For students at the University of Colorado Denver campus, the honors organic synthesis lab is the culmination of multiple semesters of undergraduate chemical education. The lab consists of an independent research project which requires the utilization of student’s chemical intuition, advanced laboratory techniques, collaboration with peers, as well as introducing students to the finer points of research and literature searches. An example project required a three step synthesis in order to investigate the para-substituent effect on the regio-selectivity of bromination across vinyl systems. The synthesis utilized many benzaldehyde derivatives where substituents varied in their electron donating/withdrawing nature. The first step consisted of the formation of homoallylic alcohols from their corresponding carbonyl compounds, an allylhalide, and various organometallic catalysts. The second synthetic step resulted in the formation of a vinyl system by performing an adapted base catalyzed dehydration of the aforementioned alcohols. Finally, the vinyl system was brominated by elemental bromine and characterized by 1H NMR and mass spectroscopy. This project not only allowed students to gain insight into organometallic chemistry, but required students to development procedures to obtain the desired vinyl intermediates based on the substituent present. The project also facilitated proficiency in complex characterizations by 1H NMR and mass spectroscopy

Introductory investigation into the substituent effect on regio-selectivity of bromination across vinyl systems: A culmination of undergraduate chemical education

249th National Meeting (2015)

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