Citation: Zhonghua Ma, Yonggang Xiang, Xiufang Cao, Jimei Ma. Designing a Classroom Teaching Methodology for Pericyclic Reactions Based on Discipline Development History[J]. University Chemistry, ;2023, 38(1): 254-261. doi: 10.3866/PKU.DXHX202201056 shu

Designing a Classroom Teaching Methodology for Pericyclic Reactions Based on Discipline Development History

College of Science, Huazhong Agricultural University, Wuhan 430070, China

Corresponding author: Zhonghua Ma, mazonghua@mail.hzau.edu.cn
Received Date: 28 January 2022

In the teaching of organic chemistry, the pericyclic reaction involves learning a large amount of theory, with a focus on explaining the reaction mechanisms in terms of molecular orbitals, apart from analyzing functional groups. The use of quantum mechanics to explain the pericyclic reaction is helpful as it can predict the products and design the synthetic route. However, classroom teaching can face immense challenges in this regard, due to the abstract theory and confusing application prospects of quantum mechanics. This article attempts to rationally simplify the complex principle of the pericyclic reaction and elucidate it from the point of view of synthesis applications. Classic cases of scientific practice in teaching, such as Fukui’s observation and prediction, Dewar-benzene conversion, and VB₁₂ synthesis are discussed. This methodology would not only enable students to understand basic principles in depth, but also cultivate in them a scientific and systematic thinking approach to solve complex problems.
- Pericyclic reaction,
- Conservation of orbital symmetry,
- Dewar-benzene,
- Stilbene,
- Vitamin B₁₂
1. [1]
2. [2]
3. [3]
4. [4]
5. [5]
  Fukui, K.; Yonezawa, T.; Shingu, H. J. Chem. Phys. 1952, 20, 722.
6. [6]
  Fukui, K.; Yonezawa, T.; Nagata, C.; Shingu, H. J. Chem. Phys. 1954, 22, 1433.
7. [7]
  Sachs, F. Ber. Deut. Chern. Ges. 1906, 39, 3006.
8. [8]
9. [9]
  Havinga, E.; Schlatmannj, J. L. M. A. Tetrahedron 1961, 16, 146.
10. [10]
  van Tamelen, E. E.; Pappas, S. P. J. Am. Chem. Soc. 1962, 84, 3789.
11. [11]
  van Tamelen, E. E.; Pappas, S. P.; Kirk, K. L. J. Am. Chem. Soc. 1971, 93, 6092.
12. [12]
13. [13]
  Blackburn, E. V.; Timmons, C. J. Q. Rev. Chem. Soc.1969, 23,482.
14. [14]
  Woodward, R. B. Pure Appl. Chem. 1968, 17 (3–4), 519.
15. [15]
  Kupchan, S. M.; Wormser, H. C. Tetrahedron Lett. 1965, 6 (6), 359.
16. [16]
  Wenkert, E.; Naemura, K. Synth. Commun. 1973, 3 (1), 45.
17. [17]
18. [18]
1. [1]
  Chengqian Mao , Yanghan Chen , Haotong Bai , Junru Huang , Junpeng Zhuang . Photodimerization of Styrylpyridinium Salt and Its Application in Silk Screen Printing. University Chemistry, 2024, 39(5): 354-362. doi: 10.3866/PKU.DXHX202312014
2. [2]
  Zeyi Yan , Ruitao Liu , Xinyu Qi , Yuxiang Zhang , Lulu Sun , Xiangyuan Li , Anchao Feng . Exploration of Suspension Polymerization: Preparation and Fluorescence Stability of Perovskite Polystyrene Microbeads. University Chemistry, 2025, 40(4): 72-79. doi: 10.12461/PKU.DXHX202405110
3. [3]
  Yukun Xing , Xiaoyu Xie , Fangfang Chen . A Sunlit Gift: Vitamin D. University Chemistry, 2024, 39(9): 28-34. doi: 10.12461/PKU.DXHX202402006
4. [4]
  Zhenhua Wang , Haoyang Feng , Xiaoyang Shao , Wenru Fan . Vitamins in Solid Propellants: Controlled Synthesis of Neutral Macromolecular Bonding Agents. University Chemistry, 2025, 40(4): 1-9. doi: 10.3866/PKU.DXHX202401007
5. [5]
  Liwei Wang , Guangran Ma , Li Wang , Fugang Xu . A Comprehensive Analytical Chemistry Experiment: Colorimetric Detection of Vitamin C Using Nanozyme and Smartphone. University Chemistry, 2024, 39(8): 255-262. doi: 10.3866/PKU.DXHX202312094
6. [6]
  Jiying Liu , Zehua Li , Wenjing Zhang , Donghui Wei . Molecular Orbital and Nucleus-Independent Chemical Shift Calculations for C₆H₆ and B₁₂H₁₂^2-: A Computational Chemistry Experiment. University Chemistry, 2025, 40(3): 186-192. doi: 10.12461/PKU.DXHX202406085
7. [7]
  Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
8. [8]
  Hong Lu , Yidie Zhai , Xingxing Cheng , Yujia Gao , Qing Wei , Hao Wei . Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction. University Chemistry, 2024, 39(5): 154-162. doi: 10.3866/PKU.DXHX202310074
9. [9]
  Jiaxun Wu , Mingde Li , Li Dang . The R eaction of Metal Selenium Complexes with Olefins as a Tutorial Case Study for Analyzing Molecular Orbital Interaction Modes. University Chemistry, 2025, 40(3): 108-115. doi: 10.12461/PKU.DXHX202405098
10. [10]
  Ke QIAO , Yanlin LI , Shengli HUANG , Guoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265
11. [11]
  Weina Wang , Lixia Feng , Fengyi Liu , Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022
12. [12]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
13. [13]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
14. [14]
  Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
15. [15]
  Zhuoyan Lv , Yangming Ding , Leilei Kang , Lin Li , Xiao Yan Liu , Aiqin Wang , Tao Zhang . Light-Enhanced Direct Epoxidation of Propylene by Molecular Oxygen over CuO_x/TiO₂ Catalyst. Acta Physico-Chimica Sinica, 2025, 41(4): 100038-. doi: 10.3866/PKU.WHXB202408015
16. [16]
  Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
17. [17]
  Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-. doi: 10.3866/PKU.WHXB202309027
18. [18]
  Jianjun LI , Mingjie REN , Lili ZHANG , Lingling ZENG , Huiling WANG , Xiangwu MENG . UV-assisted degradation of tetracycline hydrochloride by MnFe₂O₄@activated carbon activated persulfate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1869-1880. doi: 10.11862/CJIC.20240187
19. [19]
  Junjie Zhang , Yue Wang , Qiuhan Wu , Ruquan Shen , Han Liu , Xinhua Duan . Preparation and Selective Separation of Lightweight Magnetic Molecularly Imprinted Polymers for Trace Tetracycline Detection in Milk. University Chemistry, 2024, 39(5): 251-257. doi: 10.3866/PKU.DXHX202311084
20. [20]
  Jinwang Wu , Qijing Xie , Chengliang Zhang , Haifeng Shi . 自旋极化增强ZnFe_1.2Co_0.8O₄/BiVO₄ S型异质结光催化性能降解四环素. Acta Physico-Chimica Sinica, 2025, 41(5): 100050-. doi: 10.1016/j.actphy.2025.100050

Get Citation

PDF

XML

Metrics

PDF Downloads(5)
Abstract views(656)
HTML views(112)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142