The validation of the fact that the given keto ester is formed by Dieckmann condensation has to be predicted and the structure of starting diester if applicable has to be drawn. Concept introduction: An internal condensation reaction of a diester forms a ring compound. Such an internal claisen cyclization is known as a Dieckmann condensation reaction or more commonly it is known as a Dieckmann cyclization. This reaction is useful in the formation of five and six membered rings. Rings which are smaller than five carbon atoms or larger than six carbon atoms are rarely formed by this reaction.

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Answer 1

Question

Chapter 22.13, Problem 22.40P

(a)

Interpretation Introduction

Interpretation:

The validation of the fact that the given keto ester is formed by Dieckmann condensation has to be predicted and the structure of starting diester if applicable has to be drawn.

Concept introduction:

An internal condensation reaction of a diester forms a ring compound. Such an internal claisen cyclization is known as a Dieckmann condensation reaction or more commonly it is known as a Dieckmann cyclization. This reaction is useful in the formation of five and six membered rings. Rings which are smaller than five carbon atoms or larger than six carbon atoms are rarely formed by this reaction.

(b)

Interpretation Introduction

Interpretation:

The validation of the fact that the given keto ester is formed by Dieckmann condensation is to be predicted and the structure of starting diester if applicable is to be drawn.

Concept introduction:

An internal condensation reaction of a diester forms a ring compound. Such an internal claisen cyclization is known as a Dieckmann condensation reaction or more commonly it is known as a Dieckmann cyclization. This reaction is useful in the formation of five and six membered rings. Rings which are smaller than five carbon atoms or larger than six carbon atoms are rarely formed by this reaction.

(c)

Interpretation Introduction

Interpretation:

The validation of the fact that the given keto ester is formed by Dieckmann condensation is to be predicted and the structure of starting diester if applicable is to be drawn.

Concept introduction:

An internal condensation reaction of a diester forms a ring compound. Such an internal claisen cyclization is known as a Dieckmann condensation reaction or more commonly it is known as a Dieckmann cyclization. This reaction is useful in the formation of five and six membered rings. Rings which are smaller than five carbon atoms or larger than six carbon atoms are rarely formed by this reaction.

(d)

Interpretation Introduction

Interpretation:

The validation of the fact that the given keto ester is formed by Dieckmann condensation is to be predicted and the structure of starting diester if applicable is to be drawn.

Concept introduction:

An internal condensation reaction of a diester forms a ring compound. Such an internal claisen cyclization is known as a Dieckmann condensation reaction or more commonly it is known as a Dieckmann cyclization. This reaction is useful in the formation of five and six membered rings. Rings which are smaller than five carbon atoms or larger than six carbon atoms are rarely formed by this reaction.

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Don't used hand raiting and don't used Ai solution

Give the structure(s) of the product(s) the reaction below, and be sure to indicate any relative stereochemistry (you can assume that each of the Diels-Alder reactions will proceed with endo selectivity). Draw out relevant enantiomer(s) if they are expected to form. If no reaction is expected to occur under the indicated conditions, then write "no reaction" or NR, and explain why you would expect nothing to occur. If more than one product is formed, please indicate which one will be the major product or if they will be formed in equal amounts. In all cases, equimolar amounts of both components/reagents are present unless indicated otherwise I'm struggling to see how this reaction will go! I am wondering if it will cycle on itself but I'm not sure how I drew out a decagon but I'm a bit lost

Give the structure(s) of the product(s) for the reactions below, and be sure to indicate any relative stereochemistry (you can assume that each of the Diels-Alder reactions will proceed with endo selectivity). Draw out relevant enantiomer(s) if they are expected to form. If no reaction is expected to occur under the indicated conditions, then write "no reaction" or NR, and explain why you would expect nothing to occur. If more than one product is formed, please indicate which one will be the major product or if they will be formed in equal amounts. In all cases, equimolar amounts of both components/reagents are present unless indicated otherwise .

Answer 2

Question

Chapter 22.13, Problem 22.40P

(a)

Interpretation Introduction

Interpretation:

The validation of the fact that the given keto ester is formed by Dieckmann condensation has to be predicted and the structure of starting diester if applicable has to be drawn.

Concept introduction:

An internal condensation reaction of a diester forms a ring compound. Such an internal claisen cyclization is known as a Dieckmann condensation reaction or more commonly it is known as a Dieckmann cyclization. This reaction is useful in the formation of five and six membered rings. Rings which are smaller than five carbon atoms or larger than six carbon atoms are rarely formed by this reaction.

