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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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Which of the following chemical reactions could be used to distinguish between a polyunsaturated animal oil and a synthetic cooking oil containing a mixture of saturated and unsaturated hydrocarbons? Explain your reasoning.
Point out the hydrophilic and hydrophobic regions in the structures of sodium dodecyl sulfate, Nonoxynol®, and the alkylbenzenesulfonate detergent (Figure 25-6).
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.
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.
The long-term health effects of eating partially hydrogenated vegetable oils concern some nutritionists because many unnatural fatty acids are produced. Consider the partial hydrogenation of linolenic acid by the addition of one or two equivalents of hydrogen. Show how this partial hydrogenation can produce at least three different fatty acids we have not seen before.
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