The given transformation in the presence of sodium ethoxide is to be explained. Concept introduction: Electrophiles are electron deficient species that have positive or partially positive charge. Lewis acids are electrophiles that accept electron pair. Nucleophiles are electron rich species that has negative or partially negative charge. Lewis bases are nucleophiles that donate electron pair. Free radical is an atom, molecule, or ion that has an unpaired electron, which makes it highly chemically reactive. Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a functional group is substituted by any other functional group is called substitution reaction. Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction. Addition reaction: It is the reaction in which unsaturated bonds are converted to saturated molecules by the addition of molecules. The carbon-carbon bond forming reaction, useful for the synthesizing of beta keto ester, is known as Claisen condensation reaction. In Claisen condensation, reaction occur between two esters, a carbon-carbon bond formation takes place which leads to the formation of β − keto ester. Esters containing only one alpha hydrogen do not undergo Claisen condensation reaction. A Dieckmann condensation is also known as intramolecular Claisen condensation. Five and six membered rings are easily prepared by Dieckmann condensation. The rings with members less than five are disfavored due to strain.

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Answer 1

Question

Chapter 19, Problem 31P

Interpretation Introduction

Interpretation:

The given transformation in the presence of sodium ethoxide is to be explained.

Concept introduction:

Electrophiles are electron deficient species that have positive or partially positive charge. Lewis acids are electrophiles that accept electron pair.

Nucleophiles are electron rich species that has negative or partially negative charge. Lewis bases are nucleophiles that donate electron pair.

Free radical is an atom, molecule, or ion that has an unpaired electron, which makes it highly chemically reactive.

Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a functional group is substituted by any other functional group is called substitution reaction.

Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction.

Addition reaction: It is the reaction in which unsaturated bonds are converted to saturated molecules by the addition of molecules.

The carbon-carbon bond forming reaction, useful for the synthesizing of beta keto ester, is known as Claisen condensation reaction.

In Claisen condensation, reaction occur between two esters, a carbon-carbon bond formation takes place which leads to the formation of β− keto ester.

Esters containing only one alpha hydrogen do not undergo Claisen condensation reaction.

A Dieckmann condensation is also known as intramolecular Claisen condensation.

Five and six membered rings are easily prepared by Dieckmann condensation.

The rings with members less than five are disfavored due to strain.

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Give the reaction conditions which could be used to bring about the transformation shown in two steps

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3. Assuming that the compound undergoes geometric isomerization via electrophilic addition of bromine, write the mechanism for the reaction and the product formed.

Answer 2

Question

Chapter 19, Problem 31P

Interpretation Introduction

Interpretation:

The given transformation in the presence of sodium ethoxide is to be explained.

Concept introduction:

Electrophiles are electron deficient species that have positive or partially positive charge. Lewis acids are electrophiles that accept electron pair.

Nucleophiles are electron rich species that has negative or partially negative charge. Lewis bases are nucleophiles that donate electron pair.

Free radical is an atom, molecule, or ion that has an unpaired electron, which makes it highly chemically reactive.

Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a functional group is substituted by any other functional group is called substitution reaction.

Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction.

Addition reaction: It is the reaction in which unsaturated bonds are converted to saturated molecules by the addition of molecules.

The carbon-carbon bond forming reaction, useful for the synthesizing of beta keto ester, is known as Claisen condensation reaction.

In Claisen condensation, reaction occur between two esters, a carbon-carbon bond formation takes place which leads to the formation of β− keto ester.

Esters containing only one alpha hydrogen do not undergo Claisen condensation reaction.

A Dieckmann condensation is also known as intramolecular Claisen condensation.

Five and six membered rings are easily prepared by Dieckmann condensation.

The rings with members less than five are disfavored due to strain.

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Answer 3

Question

Chapter 19, Problem 31P

Interpretation Introduction

Interpretation:

The given transformation in the presence of sodium ethoxide is to be explained.

Concept introduction:

Electrophiles are electron deficient species that have positive or partially positive charge. Lewis acids are electrophiles that accept electron pair.

Nucleophiles are electron rich species that has negative or partially negative charge. Lewis bases are nucleophiles that donate electron pair.

Free radical is an atom, molecule, or ion that has an unpaired electron, which makes it highly chemically reactive.

Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a functional group is substituted by any other functional group is called substitution reaction.

Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction.

Addition reaction: It is the reaction in which unsaturated bonds are converted to saturated molecules by the addition of molecules.

The carbon-carbon bond forming reaction, useful for the synthesizing of beta keto ester, is known as Claisen condensation reaction.

In Claisen condensation, reaction occur between two esters, a carbon-carbon bond formation takes place which leads to the formation of β− keto ester.

Esters containing only one alpha hydrogen do not undergo Claisen condensation reaction.

A Dieckmann condensation is also known as intramolecular Claisen condensation.

Five and six membered rings are easily prepared by Dieckmann condensation.

The rings with members less than five are disfavored due to strain.

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Answer 4

Question

Chapter 19, Problem 31P

Interpretation Introduction

Interpretation:

The given transformation in the presence of sodium ethoxide is to be explained.

Concept introduction:

Electrophiles are electron deficient species that have positive or partially positive charge. Lewis acids are electrophiles that accept electron pair.

