Citation: Mingan Yang, Jun Li, Minsi Wu, Xiting Zhang. Analysis of Problems 9 and 10 of the Organic Chemistry in the 35th National Chemistry Olympiad Competition (Preliminary)[J]. University Chemistry, ;2023, 38(8): 341-350. doi: 10.3866/PKU.DXHX202210022 shu

Analysis of Problems 9 and 10 of the Organic Chemistry in the 35th National Chemistry Olympiad Competition (Preliminary)

Mingan Yang ^1,2 ,
Jun Li ^1,, ,
Minsi Wu ¹ ,
Xiting Zhang ^3,,

1.
Department of Chemistry, Guangdong University of Education, Guangzhou 510303, China;
2.
College of Chemistry, South China Normal University, Guangzhou 510006, China;
3.
School of Chemistry and Chemical Engineering, Guangzhou University, Guangzhou 510006, China

Corresponding author: Jun Li, Xiting Zhang,
Received Date: 10 October 2022

The article discussed organic chemistry problems 9 and 10 in the 35th National Chemistry Olympiad Competition (Preliminary) in detail from the perspective of the fundamental theories and reaction mechanisms. The scientific backgrounds and theoretical knowledge associated with the problems were expanded to arouse the curiosity of readers in exploring chemistry..
- Organic chemistry,
- Chemistry Olympiad,
- Nucleophilic substitution,
- Rearrangement reaction,
- Stereochemistry
1. [1]
  ]. https://www.chemsoc.org.cn/notice/a4486.html
2. [2]
3. [3]
4. [4]
5. [5]
  Ziegler, F. E.; Mencel, J. J. Tetrahedron Lett. 1984, 25 (2), 123.
6. [6]
  Erden, I.; Xu, F. P.; Sadoun, A.; Smith, W.; Sheff, G.; Ossun, M. J. Org. Chem. 1995, 60 (4), 813.
7. [7]
  Erden, I.; Gronert, S.; Keeffe, J. R.; Ma, J.; Ocal, N.; Gärtner, C.; Soukup, L. L. J. Org. Chem. 2014,79 (14), 6410.
8. [8]
  Zhang, X.; Nottingham, K. G.; Patel, C.; Alegre-Requena, J. V.; Levy, J. N.; Paton, R. S.; McNally, A. Nature 2021, 594 (7862), 217.
9. [9]
  Martín Castro, A. M. Chem. Rev. 2004, 104 (6), 2939.
10. [10]
  Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press:Salisbury, UK, 2012.
11. [11]
  Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92 (5), 1021.
12. [12]
13. [13]
  Li, J. J. Name Reactions:A Collection of Detailed Mechanisms and Synthetic Application, 5th ed.; Springer Science & Business Media:Heidelberg, Germany, 2014; p. 1.
14. [14]
  Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92 (5), 1021.
15. [15]
  Paderes, G. D.; Jorgensen, W. L. J. Org. Chem. 1992,57 (6), 1904.
16. [16]
17. [17]
18. [18]
  Glover, S. A. Tetrahedron 1998, 54 (26), 7229.
19. [19]
20. [20]
  Deslongchamps, P.; Lebreux, C.; Taillefer, R. Can. J. Chem. 1973, 51 (20), 3405.
21. [21]
  Kennedy, S. H.; Dherange, B. D.; Berger, K. J.; Levin, M. D. Nature 2021, 593 (7858), 223.
22. [22]
  Unsworth, W. P.; Avestro, A. J. Nature 2021, 593 (7858), 203.
23. [23]
  Leverett, C. A.; Purohit, V. C.; Johnson, A. G.; Davis, R. L.; Tantillo, D. J.; Romo, D. J. Am. Chem. Soc. 2012, 134 (32), 13348.
24. [24]
  Gutierrez, O.; Tantillo, D. J. J. Org. Chem. 2012, 77 (20), 8845.
25. [25]
  Davis, R. L.; Leverett, C. A.; Romo, D.; Tantillo, D. J. J. Org. Chem. 2011, 76 (17), 7167.
26. [26]
  Lei, X.; Li, Y.; Lai, Y.; Hu, S.; Qi, C.; Wang, G.; Tang, Y. Angew. Chem. Int. Ed. 2021,60 (8), 4221.
27. [27]
  Kocienski, P.; Barber, C. Pure Appl. Chem. 1990, 62 (10), 1933.
28. [28]
  Stocks, M.; Kocleński, P.; Donald, D. K. Tetrahedron Lett. 1990, 31 (11), 1637.
29. [29]
  Cao, J.; Wu, H.; Wang, Q.; Zhu, J. Nat. Chem. 2021, 13 (7), 671.
1. [1]
  Daojuan Cheng , Fang Fang . Exploration and Implementation of Science-Education Integration in Organic Chemistry Teaching for Pharmacy Majors: A Case Study on Nucleophilic Substitution Reactions of Alkyl Halides. University Chemistry, 2024, 39(11): 72-78. doi: 10.12461/PKU.DXHX202403105
2. [2]
  Fuxian Wan , Ying Li , Yuanhong Zhang , Shuhua Zhu , Jing Xu , Yanfang Wang , Lili Zhang . Exploration and Practice of Teaching in Agricultural Characteristic Organic Chemistry Course. University Chemistry, 2024, 39(2): 298-306. doi: 10.3866/PKU.DXHX202308041
