Abstract: . . .  oil as a model compound to illustrate the effects of catalytic hydrogenation, using palladium as the catalyst. Its molecular simplicity (monounsaturated fatty acids) makes the calculation of the fatty acid distribution straightforward. Although hydrogenation is usually done with hydrogen gas, we will use transfer hydrogenation, where hydrogen atoms are catalytically transferred from cyclohexene to the fatty acids in the triglyceride. The major component in olive oil is glyceryl trioleate. If there are no complications and the reaction goes to completion, the product is glyceryl tristearate: Page 7 7 H 2 C O C O (CH 2 )  . . .
. . .  2 C O C O (CH 2 ) 16 CH 3 H 2 C O C O (CH 2 ) 7 CH = CH (CH 2 ) 7 CH 3 H 2 C O CO (CH 2 ) 16 CH 3 PROCEDURE I. Hydrogenation of olive oil In a 5 mL conical microflask, place 400 mg of olive oil, 1 mL of cyclohexane, and 100 mg of 5% palladium on charcoal. The active ingredient in the catalyst is very finely divided Pd metal; the charcoal is an inert carrier. Add a boiling stone and a condenser, and reflux gently for 30 minutes boiling time. After refluxing, . . .
. . .  a small disposable test tube in water at various temperatures. The approach is necessary because the melting point is low, and because it is impossible to get the material in a capillary tube. B. Spectroscopic analysis Infrared and elementary proton NMR will be used to explain the observed melting point. The details will be made more clear in a handout. For now, try to digest the rudiments of NMR.  . . .
. . .  side effect of catalytic hydrogenation, can kill you. In this experiment, we will hydrogenate olive oil, examine the properties of the product, and use infrared and nuclear magnetic resonance spectroscopy to explain the results. First, however, a brief discussion of fats and oils will be helpful. Fats and oils Catalytic Hydrogenation and Arteriosclerosis Page 2 2 Fats and oils are triglycerides, which consist of glycerol molecules esterified with three fatty acids. Fatty acids are essentially long hydrocarbon chains terminating in a carboxyl group. Stearic acid (18 carbons, saturated) is an example: Triglycerides are called fats if they are oils at . . .
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