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Barberito 1
Max Barberito
12174194
CH-237-019
02/21/2023
Dehydration of Methylcyclohexanols and the Evelyn Effect
Introduction
In the 1990’s, a scientist named David Todd was conducting an experiment to clarify the results of Zaitzev’s rule and observe a mixture of alkenes. He performed alcohol dehydration and
elimination in the first order mechanisms. He then distilled his product to test the results of the mixture. During his distillation, the secretary of the chemistry department, Evelyn Jacoby, offered him an invite to lunch. His distillation was only around half done. He saved the initial distillate he collected, went to lunch, and came back to finish his distillation. When completing his distillation, he separated the distillate from before lunch from the distillate from after lunch through collecting them in different receivers. After he completed his distillation, he analyzed both of the distillates through gas chromatography. Surprisingly, the second fraction of the distillate contained a largely lower percentage of the expected 1-methylcyclohexene product. Because the reason for him having two separate distillates was the secretary’s invitation, he named this phenomenon the “Evelyn Effect.” The goal of this lab experiment was to verify the existence of the Evelyn Effect for the dehydration of 2-methylcyclohexanol and to compare the results with that of 4-methylcyclohexanol. The experimenters would add 2- or 4-
methylcyclohexanol into a flask with 85% phosphoric acid. This mixture would then be distilled in two fractions. Sodium bicarbonate was then added and removed to both distillates twice. Magnesium was then added and the remaining liquid was decanted into a pre-weighted glassware. The masses of both were then measured. Using gas chromatography results supplied
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to them, the experimenters would then analyze the results and come up with a composition of the
distillate. Structures
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Results
Theoretical yield
.15 moles 2-methylcyclohexanol + Phosphoric acid (cat) .15 moles methylcyclohexenes
Percent yield
5.99 g alkene mixture 1 + 4.28 g alkene mixture 2 = 10.27 g total
10.27 g / 96.2 g / mol = .107 moles of alkenes
.107/.15 x 100% = 71.2% yield Boiling range
88°C-110°C
Gas Chromatography 2-methylcyclohexanol
Fraction 1
– 68716830 + 14550118 + 2076623 = 85343571
68716830 / 85343571 = 80.5% 1‐methyl‐1‐cyclohexene
Fraction 2
- 79785326 + 4482960 + 8199848 = 92468134
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79785326 / 92468134 = 86.3% 1‐methyl‐1‐cyclohexene
4-methylcyclohexanol
– Total Area of Alkenes
Fraction 1
– 8861396 + 62084266 + 62084266 = 133029928
8861396 / 133029928 = 6.67% 1‐methyl‐1‐cyclohexene
Fraction 2
– 28379838 + 65277852 = 93657690
28379838 / 93657690 = 30.3% 1‐methyl‐1‐cyclohexene
Discussion
The percentage of the 1‐methyl‐1‐cyclohexene products in each fraction did change over time, but the percentage of 1‐methyl‐1‐cyclohexene in the 4-methylcyclohexanol is much lower than the 2-methylcyclohexanol. Neither of the results show the Evelyn effect, though. Although the distributions were different, the second fractions did not have lower percentages in either reaction. The Evelyn effect seems to have some play in the reaction because the percentages are different, but the second fractions’ percentages were not much lower as was expected. However, both of the cyclohexanols showed similarities in how their percentages changed. They both went up. Both of the cyclohexanols must react similarly. Conclusion
With the three different products, the elimination mechanisms must be working differently with each. 1-methyl-1-cyclohexene is the most stable of the products because of its substituted double bond. 3-methyl-1-cyclohexene is the second most stable product because it is still in the cyclohexene ring. Methylenecyclohexane is the least stable because it is a terminal alkene. The reaction goes through a E1 mechanism because the most stable major product
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undergoes a single step elimination with no carbocation intermediate. The cis- and trans- isomers
undergo different mechanisms, so the cis- isomer is more reactive and faster.
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