GC/MS analysis of the dehydration of 2-methylcyclohexanol

CHED 403

Evan C. Klein, evan.klein@duke.edu, George R. Dubay, george.dubay@duke.edu, and Holly L. Sebahar. Department of Chemistry, Duke University, Box 98464, Durham, NC 27708
The addition of GC/MS analysis to the products of an acid catalyzed dehydration of 2-methylcyclohexanol exposed the students to two new laboratory techniques and allowed for a more complete characterization of the obtained product. To analyze the sample, each of the 250 groups of undergraduate organic chemistry students diluted their sample in dichloromethane and had it analyzed by a GC/MS using an automated sampler. While previous GC analyses for this lab had indicated the presence of only 1-methylcyclohexene and 3-methylcyclohexene, by using a narrow bore fused silica capillary column methylenecyclohexane and ethylidenecyclopentane were also identified in the product mixture.