CASPiE the Friendly Ghost

The “Center for Authentic Science Practice in Education” (CASPiE), as a part of the NSF’s Undergraduate Research Centers efforts received a 4-year, 2.5 million dollar grant starting August 15th, 2004 to introduce research rich experiences to first and second year college students. As part of their dissemination requirements they are holding a series of workshops […]

Dehydration of Methylcyclohexanols Part IV

I want to pursue point #5 further by first grappling with the current literature concerning the “Evelyn Effect.” The JCE article by David Todd, “The Dehydration of 2-Methylcyclohexanol Revisited: The Evelyn Effect” observes a kinetic effect that can be explained by proposing that in a mixture of cis/trans 2-Methylcyclohexanol the cis isomer reacts much faster […]

Dehydration of Methylcyclohexanols III

There are several advantages of studying the dehydration of methylcyclohexanols in the first semester of Organic Chemistry. 1) The experiment involves reactions that are typically studied during first semester: E1, E2, and the 1,2-hydride shift. It is a time-tested protocol that has been run in hundreds of labs by thousands of students. 2) Analysis of […]

Dehydration of Methylcyclohexanols II

As predicted from the Journal of Chemical Education articles, three methylcyclohexene products were observed. Their relative abundance measured by peak height was 80, 16, and 4%. The alkene products represented by these peaks apparently correspond to 1-methycyclehexene, 3-methycyclehexene, and methylene cyclohexane respectively. The dehydration of 4-methylcyclohexanol produce two products, that can be distinguished by our […]

Dehydration of Methylcyclohexanols I

A common Sophomore Organic Chemistry laboratory experiment that has great potential for further research is the acid catalyzed dehydration of simple alcohols. The classic dehydration of 2-methylcyclohexanol experiment that was introduced in Journal of Chemical Education in 1967 Taber(1967)JCE:44,p620. The rather simple procedure of distilling an alcohol with an aqueous acid has spawned several investigations […]