The product formed in the given reaction has to be identified. Concept Introduction: Reaction of an ester having an α − hydrogen with one equivalent of a base to yield a β − keto ester. Mechanism for Claisen Condensation: A base abstracts a proton from the α − c a r b o n forms enolate ion. The enolate ion gets attached to the carbonyl carbon of another ester. The negative charge on oxygen of the carbonyl group reforms, by removing an alkoxide ion.

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Answer 1

Question

Chapter 13.8, Problem 17P

(a)

Interpretation Introduction

Interpretation:

The product formed in the given reaction has to be identified.

Concept Introduction:

Reaction of an ester having an α− hydrogen with one equivalent of a base to yield a β− keto ester.

Mechanism for Claisen Condensation:

A base abstracts a proton from the α−carbon forms enolate ion.

The enolate ion gets attached to the carbonyl carbon of another ester.

The negative charge on oxygen of the carbonyl group reforms, by removing an alkoxide ion.

(b)

Interpretation Introduction

Interpretation:

The product formed in the given reaction has to be identified.

Concept Introduction:

Reaction of an ester having an α− hydrogen with one equivalent of a base to yield a β− keto ester.

Mechanism for Claisen Condensation:

A base abstracts a proton from the α−carbon forms enolate ion.

The enolate ion gets attached to the carbonyl carbon of another ester.

The negative charge on oxygen of the carbonyl group reforms, by removing an alkoxide ion.

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Part II. Identify whether the two protons in blue are homotopic, enantiopic, diasteriotopic, or heterotopic. a) HO b) Bri H HH c) d) H H H Br 0

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Answer 2

Question

Chapter 13.8, Problem 17P

(a)

Interpretation Introduction

Interpretation:

The product formed in the given reaction has to be identified.

Concept Introduction:

Reaction of an ester having an α− hydrogen with one equivalent of a base to yield a β− keto ester.

Mechanism for Claisen Condensation:

A base abstracts a proton from the α−carbon forms enolate ion.

The enolate ion gets attached to the carbonyl carbon of another ester.

The negative charge on oxygen of the carbonyl group reforms, by removing an alkoxide ion.

(b)

Interpretation Introduction

Interpretation:

The product formed in the given reaction has to be identified.

Concept Introduction:

Reaction of an ester having an α− hydrogen with one equivalent of a base to yield a β− keto ester.

Mechanism for Claisen Condensation:

A base abstracts a proton from the α−carbon forms enolate ion.

The enolate ion gets attached to the carbonyl carbon of another ester.

The negative charge on oxygen of the carbonyl group reforms, by removing an alkoxide ion.

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Answer 3

Question

Chapter 13.8, Problem 17P

(a)

Interpretation Introduction

Interpretation:

The product formed in the given reaction has to be identified.

Concept Introduction:

Reaction of an ester having an α− hydrogen with one equivalent of a base to yield a β− keto ester.

Mechanism for Claisen Condensation:

A base abstracts a proton from the α−carbon forms enolate ion.

The enolate ion gets attached to the carbonyl carbon of another ester.

The negative charge on oxygen of the carbonyl group reforms, by removing an alkoxide ion.

(b)

Interpretation Introduction

Interpretation:

The product formed in the given reaction has to be identified.

Concept Introduction:

Reaction of an ester having an α− hydrogen with one equivalent of a base to yield a β− keto ester.

Mechanism for Claisen Condensation:

A base abstracts a proton from the α−carbon forms enolate ion.

The enolate ion gets attached to the carbonyl carbon of another ester.

The negative charge on oxygen of the carbonyl group reforms, by removing an alkoxide ion.

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Answer 4

Question

Chapter 13.8, Problem 17P

(a)

Interpretation Introduction

Interpretation:

The product formed in the given reaction has to be identified.

Concept Introduction:

Reaction of an ester having an α− hydrogen with one equivalent of a base to yield a β− keto ester.

Mechanism for Claisen Condensation:

A base abstracts a proton from the α−carbon forms enolate ion.

The enolate ion gets attached to the carbonyl carbon of another ester.

The negative charge on oxygen of the carbonyl group reforms, by removing an alkoxide ion.

