Ozonolysis of Alkenes
0 views·06:52 min
- Add 200 mg of isoeugenol, 15 mL of MeOH, and ~ 2 mg of Sudan III to a 3-necked 50- mL round bottom flask equipped with a magnetic stir bar.
- Connect the reaction flask to an oxygen tank and a bubbler.
- Turn on the flow of oxygen.
- Cool the reaction mixture with a dry ice/acetone bath.
- Switch on the ozone generator, which converts the oxygen from the tank to ozone that goes into the reaction flask. The generator will be between the oxygen tank and the reaction flask. Allow the reaction mixture to stir until the red color changes to purple/blue.
- Turn off the ozone generator, and allow oxygen to purge the reaction mixture of ozone for 5 min.
- Remove the cooling bath and add 0.2 mL of dimethyl sulfide.
- Stir the reaction mixture while warming to room temperature for 1 h.
- Remove the solvent by rotary evaporation. Make a silica plug by placing silica gel into a Büchner funnel. Dissolve the residue in 10% ethyl acetate in hexanes and pass the solution through the silica plug under vacuum to remove impurities. Wash the silica plug 2 more times with 10% ethyl acetate in hexanes. Collect the filtrate and remove the solvent by rotary evaporation to obtain vanillin as a white solid.
- Calculate the percent yield of vanillin obtained and establish its purity and identity by melting point (m.p.) and 1H NMR.
Source: Vy M. Dong and Zhiwei Chen, Department of Chemistry, University of California, Irvine, CA
This experiment will demonstrate an example of an oz…
Chapters in this video
0:00
Overview
0:46
Principles of Ozonolysis
2:35
Ozonolysis of Isoeugenol
3:51
Reductive Workup to Vanillin and Characterization
5:17
Applications
6:26
Summary
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