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  Home > JCE Print > Journal of Chemical Education > Issues > 1997  > July  >
In the Laboratory
The Microscale Laboratory
Conversion of an Alkyl Chloride to a Bromide (or Vice-Versa) by Homogeneous Nucleophile Exchange
Roger C. Hahn
Cover
July 1997
Vol. 74 No. 7
p. 836
Abstract
Quaternary salt-catalyzed bromide-chloride exchange between alkyl chlorides and alkyl bromides is used to demonstrate effects of temperature, catalyst, concentration, and substrate structure on reaction rates and chemoselectivity. Microscale reactions are monitored by GC analysis. In one experiment, a mixture of 1-chloropentane and 1-bromoheptane or of 1-bromopentane and 1-chloroheptane is equilibrated to form a mixture of all four compounds. In another experiment, bromide-chloride exchange between 1, 3-dichlorobutane and a large excess of 1-bromobutane demonstrates the greater SN2 reactivity of a primary chloride relative to that of a secondary chloride.
More Information
*  Citation
 Hahn, Roger C. . J. Chem. Educ. 1997 74 836.
*  Keywords
 Laboratory Instruction, Organic Chemistry, Catalysis, Equilibrium, Kinetics, Microscale
*  History
 Created:
Last Updated:		 July 28, 1999
June 23, 2005
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