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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]
  Zhiqiang Hao , Jinyue Li , Shiqi Zhang , Yujia Hou , Helue Sun . 维生素B₂促进的光催化氧化合成二苯甲酮. University Chemistry, 2026, 41(5): 350-357. doi: 10.12461/PKU.DXHX202510080
2. [2]
  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
3. [3]
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4. [4]
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5. [5]
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6. [6]
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7. [7]
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8. [8]
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9. [9]
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12. [12]
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13. [13]
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14. [14]
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15. [15]
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16. [16]
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17. [17]
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18. [18]
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19. [19]
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20. [20]
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