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Science Chemistry Organic Chemistry Study Guide and Solutions

(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.

(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.

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

Organic Chemistry Study Guide and Solutions

Organic Chemistry Study Guide and Solutions

6th Edition

ISBN: 9781936221868

Author: Marc Loudon, Jim Parise

Publisher: W. H. Freeman

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Concept explainers

In chemistry there are so many chemical compounds that have a hydroxyl group but a chemical compound having two hydroxyl groups (-OH) is termed as a diol. It also implies the presence of two alcohols whereas polyols contain two or more than two hydroxyl …

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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Chapter 22, Problem 22.27P

Chapter 22, Problem 22.29P

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Chapter 22 Solutions

Organic Chemistry Study Guide and Solutions

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

Ch. 22 - Prob. 22.11P Ch. 22 - Prob. 22.12P Ch. 22 - Prob. 22.13P Ch. 22 - Prob. 22.14P Ch. 22 - Prob. 22.15P Ch. 22 - Prob. 22.16P Ch. 22 - Prob. 22.17P Ch. 22 - Prob. 22.18P Ch. 22 - Prob. 22.19P Ch. 22 - Prob. 22.20P Ch. 22 - Prob. 22.21P Ch. 22 - Prob. 22.22P Ch. 22 - Prob. 22.23P Ch. 22 - Prob. 22.24P Ch. 22 - Prob. 22.25P Ch. 22 - Prob. 22.26P Ch. 22 - Prob. 22.27P Ch. 22 - Prob. 22.28P Ch. 22 - Prob. 22.29P Ch. 22 - Prob. 22.30P Ch. 22 - Prob. 22.31P Ch. 22 - Prob. 22.32P Ch. 22 - Prob. 22.33P Ch. 22 - Prob. 22.34P Ch. 22 - Prob. 22.35P Ch. 22 - Prob. 22.36P Ch. 22 - Prob. 22.37P Ch. 22 - Prob. 22.38P Ch. 22 - Prob. 22.39P Ch. 22 - Prob. 22.40P Ch. 22 - Prob. 22.41P Ch. 22 - Prob. 22.42P Ch. 22 - Prob. 22.43P Ch. 22 - Prob. 22.44P Ch. 22 - Prob. 22.45P Ch. 22 - Prob. 22.46P Ch. 22 - Prob. 22.47P Ch. 22 - Prob. 22.48P Ch. 22 - Prob. 22.49P Ch. 22 - Prob. 22.50P Ch. 22 - Prob. 22.51P Ch. 22 - Prob. 22.52P Ch. 22 - Prob. 22.53P Ch. 22 - Prob. 22.54P Ch. 22 - Prob. 22.55AP Ch. 22 - Prob. 22.56AP Ch. 22 - Prob. 22.57AP Ch. 22 - Prob. 22.58AP Ch. 22 - Prob. 22.59AP Ch. 22 - Prob. 22.60AP Ch. 22 - Prob. 22.61AP Ch. 22 - Prob. 22.62AP Ch. 22 - Prob. 22.63AP Ch. 22 - Prob. 22.64AP Ch. 22 - Prob. 22.65AP Ch. 22 - Prob. 22.66AP Ch. 22 - Prob. 22.67AP Ch. 22 - Prob. 22.68AP Ch. 22 - Prob. 22.69AP Ch. 22 - Prob. 22.70AP Ch. 22 - Prob. 22.71AP Ch. 22 - Prob. 22.72AP Ch. 22 - Prob. 22.73AP Ch. 22 - Prob. 22.74AP Ch. 22 - Prob. 22.75AP Ch. 22 - Prob. 22.76AP Ch. 22 - Prob. 22.77AP Ch. 22 - Prob. 22.78AP Ch. 22 - Prob. 22.79AP Ch. 22 - Prob. 22.80AP Ch. 22 - Prob. 22.81AP Ch. 22 - Prob. 22.82AP Ch. 22 - Prob. 22.83AP Ch. 22 - Prob. 22.84AP Ch. 22 - Prob. 22.85AP Ch. 22 - Prob. 22.86AP Ch. 22 - Prob. 22.87AP Ch. 22 - Prob. 22.88AP Ch. 22 - Prob. 22.89AP Ch. 22 - Prob. 22.90AP Ch. 22 - Prob. 22.91AP Ch. 22 - Prob. 22.92AP Ch. 22 - Prob. 22.93AP Ch. 22 - Prob. 22.94AP Ch. 22 - Prob. 22.95AP Ch. 22 - Prob. 22.96AP Ch. 22 - Prob. 22.97AP Ch. 22 - Prob. 22.98AP

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