EBK ESSENTIAL ORGANIC CHEMISTRY
EBK ESSENTIAL ORGANIC CHEMISTRY
3rd Edition
ISBN: 8220100659461
Author: Bruice
Publisher: PEARSON
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Chapter 13, Problem 33P

(a)

Interpretation Introduction

Interpretation:

To determine the number of deuterium atoms that are incorporated in palmitic acid if CD3COSR and nondeuterated malonyl thioester are used as starting materials.

Concept introduction:

For the synthesis of arachidic acid, in first step acetyl thioester and malonyl thioester undergoes Claisen condensation. The product of Claisen condensation undergoes reduction, dehydration and a second reduction to form a four-carbon thioester.

The four carbon thioester combines with another molecule of malonyl thioester and undergoes Claisen condensation, reduction, dehydration and a second reduction to form a six carbon thioester. The reaction can proceed to form a fatty acid of an even number of carbon atoms and repetition of sequence adds two carbon.

(b)

Interpretation Introduction

Interpretation:

To determine the number of deuterium atoms that are incorporated in palmitic acid if OOCCD2COSR and nondeuterated acetyl thioester are used as starting materials.

Concept introduction:

For the synthesis of arachidic acid, in first step acetyl thioester and malonyl thioester undergoes Claisen condensation.  The product of Claisen condensation undergoes reduction, dehydration and a second reduction to form a four-carbon thioester.

The four carbon thioester combines with another molecule of malonyl thioester and undergoes Claisen condensation, reduction, dehydration and a second reduction to form a six carbon thioester. The reaction can proceed to form a fatty acid of an even number of carbon atoms and repetition of sequence adds two carbon.

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