Oxidation of Borneol: Possible Side Reactions & Effects

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The oxidation of borneol can lead to several side reactions, particularly when sodium hypochlorite (NaOCl) is introduced to acetic acid, resulting in the formation of chloronium ions. The reaction produces chlorine gas, which can interact with camphor and any residual acid or base. While the primary product of this oxidation is camphor, there is a potential for the formation of cyclohexene as a minor product due to the reaction of hypochlorite with other hydrogen atoms on the borneol structure. Additionally, the presence of cyclohexanone allows for keto-enol tautomerism, which may further influence the reaction dynamics with hypochlorite or chlorine, potentially leading to additional products. Overall, the major focus remains on camphor production, with side reactions including the formation of cyclohexene and the implications of tautomerism.
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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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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?
 
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.
 
But what do you know about keto-enol tautomerism?
 
Not much. I did find out that one of the side reactions would be the formation of a cyclohexene ring (a minor product). Thanks.
 
Cyclohexanone can form a keto-enol tautomer. What is the likely reaction between that olefin and hypochlorite or Cl2?
 
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