Chapter 25: Q3P (page 1305)
Give an equation for the complete transesterification of triolein using an excess of methanol as the alcohol and sodium hydroxide as the catalyst.
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Phospholipids undergo saponification much like triglycerides. Draw the structure of a phospholipid meeting the following criteria. Then draw the products that would result from its saponification.
(a) a cephalin containing stearic acid and oleic acid
(b) a lecithin containing palmitic acid.
Show that a phosphatidic acid is chiral, even though none of its fatty acids are chiral. Where is the asymmetric carbon atom?
How would you use simple chemical tests to distinguish between the following pairs of compounds?
When an extract of parsley seed is saponified and acidified, one of the fatty acids isolated is petroselenic 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.
How would you use a simple extraction to separate a mixture of testosterone and estradiol?
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