Experiment 9_ Column Chromatography
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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.
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
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8000000
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6000000
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