agent_entropy
Hazard to Self
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Registered: 17-7-2006
Location: U.S.
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Mechanism of Peroxide Formation?
Does anyone know the general mechanism for the formation of organic peroxides? (or where I can find this information) I've searched the board to no
avail, and google yields nothing but pages about spontaneous peroxide formation in reagent bottles that are left alone too long. What I want to know
about is the chemical mechanism involved in the intentional synthesis of an organic peroxide.
I'm interested in the general mechanism and specifically in the mechanism of the synthesis of HMTD. If at all possible a diagram of the mechanism in
the curved arrow format would be preferable. (I'm a visual learner)
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guy
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Looks like in the presence of light, the C-H bond can break forming radicals which will react with oxygen to form a hydroperoxide. This will
polymerize into a peroxide.
R-C-H + hv ----> R-C* + H*
R-C* + O-O --> R-C-O-O*
R-C-O-O* + H* ---> R-C-O-O-H
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SilencePlease...
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With an H+ catalyst, water forms "hydrates" with Ketones:
CH3.CO.CH3 + H2O (+H+) -> CH3.C(OH)2.CH3
Then, as with alcohols, H2O2 can form hydroperoxides:
CH3.C(OH)(OOH).CH3
This 2-hydroperoxypropan-2-ol then trimerises to our well known Cyclic peroxide.
Look up Markovnikov, and radicals?!? never, ever, ever.....
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