When an extract of parsley seed is saponified and acidified, one of the fatty acids isolated is petroselenic acid, formulaC18H34O2. Hydrogenation of petroselenic acid gives pure stearic acid. When petroselenic acid is treated with warmpotassium permanganate followed by acidification, the only organic products are dodecanoic acid and adipic acid. TheNMR spectrum shows absorptions of vinyl protons split by coupling constants of 7 Hz and 10 Hz. Propose a structure forpetroselenic acid, and show how your structure is consistent with these observations.

When an extract of parsley seed is saponified and acidified, one of the fatty acids isolated is petroselenic acid, formulaC18H34O2. Hydrogenation of petroselenic acid gives pure stearic acid. When petroselenic acid is treated with warmpotassium permanganate followed by acidification, the only organic products are dodecanoic acid and adipic acid. TheNMR spectrum shows absorptions of vinyl protons split by coupling constants of 7 Hz and 10 Hz. Propose a structure forpetroselenic acid, and show how your structure is consistent with these observations.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter29: Organic Polymer Chemistry

Section: Chapter Questions

Problem 29.8P

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