University Chemistry ›› 2021, Vol. 36 ›› Issue (8): 2010060.doi: 10.3866/PKU.DXHX202010060

• Chemistry Laboratory • Previous Articles     Next Articles

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

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