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Abstract: . . . understand what they are talking about, point out that there is a dark side to hydrogenated vegetable oil. Hydrogenation increases the content of saturated fatty acids and trans fatty acids, both of which contribute to the formation of 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 tristearin, is a fat (mp 72 C) containing three molecules of stearic acid: H 2 C 0 C CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 . . . . . . spread the liquid over the inside surface of the flask. Finally, release the vacuum line, and cool the flask in ice. II. Characterizing the product Read Sorrell pp. 691 708 and Mohrig pp. 610-627 on proton NMR. A. 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. . . . --3000,2,750,2433,19438
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