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Transcript
Chem 343 – Organic Reactions Chapter 10 Prepared by José Laboy, MS http: www.chem.wisc.edu/areas /clc (Resource page) Reactions of Alcohols #7: Oxidation of Secondary Alcohols to Ketones H2CrO4 (Jone's Reagent) or 1) KMnO4 / NaOH , acetone OH 2) Acid workup either or both or enantiomers PCC / CH2Cl2 Mechanism for Jone’s Reagent H2O H O HO O HO Cr O O O O Cr O O H H CH 3 HO O Cr OH CH 3 O HO O OH H H H O H O Cr HO HCrO3- O O O Cr O H 3C OH2 O O HO CH H H2O Ketone a chromate ester Although chromic acid and permanganate are powerful oxidizing agents the reaction only requires a two-‐electron transfer to transform a 2° alcohol to a ketone. The same results will be obtained by the use of the PCC reagent although under milder conditions. A similar mechanism for the permanganate occurs except that the media is basic. H O O O HO O Mn O Mn O O O O CH 3 HMnO4- + H2O OH O O Mn O O H 3C O H 3 HO ketone
