Experiment 9_ Column Chromatography

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Feb 20, 2024

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1 11/14/21 Experiment 9: Column Chromatography Other lab members : Caroline and Ethan Goal : Use a TLC-like technique that uses silica gas to more accurately separate molecules based on their structure. Quantities for column load : 100 mL developing solvent - 100% Ethyl acetate (used throughout the column and in the slurry) Ethyl acetate is a polar solvent which is why this DS is used. The more polar the solvent, the greater the eluting strength. 0.12 g cis-cyclohexane-1,2-diol 0.11 g trans-cyclohexane-1,2-diol 190 μL cyclohexene Few scoops of silica (around 10 mL) TLC plates : Visualization: p-anisaldehyde, DS: 100% Ethyl acetate Blue lines on top = cyclohexene Pink spots = cis Purple dots = trans Fractions: Cyclohexene: 1-4 Cis: 4-7 Trans: 21-25 Mix of cis and trans Cis is almost separated
2 Rf values: Rf (1-3) = 6/6.2 = 0.97 Rf (4-5) = 4.7/6.2 = 0.76 Rf (6) = 5.9/6.6 = 0.89 Rf (7-9 (pink spot)) = 2/6.6 = 0.30 Rf (8-9 (purple spot)) = 1.2/6.6 = 0.18 Rf (10 (blue line)) = 6.5/6.6 = 0.99 Rf (11-25 (purple spot)) = 2/6.6 = 0.30 Rf (11-25 pink spot)) = 2.7/6.6 = 0.41 Data : Cis-cyclohexane-1,2-diol Weight (g) Pre-weighed empty vial 147.73 Vial + dried product 147.74 Product weight 0.01 Theoretical yield 0.218 Percent yield 4.59% Trans-cyclohexane-1,2-diol Weight (g) Pre-weighed empty vial 65.95 Vial + dried product 65.96 Product weight 0.01 Theoretical yield 0.218 Percent yield 4.59%
3 Calculations : The usefulness of this technique : With this TLC-like technique (upside down TLC plate), we are able to produce a continuous reaction flow that drains out compounds one at a time. Rather with LLE, it would use solubility to separate the reaction products. This increases the likelihood that the cyclohexene would extract in the organic layer and the diols would not be successfully extracted. Column chromatography is important because it allows us to clearly separate the diols one after another. In this lab, cyclohexene appeared first, then the cis diol, and finally, the trans diol.
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4 NMR : Cyclohexene 1.98 ppm 1.16 ppm Around 3.98 ppm (this is slightly off) 5.661 ppm 1.98 ppm 1.61 ppm
5 Cis-cyclohexane-1,2-diol : (standard) O-H peak H H group O-H peak H H groups
6 Trans-cyclohexane-1,2-diol : D=1.69 ppm E= 1-1.56 ppm C= 1.95 ppm A= 3.91 ppm Unnecessary peak (around 7.45 ppm) A=3.91 ppm B=3.33 ppm C=1.95 ppm D=1.69 ppm E=1-1.56 ppm
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7 IR (Did not collect in lab) : C-H (alkene) C=C - CH2 O-H C-H
8 O-H C-H
9 Theoretical NMR vs. Database NMR : Cyclohexene :
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10 These are very pretty exact - same number of peaks with similar ppms Cis-cyclohexane-1,2-diol : These two are almost exact - same peak identification but some ppms are slightly off
11 Trans-cyclohexane-1,2-diol : A B C D E B C, E, D NMRDB only shows the H, no OH groups are shown
12 Unknown Acid NMR (trans-cinnamic acid) vs. Theoretical NMR : OH peak shown
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13 These are both very similar - but the database H-NMR contains the H from the OH bond These are pretty exact - same number of peaks with similar ppms. 1 2 3 4 5 6 7 1 2 3 4 5,6 7