What is the oxidation mechanism of KMnO4 on alkanes?

In summary, the conversation is about the search for the oxidation mechanism of KMnO4 on alkanes, specifically aryl derivatives like toluene. The only information found was the overall reaction and some notes mentioning a radical character where the MnO4 anion removes hydrogens from the methyl group of toluene. Some websites deemed the mechanism as unimportant or too complicated for their purposes. The speaker asks for the reaction mechanism and provides some links for further information on the oxidation of side chains.
  • #1
PeetPb
29
0
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
  • #2
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"
 

FAQ: What is the oxidation mechanism of KMnO4 on alkanes?

What is the chemical formula for KMnO4?

The chemical formula for KMnO4 is potassium permanganate.

How does KMnO4 act as an oxidizing agent?

KMnO4 acts as an oxidizing agent by accepting electrons from other substances, causing them to be oxidized and itself being reduced in the process.

What is the mechanism of KMnO4 oxidation?

The mechanism of KMnO4 oxidation involves the transfer of oxygen atoms from the permanganate ion to the substance being oxidized.

What factors influence the rate of KMnO4 oxidation?

The rate of KMnO4 oxidation is influenced by the concentration of KMnO4, temperature, pH, and the nature of the substance being oxidized.

What are some common applications of KMnO4 oxidation?

KMnO4 oxidation is commonly used in the production of dyes, organic synthesis, and wastewater treatment. It is also used in analytical chemistry as a titrant and in the production of certain pharmaceuticals.

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