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28: Alkene Oxidations

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    Alkene Oxidations: More Pericyclics

    Osmate Hydroxylation

    Osmium tetroxide (can also be done with KMnO4 or Pb(OAc)4) can hydrolyze an alkene to form a stereospecific 1,2 diol. This reaction sequence is shown below.

    Screen Shot 2019-05-19 at 12.39.37 AM.png

    • The reaction shown above is a stereospecific oxidation; not all possible stereoisomers are formed. Draw a stepwise mechanism with all arrows clearly shown for the reactions above.

    • Predict whether formation of the osmate ester results in a syn or anti addition to the alkene?

    • Draw the stereoisomer(s) formed in this reaction.

    • Label the above product(s) with the correct R or S designation at each chiral center.

    • Draw all of the stereoisomers formed if a-pinene were treated with OsO4.

      Screen Shot 2019-05-19 at 12.40.53 AM.png

    Ozonolysis

    • Draw the Lewis dot structure of ozone (O3).

    • Draw the mechanism for ozone reacting with a generic alkene (RCH=CH2).

    • The intermediate initially formed in this reaction rearranges to form an ozonide which is then cleaved using dimethyl sulfide. This process is shown below.

      Screen Shot 2019-05-19 at 12.42.10 AM.png

    Applications:

    Ozonolyis is interesting for three reasons:

    1. Ozonolysis is one of the few C-C bond breaking reactions!

      • List all the bond breaking reactions that you know.

    2. Alkene can be a protecting group for a ketone.

      • Show a reaction for making an alkene from a ketone

      • Show how you can reverse this reaction.

    3. Ozonolysis can be used for structure elucidation.

      • The corn borer sex pheromone (shown below) was difficult to elucidate because the researchers couldn’t determine the location of the double bond. Explain how ozonolysis and GC-MS could be used to determine location of double bond.

        Screen Shot 2019-05-19 at 12.44.53 AM.png

    This page titled 28: Alkene Oxidations was last modified on Fri, 11 Jun 2021 05:31:43 GMT and is shared under a CC BY-NC-SA 4.0 license and was authored, remixed, and/or curated by Kate Graham.

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