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Kathleen S. Rein
Department of Chemistry and Biochemistry
Florida International University
Hall of Fame or Shame?: The Chemistry of a Designer Drug

This case study involves the structure elucidation of the designer steroid tetrahydrogestrinone or THG by the UCLA Olympic Analytical Laboratory. This steroid was allegedly synthesized by BALCO organic chemist Patrick Arnold and was allegedly used by the famous baseball player, Barry Bonds. Students will learn the logic of structure elucidation and the techniques used by chemists to determine molecular structure. Students are asked to make predictions with respect to the changes in the proton NMR upon conversion of gestrinone to tetrahydrogestrinone. The case was originally developed for use in an organic chemistry survey course for non-chemistry majors, but could also be used in a general/organic/biochemistry survey course or modified for use in an organic chemistry sequence. Two sets of questions are included; the first is appropriate for students who are able to interpret skeletal structures and have studied addition reactions to alkenes, including hydrogenations, while the second is more advanced. Students will need access to a 2004 paper by D.H. Catlin et al. published in Rapid Communications in Mass Spectrometry (not included in this case).

Katie‚Äôs Day at the Spa: The Chemistry of Nail Polish

This case study examines the chemistry of nail polish. Traditional nail polish is made from nitrocellulose whereas the new process of shellac manicure involves acrylic polymer. The "polish" is actually a mixture of methylmethacrylate and oligomers. The mixture is applied to the nail and exposed to UV light to "cure" the polish. The process is a free radical polymerization of methyl methacrylate using benzoyl peroxide as the free radical initiator, which is activated by UV light. The case provides an example of the central role that organic chemistry plays in many of the consumer products that students encounter on a daily basis, how these consumer products are derived, and how their chemical and physical properties lend them to specific applications. Originally developed for an organic chemistry survey course for non-chemistry majors, the case could also be used in a general/organic/ biochemistry survey type of course or modified for use in the first or second semester of a two semester organic chemistry sequence.