University Chemistry ›› 2025, Vol. 40 ›› Issue (3): 206-214.doi: 10.12461/PKU.DXHX202407022

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Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes

Weina Wang1, Lixia Feng2, Fengyi Liu1, Wenliang Wang1,3   

  1. 1 School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, China;
    2 College of Chemistry and Materials, Taiyuan Normal University, Jinzhong 030619, Shanxi Province, China;
    3 School of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, Anhui Province, China
  • Received:2024-07-01 Accepted:2024-10-16 Published:2025-03-19
  • Contact: Wenliang Wang E-mail:wlwang@snnu.edu.cn

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Abstract: The combination of computational chemistry experiments with organic chemistry courses can not only enhance students' software application capabilities and scientific research innovation thinking and abilities, but also cultivate their ability to efficiently solve chemical research problems through computational chemistry and deepen their understanding of reaction mechanisms. In this paper, the electrophilic addition of HCl to asymmetric alkenes CH2 = CHR (R = CH3, Cl, CN) is taken as an example, the Markovnikov and anti-Markovnikov addition reaction paths are constructed to obtain the thermodynamic and kinetic data. The changes in NPA charge at the stationary points along the reaction path are analyzed to explore the essence of the influence of substituents on reaction mechanism. This computational chemistry experiment is designed to deepen students’ understanding and cognition of the electrophilic addition mechanism of asymmetric alkenes, and to grasp the fundamental methods of using computational chemistry to study chemical reaction mechanisms.

Key words: Computational chemistry experiment, Asymmetric alkenes, Electrophilic addition, Density functional theory