This paper details an experiment which serves as an introduction to organic laboratory research. The reaction is the dehydration of a cis, trans mixture of 2-methylcyclohexanols. At intervals of times the reactant mixture is sampled for the cis and trans reactants. At those same intervals of times the receiver flasks of product cyclohexanes being collected are changed, such that sequential fractions of material are obtained.

To explore the effects of fluorine substitution on the highly strained [2.2.2]propellane skeleton, a new representative of this ring system, perfluorotricyclo[2.2.2.01,4]octan-2-one ethylene ketal, was prepared by a rapid and quantitative [2+2] cycloaddition to the strained alkene perfluorobicyclo[2.2.0]hex-1(4)-ene. The propellane displays impressive thermal stability, and the vulnerable C-C bond joining the bridgeheads is very resistant to attack by electrophilic reagents. On the other hand, that electron-deficient bond is cleaved quickly at room temperature by a variety of nucleophiles and mild reducing agents. The behavior of this compound contrasts dramatically with that of the only known [2.2.2]propellane lacking fluorine substituents.

A take-home exam is presented. It is based on an experiment that studied the dehydration of a cis-trans mixture of 2-methylcyclohexanols. The "givens" are the idealized kinetic and regiochemical data. The focus is strictly on the mathematics, not the experimental details. The goal is to calculate six specific rate constants using a little ingenuity and some fundamental mathematics, to show that the Saytzeff elimination rule is followed for the dehydration of each of the two reactant isomeric alcohols.

No abstract

An experiment with two different "conclusions" to be reached: one for liberal arts students, one for science students.