(b)

Interpretation Introduction

Interpretation:

The validation of the fact that the given keto ester is formed by Dieckmann condensation is to be predicted and the structure of starting diester if applicable is to be drawn.

Concept introduction:

An internal condensation reaction of a diester forms a ring compound. Such an internal claisen cyclization is known as a Dieckmann condensation reaction or more commonly it is known as a Dieckmann cyclization. This reaction is useful in the formation of five and six membered rings. Rings which are smaller than five carbon atoms or larger than six carbon atoms are rarely formed by this reaction.

(c)

Interpretation Introduction

Interpretation:

The validation of the fact that the given keto ester is formed by Dieckmann condensation is to be predicted and the structure of starting diester if applicable is to be drawn.

Concept introduction:

An internal condensation reaction of a diester forms a ring compound. Such an internal claisen cyclization is known as a Dieckmann condensation reaction or more commonly it is known as a Dieckmann cyclization. This reaction is useful in the formation of five and six membered rings. Rings which are smaller than five carbon atoms or larger than six carbon atoms are rarely formed by this reaction.

(d)

Interpretation Introduction

Interpretation:

The validation of the fact that the given keto ester is formed by Dieckmann condensation is to be predicted and the structure of starting diester if applicable is to be drawn.

Concept introduction:

An internal condensation reaction of a diester forms a ring compound. Such an internal claisen cyclization is known as a Dieckmann condensation reaction or more commonly it is known as a Dieckmann cyclization. This reaction is useful in the formation of five and six membered rings. Rings which are smaller than five carbon atoms or larger than six carbon atoms are rarely formed by this reaction.

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Answer 3

Question

Chapter 22.13, Problem 22.40P

(a)

Interpretation Introduction

Interpretation:

The validation of the fact that the given keto ester is formed by Dieckmann condensation has to be predicted and the structure of starting diester if applicable has to be drawn.

Concept introduction:

An internal condensation reaction of a diester forms a ring compound. Such an internal claisen cyclization is known as a Dieckmann condensation reaction or more commonly it is known as a Dieckmann cyclization. This reaction is useful in the formation of five and six membered rings. Rings which are smaller than five carbon atoms or larger than six carbon atoms are rarely formed by this reaction.

(b)

Interpretation Introduction

Interpretation:

The validation of the fact that the given keto ester is formed by Dieckmann condensation is to be predicted and the structure of starting diester if applicable is to be drawn.

Concept introduction:

An internal condensation reaction of a diester forms a ring compound. Such an internal claisen cyclization is known as a Dieckmann condensation reaction or more commonly it is known as a Dieckmann cyclization. This reaction is useful in the formation of five and six membered rings. Rings which are smaller than five carbon atoms or larger than six carbon atoms are rarely formed by this reaction.

(c)

Interpretation Introduction

Interpretation:

The validation of the fact that the given keto ester is formed by Dieckmann condensation is to be predicted and the structure of starting diester if applicable is to be drawn.

Concept introduction:

An internal condensation reaction of a diester forms a ring compound. Such an internal claisen cyclization is known as a Dieckmann condensation reaction or more commonly it is known as a Dieckmann cyclization. This reaction is useful in the formation of five and six membered rings. Rings which are smaller than five carbon atoms or larger than six carbon atoms are rarely formed by this reaction.

(d)

Interpretation Introduction

Interpretation:

The validation of the fact that the given keto ester is formed by Dieckmann condensation is to be predicted and the structure of starting diester if applicable is to be drawn.

Concept introduction:

An internal condensation reaction of a diester forms a ring compound. Such an internal claisen cyclization is known as a Dieckmann condensation reaction or more commonly it is known as a Dieckmann cyclization. This reaction is useful in the formation of five and six membered rings. Rings which are smaller than five carbon atoms or larger than six carbon atoms are rarely formed by this reaction.

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Answer 4

Question

Chapter 22.13, Problem 22.40P

(a)

Interpretation Introduction

Interpretation:

The validation of the fact that the given keto ester is formed by Dieckmann condensation has to be predicted and the structure of starting diester if applicable has to be drawn.

