- 1 -Organic FantasiaHalloween Skit Production of Prof. Barany’s Fall 2003 Chemistry 2301 ClassCast:Ann Stimmel — concept; musical arranger; nucleophile (bassoon)Oana Lungu — script; chiral carbonBecky Loper — leaving group (saxophone)Danielle Gaetz and Matt Kuehl — substituentsKristine Domingo — narratorTamar Meyers — video; program notesMusic by Paul Dukas (1865-1935), “The Sorcerer’s Apprentice” (1897) [as adapted forWalt Disney’s 1940 full-length animated musical cartoon movie “Fantasia”]The video starts with Kristine, the narrator, explaining the sequence of events.Next Professor Barany stalls by telling some jokes, including the scientifically provenfunniest joke, while the student thespians make last-minute preparations.Once the production starts, we see Ann playing the bassoon, acting as thenucleophile and approaching Oana, the chiral carbon. Oana is wearing red and has anewspaper on her head representing one of the four substituents (to achieve chirality, thefour substituents need to be different). Danielle and Matt represent two moresubstituents, and Becky the saxophone player is in the back and serves as the leavinggroup. As Ann begins attacking Oana from one side, Becky begins to leave from theother side. Once Ann has fully bonded to Oana, Becky has been forced to completelyleave (not obvious from Tamar’s camera angle), demonstrating how SN2 reactions occurvia backside attack. Watch carefully to notice the movements of Danielle and Matt,demonstrating inversion.In the second act, Ann once again acts as the nucleophile (but recall, most goodnucleophiles are also strong bases). This time, Ann is unable to carry out backside attackdue to steric hindrance (watch how she is aggressively pushed away by the bulky otherstudents). In desperation, Ann removes Danielle’s baseball cap, which represents aproton. Becky again leaves, and Danielle puts both arms on Oana indicating formation ofa double bond. This is known as an E2 elimination reaction, and just like SN2, it isconcerted (the students in this class heard quite a concert through this production). Forcompleteness, note that Ann who is now wearing Danielle’s cap is a protonated base(positive charge) and forms an ionic bond with Becky the leaving group (negativecharge).A short coda illustrates the concept of regiochemistry. In another E2 reaction thatoccurs because SN2 is unlikely on account of steric hindrance, Ann grabs Matt’s stockingcap, a different proton. Now, it is Matt’s turn to put both arms on Oana, showingformation of a different double bond which means a different product has been created.-At the end of the video, the cast members are introduced, and take their individualand group bows. Prof. Barany points out a couple of special guests from the ChemistryDepartment team who took time out from their busy schedules to watch the show.For notes about the music, please see:http://www.musicweb.uk.net/Programme_Notes/dukas_sorcerer.htmand http://www.galvestonsymphony.org/composers/Dukas_Sorcerer.htmlFor information about the Disney film, see: http://imdb.com/title/tt0032455/For more on the scientific search for the world’s funniest joke, see:http://www.laughlab.co.uk/, which gets you to http://www.laughlab.co.uk/winner.htmlFile is 155 MB, and plays on Quick Time or a related program.Running time, approximately 6
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