Regioselective bromination of aromatic ketones: Discovery in the organic chemistry laboratory

CHED 1843

C. Eric Ballard, eballard@ut.edu1, John A. Struss2, Scott E. Allen1, and L. Michael Carastro1. (1) Department of Chemistry and Physics, University of Tampa, 401 West Kennedy Boulevard, Campus Box U, Tampa, FL 33606-1490, (2) Department of Chemistry & Physics, University of Tampa, 401 W. Kennedy Blvd., Tampa, FL 33606
The reactivities of two aromatic ketones with N-bromosuccinimide were examined. The less electron-rich ketone selectively reacted alpha to the carbonyl group while the more electron-rich ketone brominated exclusively on the aromatic ring. Students analyzed their products by 1H NMR spectroscopy to determine which products they made. Based on the contrasting results for the two substrates, the students were asked to explain the difference in reactivity. In this sense, the experiment offered an element of “discovery” for the students. In addition, since the reactions were conducted without organic solvent, principles of green chemistry and sustainable development could be introduced. The results of implementing this experiment during one semester with six sections (about 100 students) of organic laboratory will be discussed.

 

Bringing Research to the Undergraduate Course Curriculum
1:00 PM-4:05 PM, Thursday, March 29, 2007 McCormick Place North -- Room N227B, Level 2, Oral

Division of Chemical Education

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007