Concept introduction:

An internal condensation reaction of a diester forms a ring compound. Such an internal claisen cyclization is known as a Dieckmann condensation reaction or more commonly it is known as a Dieckmann cyclization. This reaction is useful in the formation of five and six membered rings. Rings which are smaller than five carbon atoms or larger than six carbon atoms are rarely formed by this reaction.

(b)

Interpretation Introduction

Interpretation:

The validation of the fact that the given keto ester is formed by Dieckmann condensation is to be predicted and the structure of starting diester if applicable is to be drawn.

Concept introduction:

An internal condensation reaction of a diester forms a ring compound. Such an internal claisen cyclization is known as a Dieckmann condensation reaction or more commonly it is known as a Dieckmann cyclization. This reaction is useful in the formation of five and six membered rings. Rings which are smaller than five carbon atoms or larger than six carbon atoms are rarely formed by this reaction.

(c)

Interpretation Introduction

Interpretation:

The validation of the fact that the given keto ester is formed by Dieckmann condensation is to be predicted and the structure of starting diester if applicable is to be drawn.

Concept introduction:

An internal condensation reaction of a diester forms a ring compound. Such an internal claisen cyclization is known as a Dieckmann condensation reaction or more commonly it is known as a Dieckmann cyclization. This reaction is useful in the formation of five and six membered rings. Rings which are smaller than five carbon atoms or larger than six carbon atoms are rarely formed by this reaction.

(d)

Interpretation Introduction

Interpretation:

The validation of the fact that the given keto ester is formed by Dieckmann condensation is to be predicted and the structure of starting diester if applicable is to be drawn.

Concept introduction:

An internal condensation reaction of a diester forms a ring compound. Such an internal claisen cyclization is known as a Dieckmann condensation reaction or more commonly it is known as a Dieckmann cyclization. This reaction is useful in the formation of five and six membered rings. Rings which are smaller than five carbon atoms or larger than six carbon atoms are rarely formed by this reaction.

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Answer 5

Chapter 22.13, Problem 22.40P

(a)

Interpretation Introduction

Interpretation:

The validation of the fact that the given keto ester is formed by Dieckmann condensation has to be predicted and the structure of starting diester if applicable has to be drawn.

Concept introduction:

An internal condensation reaction of a diester forms a ring compound. Such an internal claisen cyclization is known as a Dieckmann condensation reaction or more commonly it is known as a Dieckmann cyclization. This reaction is useful in the formation of five and six membered rings. Rings which are smaller than five carbon atoms or larger than six carbon atoms are rarely formed by this reaction.

(b)

Interpretation Introduction

Interpretation:

The validation of the fact that the given keto ester is formed by Dieckmann condensation is to be predicted and the structure of starting diester if applicable is to be drawn.

Concept introduction:

An internal condensation reaction of a diester forms a ring compound. Such an internal claisen cyclization is known as a Dieckmann condensation reaction or more commonly it is known as a Dieckmann cyclization. This reaction is useful in the formation of five and six membered rings. Rings which are smaller than five carbon atoms or larger than six carbon atoms are rarely formed by this reaction.

(c)

Interpretation Introduction

Interpretation:

The validation of the fact that the given keto ester is formed by Dieckmann condensation is to be predicted and the structure of starting diester if applicable is to be drawn.

Concept introduction:

An internal condensation reaction of a diester forms a ring compound. Such an internal claisen cyclization is known as a Dieckmann condensation reaction or more commonly it is known as a Dieckmann cyclization. This reaction is useful in the formation of five and six membered rings. Rings which are smaller than five carbon atoms or larger than six carbon atoms are rarely formed by this reaction.

(d)

Interpretation Introduction

Interpretation:

The validation of the fact that the given keto ester is formed by Dieckmann condensation is to be predicted and the structure of starting diester if applicable is to be drawn.

Concept introduction:

An internal condensation reaction of a diester forms a ring compound. Such an internal claisen cyclization is known as a Dieckmann condensation reaction or more commonly it is known as a Dieckmann cyclization. This reaction is useful in the formation of five and six membered rings. Rings which are smaller than five carbon atoms or larger than six carbon atoms are rarely formed by this reaction.

Answer 6

Chapter 22.13, Problem 22.40P

(a)

Interpretation Introduction

Interpretation:

The validation of the fact that the given keto ester is formed by Dieckmann condensation has to be predicted and the structure of starting diester if applicable has to be drawn.

