Exercise 46. Potassium Permanganate

Exercise 15-31 Show the mechanistic steps you expect to be involved in the oxidation of benzenecarbaldehyde (benzaldehyde) to benzenecarboxylic (benzoic) acid in an alkaline solution of potassium permanganate. 

Exercise 15-32 Explain why oxidation of secondary alcohols with 180-labeled potassium permanganate produces an 1sO-containing ketone in acidic solution, but not in basic solution. 

Exercise 15-33 The oxidation of (CH3)2CDOH is one seventh as fast as the oxidation of (CH3)2CHOH using potassium permanganate in acidic solution. What does this tell us about the mechanism of the reaction in acidic solution ... 

Exercise 16-37 An elegant modification of the two-step procedure to prepare ketones from alkenes by hydroxylation and oxidative cleavage of the diol formed uses a small amount of potassium permanganate (or osmium tetroxide, 0s04) as the catalyst and sodium periodate as the oxidizing agent ... 

Sulfuric acid and potassium permanganate are used to dispose of doxorubicin or daunorubicin wastes. Doxorubicin shows mutagenicity only at high concentrations. Care must be exercised by wearing protective clothing when handling urine and feces after administration of doxorubicin, etoposides, fluorouracil, methotrexate, mitoxantrone, mustine, procarbazine, melphalan, mercaptopurine, vinblastine, vincristine, and hydroxyurea.217... 

This reaction used to be commonly employed in first-year chemistry laboratory exercises, but reports of isolated explosions have forced its elimination from such situations. Great care should be used in preparing oxygen in this manner. A safer method is to oxidize a mild solution of hydrogen peroxide with potassium permanganate in acid solution, as shown in Equation (11.3) ... 

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