of the enamine to eliminate the amine v) Abstraction of a proton from the diketone vi) Internal aldol reaction to form the second ring vii) Protonation and dehydration.

To give:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation.

Answer 8

Interpretation Introduction

b)

Interpretation:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation is to be shown.

Concept introduction:

The steps involved in the reaction are i) Reaction of the cyclic ketone with pyrrolidine ii) Michael addition of enamine to cyclohexanone iii) A proton transfer iv) Hydrolysis of the enamine to eliminate the amine v) Abstraction of a proton from the diketone vi) Internal aldol reaction to form the second ring vii) Protonation and dehydration.

To give:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation.

Answer 9

Interpretation Introduction

b)

Interpretation:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation is to be shown.

Concept introduction:

The steps involved in the reaction are i) Reaction of the cyclic ketone with pyrrolidine ii) Michael addition of enamine to cyclohexanone iii) A proton transfer iv) Hydrolysis of the enamine to eliminate the amine v) Abstraction of a proton from the diketone vi) Internal aldol reaction to form the second ring vii) Protonation and dehydration.

To give:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation.

Answer 10

Interpretation Introduction

c)

Interpretation:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation is to be shown.

Concept introduction:

The steps involved in the reaction are i) Reaction of the cyclic ketone with pyrrolidine ii) Michael addition of enamine to cyclohexanone iii) A proton transfer iv) Hydrolysis of the enamine to eliminate the amine v) Abstraction of a proton from the diketone vi) Internal aldol reaction to form the second ring vii) Protonation and dehydration.

To give:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation.

Answer 11

Interpretation Introduction

c)

Interpretation:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation is to be shown.

Concept introduction:

The steps involved in the reaction are i) Reaction of the cyclic ketone with pyrrolidine ii) Michael addition of enamine to cyclohexanone iii) A proton transfer iv) Hydrolysis of the enamine to eliminate the amine v) Abstraction of a proton from the diketone vi) Internal aldol reaction to form the second ring vii) Protonation and dehydration.

To give:

How to prepare the cyclohexanone shown by combining a Stork enamine reaction with an intramolecular aldol condensation.

Answer 12

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Answer 23

Ch. 23.1 - Prob. 1P Ch. 23.1 - Prob. 2P Ch. 23.3 - Prob. 3P Ch. 23.3 - Prob. 4P Ch. 23.4 - Prob. 5P Ch. 23.4 - 1-Butanol is prepared commercially by a route that...Ch. 23.4 - Prob. 7P Ch. 23.5 - Prob. 8P Ch. 23.6 - Prob. 9P Ch. 23.6 - What product would you Expect to obtain from base...

Solution Summary: The author explains how to prepare the cyclohexanone by combining a Stork enamine reaction with an intramolecular aldol condensation.

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