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

Show a reasonable mechanism for the following reaction (Hint: Michael addition followed by intramolecular aldol condensation) ☆ NaOEt, EtOH A

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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