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ERIC Number: EJ1011395
Record Type: Journal
Publication Date: 2013-Jan
Pages: 4
Abstractor: As Provided
Reference Count: 15
ISBN: N/A
ISSN: ISSN-0021-9584
Aerobic Alcohol Oxidation Using a Copper(I)/TEMPO Catalyst System: A Green, Catalytic Oxidation Reaction for the Undergraduate Organic Chemistry Laboratory
Hill, Nicholas J.; Hoover, Jessica M.; Stahl, Shannon S.
Journal of Chemical Education, v90 n1 p102-105 Jan 2013
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 Cu [superscript I]/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. (Contains 3 schemes and 1 table.)
Division of Chemical Education, Inc and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education; Postsecondary Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A