SOME OXIDIZING AGENTS IN ORGANIC CHEMISTRY

alkane H2CrO4 CrO3, Py (PCC) CrO2Cl2 KMnO4,OH! KMnO4, H+ Cl2, Br2, I2 NBS RCO3H HOOH O2 O3 HNO3 HNO2 SO3 OsO4 NaIO4 Pb(OAc)4 Ag(NH3)2+, Ag2O Cu++(Fehling) Pt (or Pd) +(!H2) alkane alkene alkyne aromatic benzyl or allyl alkyl halide +?(!H2) alcohol p or s ether p or s aldehyde ketone + ? + + ? +(diol) +(diol) + + + + amine organometallic sulfide + + +(tert) + + +(light) + + ? +(light) + +(FeSO4) + + +(H2SO4) +(H2SO4) +(H2SO4) + + + +(light) +(light) + + ? + + + + + + + + +(Fe) + + + + + +(heat) alkene + + alkyne + +? aromatic benzyl or allyl + + + + alkyl halide alcohol p or s + + + + + + + + + ether p or s + Aldehyde + ! ! + + + +(CH) + + +(slow) +(CH) +(CH) + +(CH) + + + + ? + + + + + + + + + ? ! ! +(CH3) + + ketone amine organometallic sulfide ? ? + +

Ethers usually form explosive peroxides when oxidized and are nearly as reactive as alcohols. BEWARE!!! + reacts by oxidizing the functional group ! no oxidation

Groups not included are generally not oxidized (e.g. CO2H)

? or +? expect oxidation but found no examples L. M. SWEETING 1995

A blank space means that information was not readily available or there were examples of + and !; contributions welcome.