An information-rich experiment in organic chemistry for chemistry majors: Synthesis of 1-(halobenzyl)-4-(halophenoxy)methyl triazoles

CHED 87

Robert N. Hanson, r.hanson@neu.edu, Ian Kendrick, Danielle Falcone, falcone.da@neu.edu, John Bottomy, and Graham Jones. Department of Chemistry and Chemical Biology, Northeastern University, 360 Huntington Avenue, Boston, MA 02115
The culmination of our organic chemistry laboratory for chemistry majors involves undertaking the synthesis and characterization of novel compounds with potentially interesting biological activity. Because the target compounds have not been previously reported, a survey of the literature is initially required to ascertain the general synthetic procedures. Experimental design is critical to ensure that the reactions, work up and characterization can be accomplished within a single 5 hour timeframe per step. In the first half of experiment we devised, half of the class would prepare a series of four (substituted)benzyl azides while the other half would prepare (substituted)phenyl propargyl ethers. In the second half of the experiment, each group would take one benzyl azide and one propargyl ether to perform the Huisgen [3+2] cycloaddition (click) reaction. In this presentation we will describe our modifications in experimental design that would allow the reactions to be done safely within the time constraints imposed by the class and to permit a rapid purification and characterization of the products.
 

General Posters
7:30 PM-9:30 PM, Sunday, August 19, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Chemical Education

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007