The accreditors of this session require that you periodically check in to verify that you are still attentive.
Please click the button below to indicate that you are.
3557499
Rescuing student learning outcomes from the organic waste container
Session: Undergraduate Research Posters: Organic Chemistry:
A perennial frustration for students and faculty alike is the “make it and dump it” cycle characteristic of some second-year undergraduate organic chemistry laboratories. We seek to change this paradigm by rescuing student products and by-products from the waste container and using them to extend student learning outcomes either in an enriched second-year experience or in an upper-division undergraduate course. This poster demonstrates the new paradigm in a classic Claisen-Schmidt condensation, the base-catalyzed formation of 4-methoxychalcone (p-anisalacetophenone) from 4-methoxybenzaldehyde (p-anisaldehyde) and acetophenone. One appeal of this reaction is that the desired product precipitates from the reaction mixture and is readily isolated by vacuum filtration. The filtrate is typically discarded as waste. However, analysis of this filtrate by thin-layer chromatography on silica gel plates resolved with 4:1 hexanes:ethyl acetate reveals, in addition to the expected 4-methoxychalcone (Rf = 0.54), a prominent peak at a lower Rf value (0.41). Students may be set to the task of performing the isolation of this unknown species and elucidating its structure using NMR spectroscopy. In addition, students may propose a mechanism for the formation of this by-product that turns out to be a Michael adduct. In summary, a by-product normally sent to the waste container is repurposed, with the net effect of extending the learning outcomes of the laboratory. A new protocol will be presented, suitable for either the second-year or upper-division undergraduate laboratory.
Patchoulol synthase catalyzes the conversion of farnesyl diphosphate, a linear compound, into patchouli alcohol, which is a tricyclic tertiary alcohol that provides the characteristic fragrance note of patchouli oil…
Deuteration is a well-established technique for the investigation of molecular structure and function, yet this chemistry is underrepresented in the undergraduate curriculum…
This conference presentation proposes to illustrate that achievement is borne of failure, with stories shared in the hopes of encouraging, supporting, and affirming our work to emphasize the invaluableness of resilience…
Sesquiterpene cyclases catalyze the conversion of farnesyl diphosphate, a linear compound, into a dizzying array of molecular structures including monocyclic, bicyclic, tricyclic, and even tetracyclic products…