Kinetic vs. thermodynamic control in the dehydration of 2-Methylcyclopentanol

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Title: Kinetic vs. thermodynamic control in the dehydration of 2-Methylcyclopentanol
Author: Poon, Thomas; Mundy, Bradford; McIntyre, Jean; Woods, Lesley; Favaloro, Frank; Goudreau, Christina; Collison, Christina
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.
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Date: 1997-10

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