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ERIC Number: EJ941061
Record Type: Journal
Publication Date: 2011-Aug
Pages: 3
Abstractor: As Provided
ISSN: ISSN-0021-9584
A Multistep Organocatalysis Experiment for the Undergraduate Organic Laboratory: An Enantioselective Aldol Reaction Catalyzed by Methyl Prolinamide
Wade, Edmir O.; Walsh, Kenneth E.
Journal of Chemical Education, v88 n8 p1152-1154 Aug 2011
In recent years, there has been an explosion of research concerning the area of organocatalysis. A multistep capstone laboratory project that combines traditional reactions frequently found in organic laboratory curriculums with this new field of research is described. In this experiment, the students synthesize a prolinamide-based organocatalyst that is then used to perform an enantioselective aldol reaction between acetone and 4-nitrobenzaldehyde. The enantiomeric excess (ee) of the reaction is determined by chiral HPLC and polarimetry. Students obtained ee values ranging from 46 to 59%. This experiment is designed to be adaptable and can be performed with minimal equipment (glassware, IR, and polarimeter). It also provides flexibility to the instructor, due to the wide range of topics that may be emphasized in the experience. (Contains 1 figure and 2 schemes.)
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:; Web site:
Publication Type: Journal Articles; Reports - Research
Education Level: Higher Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A