大学化学 >> 2024, Vol. 39 >> Issue (7): 361-367.doi: 10.3866/PKU.DXHX202311029

化学实验 上一篇    下一篇

核磁共振氢谱多维度探究1,3-二羰基化合物的酮-烯醇互变异构规律

梁倬铭, 陈铭, 郑智文, 陈凯   

  1. 中南大学化学化工学院, 长沙 410083
  • 收稿日期:2023-11-08 录用日期:2024-03-13 发布日期:2024-03-21
  • 通讯作者: 陈凯 E-mail:kaichen@email.com
  • 基金资助:
    国家自然科学基金青年项目(22003077)；中南大学教育教学改革研究项目(2022jy081)

Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By 1H NMR

Zhuoming Liang, Ming Chen, Zhiwen Zheng, Kai Chen   

  1. College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, China
  • Received:2023-11-08 Accepted:2024-03-13 Published:2024-03-21
  • Contact: Kai Chen E-mail:kaichen@email.com

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摘要： 针对大学有机化学实验“核磁共振氢谱测定乙酰乙酸乙酯互变异构体”存在内容单一、教学深度与广度不足等问题进行了改进创新。实验内容由认识酮-烯醇互变异构的存在，拓展到探究时间、取代基以及溶剂三个维度对β-二羰基化合物的酮-烯醇互变异构平衡的影响。此外，在研究甲醇溶剂对平衡的影响时，可以观测到氢氘交换现象，有助于进一步理解异构过程的机理。本实验可针对化学相关专业高年级本科生开展，有助于加深学生对酮性质的理解，掌握核磁共振波谱在有机化学中的应用，从而巩固有机化学和仪器分析的理论知识，以及培养学生分析问题、解决问题的能力。

关键词: 乙酰乙酸乙酯, 互变异构, 核磁共振氢谱

Abstract: Herein, the classic organic chemistry experiment titled "Determination of Ethyl Acetoacetate Tautomers by 1H Nuclear Magnetic Resonance" was redesigned to enhance its scope and depth. This new experiment goes beyond simply recognizing the keto-enol tautomeric phenomenon. It delves into the kinetics, the impact of substituents, and the influence of solvents on the keto-enol tautomerization. It's worth noting that the hydrogen-deuterium exchange phenomenon can be observed, providing valuable insights into the ketone-enol tautomeric mechanism. This well-crafted experiment is designed for senior undergraduate students pursuing chemistry-related majors. It not only deepens their comprehension of ketone properties but also fosters expertise in utilizing nuclear magnetic resonance spectroscopy in the field of organic chemistry. This, in turn, solidifies their theoretical knowledge in organic chemistry and instrumental analysis and hones their problem-solving and analytical skills.

Key words: Ethyl acetoacetate, Tautomerism, 1H NMR