ERIC Number: EJ918437
Record Type: Journal
Publication Date: 2010-Jul
Pages: 4
Abstractor: As Provided
ISBN: N/A
ISSN: ISSN-0021-9584
EISSN: N/A
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.)
Descriptors: Organic Chemistry, Science Instruction, Scientific Concepts, Science Laboratories, Majors (Students), College Science, Science Experiments, Thermodynamics, Cooperative Learning, Molecular Structure
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 - Descriptive
Education Level: Higher Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A
Grant or Contract Numbers: N/A