The Passerini multicomponent reaction is a chemical reaction in which a carboxylic acid, an aldehyde, and an isocyanide react to form an a-acyloxy amide.  Recent findings suggest that the Passerini reaction can be carried out in water instead of traditional organic solvents, such as methylene chloride or MeOH.   In fact, the rate of this reaction is accelerated when carried out in water.  In an attempt to design a green, guided-inquiry, collaborative experiment for the teaching lab, we have carried out a series of Passerini reactions in water while varying  electron donating and withdrawing substituents on benzoic acid and benzaldehyde.  The various combinations of reactants offer a valuable and environmentally friendly way to allow students in an advanced undergraduate chemistry lab course to identify Passerini products through various spectroscopic techniques. The lab has been designed to be a guided-inquiry, puzzle experiment that students work on in teams.  Experimental procedures, spectroscopic data, and teaching results will be presented.

Green, guided-inquiry, collaborative puzzle for the undergraduate teaching lab

245th National Meeting (2013)

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