CHED 186 |
| The dehydration of 2-methylcyclohexanol and 4-methylcyclohexanol in acid is commonly used as an experiment in organic chemistry laboratories. An interesting complication is the occurrence of the Evelyn Effect, which is the phenomenon of changing product ratios as the reaction proceeds. Our previous work focused on combining experimental results with molecular modeling to conclude which mechanisms could take place during this dehydration and account for the observance of the Evelyn Effect. This report adds results when the reaction is run with pure isomers and investigates the possibility of reprotonation as an alternative to rearrangement. As before the two mechanisms (E1 vs. E2) were found to be competitive and both operative. The mechanism preference is principally determined by the stereochemistry of the conformations of the methylcyclohexanols. |
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General Posters
7:30 PM-9:30 PM, Sunday, March 25, 2007 Hyatt Regency Chicago -- Riverside Center, Poster
Division of Chemical Education |