So, KMnO4 oxidizes an aldehyde to a carboxylic acid and a ketone to a diol, right? The mechanism for aldehyde is in the KBB but not for ketone. Please correct me if I am wrong! Thanks.
KMnO4 oxidizes ketone to diol?
- Thread starter dental17
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How about when it's dilute KMnO4? A question in the KBB asked which reagent would oxidize a ketone to a secondary alcohol. One of the options was dilute KMnO4. In the solutions section it explained that dilute KMnO4 would oxidize the ketone to a diol and not a secondary alcohol. I picked the right reagent (PCC) but couldn't find anything in the chapter that verified that KMnO4 produced a diol from a ketone.
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they can't be oxidized any further
the only one that could be oxidized another step is an aldehyde which is to a carboxylic acid
primary alcohol-->aldehyde (via PCC)-->carboxylic acid via k2cr2o7/h2cr2o7/etc etc
and dilute KMnO4 adds in a syn fashion to alkenes
the only one that could be oxidized another step is an aldehyde which is to a carboxylic acid
primary alcohol-->aldehyde (via PCC)-->carboxylic acid via k2cr2o7/h2cr2o7/etc etc
and dilute KMnO4 adds in a syn fashion to alkenes
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the only way that i can think of to go from a ketone to diol would be to reduce it, treat it with acid and heat and then add KMnO4...
anyone?
anyone?
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cold, dilute KMnO4 will do syn hydroxylation
hot, conc KMnO4 will do oxidative cleavage of an alkene--- Ketones will stay ketones, and aldehydes will oxidize to COOH
hot, conc KMnO4 will do oxidative cleavage of an alkene--- Ketones will stay ketones, and aldehydes will oxidize to COOH
