Abstract: Porphyrin compounds, as naturally occurring nitrogen-containing heterocyclic functional molecules, hold significant importance in both natural systems and life sciences. The organic chemistry experiment designed for the 13th National Undergraduate Chemistry Experiment Competition Finals specifically focused on the synthesis of 5-phenyl-dipyrromethane, a fundamental structural unit for constructing diverse porphyrin compounds. In this experiment, students were required to synthesize the target molecule through a one-step condensation reaction of benzaldehyde and pyrrole solvent, using indium trichloride as the catalyst. The competition results revealed that while students demonstrated proficiency in basic laboratory techniques such as simple distillation, instrument assembly, and thin layer chromatography (TLC) monitoring, certain aspects of their fundamental experimental skills still require improvement. Furthermore, the majority of participants exhibited limited understanding of the catalytic mechanism of indium trichloride. These findings underscore the necessity of emphasizing both basic experimental skill development and the integration of theoretical knowledge with practical operations in future experimental instruction.

Key words: Chemistry experiment competition, Organic chemistry experiment, Exam question analysis, 5-Phenyldipyrromethane, Indium trichloride