Aerobic Alcohol Oxidation Using a Copper(I)/TEMPO Catalyst System: A Green, Catalytic Oxidation Reaction for the Undergraduate Organic Chemistry Laboratory
Year: 2012
Type: article
Abstract: 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.
Source: Journal of Chemical Education
DOI: 10.1021/ed300368q
Institution: University of Wisconsin–Madison
Language: English
Subfield: Physical and Theoretical Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,500
OpenAlex ID: W2077140551