Dehydration of Methalcyclohexanols

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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

Calculations:

2-Methylcyclohexanol

Mass: (20mmol/1)(1mol/1000mmol)(114.2g/1mol) = 2.284g

Volume: (2.284g)(1mL/.930g) = 2.46 mL

Theoretical Yield: (.02mol) (1mol/1mol) (96.1702g/mol) = 1.924g methycyclohexene

Actual Percent Yield:

Distillate 1:

Mass: 24.543g – 24.130g = .413g

Percent Yield: (.413)/(1.924) X 100 = 21.47%

Distillate 2:

Mass: 39.075g – 38.825g = .25g

Percent Yield: (.25)/(1.924) X100 = 12.1 %

Data, Results and Observations:

Table 1: Measurements
T1| 75° C|
T2| 90° C|
T3| 99° C|
Beaker 1| 24.130g|
Beaker 2| 38.825g|
Beaker 1 w/ Product| 24.543g|
Beaker 2 w/ Product| 39.075g|

Table 2: Gas Chromatography for Distillate 1

Peak #| Ret. Time| Area|
1| 1.711| 5.8029%|
2| 1.758| 5.2536%|
3| 1.784| 6.6098%|
4| 1.830| 5.5547%|
5| 2.031| 1.6967%|
6| 2.110| 20.7735%|
7| 2.183| 32.8520%|
8| 2.229| 21.3453%|

Table 3: Gas Chromatography for Distillate 2

Peak #| Ret. Time| Area|
1| 1.774| .5729%|
2| 1.821| 9.7434%|
3| 2.073| 7.7451%|
4| 2.148| 40.7443%|
5| 2.205| 41.1523%|
6| 2.391| .0419%|

Discussion:

This experiment involved...
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