Lab Report 4

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University of Alabama *

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237

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Chemistry

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Feb 20, 2024

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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
Barberito 2 to them, the experimenters would then analyze the results and come up with a composition of the distillate. Structures
Barberito 3 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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Barberito 4 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
Barberito 5 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.