Organic Chemistry
Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 23, Problem 17P

Gadoleic acid ( C 20 H 38 O 2 ) , a fatty acid that can be isolated from cod-liver oil, can be cleaved by hydroxylation and subsequent treatment with periodic acid to C H 3 ( C H 2 ) 9 C H O and C H O ( C H 2 ) 7 C O 2 H .

(a) What two stereoisomeric structures are possible for gadoleic acid?

(b) What spectroscopic technique would make possible a decision as to the actual structure of gadoleic acid?

(c) What peaks would you look for?

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