Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 23, Problem 13PP
Interpretation Introduction

Interpretation:

The organic compounds produced by the complete hydrolysis of the given compounds need to be identified.

Concept Introduction:

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Phospholipids are derived from phosphatidic acid. The phosphatidic acid has two hydroxyl groups of a glycerol unit, joined to fatty acids through ester linkages. The other terminal hydroxyl group is joined to the phosphoric acid through an ester linkage.

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When the phosphate group of the phosphatidic acid is connected to a nitrogen containing compound such as choline, 2-aminiethanol and L-serine through another phosphate ester linkage, a phosphatide is formed. Lecithin, cephalin, phosphatidylserines and plasmalogens are important groups of phosphatides.

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Lecithin finds wide application in food industry. To enhance their compatibility and performance with the product they are used with, lecithin molecules are hydrolyzed enzymatically.

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The hydrolysis of lecithin results in the production of glycerol, fatty acids, phosphoric acid, and choline molecules

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The hydrolysis of cephalin results in the breakdown of carboxy ester and phosphoester bonds to produce glycerol, fatty acids, phosphoric acid, and ethanolamine molecules.

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The hydrolysis of choline-based plasmalogen gives glycerol, fatty acid, phosphoric acid, and an unsaturated aldehyde

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Answer ALL parts of this question. (a) Provide the structure and name of the aldehyde with the formula, C2H4O. (b) Draw the two steps of the Strecker synthesis used for the conversion of the aldehyde in part (a) into racemic alanine. (c) Draw the (R) and (S) enantiomers of alanine. Which is the naturally occurring enantiomer? (d) Draw the structure of the dipeptide, Ala-Gly.
23.14
23.1(b,d and e)
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