Oxidation Reagents
| Reagent | Preferred Solvents | Functions Oxidized | Reaction Work-up |
|---|---|---|---|
|
Jones Reagent H2CrO4 |
aqueous sulfuric acid & acetone (avoid acid sensitive systems) |
1°-alcohols to carboxylic acids aldehydes to carboxylic acids 2°-alcohols to ketones avoid amines and sufides |
1) destroy excess reagent 2) extract product |
|
Collins Reagent CrO3 • 2 C5H5N |
methylene chloride (CH2Cl2) |
1°-alcohols to aldehydes 2°-alcohols to ketones |
1) filter inorganic salts 2) wash with aqueous acid 3) remove CH2Cl2 solvent |
|
Pyridinium Chlorochromate ClCrO3 • C5H5NH |
methylene chloride (CH2Cl2) |
1°-alcohols to aldehydes 2°-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
1°-alcohols to aldehydes 2°-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 2°-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 |