Owen Priest - Identifying Passerini Products Using a Green, Guided-Inquiry, Collaborative Approach Combined with Spectroscopic Lab Techniques

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      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.

      Abstract:

        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. 

         

       

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