大学化学 >> 2025, Vol. 40 >> Issue (11): 427-434.doi: 10.12461/PKU.DXHX202412125

竞赛园地 上一篇    

第13届全国大学生化学实验竞赛总决赛有机化学实验试题解析

刘刚, 张永强, 李晓苗, 李庆爽, 孙继超, 徐政虎, 李晓燕   

  1. 山东大学化学与化工学院, 济南 250100
  • 收稿日期:2024-12-30 录用日期:2025-04-17 发布日期:2025-11-21
  • 通讯作者: 李晓燕, 徐政虎 E-mail:xli63@sdu.edu.cn;xuzh@sdu.edu.cn Xiaoyan Li, Zhenghu Xu
  • 基金资助:
    山东省自然科学基金重大基础研究项目(ZR2019ZD46)；山东大学实验室建设与管理研究项目(sy20232204)；山东大学仪器设备育人项目(yr20240204)；山东大学公共技术平台仪器设备能力提升项目(ts20230208)；山东大学本科教育教学改革研究一般项目(2024Y119)；山东大学实验室建设与管理研究重大项目(sy20221201)；山东省本科教学改革研究项目(Z2024043,M2024007)

Analysis of Organic Chemistry Experiment Questions in the 13th National Undergraduate Chemistry Experiment Competition Finals

Gang Liu, Yongqiang Zhang, Xiaomiao Li, Qingshuang Li, Jichao Sun, Zhenghu Xu, Xiaoyan Li   

  1. School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, China
  • Received:2024-12-30 Accepted:2025-04-17 Published:2025-11-21
  • Contact: Xiaoyan Li, Zhenghu Xu E-mail:xli63@sdu.edu.cn;xuzh@sdu.edu.cn

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摘要： 卟啉类化合物作为天然氮杂环功能分子，在自然界和生命科学中具有重要地位。第13届全国大学生化学实验竞赛总决赛有机化学实验试题的设计特别关注了5-苯基-二吡咯甲烷的合成，这种化合物是构建多样化卟啉类化合物的基本结构单元。本实验让学生使用三氯化铟作为催化剂，利用苯甲醛和吡咯溶剂一步缩合合成目标分子。竞赛结果显示，学生在简单蒸馏、仪器组装和薄层层析(TLC)追踪等基本操作方面表现良好，但仍有部分学生的基本操作技能有待提升。另外，大多数学生对三氯化铟催化剂作用机制的理解还不够深入。这提示我们在今后的实验教学中，在注重基本操作技能训练的同时，仍需加强理论知识与实验操作的结合。

关键词: 化学实验竞赛, 有机化学实验, 试题解析, 5-苯基二吡咯甲烷, 三氯化铟

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