Nucleophiles are electron rich species that has negative or partially negative charge. Lewis bases are nucleophiles that donate electron pair.

Free radical is an atom, molecule, or ion that has an unpaired electron, which makes it highly chemically reactive.

Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a functional group is substituted by any other functional group is called substitution reaction.

Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction.

Addition reaction: It is the reaction in which unsaturated bonds are converted to saturated molecules by the addition of molecules.

The carbon-carbon bond forming reaction, useful for the synthesizing of beta keto ester, is known as Claisen condensation reaction.

In Claisen condensation, reaction occur between two esters, a carbon-carbon bond formation takes place which leads to the formation of β− keto ester.

Esters containing only one alpha hydrogen do not undergo Claisen condensation reaction.

A Dieckmann condensation is also known as intramolecular Claisen condensation.

Five and six membered rings are easily prepared by Dieckmann condensation.

The rings with members less than five are disfavored due to strain.

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Answer 5

Chapter 19, Problem 31P

Interpretation Introduction

Interpretation:

The given transformation in the presence of sodium ethoxide is to be explained.

Concept introduction:

Electrophiles are electron deficient species that have positive or partially positive charge. Lewis acids are electrophiles that accept electron pair.

Nucleophiles are electron rich species that has negative or partially negative charge. Lewis bases are nucleophiles that donate electron pair.

Free radical is an atom, molecule, or ion that has an unpaired electron, which makes it highly chemically reactive.

Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a functional group is substituted by any other functional group is called substitution reaction.

Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction.

Addition reaction: It is the reaction in which unsaturated bonds are converted to saturated molecules by the addition of molecules.

The carbon-carbon bond forming reaction, useful for the synthesizing of beta keto ester, is known as Claisen condensation reaction.

In Claisen condensation, reaction occur between two esters, a carbon-carbon bond formation takes place which leads to the formation of β− keto ester.

Esters containing only one alpha hydrogen do not undergo Claisen condensation reaction.

A Dieckmann condensation is also known as intramolecular Claisen condensation.

Five and six membered rings are easily prepared by Dieckmann condensation.

The rings with members less than five are disfavored due to strain.

Answer 6

Chapter 19, Problem 31P

Interpretation Introduction

Interpretation:

The given transformation in the presence of sodium ethoxide is to be explained.

Concept introduction:

Electrophiles are electron deficient species that have positive or partially positive charge. Lewis acids are electrophiles that accept electron pair.

Nucleophiles are electron rich species that has negative or partially negative charge. Lewis bases are nucleophiles that donate electron pair.

Free radical is an atom, molecule, or ion that has an unpaired electron, which makes it highly chemically reactive.

Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a functional group is substituted by any other functional group is called substitution reaction.

Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction.

Addition reaction: It is the reaction in which unsaturated bonds are converted to saturated molecules by the addition of molecules.

The carbon-carbon bond forming reaction, useful for the synthesizing of beta keto ester, is known as Claisen condensation reaction.

In Claisen condensation, reaction occur between two esters, a carbon-carbon bond formation takes place which leads to the formation of β− keto ester.

Esters containing only one alpha hydrogen do not undergo Claisen condensation reaction.

A Dieckmann condensation is also known as intramolecular Claisen condensation.

Five and six membered rings are easily prepared by Dieckmann condensation.

The rings with members less than five are disfavored due to strain.

Answer 7

Chapter 19, Problem 31P

Interpretation Introduction

Interpretation:

The given transformation in the presence of sodium ethoxide is to be explained.

Concept introduction:

Electrophiles are electron deficient species that have positive or partially positive charge. Lewis acids are electrophiles that accept electron pair.

Nucleophiles are electron rich species that has negative or partially negative charge. Lewis bases are nucleophiles that donate electron pair.

Free radical is an atom, molecule, or ion that has an unpaired electron, which makes it highly chemically reactive.

Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a functional group is substituted by any other functional group is called substitution reaction.

Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction.

Addition reaction: It is the reaction in which unsaturated bonds are converted to saturated molecules by the addition of molecules.

The carbon-carbon bond forming reaction, useful for the synthesizing of beta keto ester, is known as Claisen condensation reaction.

In Claisen condensation, reaction occur between two esters, a carbon-carbon bond formation takes place which leads to the formation of β− keto ester.

Esters containing only one alpha hydrogen do not undergo Claisen condensation reaction.

A Dieckmann condensation is also known as intramolecular Claisen condensation.

Five and six membered rings are easily prepared by Dieckmann condensation.

The rings with members less than five are disfavored due to strain.

Answer 8

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Answer 10

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Answer 11

Ch. 19 - PRACTICE PROBLEM 19.1 (a) Write a mechanism. for...Ch. 19 - Practice Problem 19.2 Since the products obtained...Ch. 19 - Prob. 3PP Ch. 19 - PRACTICE PROBLEM 19.4 Write mechanisms that...Ch. 19 - Prob. 5PP Ch. 19 - Prob. 6PP Ch. 19 - Practice Problem 19.7 The acid-catalyzed aldol...Ch. 19 - Prob. 8PP Ch. 19 - Practice Problem 19.9 (a) Provide a mechanism for...Ch. 19 - Prob. 10PP

Solution Summary: The author explains that the given transformation occurs in a two-stage reaction in the presence of sodium ethoxide.

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Chapter 19 Solutions