3. [3]
  Zhichang Xiao , Xiaohui Li , Ling Zhang , Huimin Liu . Exploration of Ideological and Political Construction in University Foundation Course of Organic Chemistry. University Chemistry, 2024, 39(2): 314-320. doi: 10.3866/PKU.DXHX202308058
4. [4]
  Fei Xie , Shichong Yu , Ting Wang , Yongsheng Jin , Dazhi Zhang , Yumeng Hao . Practice and Exploration of O-PIRTAS Flipped Classroom in Organic Chemistry Course. University Chemistry, 2024, 39(4): 238-243. doi: 10.3866/PKU.DXHX202310055
5. [5]
  Hui Liu , Shupeng Zhang , Yuntian Zhang , Wei Dong , Yuji Liu , Bingxin Deng , Dongping Chen , Yongxing Tang . Research on the Application of Virtual Reality (VR) Technology in the Teaching of Organic Chemistry. University Chemistry, 2024, 39(8): 64-71. doi: 10.3866/PKU.DXHX202312028
6. [6]
  Yong Wang , Yingying Zhao , Boshun Wan . Analysis of Organic Questions in the 37th Chinese Chemistry Olympiad (Preliminary). University Chemistry, 2024, 39(11): 406-416. doi: 10.12461/PKU.DXHX202403009
7. [7]
  Yong Zhao , Yunmei Bi , Liqin Wang , Rui Zhan , Guoli Huang . Construction and Practice of Organic Chemistry Course in Normal Universities from the Perspective of First-Class Curriculum. University Chemistry, 2024, 39(8): 54-63. doi: 10.3866/PKU.DXHX202312088
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]
  Yuting Zhang , Zhiqian Wang . Methods and Case Studies for In-Depth Learning of the Aldol Reaction Based on Its Reversible Nature. University Chemistry, 2024, 39(7): 377-380. doi: 10.3866/PKU.DXHX202311037
10. [10]
  Houjin Li , Wenjian Lan . Name Reactions in University Organic Chemistry Laboratory. University Chemistry, 2024, 39(4): 268-279. doi: 10.3866/PKU.DXHX202310016
11. [11]
  Wentao Lin , Wenfeng Wang , Yaofeng Yuan , Chunfa Xu . Concerted Nucleophilic Aromatic Substitution Reactions. University Chemistry, 2024, 39(6): 226-230. doi: 10.3866/PKU.DXHX202310095
12. [12]
  Zhanhui Yang , Jiaxi Xu . (m+n+…) or [m+n+…]cycloaddition?. University Chemistry, 2025, 40(3): 387-389. doi: 10.12461/PKU.DXHX202406032
13. [13]
  Gang Liu , Heng Zhang , Ying Ma , Shiling Yuan , Qisheng Song , Zhenghu Xu , Jichao Sun . Exploration and Practice on Improving the Teaching Quality of Organic Chemistry Laboratory Course. University Chemistry, 2024, 39(4): 70-74. doi: 10.3866/PKU.DXHX202309079
14. [14]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
15. [15]
  Jiabo Huang , Quanxin Li , Zhongyan Cao , Li Dang , Shaofei Ni . Elucidating the Mechanism of Beckmann Rearrangement Reaction Using Quantum Chemical Calculations. University Chemistry, 2025, 40(3): 153-159. doi: 10.12461/PKU.DXHX202405172
16. [16]
  Tingbo Wang , Yao Luo , Bingyan Hu , Ruiyuan Liu , Jing Miao , Huizhe Lu . Quantitative Computational Study on the Claisen Rearrangement Reaction of Allyl Phenyl Ethers: An Introduction to a Computational Chemistry Experiment. University Chemistry, 2024, 39(11): 278-285. doi: 10.12461/PKU.DXHX202403082
17. [17]
  Biaolin Yin , Yuanfu Deng , Dongen Lin . Exploration and Practice of Integrating Ideological and Political Education and Innovative Thinking into “Organic Chemistry” Teaching. University Chemistry, 2024, 39(2): 286-291. doi: 10.3866/PKU.DXHX202308026
18. [18]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
19. [19]
  Mengchen Liao , Hua Yang , Younian Liu , Zhen He , Maolin Zhang , Qing Liu , Jiwen Ding . Exploration and Implementation of Refined Management Practices in Basic Organic Chemistry Laboratories. University Chemistry, 2024, 39(10): 164-173. doi: 10.3866/PKU.DXHX202403041
20. [20]
  Renqing Lü , Shutao Wang , Fang Wang , Guoping Shen . Computational Chemistry Aided Organic Chemistry Teaching: A Case of Comparison of Basicity and Stability of Diazine Isomers. University Chemistry, 2025, 40(3): 76-82. doi: 10.12461/PKU.DXHX202404119

Get Citation

PDF

XML

Metrics

PDF Downloads(28)
Abstract views(1248)
HTML views(104)

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