Abstract: . . .  arterioscleroic plaque, with subsequent infarctions and heart attack. Apparently, cis-trans isomerization, which is a 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 (low melting point) and fats if they are solid (higher melting point). For instance, glyceryl tristearate, also called . . .
. . .  Melting point Determine the melting point of the hydrogenated olive oil by placing it in 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.  . . .
. . .  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, cool the flask to room temperature before removing the condenser (to prevent evaporation), and filter in a pasteur pipet to remove the catalyst. Prepare a large-diameter pasteur pipet by pushing a small piece of cotton down to the constriction and packing it tightly, then adding about 1 cm of Celite on top of it. Clamp the filter pipet upright, and use another pipet to transfer the reaction mixture to the filter pipet. Force the solution into small, dry, disposable . . .
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