(a) Interpretation: The stepwise mechanism for the reaction of ethyl hexa-2, 4-dienoate with diethyl oxalate in the presence of base is to be drawn. 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 compound to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β -ketoester.

Question

Q1: Predict the major organic product(s) of the following reactions. Include stereochemistry when necessary. Write NR if no reaction, try to explain. 1.) LDA, THF 2.) СОН CI OH H2SO4, heat OH m...... OH 1.) PCC, CH2Cl2 2.) CH3CH2MgBr, THF 3.) H3O+ 4.) TsCl, pyr 5.) tBuOK, tBuOH 1.) SOCI 2, CHCI 3 2.) CH3CH2ONA, DMF OH 1.) HBr 2.) Mg, THF 3.) H₂CO, THE 4.) H3O+ OH NaH, THF

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 22, Problem 59P

Interpretation Introduction

(a)

Interpretation: The stepwise mechanism for the reaction of ethyl hexa-2, 4-dienoate with diethyl oxalate in the presence of base is to be drawn.

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 compound 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: An explanation regarding the formation of a new carbon-carbon bond on C6 with the help of mechanism is to be stated.

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 compound to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

Interpretation Introduction

(c)

Interpretation: The reason as to why the given reaction is an example of a crossed Claisen reaction is to be stated.

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 compound to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Students have asked these similar questions

Q1: Predict the major organic product(s) of the following reactions. Include stereochemistry when necessary. Write NR if no reaction, try to explain. 1.) LDA, THF 2.) СОН CI OH H2SO4, heat OH m...... OH 1.) PCC, CH2Cl2 2.) CH3CH2MgBr, THF 3.) H3O+ 4.) TsCl, pyr 5.) tBuOK, tBuOH 1.) SOCI 2, CHCI 3 2.) CH3CH2ONA, DMF OH 1.) HBr 2.) Mg, THF 3.) H₂CO, THE 4.) H3O+ OH NaH, THF

What is the stepwise mechanism for this reaction?

Draw the major product of this reaction

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 22, Problem 59P

Interpretation Introduction

(a)

Interpretation: The stepwise mechanism for the reaction of ethyl hexa-2, 4-dienoate with diethyl oxalate in the presence of base is to be drawn.

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 compound 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: An explanation regarding the formation of a new carbon-carbon bond on C6 with the help of mechanism is to be stated.

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 compound to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

Interpretation Introduction

(c)

Interpretation: The reason as to why the given reaction is an example of a crossed Claisen reaction is to be stated.

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 compound to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

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 22, Problem 59P

Interpretation Introduction

(a)

Interpretation: The stepwise mechanism for the reaction of ethyl hexa-2, 4-dienoate with diethyl oxalate in the presence of base is to be drawn.

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 compound 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: An explanation regarding the formation of a new carbon-carbon bond on C6 with the help of mechanism is to be stated.

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 compound to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

Interpretation Introduction

(c)

Interpretation: The reason as to why the given reaction is an example of a crossed Claisen reaction is to be stated.

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 compound to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

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 22, Problem 59P

Interpretation Introduction

(a)

Interpretation: The stepwise mechanism for the reaction of ethyl hexa-2, 4-dienoate with diethyl oxalate in the presence of base is to be drawn.

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 compound 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: An explanation regarding the formation of a new carbon-carbon bond on C6 with the help of mechanism is to be stated.

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 compound to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

Interpretation Introduction

(c)

Interpretation: The reason as to why the given reaction is an example of a crossed Claisen reaction is to be stated.

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 compound to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Answer 5

Chapter 22, Problem 59P

Interpretation Introduction

(a)

Interpretation: The stepwise mechanism for the reaction of ethyl hexa-2, 4-dienoate with diethyl oxalate in the presence of base is to be drawn.

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 compound 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: An explanation regarding the formation of a new carbon-carbon bond on C6 with the help of mechanism is to be stated.

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 compound to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

Interpretation Introduction

(c)

Interpretation: The reason as to why the given reaction is an example of a crossed Claisen reaction is to be stated.

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 compound 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 22, Problem 59P

Interpretation Introduction

(a)

Interpretation: The stepwise mechanism for the reaction of ethyl hexa-2, 4-dienoate with diethyl oxalate in the presence of base is to be drawn.

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 compound 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 22, Problem 59P

Interpretation Introduction

(a)

Interpretation: The stepwise mechanism for the reaction of ethyl hexa-2, 4-dienoate with diethyl oxalate in the presence of base is to be drawn.

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 compound 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: An explanation regarding the formation of a new carbon-carbon bond on C6 with the help of mechanism is to be stated.

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 compound 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: An explanation regarding the formation of a new carbon-carbon bond on C6 with the help of mechanism is to be stated.

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 compound to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

Answer 10

Interpretation Introduction

(c)

Interpretation: The reason as to why the given reaction is an example of a crossed Claisen reaction is to be stated.

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 compound to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

Answer 11

Interpretation Introduction

(c)

Interpretation: The reason as to why the given reaction is an example of a crossed Claisen reaction is to be stated.

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 compound to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

Answer 12

Expert Solution & Answer

Answer 13

Expert Solution & Answer

Answer 14

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Answer 15

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Answer 16

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Answer 17

Trending nowThis is a popular solution!

Answer 18

Trending nowThis is a popular solution!

Answer 19

Trending nowThis is a popular solution!

Answer 20

Trending now

Answer 21

This is a popular solution!

Answer 22

See solution

Check out sample textbook solution

Answer 23

Ch. 22.1 - Prob. 1P Ch. 22.1 - Prob. 2P Ch. 22.1 - Problem 24.3 What unsaturated carbonyl compound is...Ch. 22.1 - Prob. 4P Ch. 22.1 - Prob. 5P Ch. 22.2 - Prob. 6P Ch. 22.2 - Problem 24.7 Draw the products formed in each...Ch. 22.4 - Prob. 15P Ch. 22.4 - Prob. 16P Ch. 22.5 - Problem 24.16 What ester is formed when each...

Concept explainers

Chapter 22 Solutions