Exploring Electrosynthesis: Bulk Electrolysis and Cyclic Voltammetry Analysis of the Shono Oxidation
Abstract
As electrochemistry continues to gain broader acceptance and use within the organic chemistry community, it is important that advanced undergraduate students are exposed to fundamental and practical knowledge of electrochemical applications for chemical synthesis. Herein, we describe the development of an undergraduate laboratory experience that introduces synthetic and analytical electrochemistry concepts to an advanced organic chemistry class. Experiments focus on the electrooxidative α-functionalization of carbamates, more generally known as the Shono oxidation, and include cyclic voltammetry analysis of two cyclic carbamates and a constant current bulk electrolysis reaction. Here, the exercise offers students an authentic experience in organic electrochemistry, lays a practical and theoretical foundation for future engagement with concepts in electrochemistry and redox chemistry, and strengthens fundamental organic chemistry skills.
- Authors:
-
[1];
[1];
[1];
[1];
[2]
- Univ. of Wisconsin, Madison, WI (United States)
- Univ. of MIssouri, Kansas City, MO (United States)
- Publication Date:
- Research Org.:
- Great Lakes Bioenergy Research Center (GLBRC), Madison, WI (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Biological and Environmental Research (BER)
- OSTI Identifier:
- 1893530
- Grant/Contract Number:
- SC0018409; FC02-07ER64494
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Journal of Chemical Education
- Additional Journal Information:
- Journal Volume: 99; Journal Issue: 9; Journal ID: ISSN 0021-9584
- Publisher:
- American Chemical Society
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Upper-Division Undergraduate; Laboratory Instruction; Organic Chemistry; Electrochemistry; Hands-On Learning/Manipulatives; Problem Solving/Decision Making; Computational Chemistry; NMR Spectroscopy; Electrodes; Electrolysis; Oxidation; Students
Citation Formats
Goes, Shannon L., Nutting, Jordan E., Hill, Nicholas J., Stahl, Shannon S., and Rafiee, Mohammad. Exploring Electrosynthesis: Bulk Electrolysis and Cyclic Voltammetry Analysis of the Shono Oxidation. United States: N. p., 2022.
Web. doi:10.1021/acs.jchemed.2c00221.
Goes, Shannon L., Nutting, Jordan E., Hill, Nicholas J., Stahl, Shannon S., & Rafiee, Mohammad. Exploring Electrosynthesis: Bulk Electrolysis and Cyclic Voltammetry Analysis of the Shono Oxidation. United States. https://doi.org/10.1021/acs.jchemed.2c00221
Goes, Shannon L., Nutting, Jordan E., Hill, Nicholas J., Stahl, Shannon S., and Rafiee, Mohammad. Tue .
"Exploring Electrosynthesis: Bulk Electrolysis and Cyclic Voltammetry Analysis of the Shono Oxidation". United States. https://doi.org/10.1021/acs.jchemed.2c00221. https://www.osti.gov/servlets/purl/1893530.
@article{osti_1893530,
title = {Exploring Electrosynthesis: Bulk Electrolysis and Cyclic Voltammetry Analysis of the Shono Oxidation},
author = {Goes, Shannon L. and Nutting, Jordan E. and Hill, Nicholas J. and Stahl, Shannon S. and Rafiee, Mohammad},
abstractNote = {As electrochemistry continues to gain broader acceptance and use within the organic chemistry community, it is important that advanced undergraduate students are exposed to fundamental and practical knowledge of electrochemical applications for chemical synthesis. Herein, we describe the development of an undergraduate laboratory experience that introduces synthetic and analytical electrochemistry concepts to an advanced organic chemistry class. Experiments focus on the electrooxidative α-functionalization of carbamates, more generally known as the Shono oxidation, and include cyclic voltammetry analysis of two cyclic carbamates and a constant current bulk electrolysis reaction. Here, the exercise offers students an authentic experience in organic electrochemistry, lays a practical and theoretical foundation for future engagement with concepts in electrochemistry and redox chemistry, and strengthens fundamental organic chemistry skills.},
doi = {10.1021/acs.jchemed.2c00221},
journal = {Journal of Chemical Education},
number = 9,
volume = 99,
place = {United States},
year = {Tue Aug 02 00:00:00 EDT 2022},
month = {Tue Aug 02 00:00:00 EDT 2022}
}
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