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The Chemical Educator

ISSN: 1430-4171 (electronic version)

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Abstract Volume 18 (2013) pp 290-294
DOI 10.1007/s00897132493

An Undergraduate Research-based Organic Chemistry Lab Project on Guided Inquiry Green Synthesis of Novel Crystalline Diels-Alder Monomers for Ring Opening Metathesis Polymerization (ROMP)

Joseph K. Rugutt*^,†, Travis L. Pohl^†, Benton G. Grills^†, Taewan Park^†, Chulapol Thanomsing^†, Nicole Christian^‡, Kipngeno J. Rugutt^§, Joel Koech**, Millie Chepkemoi Obel**, Gilbert Cheruiyot**, Denis Chirchir**, and Ronald Rop^††

†Math and Science Division, Missouri State University-West Plains, 128 Garfield, West Plains, MO, 95775, JRugutt@MissouriState.edu; ‡ Department of Chemistry, Columbus State University, 4225 University Avenue, Columbus, GA 31907; §Illinois State University, Department of Educational Administration and Foundations, College of Education, DeGarmo 331, Campus Box 5900, Normal, IL 61790-590; **School of Science and Technology, Department of Biological Sciences, University of Kabianga, Main Campus, P.O. Box 2030, 20200, Kericho City, Kenya; ‡‡Laser and Optical Sciences Group, Department of Physics, Egerton University, P.O. Box 536, Egerton 20115, Nakuru City, Kenya
Received March 16, 2013. Accepted May 7, 2013.

Published: 28 October 2013

Abstract. The overarching goal of our ongoing guided inquiry project is to develop a range of green Nobellaureate-type experiments that can be used in several undergraduate science lab courses. Nobel green chemistry reactions are beneficial to mankind because they are environmentally friendly and also reduce the waste disposal costs. Our project was guided by a specific chemistry research question, i.e., in the Diels-Alder reactions between maleic anhydride and dienes (e.g., furan, pyrrole, and thiophene), which experimental conditions produce the most crystalline monomers? Maleic anhydride, furan, 2-methyl furan, pyrrole, thiopene, and solvent (tetrahydrofuran or o-xylene) were mixed, refluxed and then left to stand for one week at room temperature. The crystalline products were analyzed by various techniques including melting point, thin-layer chromatography (TLC), high performance liquid chromatography (HPLC), Infrared (IR) spectroscopy, and Nuclear Magnetic Resonance (NMR) spectroscopy.

Key Words: Laboratories and Demonstrations; organic chemistry; Diels-Alder; metathesis

(*) Corresponding author. (E-mail: JRugutt@MissouriState.edu)

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