Conformational Analysis, Modeling, Stereochemistry and Optical Activity of Cyclohexane Derivatives

Cyclohexane derivative stability is investigated using a combination of molecular modeling kits, conformational analysis, computational chemistry and polarimetry. Students build selected mono- and disubstituted cyclohexanes using model kits, predict the most stable conformation and calculate conformational equilibria. Students also construct cis-1,2-dimethylcyclohexane and trans-1,2-dimethylcyclohexane using the Avogadro computational chemistry program, optimize the structures and confirm the lowest energy conformations. Students utilize a polarimeter to measure the optical activity of several unknown cyclohexane derivatives and identify them from a list of possible (±) menthol and (±) carvone stereoisomers.