Advanced organic chemistry laboratory at Stanford emphasizes techniques in synthesis and spectroscopy with a focus on organometallic chemistry and catalysis. In accord with this objective, a new laboratory was developed in which students explored a rhodium-catalyzed C-H amination reaction on simple hydrocarbon substrates.  This laboratory offered students a first-hand look at modern catalytic methods for fine-chemical synthesis, and provided students with the opportunity to conduct reactions from the initial set-up through product isolation by chromatography. The second part of the lab involved performing competition experiments to compare the relative reactivity of ethyl benzene against para-substituted ethyl benzenes.  Reaction outcomes were analyzed and quantitated using NMR analysis against an internal standard. Data obtained from these experiments allowed for construction of a Hammett plot, and a discussion of reaction mechanism and the influence of electron-donating and electron-withdrawing groups on substrate reactivity. This presentation will describe the design, implementation, and take home lessons of this undergraduate teaching lab.

Modern C-H oxidation catalysis as an advanced organic chemistry lab

248th National Meeting (2014)

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