Exp 4 - Dehydration of Methylcyclohexanols Tyler Argent Exp...

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Dehydration of Methylcyclohexanols 10/13/08 Tyler Argent Exp. 4 CH 237 Lehman, John W. Operational Organic Chemistry, (Exp. 21 p.156 in text) I. Pre-Lab: (Attached) II. Experiment Notes and Observations: (Refer to Pre-Lab) III. Results: Table of Reagents Compound MW (g/mol) Amt. Used Moles Used Physical Constants 2-Methylcyclohexanol* 114.2 (g/mol) 18.7 mL .15 mol Flammable b.p.=166°C d=0.930 g/mL 4-Methylcyclohexanol* 114.2 (g/mol) 18.7 mL .15 mol Flammable b.p.=173°C d=1.70 g/mL Phosphoric Acid 98.0 (g/mol) 5 .0 mL .074 mol Corrosive D=1.70 g/mL M =14.7 mol/L 1-Methylcyclohexene 96.2 (g/mol) Flammable b.p.=110°C d=0.813 g/mL 3-Methylcyclohexene 96.2 (g/mol) Flammable b.p.=104°C d=0.801 g/mL 4-Methylcyclohexene 96.2 (g/mol) Flammable b.p.=102°C d=0.799 g/mL *Mixture of cis- and trans- isomers. Theoretical Yield:
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(150 mmol 4-methylcyclohexanol) x (1mol/1000mmol) x (96.2g cyclohexene) = 14.43 g Actual Yield: - Amount Recovered for both fractions: 10.6 g 10.6 g/14.43g x 100= 74% -b.p. range: 110C- 115C Average Product Distribution: IV. Discussion: The purpose of this experiment was to carry out the dehydration of 4- methylcyclohexanol by heating the alcohol in the presence of phosphoric acid. The alcohol was a mixture of cis and trans isomers so it could exhibit the Evelyn effect which was one of the main objectives to discover. By protonating an alcohol, the acid catalyst converts the poor leaving group—OH to a much better leaving group—+H2O. Elimination of H+ and H2O from the protonated alcohol yields an alkene, with the
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This note was uploaded on 04/19/2010 for the course CH 237 taught by Professor Staff during the Spring '08 term at Alabama.

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Exp 4 - Dehydration of Methylcyclohexanols Tyler Argent Exp...

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