Inquiry Experiment Based on Regioselectivity Regulation of Aromatic Nitration Reaction
YUAN Jia-Qi1, SU You-Rui1, YANG Zhi-Rui1, CHEN Jian-Ye2, YANG Yu-Dong1**
1. Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China; 2. Development and Planning Division, Sichuan University, Chengdu 610064, China
Abstract Aromatic electrophilic substitution is a hallmark reaction of aromatic compounds and constitutes a core component of both theoretical and laboratory courses in basic organic chemistry.Current university laboratory textbooks typically employ the para-nitration of acetanilide as a model system for teaching this reaction,but lack exploration into ortho-nitration and the regulation of reaction regioselectivity.This limitation fails to adequately address students’ needs for in-depth comprehension of reaction mechanisms.To deepen students’ understanding of the mechanism of aromatic electrophilic substitution and the key factors governing selectivity control,and to improve their innovative experimental skills and personalized inquiry abilities,this study designed a novel inquiry-based experiment focusing on the regioselectivity regulation of acetanilide nitration.The experiment integrates modern analytical techniques including nuclear magnetic resonance spectroscopy,gas chromatography-mass spectrometry,and high-performance liquid chromatography,guiding students through the complete inquiry process of“chemical synthesis-structural identification-mechanism discussion”.This approach thereby further fosters students’ scientific research thinking and comprehensive capabilities in analyzing and solving complex problems.
YUAN Jia-Qi, SU You-Rui, YANG Zhi-Rui, CHEN Jian-Ye, YANG Yu-Dong. Inquiry Experiment Based on Regioselectivity Regulation of Aromatic Nitration Reaction[J]. Chinese Journal of Chemical Education, 2026, 47(14): 41-45.
