Design of Comprehensive Organic Chemistry Experiment:Preparation and Characterization of N-(4-Methylphenyl)Pyrrole-2,5-Dione
JIANG Shuang, JIN Xiao-Ning, ZHANG Wan-Dong**
School of Science,Tianjin University,National Demonstration Center for Experimental Chemistry & Chemical Engineering Education(Tianjin University),National Virtual Simulation Experimental Teaching Center for Chemistry & Chemical Engineering Education(Tianjin University),Tianjin 300354,China
Abstract On the basis of the foundational experiment of acetanilide preparation,a comprehensive organic chemistry experiment of“preparation and characterization of N-(4-methylphenyl)pyrrole-2,5-dione”was developed.In this experiment,maleic anhydride and p-toluidine were employed as starting materials to synthesize N-(4-methylphenyl)pyrrole-2,5-dione via a two-step process:ring-opening amidation followed by cyclization and dehydration,using triethylamine as a catalyst and acetic anhydride as a dehydrating agent.The product was characterized through melting point measurement and spectroscopic techniques including IR,1H NMR and 13C NMR.The experimental procedure involved a series of fundamental organic laboratory operations,such as constant pressure addition,ice-water bath cooling,reflux heating,recrystallization,vacuum filtration,oil bath heating,and drying.This experiment not only deepens students’ understanding of essential organic reaction mechanisms and reinforces basic laboratory skills,but also broadens their academic perspective and stimulates enthusiasm for learning,which plays an important role in the cultivation of high-level innovative talent.
JIANG Shuang, JIN Xiao-Ning, ZHANG Wan-Dong. Design of Comprehensive Organic Chemistry Experiment:Preparation and Characterization of N-(4-Methylphenyl)Pyrrole-2,5-Dione[J]. Chinese Journal of Chemical Education, 2026, 47(6): 46-52.
