Publication Details (including relevant citation information):
Serafin, M.; Priest, O.P.; “Identifying Passerini Products Using a Green, Guided-Inquiry, Collaborative Approach Combined with Spectroscopic Lab Techniques,” J. Chem. Educ. 2015, 92, 579-581.
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. The Passerini reaction can be carried out in water instead of traditional organic solvents, such as methylene chloride or MeOH, and the rate of this reaction is accelerated when carried out in water. A green, guided-inquiry, collaborative experiment has been developed for the teaching lab where a series of Passerini reactions have been conducted in water while varying electron donating and withdrawing substituents on benzoic acids and benzaldehydes. 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 may work on in teams.