2-Methylcyclohexanol Dehydration

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Dehydration of Methylcyclohexanols
Balie Zander
Date Conducted: March 27, 2013
Date Submitted: April 3, 2013

Introduction:
The purpose of this experiment was to demonstrate the application of Zaitzev’s rule, the Evelyn Effect and the occurrence of an E1 mechanism in an alcohol dehydration reaction. Specifically this experiment involved the dehydration of 2-methylcylcohexanol by heating this alcohol in the presence of phosphoric acid and then to based on the results of the gas chromatography of the product to determine whether the alcohol exhibited the Evelyn Effect. The reaction taking place for both the Cis and the Trans isomers for Methylcyclohexanol are as follows: E1 Mechanism for Cis Methylcyclohexanol

E1 Mechanism for Trans methylcyclohexanol
…show more content…
The 2-methylcyclohexanol alcohol used in this experiment was a mixture of both cis and trans isomers. The way this reaction occurs is as follows. Through protonation, the acid-catalyst converts the already present, poor leaving group (-OH) to a much better leaving group (H2O+). Then once the H2O and the H+ are eliminated the reaction yields an alkene in which the un-protonated alcohol serves as the reaction solvent. This experiment then called for the distillation of this mixture, using a distillation apparatus. As this distillation took place the products, alkenes and water continuously distilled from the reaction mixture into a Hickman still as they were formed. The removal of these elements shifted the equilibrium to the right, ultimately increasing the yield of alkene, this is also known as Le Chatelier’s Principle. Then both fractions were washed with 1.5mL of 5% aqueous sodium bicarbonate, the reason or this is that the sodium bicarbonate gets rid of the excess acid present. In order to analyze the fractions, both were put through gas

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