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  Home > JCE Print > Journal of Chemical Education > Issues > 1997  > October  >
In the Laboratory
Kinetic versus Thermodynamic Control in the Dehydration of 2-Methylcyclopentanol: A Two-Part Laboratory Experiment Utilizing the Gignard Reaction and GC-MS
Thomas Poon, Bradford P. Mundy, Jean McIntyre, Lesley Woods, Frank G. Favaloro Jr., and Christina A. Goudreau
Department of Chemistry, Colby College, 5750 Mayflower Hill, Waterville, ME 04901-8857
Cover
October 1997
Vol. 74 No. 10
p. 1218
Abstract
A two part organic laboratory experiment illustrating the Grignard reaction and the concept of kinetic versus thermodynamic control is described. The reaction of phenylmagnesium bromide with 2-methylcyclopentanone yileds an unsymmetrical benzylic alcohol which can be dehydrated using toluenesulfonic acid to give predominately the less substituted alkene. Application of heat to the reaction mixture over a period of two hours reverses the trend to give the more substituted alkene as the major product in 91% relative yield. The dehydration is monitored by GC/MS and the experiment can be performed using macro and microscale techniques.
More Information
*  Citation
 Poon, Thomas; Mundy, Bradford P.; MnIntyre, Jean; Woods, Lesley; Favaloro Jr.; Frank G.; Goudreau, Christina A. J. Chem. Educ. 1997 74 1218.
*  Keywords
 Laboratory, Organic Chemistry, Chromatography, Organic Synthesis, and Time-Dependent Reactions
*  History
 Created:
Last Updated:		 July 27, 1999
June 23, 2005
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