Lab 9 Betulin - E xperiment #9- Isolation of Betulin and...

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Experiment #9- Isolation of Betulin and Rearrangement to Allobetulin 11/19/09
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Purpose The purpose of this experiment was to extract and isolate Betulin, a pentacyclic triterpene, from a sample of dry Birch Bark. The product was then positively identified and analyzed. Next, the Betulin was then rearranged to Allobetulin by adding p-TSA and this product was identified and analyzed as well. Results (also see attached IRs) 1. Melting Point of Suspected Betulin= 226-230 degrees C 2. Melting Point of Suspected Allobetulin= 224-229 degrees C 3. Mass of Allobetulin crystals: 0.02g 4. TLC of Betulin extraction (spot at 2.2cm with a front of 5.9cm):
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Calculations 1. Percent Error in Melting Points (Standards obtained from Lab #9 Handout): a. Betulin: (256.5-228)/256.5 = 11% b. Allobetulin: (259-226.5)/259 = 12.5% 2. Rf of betulin TLC: 2.2cm / 5.9cm = 0.37 3. Percent Yield of Allobetulin from total process: .02g/.25g= 4% Mechanisms (See attached Mechanism Sheet) Discussion The first task was to extract the betulin from the birch bark into a chloroform solution. The presence of betulin in the chloroform was confirmed by taking a small sample to run an IR, a TLC, and a melting point test. The presence of a single spot on the TLC with an Rf of about 0.37 indicates that
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Lab 9 Betulin - E xperiment #9- Isolation of Betulin and...

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