ERIC Number: EJ1443734
Record Type: Journal
Publication Date: 2023-Feb
Pages: 5
Abstractor: As Provided
ISBN: N/A
ISSN: ISSN-0021-9584
EISSN: EISSN-1938-1328
Updating the Benzoin Condensation of Benzaldehyde Using Microwave-Assisted Organic Synthesis and N-Heterocyclic Carbene Catalysis
John P. Morgan; Elizabeth E. Torres; Richard Averill; Alex M. Brody
Journal of Chemical Education, v100 n2 p986-990 2023
The benzoin condensation of benzaldehyde is a staple of the undergraduate organic chemistry laboratory, introducing the current topic of nucleophilic carbene organocatalysis. Our procedure makes notable improvements to current practice, including the elimination of solvent waste and an "18-fold reduction of reaction time." We have demonstrated that microwave heating provides yields comparable to current practice in 5 min, using significantly less power (70 W) than traditional heating methods. The highest yields were obtained with N,N'-(2,4,6-trimethylphenyl)imidazolium chloride (IMes·HCl) as the catalyst and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as the base. Our procedure has been successfully executed by multiple cohorts of organic chemistry undergraduates, both with and without pandemic social distancing constraints.
Descriptors: Science Instruction, Organic Chemistry, Laboratory Experiments, Laboratory Procedures, Reaction Time, Wastes, Hazardous Materials, Heat, Comparative Analysis, Undergraduate Students, Pandemics, COVID-19, Barriers
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 - Research
Education Level: Higher Education; Postsecondary Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A
Grant or Contract Numbers: N/A