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 the experiment involves the understanding of all three mechanisms mentioned previously and how they may compete with each other. In other words, it is a simple experiment that demands a rather involved interpretation of results.

3) It shows that textbooks “rules” such as the Zaitzev’s rule in this case, are not necessarily rules as such, but rather astute observations of general trends that can vary experimentally depending on the reactant and the reaction conditions.

4) Analytically, we are observing/measuring the presence of 3 known methylcyclohexene and methylene cyclohexane products that can be separated and detected by Gas Chromatography. I believe that the product mixtures can also be analyzed by NMR.

5) The reaction lends itself to an inquiry format that involves the study different reactants and reaction conditions on the ratio of products. In fact, this experiment, in my opinion, is an ideal candidate for a multi-institution collaborative study that combines and interprets student data.

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