ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
10th Edition
ISBN: 9781260028355
Author: Carey
Publisher: MCG CUSTOM
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Chapter 18, Problem 54DSP
Interpretation Introduction

Interpretation:

The configuration at the carbon in the product isto be determined.

Concept Introduction:

During the Baeyer Villiger oxidation of ketones, an oxygen atom is inserted between the carbonyl group and one of the carbons attached to it. The product formed is an ester.

Usually, the oxygen atom is inserted between the carbonyl and the larger of the two groups attached to the carbonyl.

The ketone is converted to the conjugate acid of the ester. Further hydrolysis of the conjugate acid forms the ester.

The peroxy acid used is converted to the corresponding carboxylic acid.

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An esterification and a claisen condensation are the reverse of each other. Write a single equilibrium reaction that is appropriate for both reactions and discuss the experimental conditions that can drive this equilibrium toward one side or the other of this reaction.  The reactions are:  Esterification Reaction: acetic acid is reacted with methanol and sulfuric acid catalyst under heated conditions to produce methyl acetate.  Claisen Condensation:  methyl acetate is reacted with water and sulfuric acid catalyst under heated conditions to produce acetic acid
describe how steric and electronic effects influence the postion of equilibrium when the electrophilic center of an aldehyde or ketone is under nucleophilic attack.

Chapter 18 Solutions

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