What side reactions occur when oxidizing borneol with NaOCl?

[lexia925]

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.

 

[chemisttree]

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?

 

[lexia925]

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.

 

[chemisttree]

But what do you know about keto-enol tautomerism?

 

[lexia925]

Not much. I did find out that one of the side reactions would be the formation of a cyclohexene ring (a minor product). Thanks.

 

[chemisttree]

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