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8421072 
Journal Article 
Aerobic alcohol oxidation using a copper(I)/TEMPO catalyst system: A green, catalytic oxidation reaction for the undergraduate organic chemistry laboratory 
Hill, NJ; Hoover, JM; Stahl, SS 
2013 
Yes 
Journal of Chemical Education
ISSN: 0021-9584 
90 
1 
102-105 
English 
Modern undergraduate organic chemistry textbooks provide detailed discussion of stoichiometric Cr- and Mn-based reagents for the oxidation of alcohols, yet the use of such oxidants in instructional and research laboratories, as well as industrial chemistry, is increasingly avoided. This work describes a laboratory exercise that uses ambient air as the source of oxidant and a readily available CuI/TEMPO catalyst system to convert benzyl alcohols to the corresponding aldehydes in standard glassware at room temperature. The procedure is well suited for a high-enrollment undergraduate course, and the complete exercise fits easily within a 3-h lab period. The structures of the organic starting materials and products are determined by NMR spectroscopy and EI-MS. The protocol is adapted from the contemporary research literature and provides students with practical experience of a modern, "green" oxidation method. In addition to the practical aspects, the experiment encourages student discussion and exploration of transition-metal- catalyzed reactions, a topic that is underrepresented in the contemporary undergraduate organic chemistry curriculum. © 2012 The American Chemical Society and Division of Chemical Education, Inc. 
Alcohols; Catalysis; Green Chemistry; Hands-On Learning/Manipulatives; Inorganic Chemistry; Inquiry-Based/Discovery Learning; Laboratory Instruction; Organic Chemistry; Oxidation/Reduction; Second-Year Undergraduate