ERIC Number: EJ1011395
Record Type: Journal
Publication Date: 2013-Jan
Pages: 4
Abstractor: As Provided
ISBN: N/A
ISSN: ISSN-0021-9584
EISSN: N/A
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.)
Descriptors: Organic Chemistry, College Science, Science Instruction, Undergraduate Students, Science Laboratories, Laboratory Experiments, Spectroscopy, Hands on Science, Science Activities
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
Grant or Contract Numbers: N/A