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Kinetic versus Thermodynamic Control in the Dehydration of 2-Methylcyclopentanol: A Two-Part Laboratory Experiment Utilizing the Gignard Reaction and GC-MS

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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

J. Chem. Educ., 1997, 74 (10), p 1218

DOI: 10.1021/ed074p1218

Publication Date (Web): October 1, 1997

Section:

History, Education, and Documentation

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.

Keywords (Audience):

Upper-Division Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Chromatography

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This article has been cited by 3 ACS Journal articles (3 most recent appear below).

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- Diastereoselective Synthesis of (+/-)-1,2-Diphenyl-1,2-propanediol. A Discovery-Based Grignard Reaction Suitable for a Large Organic Lab Course
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  Journal of Chemical Education2001 78 (4), 531
  We have developed an undergraduate organic laboratory experiment that probes the diastereoselectivity of the reaction between a Grignard reagent and a common, inexpensive α-chiral ketone. Students isolate a single diastereomer of (+/-)-1,2-diphenyl-1,2-...
  Abstract | Hi-Res PDF | PDF w/ Links