What is the oxidation mechanism of KMnO4 on alkanes?

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SUMMARY

The oxidation mechanism of KMnO4 (potassium permanganate) on alkanes, specifically aryl derivatives like toluene, involves the formation of free radicals. The MnO4 anion abstracts hydrogen atoms from the methyl group of toluene, resulting in a radical intermediate. This reaction occurs in the presence of diluted or concentrated sulfuric acid, ultimately leading to the formation of benzoic acid. Relevant resources include detailed presentations on the oxidation of side chains and the specific reaction mechanisms involved.

PREREQUISITES
  • Understanding of organic chemistry principles, particularly oxidation reactions.
  • Familiarity with the structure and reactivity of toluene and its derivatives.
  • Knowledge of potassium permanganate as an oxidizing agent.
  • Basic grasp of radical chemistry and reaction mechanisms.
NEXT STEPS
  • Research the detailed oxidation mechanism of toluene with KMnO4 and sulfuric acid.
  • Study the formation and stability of free radicals in organic reactions.
  • Explore the synthesis of benzoic acid from toluene via oxidation.
  • Investigate other reagents that can oxidize methyl side chains in aromatic compounds.
USEFUL FOR

Chemistry students, organic chemists, and researchers interested in oxidation reactions and the behavior of aromatic compounds under oxidative conditions.

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Hi,
I've been searching for the oxidation mechanism of KMnO4 on alkanes (aryl derivatives like toluene). All I found was some web sites telling me the overall reaction and that the mechanism is either unimportant or too complicated for their purposes. I found some little notes that it has a radical character something like the MnO4 anion removes the hydrogens from the methyl group of toluene and leaves a free radical. Beyond that I couldn't get anything. Please if you can tell me the reaction mechanism I'd be very happy ...

thanx
 
Chemistry news on Phys.org
wiki- toluene

"With other reagents the methyl side chain in toluene may react, undergoing oxidation. Reaction with potassium permanganate and diluted acid (e.g., sulfuric acid) or potassium permanganate with concentrated sulfuric acid, leads to benzoic acid"

here are some notes:
faculty.philau.edu/milkevitchm/Microscale_Oxid_Toluene.ppt

and another
phs244.wikispaces.com/file/view/Side+chain.pptx

I haven't played with those types of reactions yet so I'm not sure how helpful this will be. Look for "oxidation of side chains"
 

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