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 [...]
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 [...]
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 the experiment [...]
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 current [...]
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 [...]
