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Oxidation is a ubiquitous reaction in organic chemistry and as such we felt it was necessary to include it in our laboratory curriculum. Among oxidants, nitric acid is dangerous, and salts of manganese or chromium are environmentally harmful and often messy; therefore, we sought other oxidizing agents devoid of these drawbacks and commercial bleach seemed appropriate.
In 1985 Mohrig et al.(1) published in this Journal a seminal paper on the use of household bleach in the oxidation of alcohols and the described procedure was then taken up by various laboratory textbooks (2). More recently, in this Journal Straub (3) published an oxidation procedure using TEMPO and bromide ion with commercial bleach to obtain benzil from benzoin. Moreover, alcohols and amines have been oxidized by bleach alone using phase transfer catalysis (4); this technique is now widely used in the laboratory (4) and could be included in the oxidation procedure as a demonstration of its usefulness. Therefore, we propose a procedure for the oxidation of benzhydrol to benzophenone, using bleach as the oxidant, ethyl acetate as the organic phase, and tetrabutylammonium hydrogen sulfate as the PTC...