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Oxidation of Borneol

  1. Jan 29, 2008 #1
    What possible side reactions could occur in the oxidation of borneol? Since an acid-base rxn takes place when the NaOCl is added to the acetic acid, could that be considered a side-reaction since it gives rise to the chloronium ion or is there something else that happens after the production of camphor? Thanks.
     
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  3. Jan 31, 2008 #2

    chemisttree

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    When you treat hypochlorite with acid, chlorine is produced. What will happen to champhor in the presence of chlorine and whatever base (or acid) might be left over?
     
  4. Jan 31, 2008 #3
    From what I could find (and learned from the professor) is that if the OCl attacks the other H (not the one with the O-) then it would form a double bond allowing the OCl to leave. However the major product would be the formation of the ketone (camphor) and not the cyclohexene.
     
  5. Feb 1, 2008 #4

    chemisttree

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    But what do you know about keto-enol tautomerism?
     
  6. Feb 2, 2008 #5
    Not much. I did find out that one of the side reactions would be the formation of a cyclohexene ring (a minor product). Thanks.
     
  7. Feb 4, 2008 #6

    chemisttree

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    Cyclohexanone can form a keto-enol tautomer. What is the likely reaction between that olefin and hypochlorite or Cl2?
     
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