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ERIC Number: EJ918437
Record Type: Journal
Publication Date: 2010-Jul
Pages: 4
Abstractor: As Provided
Reference Count: 5
ISSN: ISSN-0021-9584
Rearrangements of Allylic Sulfinates to Sulfones: A Mechanistic Study
Ball, David B.; Mollard, Paul; Voigtritter, Karl R.; Ball, Jenelle L.
Journal of Chemical Education, v87 n7 p717-720 Jul 2010
Most current organic chemistry textbooks are organized by functional groups and those of us who teach organic chemistry use functional-group organization in our courses but ask students to learn organic chemistry from a mechanistic approach. To enrich and extend the chemical understanding and knowledge of pericyclic-type reactions for chemistry majors, we introduced into the chemistry-major organic chemistry laboratory a discovery-based, collaborative experiment on the thermal rearrangement of allylic sulfinates to thermodynamically more stable allylic sulfones. The sensitivity of the sulfinate-sulfone rearrangement pathway to substrate structure in this experiment allows the students to investigate the structure-reaction relationship of organic chemistry. Students also encounter the chemical and spectral properties of diasteromers and the necessity of deuterium labeling for product identification. (Contains 8 notes, 2 tables, 1 figure and 4 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 - Descriptive
Education Level: Higher Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A