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An organic chemistry laboratory experiment illustrating the oxidation of primary and secondary alcohols to their corresponding aldehyde or ketones, respectively, is described. The procedure uses 30% aqueous hydrogen peroxide in the presence of tungsten catalyst (sodium tungstate) using phase transfer catalysis. The described experiments illustrate basic organic reaction chemistry and techniques and may be used to introduce gas chromatography and 1H NMR spectroscopy to evaluate product composition and purity and infrared spectroscopy to confirm functional group transformation and describe product composition. The procedure illustrates the use of an environmental benign, organic-solvent-free oxidation system for functional group transformations. .
Supplemental materials are provided on the J. Chem. Educ. website and include laboratory procedures, instructors notes, tables of reagents and products and spectra.
Summary prepared May 2005 by Julie A. Haack, Department of Chemistry at the University of Oregon.
Hulce, M.; Marks, D. W. J. Chem. Educ., Print 2001, 78, pp 66-67.