This may be aided by the solvation (solubilising) of PDC in DMF. So given that, it may be concluded that DMF causes PDC to over-oxidise due to following reasons (possible):ĭecomposition of PDC in DMF to form water molecules, so that hydrate formation of intermediate aldehyde occurs and then conversion into carboxylic acid. The water necessary for the formation of the intermediate aldehyde hydrate may proceed from the decomposition of PDC. This oxidation into carboxylic acids succeeds when the intermediate aldehyde equilibrates with a sizeable proportion of hydrate (when the intermediate aldehyde belongs to the aliphatic kind and is not highly hindered). Of certain alcohols into acids, something that may happen even Now, coming to your question the interesting thing is that DMF, which is very efficient in dissolving PDC,causes the over-oxidation PDC is far more reactive in more polar solvents like water. The water necessary for the formation of the intermediate aldehyde hydrate may proceed from the decomposition of PDC.$^$, ethyl acetate, benzene, methyl cyanide or chloroform. As stated in the previously posted answer:Ĭarboxylic acids succeeds when the intermediate aldehyde equilibrates with a liberal proportion of hydrate that is, when the intermediate aldehyde belongs to the aliphatic kind and is not highly hindered.
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