(a) Interpretation: An explanation as to why compound A when treated with one equivalent of NaOEt followed by acidification is completely converted to compound B is to be stated. Concept introduction: The Claisen condensation takes place between two esters or between an ester and a ketone . In cross Claisen condensation reaction, the base abstracts an acidic proton from the α-carbon atom of carbonyl compound to form enolate. This enolate reacts with carbonyl group of other carbonyl compound that leads to the formation of β-keto ester. The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

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Answer 1

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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 22.28P

Interpretation Introduction

(a)

Interpretation:

An explanation as to why compound A when treated with one equivalent of NaOEt followed by acidification is completely converted to compound B is to be stated.

Concept introduction:

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

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

Interpretation Introduction

(b)

Interpretation:

The curved arrow mechanism for the given conversion is to be stated.

Concept introduction:

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

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

Interpretation Introduction

(c)

Interpretation:

The structure of the only product formed when diethyl α- methyladipate reacts in the Dieckmann condensation is to be shown.

Concept introduction:

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

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

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1. Predict the organic product(s) of the following reactions. Assume excess of reagents unless otherwise noted. a) &l BH3 •THF b) 1) NaOH 2) H3O+ solve d) ala 1) EtMgBr 2) H3O+ e) H2N سكر CuLi NH2 1) SOCI2 2) EtMgBr 3) H3O+ NC H3O+ Δ

There are 48 pairs of students in the following table. Each pair has quantitatively determined the mass of taurine in a 250 mL can of the popular energy drink marketed as “Munster” using High Performance Liquid Chromatography (HPLC). The class results are presented below: QUESTION: Summarise and report these results including an indication of measurement uncertainty. In both calculation samples calculate if an outlier is present, max value, number of samples, mean, standard deviation, g (suspect), g (critical) and t (critical). Mass of Taurine (mg) Mass of Taurine (mg) (Table continued) 152.01 152.23 151.87 151.45 154.11 152.64 152.98 153.24 152.88 151.45 153.49 152.48 150.68 152.33 151.52 153.63 152.48 151.68 153.17 153.40 153.77 153.67 152.34 153.16 152.57 153.02 152.86 151.50 151.23 152.57 152.72 151.54 146.47 152.38 152.44 152.54 152.53 152.54 151.32…

Indicate the rate expressions for reactions that have order 0, 1, and 2.

Answer 2

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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 22.28P

Interpretation Introduction

(a)

Interpretation:

An explanation as to why compound A when treated with one equivalent of NaOEt followed by acidification is completely converted to compound B is to be stated.

Concept introduction:

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

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

Interpretation Introduction

(b)

Interpretation:

The curved arrow mechanism for the given conversion is to be stated.

Concept introduction:

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

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

Interpretation Introduction

(c)

Interpretation:

The structure of the only product formed when diethyl α- methyladipate reacts in the Dieckmann condensation is to be shown.

Concept introduction:

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

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

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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 22.28P

Interpretation Introduction

(a)

Interpretation:

An explanation as to why compound A when treated with one equivalent of NaOEt followed by acidification is completely converted to compound B is to be stated.

Concept introduction:

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

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

Interpretation Introduction

(b)

Interpretation:

The curved arrow mechanism for the given conversion is to be stated.

Concept introduction:

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

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

Interpretation Introduction

(c)

Interpretation:

The structure of the only product formed when diethyl α- methyladipate reacts in the Dieckmann condensation is to be shown.

Concept introduction:

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

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

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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 22.28P

Interpretation Introduction

(a)

Interpretation:

An explanation as to why compound A when treated with one equivalent of NaOEt followed by acidification is completely converted to compound B is to be stated.

Concept introduction:

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

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

Interpretation Introduction

(b)

Interpretation:

The curved arrow mechanism for the given conversion is to be stated.

Concept introduction:

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

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

Interpretation Introduction

(c)

Interpretation:

The structure of the only product formed when diethyl α- methyladipate reacts in the Dieckmann condensation is to be shown.

Concept introduction:

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

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

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Answer 5

Chapter 22, Problem 22.28P

Interpretation Introduction

(a)

Interpretation:

An explanation as to why compound A when treated with one equivalent of NaOEt followed by acidification is completely converted to compound B is to be stated.

Concept introduction:

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

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

Interpretation Introduction

(b)

Interpretation:

The curved arrow mechanism for the given conversion is to be stated.

Concept introduction:

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

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

Interpretation Introduction

(c)

Interpretation:

The structure of the only product formed when diethyl α- methyladipate reacts in the Dieckmann condensation is to be shown.

Concept introduction:

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

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

Answer 6

Chapter 22, Problem 22.28P

Interpretation Introduction

(a)

Interpretation:

An explanation as to why compound A when treated with one equivalent of NaOEt followed by acidification is completely converted to compound B is to be stated.

Concept introduction:

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

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

Answer 7

Chapter 22, Problem 22.28P

Interpretation Introduction

(a)

Interpretation:

An explanation as to why compound A when treated with one equivalent of NaOEt followed by acidification is completely converted to compound B is to be stated.

Concept introduction:

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

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The curved arrow mechanism for the given conversion is to be stated.

Concept introduction:

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

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The curved arrow mechanism for the given conversion is to be stated.

Concept introduction:

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

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

Answer 10

Interpretation Introduction

(c)

Interpretation:

The structure of the only product formed when diethyl α- methyladipate reacts in the Dieckmann condensation is to be shown.

Concept introduction:

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

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

Answer 11

Interpretation Introduction

(c)

Interpretation:

The structure of the only product formed when diethyl α- methyladipate reacts in the Dieckmann condensation is to be shown.

Concept introduction:

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

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

Answer 12

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Answer 13

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Answer 15

Ch. 22 - Prob. 22.1P Ch. 22 - Prob. 22.2P Ch. 22 - Prob. 22.3P Ch. 22 - Prob. 22.4P Ch. 22 - Prob. 22.5P Ch. 22 - Prob. 22.6P Ch. 22 - Prob. 22.7P Ch. 22 - Prob. 22.8P Ch. 22 - Prob. 22.9P Ch. 22 - Prob. 22.10P

Solution Summary: The author explains how compound A is converted to compound B when treated with NaOEt followed by acidification.

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Chapter 22 Solutions