大学化学 >> 2021, Vol. 36 >> Issue (8): 2010060.doi: 10.3866/PKU.DXHX202010060

化学实验 上一篇    下一篇

(-)-薄荷酮的制备及比旋光度测定——介绍一个研究型有机化学实验

韩杰(), 陈文彬, 李玉新, 马如江, 贺峥杰()   

  • 收稿日期:2020-10-26 录用日期:2020-12-15 发布日期:2021-01-04
  • 通讯作者: 韩杰,贺峥杰 E-mail:hanjie@nankai.edu.cn;zhengjiehe@nankai.edu.cn
  • 作者简介:Email: zhengjiehe@nankai.edu.cn(贺峥杰)
    Email: hanjie@nankai.edu.cn(韩杰)
  • 基金资助:
    南开大学实验教学课程改革项目及南开大学科研反哺教学项目(NKJ2020006)

Synthesis and Specific Rotation Determination of (-)-Menthone: A Research-Oriented Fundamental Organic Chemistry Experiment

Jie Han(), Wenbin Chen, Yuxin Li, Rujiang Ma, Zhengjie He()   

  • Received:2020-10-26 Accepted:2020-12-15 Published:2021-01-04
  • Contact: Jie Han,Zhengjie He E-mail:hanjie@nankai.edu.cn;zhengjiehe@nankai.edu.cn

摘要:

以(-)-薄荷醇为原料,采用重铬酸钠或次氯酸钠为氧化剂制备(-)-薄荷酮,比较了不同氧化方法的特点。测定了产物的比旋光度,并通过气相色谱对实验结果进行了分析,讨论了(-)-薄荷酮与(+)-薄荷酮之间的差向异构化作用对比旋光度的影响。本实验涉及加热回流、蒸馏、萃取、过滤等基本操作以及气相色谱表征与比旋光度的测定与分析,有利于培养学生基本操作技能,培养综合分析能力。

关键词: 有机化学实验, (-)-薄荷酮, 比旋光度, 差向异构化

Abstract:

(-)-Menthone has been prepared by oxidation of (-)-menthol with sodium dichromate in dilute sulfuric acid or sodium hypochlorite in acetonitrile, and the preparation methods have been reviewed briefly. The specific rotation of (-)-menthone was determined and discussed with respect to the epimerization between (-)-menthone and (+)-menthone, which was corroborated by gas chromatography. This experiment covers the training in fundamental experimental skills such as reflux, distillation, extraction, filtration, gas chromatography characterization and specific rotation determination, and may help the undergraduates improve their integrative abilities and learn the knowledge of chiral compounds.

Key words: Organic chemistry experiment, (-)-Menthone, Specific rotation, Epimerization

MSC2000: 

  • G64