第11届全国大学生化学实验邀请赛有机化学实验试题解析

doi:10.3866/PKU.DXHX201909011

University Chemistry ›› 2020, Vol. 35 ›› Issue (9): 214-218.doi: 10.3866/PKU.DXHX201909011

• Chemical Olympiad Competition • Previous Articles

The Analysis of Organic Chemistry Lab for the 11st National Undergraduate Chemistry Lab Tournament

Shaohua Wu(), Jianfeng Yan, Jiajia Chen, Qiaohua Wei, Jing Tang, Yaofeng Yuan()

College of Chemistry, Fuzhou University, Fuzhou 350116, P. R. China

Received:2019-09-04 Accepted:2019-11-11 Published:2019-11-15
Contact: Shaohua Wu,Yaofeng Yuan E-mail:wsh@fzu.edu.cn;yaofeng_yuan@fzu.edu.cn

Abstract

Shaohua Wu, Jianfeng Yan, Jiajia Chen, Qiaohua Wei, Jing Tang, Yaofeng Yuan. The Analysis of Organic Chemistry Lab for the 11st National Undergraduate Chemistry Lab Tournament[J].University Chemistry, 2020, 35(9): 214-218.

思考题(10分)	参考答案
(1)结合本实验产物的¹H NMR谱图(图1)及其局部放大的二维¹H–¹H NMR谱图(图2)，对其苯环上Ha、Hb、Hc、Hd 4种氢进行归属，并说明归属的理由	答：从左到右依次为：Ha、Hc、Hb、Hd，如图1所示苯环上的H的化学位移δ在8.5–7.0之间，图1可以看出该区域的H出现两种不同的分裂耦合峰(双重耦合峰和三重耦合峰)，Ha、Hd为双重耦合峰，而Hb、Hc为三重耦合峰。由于Ha比Hd更接近吸电子羰基，因此Ha的化学位移在较低场8.09，Hd的化学位移在较高场7.30 Hc在羰基对位，Hb在羰基间位，Hc受到吸电子羰基的影响更强，因此Hc的化学位移比Hb更在低场，分别为7.55和7.37 从图2局部放大的二维¹H–¹H NMR谱图可以看出化学位移位于7.37的三重耦合峰与化学位移8.09的双重耦合峰的相关，由此推断化学位移7.37的三重耦合峰为Hb的信号峰；同样化学位移7.55的三重耦合峰与化学位移7.30的双重耦合峰的相关，由此推断化学位移7.55的三重耦合峰为Hc的信号峰
(2)本实验选用300–400目的硅胶用于柱色谱。如果选用100–200目的硅胶，实验现象和结果有什么不同？说明理由	答：本实验如果选用100–200目的硅胶，可能会导致分离时间变短，但分离效果不理想。因为硅胶目数越大，粒径越小，比表面积大，吸附能力强，分离较慢，分离效果好。相反，目数小，粒径大，比表面积小，吸附能力弱，分离较快，分离效果不理想

考查项目	得分	所占比例/%
实验操作(30分)	≥ 24	33.3
	18–24	33.3
	＜18	33.3
实验报告(20分)	≥ 16	23.8
	12–16	31.0
	＜12	45.2
思考题(10分)	≥ 8	9.5
	6–8	23.8
	＜6	66.7
产率(10分)	≥ 8	21.4
	6–8	16.7
	＜6	61.9
产物纯度(30分)	≥ 24	21.4
	18–24	38.1
	＜18	40.5

1	Su X. ; Huang H. ; Yuan Y. ; Li Y. Angew. Chem. Int. Ed. 2017, 56 (5), 1338. doi: 10.1002/anie.201608507
2	兰州大学.有机化学实验.第3版.王清廉,李瀛,高坤,许鹏飞,曹小平,修订.北京:高等教育出版社, 2010.
3	北京大学.有机化学实验.第3版.张奇涵,关烨,关玲,修订.北京:北京大学出版社, 2015.
4	段连运. 大学化学, 2002, 17 (5), 64.
5	赵斌; 章文伟; 张剑荣. 大学化学, 2016, 31 (11), 111. doi: 10.3866/pku.DXHX201609016

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The Analysis of Organic Chemistry Lab for the 11st National Undergraduate Chemistry Lab Tournament

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