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When an extract of parsley seed is saponified and
Chapter 26, Problem 28SP(choose chapter or problem)
Problem 28SP
When an extract of parsley seed is saponified and acidified, one of the fatty acids isolated ispetroselenic acid, formula C18H34O2 .Hydrogenation of petroselenic acid gives pure stearic acid. When petroselenic acid is treated with warm potassium permanganate followed by acidification, the only organic products are dodecanoic acid and adipic acid. The NMR spectrum shows absorptions of vinyl protons split by coupling constants of 7 Hz and 10 Hz. Propose a structure for petroselenic acid, and show how your structure is consistent with these observations.
Questions & Answers
QUESTION:
Problem 28SP
When an extract of parsley seed is saponified and acidified, one of the fatty acids isolated ispetroselenic acid, formula C18H34O2 .Hydrogenation of petroselenic acid gives pure stearic acid. When petroselenic acid is treated with warm potassium permanganate followed by acidification, the only organic products are dodecanoic acid and adipic acid. The NMR spectrum shows absorptions of vinyl protons split by coupling constants of 7 Hz and 10 Hz. Propose a structure for petroselenic acid, and show how your structure is consistent with these observations.
ANSWER:
Solution 28SP
Step 1
