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Integrating Bifunctional Catalysis into Senior Undergraduate Organic Chemistry: A Laboratory Experiment on the Asymmetric Michael Addition Reaction

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Title: Integrating Bifunctional Catalysis into Senior Undergraduate Organic Chemistry: A Laboratory Experiment on the Asymmetric Michael Addition Reaction
Language: English
Authors: Lei Li, Fu Pi, Gu Zhan (ORCID 0000-0002-5263-8263), Qian-Qian Yang (ORCID 0000-0003-2890-1532), Ying-Chun Chen (ORCID 0000-0003-1902-0979), Zhi-Chao Chen, Wei Du (ORCID 0000-0003-4162-1471)
Source: Journal of Chemical Education. 2024 101(8):3480-3484.
Availability: 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
Peer Reviewed: Y
Page Count: 5
Publication Date: 2024
Document Type: Journal Articles
Reports - Research
Education Level: Higher Education
Postsecondary Education
Descriptors: Undergraduate Students, College Science, Organic Chemistry, Laboratory Experiments, Spectroscopy, Laboratory Training, Science Process Skills
DOI: 10.1021/acs.jchemed.4c00510
ISSN: 0021-9584
1938-1328
Abstract: An organic chemistry experiment designed for senior undergraduates focuses on bifunctional catalysis, a critical yet often omitted topic at the undergraduate level, but essential for advanced studies in chemistry. By utilization of a tertiary amine-thiourea catalyst in the asymmetric Michael addition reaction, the experiment showcases the superiority of bifunctional catalysis over traditional monofunctional approaches. Comprehensive training in designing control experiments, performing flash chromatography, and analyzing results with NMR and HPLC techniques equip students with modern synthetic skill sets. This experiment features easy operation and a relatively short time (4.5h, including 2-2.5 h reaction time). More importantly, it bridges the educational gap in understanding advanced catalytic mechanisms and techniques in organic chemistry.
Abstractor: As Provided
Entry Date: 2024
Accession Number: EJ1437997
Database: ERIC
FullText Text:
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  Data: Integrating Bifunctional Catalysis into Senior Undergraduate Organic Chemistry: A Laboratory Experiment on the Asymmetric Michael Addition Reaction
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  Data: <searchLink fieldCode="AR" term="%22Lei+Li%22">Lei Li</searchLink><br /><searchLink fieldCode="AR" term="%22Fu+Pi%22">Fu Pi</searchLink><br /><searchLink fieldCode="AR" term="%22Gu+Zhan%22">Gu Zhan</searchLink> (ORCID <externalLink term="https://orcid.org/0000-0002-5263-8263">0000-0002-5263-8263</externalLink>)<br /><searchLink fieldCode="AR" term="%22Qian-Qian+Yang%22">Qian-Qian Yang</searchLink> (ORCID <externalLink term="https://orcid.org/0000-0003-2890-1532">0000-0003-2890-1532</externalLink>)<br /><searchLink fieldCode="AR" term="%22Ying-Chun+Chen%22">Ying-Chun Chen</searchLink> (ORCID <externalLink term="https://orcid.org/0000-0003-1902-0979">0000-0003-1902-0979</externalLink>)<br /><searchLink fieldCode="AR" term="%22Zhi-Chao+Chen%22">Zhi-Chao Chen</searchLink><br /><searchLink fieldCode="AR" term="%22Wei+Du%22">Wei Du</searchLink> (ORCID <externalLink term="https://orcid.org/0000-0003-4162-1471">0000-0003-4162-1471</externalLink>)
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  Data: 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
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  Data: 10.1021/acs.jchemed.4c00510
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  Data: 0021-9584<br />1938-1328
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  Data: An organic chemistry experiment designed for senior undergraduates focuses on bifunctional catalysis, a critical yet often omitted topic at the undergraduate level, but essential for advanced studies in chemistry. By utilization of a tertiary amine-thiourea catalyst in the asymmetric Michael addition reaction, the experiment showcases the superiority of bifunctional catalysis over traditional monofunctional approaches. Comprehensive training in designing control experiments, performing flash chromatography, and analyzing results with NMR and HPLC techniques equip students with modern synthetic skill sets. This experiment features easy operation and a relatively short time (4.5h, including 2-2.5 h reaction time). More importantly, it bridges the educational gap in understanding advanced catalytic mechanisms and techniques in organic chemistry.
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