What is another method/reagent for achieving the same overall transformation from Olefin 9 to ketone 10? How does this method compare to the one used? Another method is to use potassium permanganate instead of osmium tetroxide (OsO4). Potassium permanganate is a very powerful oxidizing agent. The mechanism for potassium permanganate is very similar to that of osmium tetroxide. The general reaction scheme is shown below:(1) |
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Potassium permanganate is not as effective as osmium tetroxide because it is too powerful for our reaction. However, there are many benefits of potassium permanganate. It is inexpensive, water-soluble, and is soluble in non-polar solvents (ie dichloromethane).1 In addition, the product can be easily isolated because potassium permanganate can be removed by filtration and flash evaporation (evaporation that separates the product based on boiling points) (2,3) Works Cited 1. Lee, Donald G., Maria Ribagorda, and Javier Adrio. "Potassium Permanganate." Encyclopedia of Reagents for Organic Synthesis. 2007. Web. 7 Apr. 2010. <http://www.mrw.interscience.wiley.com/eros/articles/rp244/sect0-fs.html>. 2. Lee, Donald G. "Potassium Permanganate–Copper(II) Sulfate." Encyclopedia of Reagents for Organic Synthesis. 2001. Web. 7 Apr. 2010. <http://www.mrw.interscience.wiley.com/eros/articles/rp245/sect0-fs.html>. 3. "Flash Distillation." Rensselaer Polytechnic Institute. Web. 07 Apr. 2010. <http://www.rpi.edu/dept/chem-eng/Biotech- Environ/Environmental/desal/flash.html>. |
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