Dehydration and Gas Chromatography of Methylcyclohexanols.
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Chase A. Hurst CHM 215 11 Dr. Daniel Ketcha October 28, 2004 Dehydration and Gas Chromatography of Methylcyclohexanols Introduction The experimental confirmation of the "Evelyn Effect" was performed in this report. This effect, first described by David Todd of Pomona College in 1994, describes the formation of 1-methylcyclohexene and 3-Methylcyclohexene (structures shown below) derived from the dehydration and distillation of a mixture of cis-2-methylcyclohexanol and trans-2-methylcyclohexanol (structures shown below) when reacted with phosphoric acid. Figure 1. Stereochemical Structures of Methylcyclohexanols. This reaction was carried out according to the following mechanisms. Figure 2. Reaction Mechanism of Dehydration of cis/trans-2-methcylohexanol Mixture. Procedure 150 mmol (˜ 18.419 g) of 2-methylcyclohexanol (cis - trans mixture) was placed into a 50 mL round bottom flask. Mixed in this flask was 5 mL of 85% phosphoric acid, 3 drops of sulfuric acid (to quicken reaction), and a few acid resistant boiling chips. A simple apparatus for distillation was assembled and two 10 mL graduated cylinders...