(b)

Interpretation Introduction

Interpretation:

The product formed in the given reaction has to be identified.

Concept Introduction:

Reaction of an ester having an α− hydrogen with one equivalent of a base to yield a β− keto ester.

Mechanism for Claisen Condensation:

A base abstracts a proton from the α−carbon forms enolate ion.

The enolate ion gets attached to the carbonyl carbon of another ester.

The negative charge on oxygen of the carbonyl group reforms, by removing an alkoxide ion.

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Answer 5

Chapter 13.8, Problem 17P

(a)

Interpretation Introduction

Interpretation:

The product formed in the given reaction has to be identified.

Concept Introduction:

Reaction of an ester having an α− hydrogen with one equivalent of a base to yield a β− keto ester.

Mechanism for Claisen Condensation:

A base abstracts a proton from the α−carbon forms enolate ion.

The enolate ion gets attached to the carbonyl carbon of another ester.

The negative charge on oxygen of the carbonyl group reforms, by removing an alkoxide ion.

(b)

Interpretation Introduction

Interpretation:

The product formed in the given reaction has to be identified.

Concept Introduction:

Reaction of an ester having an α− hydrogen with one equivalent of a base to yield a β− keto ester.

Mechanism for Claisen Condensation:

A base abstracts a proton from the α−carbon forms enolate ion.

The enolate ion gets attached to the carbonyl carbon of another ester.

The negative charge on oxygen of the carbonyl group reforms, by removing an alkoxide ion.

Answer 6

Chapter 13.8, Problem 17P

(a)

Interpretation Introduction

Interpretation:

The product formed in the given reaction has to be identified.

Concept Introduction:

Reaction of an ester having an α− hydrogen with one equivalent of a base to yield a β− keto ester.

Mechanism for Claisen Condensation:

A base abstracts a proton from the α−carbon forms enolate ion.

The enolate ion gets attached to the carbonyl carbon of another ester.

The negative charge on oxygen of the carbonyl group reforms, by removing an alkoxide ion.

Answer 7

Chapter 13.8, Problem 17P

(a)

Interpretation Introduction

Interpretation:

The product formed in the given reaction has to be identified.

Concept Introduction:

Reaction of an ester having an α− hydrogen with one equivalent of a base to yield a β− keto ester.

Mechanism for Claisen Condensation:

A base abstracts a proton from the α−carbon forms enolate ion.

The enolate ion gets attached to the carbonyl carbon of another ester.

The negative charge on oxygen of the carbonyl group reforms, by removing an alkoxide ion.

Answer 8

(b)

Interpretation Introduction

Interpretation:

The product formed in the given reaction has to be identified.

Concept Introduction:

Reaction of an ester having an α− hydrogen with one equivalent of a base to yield a β− keto ester.

Mechanism for Claisen Condensation:

A base abstracts a proton from the α−carbon forms enolate ion.

The enolate ion gets attached to the carbonyl carbon of another ester.

The negative charge on oxygen of the carbonyl group reforms, by removing an alkoxide ion.

Answer 9

(b)

Interpretation Introduction

Interpretation:

The product formed in the given reaction has to be identified.

Concept Introduction:

Reaction of an ester having an α− hydrogen with one equivalent of a base to yield a β− keto ester.

Mechanism for Claisen Condensation:

A base abstracts a proton from the α−carbon forms enolate ion.

The enolate ion gets attached to the carbonyl carbon of another ester.

The negative charge on oxygen of the carbonyl group reforms, by removing an alkoxide ion.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 13.1 - Identify the most acidic hydrogen in each...Ch. 13.1 - Prob. 2P Ch. 13.1 - Prob. 3P Ch. 13.1 - Prob. 4P Ch. 13.1 - Explain why HO cannot remove a proton from the...Ch. 13.2 - Prob. 6P Ch. 13.2 - Prob. 7P Ch. 13.3 - Prob. 8P Ch. 13.3 - Prob. 9P Ch. 13.3 - Prob. 10P

Solution Summary: The author explains the mechanism of Claisen Condensation, wherein a proton is abstracted from the alpha -carbon and attached to the carbonyl carbon of another ester.

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