(a) Interpretation: The carbonyl compounds needed to synthesize octinoxate using a condensation reaction is to be predicted. Concept introduction: Claisen condensation takes place between two esters or between an ester and a ketone . In crossed Claisen condensation reaction, a base abstracts an acidic proton from an α carbon atom of carbonyl group to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β -ketoester.

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Answer 1

Question

Chapter 24, Problem 24.66P

Interpretation Introduction

(a)

Interpretation: The carbonyl compounds needed to synthesize octinoxate using a condensation reaction is to be predicted.

Concept introduction: Claisen condensation takes place between two esters or between an ester and a ketone. In crossed Claisen condensation reaction, a base abstracts an acidic proton from an α carbon atom of carbonyl group to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

Interpretation Introduction

(b)

Interpretation: Synthesis of octinoxate is to be devised from the given starting materials and other needed reagents is to be devised.

Concept introduction: In Aldol condensation reaction, the base abstracts the acidic proton from α carbon atom to form enolate. This enolate or enol reacts with carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Claisen condensation takes place between two esters or between an ester and a ketone. In crossed Claisen condensation reaction, a base abstracts an acidic proton from an α carbon atom of carbonyl group to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

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Octinoxate is an unsaturated ester used as an active ingredient in sunscreens. (a) What carbonyl compounds are needed to synthesize this compound using a condensation reaction? (b) Devise a synthesis of octinoxate from the given organic starting materials and any other needed reagents.

Provide reagents

Synthesize the compound from ethyl acetoacetate. You may use any other organic compounds or inorganic reagents.

Answer 2

Question

Chapter 24, Problem 24.66P

Interpretation Introduction

(a)

Interpretation: The carbonyl compounds needed to synthesize octinoxate using a condensation reaction is to be predicted.

Concept introduction: Claisen condensation takes place between two esters or between an ester and a ketone. In crossed Claisen condensation reaction, a base abstracts an acidic proton from an α carbon atom of carbonyl group to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

Interpretation Introduction

(b)

Interpretation: Synthesis of octinoxate is to be devised from the given starting materials and other needed reagents is to be devised.

Concept introduction: In Aldol condensation reaction, the base abstracts the acidic proton from α carbon atom to form enolate. This enolate or enol reacts with carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Claisen condensation takes place between two esters or between an ester and a ketone. In crossed Claisen condensation reaction, a base abstracts an acidic proton from an α carbon atom of carbonyl group to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

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Answer 3

Question

Chapter 24, Problem 24.66P

Interpretation Introduction

(a)

Interpretation: The carbonyl compounds needed to synthesize octinoxate using a condensation reaction is to be predicted.

Concept introduction: Claisen condensation takes place between two esters or between an ester and a ketone. In crossed Claisen condensation reaction, a base abstracts an acidic proton from an α carbon atom of carbonyl group to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

Interpretation Introduction

(b)

Interpretation: Synthesis of octinoxate is to be devised from the given starting materials and other needed reagents is to be devised.

Concept introduction: In Aldol condensation reaction, the base abstracts the acidic proton from α carbon atom to form enolate. This enolate or enol reacts with carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Claisen condensation takes place between two esters or between an ester and a ketone. In crossed Claisen condensation reaction, a base abstracts an acidic proton from an α carbon atom of carbonyl group to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

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Answer 4

Question

Chapter 24, Problem 24.66P

Interpretation Introduction

(a)

Interpretation: The carbonyl compounds needed to synthesize octinoxate using a condensation reaction is to be predicted.

Concept introduction: Claisen condensation takes place between two esters or between an ester and a ketone. In crossed Claisen condensation reaction, a base abstracts an acidic proton from an α carbon atom of carbonyl group to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

Interpretation Introduction

(b)

Interpretation: Synthesis of octinoxate is to be devised from the given starting materials and other needed reagents is to be devised.

Concept introduction: In Aldol condensation reaction, the base abstracts the acidic proton from α carbon atom to form enolate. This enolate or enol reacts with carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Claisen condensation takes place between two esters or between an ester and a ketone. In crossed Claisen condensation reaction, a base abstracts an acidic proton from an α carbon atom of carbonyl group to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

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Answer 5

Chapter 24, Problem 24.66P

Interpretation Introduction

(a)

Interpretation: The carbonyl compounds needed to synthesize octinoxate using a condensation reaction is to be predicted.

Concept introduction: Claisen condensation takes place between two esters or between an ester and a ketone. In crossed Claisen condensation reaction, a base abstracts an acidic proton from an α carbon atom of carbonyl group to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

Interpretation Introduction

(b)

Interpretation: Synthesis of octinoxate is to be devised from the given starting materials and other needed reagents is to be devised.

Concept introduction: In Aldol condensation reaction, the base abstracts the acidic proton from α carbon atom to form enolate. This enolate or enol reacts with carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Claisen condensation takes place between two esters or between an ester and a ketone. In crossed Claisen condensation reaction, a base abstracts an acidic proton from an α carbon atom of carbonyl group to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

Answer 6

Chapter 24, Problem 24.66P

Interpretation Introduction

(a)

Interpretation: The carbonyl compounds needed to synthesize octinoxate using a condensation reaction is to be predicted.

Concept introduction: Claisen condensation takes place between two esters or between an ester and a ketone. In crossed Claisen condensation reaction, a base abstracts an acidic proton from an α carbon atom of carbonyl group to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

Answer 7

Chapter 24, Problem 24.66P

Interpretation Introduction

(a)

Interpretation: The carbonyl compounds needed to synthesize octinoxate using a condensation reaction is to be predicted.

Concept introduction: Claisen condensation takes place between two esters or between an ester and a ketone. In crossed Claisen condensation reaction, a base abstracts an acidic proton from an α carbon atom of carbonyl group to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

Answer 8

Interpretation Introduction

(b)

Interpretation: Synthesis of octinoxate is to be devised from the given starting materials and other needed reagents is to be devised.

Concept introduction: In Aldol condensation reaction, the base abstracts the acidic proton from α carbon atom to form enolate. This enolate or enol reacts with carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Claisen condensation takes place between two esters or between an ester and a ketone. In crossed Claisen condensation reaction, a base abstracts an acidic proton from an α carbon atom of carbonyl group to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

Answer 9

Interpretation Introduction

(b)

Interpretation: Synthesis of octinoxate is to be devised from the given starting materials and other needed reagents is to be devised.

Concept introduction: In Aldol condensation reaction, the base abstracts the acidic proton from α carbon atom to form enolate. This enolate or enol reacts with carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone.

Claisen condensation takes place between two esters or between an ester and a ketone. In crossed Claisen condensation reaction, a base abstracts an acidic proton from an α carbon atom of carbonyl group to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

Answer 10

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Answer 13

Ch. 24 - Prob. 24.1P Ch. 24 - Prob. 24.2P Ch. 24 - Problem 24.3 What unsaturated carbonyl compound is...Ch. 24 - Acid-catalyzed dehydration of hydroxy carbonyl...Ch. 24 - Prob. 24.5P Ch. 24 - Prob. 24.6P Ch. 24 - Prob. 24.7P Ch. 24 - Problem 24.8 Draw the products formed in the...Ch. 24 - Prob. 24.9P Ch. 24 - Prob. 24.10P

Solution Summary: The author explains that the carbonyl compounds needed to synthesize octinoxate using a condensation reaction are shown in Figure 1.

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Chapter 24 Solutions