Integrating iSpartan into a Classic Organic Chemistry Laboratory Experiment

Abstract

The dehydration of 2- or 4-methylcyclohexanol to obtain isomers of methylcyclohexene is a classic organic chemistry experiment. Students perform a distillation, collecting samples to analyze the progress of the reaction. The reaction produces a major product that can be explained on the basis of the regiochemistry of the π bond formation for the α–β elimination process. Minor products can be attributed to the possible rearrangement of the carbocation through a hydride shift. We have added computational analysis to this classic experiment to help students understand alkene stability. The experiment was performed early in the sophomore organic chemistry laboratory, before students were introduced to the mechanistic perspectives that govern the reaction. The iSpartan analysis of the possible methylcyclohexene products combined with gas chromatography data provides students with an inquiry-based laboratory experience. A novice student can analyze the computational information about the products to determine the trend in product stability and determine if a double-bond is formed at an unexpected location in the molecule. The integration of computational tools provides more information to students than performing the experiment in isolation.