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

Author(s): 
Sloop, J.C.; Anagho, L.; Coppock, P.; Giles, G.; Park, S.; Pennington, R.; Pursell, D.; Rudd, G.; Tsoi, M.Y.
Author Affiliation: 
Georgia Gwinnett College
Journal: 
Journal of Laboratory Chemical Education
Year: 
2013
Volume: 
3
Pages: 
39-44
Abstract: 

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.

Abstract reproduced with permission. Copyright: 
Scientific & Academic Publishing
Organic topics: 
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