Disparlure, C19H38O, is a sex attractant released by the female gypsy moth, Lymantria dispar. The 1H NMR spectrum of disparlure shows a large absorption in
Disparlure, C19H38O, is a sex attractant released by the female gypsy moth, Lymantria dispar. The 1H NMR spectrum of disparlure shows a large absorption in the alkane region, 1 to 2 δ, and a triplet at 2.8 δ. Treatment of disparlure, first with aqueous acid and then with KMnO4, yields two carboxylic acids identified as undecanoic acid and 6-methyiheptanoic acid. (KMnO4 cleaves 1, 2-diols to yield carboxylic acids.) Neglecting stereochemistry, propose a structure for disparlure. The actual compound is a chiral molecule with 7R, 8S stereochemistry. Draw disparlure, showing the correct stereochemistry.
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Authors: John McMurry
7 Edition
978-0495112587, 0495112585
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