Concept introduction:

An internal condensation reaction of a diester forms a ring compound. Such an internal claisen cyclization is known as a Dieckmann condensation reaction or more commonly it is known as a Dieckmann cyclization. This reaction is useful in the formation of five and six membered rings. Rings which are smaller than five carbon atoms or larger than six carbon atoms are rarely formed by this reaction.

Answer 7

Chapter 22.13, Problem 22.40P

(a)

Interpretation Introduction

Interpretation:

The validation of the fact that the given keto ester is formed by Dieckmann condensation has to be predicted and the structure of starting diester if applicable has to be drawn.

Concept introduction:

An internal condensation reaction of a diester forms a ring compound. Such an internal claisen cyclization is known as a Dieckmann condensation reaction or more commonly it is known as a Dieckmann cyclization. This reaction is useful in the formation of five and six membered rings. Rings which are smaller than five carbon atoms or larger than six carbon atoms are rarely formed by this reaction.

Answer 8

(b)

Interpretation Introduction

Interpretation:

The validation of the fact that the given keto ester is formed by Dieckmann condensation is to be predicted and the structure of starting diester if applicable is to be drawn.

Concept introduction:

An internal condensation reaction of a diester forms a ring compound. Such an internal claisen cyclization is known as a Dieckmann condensation reaction or more commonly it is known as a Dieckmann cyclization. This reaction is useful in the formation of five and six membered rings. Rings which are smaller than five carbon atoms or larger than six carbon atoms are rarely formed by this reaction.

Answer 9

(b)

Interpretation Introduction

Interpretation:

The validation of the fact that the given keto ester is formed by Dieckmann condensation is to be predicted and the structure of starting diester if applicable is to be drawn.

Concept introduction:

An internal condensation reaction of a diester forms a ring compound. Such an internal claisen cyclization is known as a Dieckmann condensation reaction or more commonly it is known as a Dieckmann cyclization. This reaction is useful in the formation of five and six membered rings. Rings which are smaller than five carbon atoms or larger than six carbon atoms are rarely formed by this reaction.

Answer 10

(c)

Interpretation Introduction

Interpretation:

The validation of the fact that the given keto ester is formed by Dieckmann condensation is to be predicted and the structure of starting diester if applicable is to be drawn.

Concept introduction:

An internal condensation reaction of a diester forms a ring compound. Such an internal claisen cyclization is known as a Dieckmann condensation reaction or more commonly it is known as a Dieckmann cyclization. This reaction is useful in the formation of five and six membered rings. Rings which are smaller than five carbon atoms or larger than six carbon atoms are rarely formed by this reaction.

Answer 11

(c)

Interpretation Introduction

Interpretation:

The validation of the fact that the given keto ester is formed by Dieckmann condensation is to be predicted and the structure of starting diester if applicable is to be drawn.

Concept introduction:

An internal condensation reaction of a diester forms a ring compound. Such an internal claisen cyclization is known as a Dieckmann condensation reaction or more commonly it is known as a Dieckmann cyclization. This reaction is useful in the formation of five and six membered rings. Rings which are smaller than five carbon atoms or larger than six carbon atoms are rarely formed by this reaction.

Answer 12

(d)

Interpretation Introduction

Interpretation:

The validation of the fact that the given keto ester is formed by Dieckmann condensation is to be predicted and the structure of starting diester if applicable is to be drawn.

Concept introduction:

An internal condensation reaction of a diester forms a ring compound. Such an internal claisen cyclization is known as a Dieckmann condensation reaction or more commonly it is known as a Dieckmann cyclization. This reaction is useful in the formation of five and six membered rings. Rings which are smaller than five carbon atoms or larger than six carbon atoms are rarely formed by this reaction.

Answer 13

(d)

Interpretation Introduction

Interpretation:

The validation of the fact that the given keto ester is formed by Dieckmann condensation is to be predicted and the structure of starting diester if applicable is to be drawn.

Concept introduction:

An internal condensation reaction of a diester forms a ring compound. Such an internal claisen cyclization is known as a Dieckmann condensation reaction or more commonly it is known as a Dieckmann cyclization. This reaction is useful in the formation of five and six membered rings. Rings which are smaller than five carbon atoms or larger than six carbon atoms are rarely formed by this reaction.

Answer 14

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Answer 15

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Answer 16

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Answer 17

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 how Dieckmann condensation forms a ring compound, which is useful in the formation of five and six-membered rings.

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Chapter 22 Solutions