Identifying Passerini products using a green, guided-inquiry, collaborative approach combined with spectroscopic lab techniques

Matthew Serafin, Owen Patrick Priest*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

The Passerini multicomponent reaction is a chemical reaction in which a carboxylic acid, an aldehyde, and an isocyanide react to form an α-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 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.

Original languageEnglish (US)
Pages (from-to)579-581
Number of pages3
JournalJournal of Chemical Education
Volume92
Issue number3
DOIs
StatePublished - Jan 1 2015

Keywords

  • Aqueous Solution Chemistry
  • Aromatic Compounds
  • Collaborative/Cooperative Learning
  • Green Chemistry
  • Hands-On Learning/Manipulatives
  • Inquiry-Based/Discovery Learning
  • Laboratory Instruction
  • NMR Spectroscopy
  • Organic Chemistry
  • Second-Year Undergraduate

ASJC Scopus subject areas

  • Chemistry(all)
  • Education

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