大学化学 >> 2023, Vol. 38 >> Issue (4): 53-57.doi: 10.3866/PKU.DXHX202211025

所属专题： 第3届全国大学生化学实验创新设计竞赛

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一锅法两步合成香茅醛

王婷, 吴锦娇, 张莹, 柴新怡, 安鹏(), 史勇()   

  • 收稿日期:2022-11-07 录用日期:2022-12-20 发布日期:2023-03-09
  • 通讯作者: 安鹏,史勇 E-mail:anp@ynu.edu.cn;yshi@ynu.edu.cn

One-Pot Two-Step Synthesis of Citronellal

Ting Wang, Jinjiao Wu, Ying Zhang, Xinyi Chai, Peng An(), Shi Yong()   

  • Received:2022-11-07 Accepted:2022-12-20 Published:2023-03-09
  • Contact: Peng An, Shi Yong E-mail:anp@ynu.edu.cn;yshi@ynu.edu.cn

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摘要：

烯烃亲电加成反应和卤代烃消除反应在本科生有机化学基础理论知识学习中十分重要，与之有关的教学实验却不多，理论与实践的脱节导致学生对其反应原理的理解不尽如人意。本实验采用异蒲勒醇为原料，经过烯烃双键的亲电加成和Grob碎裂这一特殊的卤代烃消除反应，在室温下以“一锅两步”的方式合成价格高昂的R构型香茅醛。实验具有原料易得、操作简单、条件温和、训练全面等特点，适合本科教学，可帮助学生在熟练实验操作的同时，增强对理论知识的理解。

关键词: 异蒲勒醇, R-香茅醛, 亲电加成, Grob碎裂, 一锅法

Abstract:

The electrophilic addition reactions of alkenes and the elimination reactions of alkyl halides are two fundamental reactions that undergraduates should master in basic organic chemistry course, but are rarely included in the laboratory course. The disconnection between theory and practice leads to the poor understanding of the reaction mechanisms. To address this disconnection in organic chemistry instruction, we design an experiment containing an electrophilic addition reaction and an elimination reaction. In this experiment, we use isopulegol as the starting material to synthesize the expensive R-citronellal in a one-pot two-step manner at room temperature through an electrophilic addition and a Grob fragmentation (a special elimination). The experiment features low cost of reagents, simple operation, mild reaction conditions and comprehensive skill training, therefore, it is a qualified teaching experiment that could help students deepen their understanding of theoretical knowledge while polishing their organic laboratory techniques.

Key words: Lsopulegol, R-citronellal, Electrophilic addition, Grob fragmentation, One-pot method