Experiment 13 - Kelsey Simpson

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University of Nebraska, Lincoln *

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253

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Chemistry

Date

Dec 6, 2023

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docx

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3

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Kelsey Simpson Partner: Emma W Chem 253 – TA: Noelle Waltenburg Nov. 9, 2023 Formation of Cyclohexane from Cyclohexanol Purpose To separate cyclohexane from cyclohexanol using an acid. The reaction will separate through dehydration. Theory We began the experiment with cyclohexanol and reached a final product of cyclohexane. We used phosphoric acid to react the solution to form the distillate. We then separated the organic layer from the inorganic layer. We then ran the product through the GC and the NMR to determine the chemical formula of the compound. Methodology The procedure was found on pages 95 – 101 in the Chem 253 Organic Chemistry Lab Manual. There was no changes. Reaction Reaction: Cyclohexanol + Phosphoric Acid Cyclohexane + Water Data GCM This graph tells us that not only are Acetone and Cyclohexanol present but there are also small portions of Cyclohexene in the sample. We can tell because of the small peak between 1.6 and 1.7.
NMR This graph shows us that there is still possibly some cyclohexanol in the sample. As well as quite a bit of CH bonds present. Beginning Ending BP cyclohexanol+PA 31º C 110º C BP Organic 55º C 86º C Calculation Cyclohexanol = 10 (9.624 g*mole/100.161 g) = 0.96 mol Phosphoric Acid = 2.5 (1.885 g*mole/97.994 g) = 0.48 mol Observation/Results The presence of the cyclohexanol in the solution I believe messed up our graphs and numbers. However, we were able to identify the organic and inorganic layer during the experiment to separate them as best as we could. The distillation process also went fairly smooth, I believe we distilled slightly to fast, however, it did speed up the experiment. Discussion/Conclusion I believe that there was some error within our experiment that came from the rate of distillation within our apparatus. I the separation step causing percent error within our yield calculation. There was also definitely cyclohexanol still present in the solution, so we did not fully separate the two compounds. Other than those errors, I believe that the experiment went as planned. Exercises 1. Write a detailed mechanism for the dehydration of cyclohexanol
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