Lab 6A - 6A Hydrogenation of a Fatty Acid Author: Holly...

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6A Hydrogenation of a Fatty Acid Author: Holly Polk Instructor: Oleksandr Zhurakovskyi Organic Chemistry Lab 243A, Section 010 Date Work Performed: March 5, 2009 Date Submitted: March 12, 2009 Abstract The purpose of this experiment was to force methyl oleate to undergo hydrogenation thus creating methyl stearate. The synthesized methyl stearate had a melting point very close to the known literature value (34-37 ° C, 39 ° C respectively), a % yield of 63%, semi-solid consistency, as well as a negative result from the bromine/DCM test. The known literature methyl oleate IR spectrum was compared to the experimental methyl stearate IR spectrum, and the methyl stearate lacked the all of the methyl oleate peaks like the alkane peak at 1650, demonstrating that the reaction was complete.
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This experiment required the hydrogenation of a fatty acid, which was in this case methyl oleate. Methyl oleate is an un-saturated fatty acid. Which regards to chemistry, if an alkyl chain has no double or triple bonds, it is considered saturated, meaning that each carbon has the maximum number of allowed hydrogen atoms. Oppositely, if an alkyl chain has a double or triple bond it is considered un-saturated, meaning that each carbon does not have the maximum amount of attached hydrogen atoms because there is a double or triple bond that reduces the ability of the carbon to bond with the maximum number of hydrogen atoms. The process of hydrogenation takes an un-saturated alkyl chain and reduces the double bonds in the chain by forcing the pi bonds within the chain to bond with excess hydrogen. Methyl oleate contains a double bond, thus it is unsaturated. In this experiment, hydrogenation reduces the double bond within the methyl oleate molecule and adds hydrogen to the reduced carbon. In hydrogenation, excess amounts of hydrogen are introduced to the system to allow for the double bond to reduce. However, this reaction is extremely slow and the addition of a catalyst speeds up the reaction. Whenever a catalyst is added to a chemical reaction, it acts to reduce the activation energy required for the reaction to move from reactants to products; thus, the reaction is sped up. In this particular reaction a palladium-carbon catalyst is utilized. Palladium is not organic and thus does not dissolve in an organic solvent. Thus when palladium is added to the system, it remains in a solid state. The hydrogen being added to the system is in a gaseous state (attached to the system in a balloon). This is therefore a
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Lab 6A - 6A Hydrogenation of a Fatty Acid Author: Holly...

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