Sunday, May 5, 2013

Mechanism: Ozonolysis

Unfortunately, my computer had technical difficulties with ChemDraw. So, I had to do it the old-fashioned way and draw the mechanism by hand. I chose to do ozonolysis, a mechanism we briefly discussed in our final class period. It uses Ozone (O3), Zinc and H2O. Zinc is actually used to to reduce the hydrogen peroxide which is generated in the hydrolysis of the ozonide intermediate. This rxn is fairly easy to remember. You cleave at the alkene and add two carbon-oxygen double bonds at that "cut". Below I have included the mechanism: 



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2 comments:

  1. AnonymousMay 5, 2013 at 4:50 PM

    *Correction: the structure labeled "ozonide" should be molozonide.
    The mechanism involves the alkene and ozone forming an intermediate molozonide. Next, the molozonide reverts to its corresponding carbonyl oxide and carbonyl (notice that the carbonyl flips). The oxide and carbonyl react again to produce a pretty stable ozonide intermediate. Ozonide is then converted into the two carbonyl products.

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  2. AnonymousMay 6, 2013 at 12:04 AM

    Thanks! This is really helpful for the test! I was having problems with this when i did the practice questions. Good Luck on the Test.

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