Oxidation Reagents
| Reagent | Preferred Solvents | Functions Oxidized | Reaction Work-up |
|---|---|---|---|
| Jones Reagent H2CrO4 |
aqueous sulfuric acid & acetone (avoid acid sensitive systems) |
1º-alcohols to carboxylic acids aldehydes to carboxylic acids 2º-alcohols to ketones avoid amines and sufides |
1) destroy excess reagent 2) extract product |
| Collins Reagent CrO3 • 2 C5H5N |
methylene chloride (CH2Cl2) |
1º-alcohols to aldehydes 2º-alcohols to ketones |
1) filter inorganic salts 2) wash with aqueous acid 3) remove CH2Cl2 solvent |
| Pyridinium Chlorochromate ClCrO3 • C5H5NH |
methylene chloride (CH2Cl2) |
1º-alcohols to aldehydes 2º-alcohols to ketones |
1) filter inorganic salts 2) wash with aqueous acid 3) remove CH2Cl2 solvent |
| Dimethyl Sulfoxide (CH3)2S=O & DCC or Ac2O or (CF3CO)2O or SO3 or (COCl)2 |
CH2Cl2 or ethers or DMSO |
A Mild Procedure
1º-alcohols to aldehydes 2º-alcohols to ketones |
1) neutralize reactants 2) remove solvents |
| Potassium Permanganate KMnO4 Osmium Tetroxide OsO4 |
water and aqueous solvent mixtures pyridine often used catalytically |
aldehydes to carboxylic acids 2º-alcohols to ketones alkenes to vicinal-diols (vic.-glycols) alkynes to carboxylic acids avoid amines and sufides alkenes to vicinal-diols (vic.-glycols) |
1) destroy excess reagent 2) extract product |
| Periodic Acid HIO4 Lead Tetraacetate Pb(OCOCH3)4 |
water or aqueous mixtures benzene or acetic acid |
vic.-glycols to carbonyl compounds vic.-glycols to carbonyl compounds |
1) destroy excess reagent 2) extract product |
| Peracids CH3CO3H C6H5CO3H, etc. |
CH2Cl2 or ethers | alkenes to epoxides ketones to esters avoid amines and sufides |
1) destroy excess reagent 2) extract product |
| Ozone O3 |
CH2Cl2 or CHCl3
(sometimes alcohol) |
cleaves alkenes & alkynes avoid benzene derivatives amines and sufides |
1) destroy excess reagent & ozonides 2) extract product |