Citation: Yihui Bai, Qianyun Mao, Tian Zhang, Ruizhe Wang. Iodine-Catalyzed Chlorination of Chlorobenzene: Application of Theoretical and Computational Chemistry for the In-Depth Analysis of a College Entrance Exam Question[J]. University Chemistry, ;2023, 38(10): 306-312. doi: 10.3866/PKU.DXHX202301017 shu

Iodine-Catalyzed Chlorination of Chlorobenzene: Application of Theoretical and Computational Chemistry for the In-Depth Analysis of a College Entrance Exam Question

1.
College of Chemistry and Material Science, Zhejiang Normal University, Jinhua 321004, Zhejiang Province, China;
2.
College of Education, Zhejiang Normal University, Jinhua 321004, Zhejiang Province, China

Corresponding author: Yihui Bai, baiyihui@zjnu.cn
Received Date: 12 January 2023
Revised Date: 10 March 2023

Which of the processes affords a higher yield in the chlorination of chlorobenzene under iodine catalysis, o-chlorination or p-chlorination? Based on a college entrance exam question involving this topic, the reaction mechanism of the chlorination of chlorobenzene catalyzed by iodine is discussed in this paper using computational chemistry. Further, the reaction processes of o-chlorination and p-chlorination are simulated, and the relative energy of each species in the reaction paths is obtained. Thus, a comprehensive analysis of the examination question is carried out, and the calculated results are compared with the corresponding reference experimental results. Additionally, the rationale of the examination question is discussed, and some suggestions are put forth for future related examination questions. This study serves as a support for studies on other iodine-catalyzed chlorination reactions, serves a reference for preparing related examination questions, and provides teaching resources for students to better understand the mechanism of the chlorination of benzene.
- Analysis of a college entrance exam question,
- Iodine catalysis,
- Chlorination of chlorobenzene,
- Theoretical calculation
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