Lab 6 - Dehydration of 2-Methylcyclohexanol Experiment #6...

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Unformatted text preview: Dehydration of 2-Methylcyclohexanol Experiment #6 Dan Guerra Section: 6 TA: Yi and Luke 10/24/11 Purpose: The purpose of this experiment was to synthesize 1-methylcyclohexene and 3- methylcyclohexene via the dehydration of 2-methylcyclohexanol, and determine the amount of product formed through the calculation of percent yield. Additionally, it was to analyze the product through TLC, IR, bromine and gas chromatography tests, to determine overall success of the experiment and the products purity. Finally it was to determine if the reaction abided by Zaitefs rule. Results and Discussion: Upon mixing the sample of 2-methylcyclohexanol with liquid phosphoric acid, the mixture was fractionally distilled. The drops began to accumulate between 75-80 C, and continued as less and less 1-methycyclohexene and 3-methylcyclohexene was present in the reaction flask. This is a viable indicator that the separation was a success. While the boiling points of 1-methylcyclohexene and 3-methylcyclohexene are 110 C and 104 C, respectively, the lowered melting point is an indication of the mixture of water and the alkenes. 2-methylcyclohexanols boiling point is 164 C; therefore the significantly lower boiling point of the distillate makes it likely that 2- methylcyclohexanol is not part of it. The first test conducted was the bromine test. For this, the obtained product, 2- methylcyclohexanol, cyclohexane and cyclohexene were tested. The bromine test tests compounds for saturation. If a compound is saturated or contains no double or triple bonds, such as cyclohexane, then the addition of bromine to the compound in solution should cause the solution to become discolored. In the case of compounds containing double or triple bonds, such as cyclohexene, the solution would remain clear upon the addition of bromine. From this information, it was expected that cyclohexane and 2- methylcyclohexanol would become discolored upon the addition of bromine, as both compounds are saturated. While the obtained product and cyclohexene would remain clear upon the addition of bromine. The following results were obtained: Compound...
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This note was uploaded on 02/15/2012 for the course ORGO 101 taught by Professor Staff during the Fall '11 term at Syracuse.

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Lab 6 - Dehydration of 2-Methylcyclohexanol Experiment #6...

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