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The Chemical Educator

ISSN: 1430-4171 (electronic version)

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Abstract Volume 19 (2014) pp 247-251

Fluorous Solvents for Slow Chlorination and Bromination of Alcohols

Elisabeth Rukmini Goei, Susan Sonchik Marine*,‡, Richard T. Taylor, Angela French, Amanda E. Stewart

Department of Chemistry and Biochemistry, Miami University, 651 East High St.; Oxford, OH 45056; Department of Chemistry and Biochemistry, Miami University Middletown, 4200 North University Blvd.; Middletown, OH 45042, mariness@MiamiOH.edu
Received April 24, 2014. Accepted June 28, 2014.

Published: 14 August 2014

Abstract. By constructing a fluorous liquid membrane between two organic phases, one can mediate the mixing of reagents between the phases. Curran [1] showed that alcohols could be converted to chlorides by the action of thionyl chloride through the fluorous phase. Most of Curran’s examples were alcohols incapable of rearrangement or elimination. In a discovery-based experiment, a sophomore organic chemistry class and a chemical technology class examined this reaction using a diverse set of alcohols. The products were analyzed by GC/MS, and the product ratios could be related to the competition between substitution, elimination, and rearrangement. Similar conversions of alcohols to bromides using SOBr2 and PBr3 were also undertaken. The experiment provided an introduction to fluorous chemistry and allowed students to explore the relationship between reaction mechanisms.

Key Words: Laboratories and Demonstrations; organic chemistry

(*) Corresponding author. (E-mail: mariness@MiamiOH.edu)

Article in PDF format (242 KB) HTML format

Supporting Materials:

Two supporting files are available. Student Handout for an Undergraduate Organic Laboratory: “Fluorous Chemistry Lab” and Student Handout for a Chemical Technology Laboratory: “Triphasic Chlorination of Alcohols”e (176 KB).



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