Casting away the cookbook: Bringing independent experimental design into an organic chemistry laboratory experiment

CHED 390

Paul A. Bonvallet, pbonvallet@wooster.edu and Judith C. Amburgey-Peters, jamburgey@asc.wooster.edu. Department of Chemistry, The College of Wooster, 943 College Mall, Wooster, OH 44691
A sophomore organic laboratory experiment has been redesigned to introduce the fundamentals of independent experimental design at an early stage in the undergraduate curriculum. As part of a capstone laboratory practical exercise in the first semester, each student selected an isomer of methylcyclohexanol from which to synthesize a specific target alkene via an acid-catalyzed dehydration reaction. Each student individually designed, executed, and evaluated their experimental procedure using only their notebook entries from earlier in the semester. This experiment reinforces the classroom concepts of retrosynthetic analysis, mechanism, and E1 elimination as well as the practical application of distillation, extraction, chromatography, and spectroscopic characterization to a genuine scientific problem in which the outcome is not predetermined. Realizing that the E1 reaction provides a mixture of alkenes via carbocation rearrangements, the students also proposed a new and more effective synthetic scheme from their current work in the classroom.