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.
Publication Date
1997
Document Type
Article
Department, Program, or Center
School of Chemistry and Materials Science (COS)
Recommended Citation
Journal of Chemical Education 74N10 (1997) 1218-1220
Campus
RIT – Main Campus
Comments
This article may be accessed on the publisher's website (additional fees may apply) at: http://jchemed.chem.wisc.edu/Journal/Issues/1997/Oct/abs1218.html Support through a Bristol-Myers Squibb Award of Research Corporation is gratefully acknowledged. Paul Schupf and the National Science Foundation are acknowledged for their support of the Colby Chemistry Computational Facilities. T.P. and B.P.M. gratefully acknowledge support from the Camille and Henry Dreyfus Foundation.ISSN:0021-9584 Note: imported from RIT’s Digital Media Library running on DSpace to RIT Scholar Works in February 2014.