碘催化下氯苯的氯代反应——用理论计算化学方法深度分析一道高考试题

引用本文: 柏一慧, 毛倩芸, 张恬, 王瑞哲. 碘催化下氯苯的氯代反应——用理论计算化学方法深度分析一道高考试题[J]. 大学化学, 2023, 38(10): 306-312. doi: 10.3866/PKU.DXHX202301017 shu

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

碘催化下氯苯的氯代反应——用理论计算化学方法深度分析一道高考试题

柏一慧 ^{1,
,} ,
毛倩芸 ^2, ,
张恬 ^2, ,
王瑞哲 ^2,

1.
浙江师范大学化学与材料科学学院, 浙江金华 321004;
2.
浙江师范大学教育学院, 浙江金华 321004

通讯作者: 柏一慧,Email:baiyihui@zjnu.cn

基金项目:
浙江省一流本科课程项目(2022年)

摘要: 碘催化下氯苯发生氯代反应的产物比例到底是邻二氯苯还是对二氯苯比较高？本文基于涉及该问题的一道比较有争议的高考试题，借助理论计算化学方法，对碘催化下氯苯的氯代反应的反应机理进行了探讨，对反应过程中邻氯代和对氯代两条反应路径进行了模拟，得到了反应路径中各物种的相对能量；在此基础上，对该高考试题进行了全面的分析，将计算结果与参考文献中提供的相应实验结果进行了对照，并对该试题的合理性进行了探讨，为后续的相关试题命题工作提出了建议。本研究可以为其他碘催化下的氯代反应的研究提供依据、为相关试题的编制提供参考、也可在教学中为使学生更好地理解苯的氯代反应的实质提供更丰富的教学资源。

关键词:

English

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

Abstract: 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.

Key words:

Analysis of a college entrance exam question
/ Iodine catalysis
/ Chlorination of chlorobenzene
/ Theoretical calculation

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沈阳化工大学材料科学与工程学院沈阳 110142

碘催化下氯苯的氯代反应——用理论计算化学方法深度分析一道高考试题

通讯作者: 柏一慧,Email:baiyihui@zjnu.cn

English

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

Corresponding author: Yihui Bai, baiyihui@zjnu.cn

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

碘催化下氯苯的氯代反应——用理论计算化学方法深度分析一道高考试题

通讯作者: 柏一慧,Email:baiyihui@zjnu.cn

English

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

Corresponding author: Yihui Bai, baiyihui@zjnu.cn

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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