大学化学 >> 2026, Vol. 41 >> Issue (5): 50-61.doi: 10.12461/PKU.DXHX202511129

所属专题： 第5届全国大学生化学实验创新设计大赛

专题 上一篇    

通过格氏试剂与环氧苯乙烯的反应认识其组成与性质的复杂性

张皓淇, 姚博睿, 张蕴, 宋志光, 王博   

  1. 吉林大学化学学院, 吉林 长春 130012
  • 收稿日期:2025-11-20 录用日期:2026-02-25 发布日期:2026-05-21
  • 通讯作者: 宋志光, 王博 E-mail:szg@jlu.edu.cn;bwang_chem@jlu.edu.cn Zhiguang Song, Bo Wang
  • 基金资助:
    吉林省高教科研重点自筹课题(JGJX24C002)；吉林省高等教育教学改革研究课题(JLJY202241289021)

Exploring complicated structure and reactivity of Grignard reagents via their reactions with styrene oxide

Haoqi Zhang, Borui Yao, Yun Zhang, Zhiguang Song, Bo Wang   

  1. College of Chemistry, Jilin University, Changchun 130012, Jilin Province, China
  • Received:2025-11-20 Accepted:2026-02-25 Published:2026-05-21
  • Contact: Zhiguang Song, Bo Wang E-mail:szg@jlu.edu.cn;bwang_chem@jlu.edu.cn

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摘要： Grignard试剂的制备与反应是有机实验教学中必做的经典实验。但目前普遍采用的由1-溴丁烷和镁屑制备正丁基格氏试剂，再对丙酮加成合成2-甲基己-2-醇的方案不能引导学生认识Grignard试剂的组成与结构复杂性及对Grignard试剂反应性的影响。本实验设计使用既有原料，但是将方案改进为安排学生分组使用不同的醚类溶剂分别制备正丁基格氏试剂，将这些Grignard试剂以及二(正丁基)镁分别与环氧苯乙烯反应获得不同产物。在实验报告中要求学生通过对产物的核磁共振氢谱分析及与标准样品的对照，确定产物的结构及比例。基于产物的差异，以及对格氏试剂Schlenk平衡的自主学习，引导学生思考Grignard试剂的组成与结构复杂性，以及因Schlenk平衡而存在的Lewis酸性MgX2对Grignard试剂反应性的显著影响。此项对Grignard试剂制备及反应实验的研究型改进，在对学生进行无氧无水反应基本操作训练的基础上，加强学生对分子结构解析的能力，引导学生学习实验研究方法，对提升学习兴趣、拓展创新思维具有显著效果。

关键词: Grignard试剂, 改进实验, Schlenk平衡, 性质研究, 环氧苯乙烯

Abstract: The preparation and reactions of Grignard reagents constitute fundamental experiments in organic chemistry laboratory courses. However, the conventional experiment involving the preparation of n-butyl Grignard reagent from 1-bromobutane and magnesium turnings, followed by its addition to acetone to yield 2-methylhexan-2-ol, fails to demonstrate the compositional and structural complexity of Grignard reagents and their impact on reactivity. In this study, we present a modified experimental design using existing materials, where student groups prepare n-butyl Grignard reagents in different ethereal solvents. These reagents, along with di(n-butyl)magnesium, are then reacted with styrene oxide to produce distinct products. Students analyze the resulting products through 1H-nuclear magnetic resonance (1H-NMR) spectroscopy and comparison with reference standards to determine product structures and distributions. By examining these experimental results and studying the Schlenk equilibrium through self-directed learning, students gain insights into the compositional complexity of Grignard reagents and the significant influence of Lewis acidic MgX2 on their reactivity due to the Schlenk equilibrium. This research-oriented modification not only reinforces fundamental skills in air- and moisture-free synthesis but also enhances students’ abilities in molecular structure analysis and experimental methodology, thereby stimulating their scientific curiosity and fostering innovative thinking.

Key words: Grignard reagent, Improved experiment, Schlenk equilibrium, Property investigation, Styrene oxide