Oxidation of Borneol: Possible Side Reactions & Effects

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SUMMARY

The oxidation of borneol primarily yields camphor as the major product, with potential side reactions involving the formation of chloronium ions when sodium hypochlorite (NaOCl) is added to acetic acid. Chlorine production occurs when hypochlorite reacts with acid, which may affect camphor's stability. A minor product, cyclohexene, can form through the attack of hypochlorite on borneol, leading to a double bond formation. Additionally, cyclohexanone can undergo keto-enol tautomerism, which may influence its reactivity with hypochlorite or chlorine.

PREREQUISITES
  • Understanding of oxidation reactions, specifically borneol oxidation.
  • Familiarity with sodium hypochlorite (NaOCl) and its reactions with acids.
  • Knowledge of keto-enol tautomerism and its implications in organic chemistry.
  • Basic concepts of chlorination reactions and their effects on organic compounds.
NEXT STEPS
  • Research the mechanisms of borneol oxidation to camphor using NaOCl.
  • Study the formation and stability of chloronium ions in acid-base reactions.
  • Explore the implications of keto-enol tautomerism in organic synthesis.
  • Investigate the reactivity of cyclohexene with hypochlorite and chlorine.
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Chemistry students, organic chemists, and researchers interested in oxidation reactions and the behavior of chlorinated compounds in organic synthesis.

lexia925
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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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