{"title":"基于核磁共振的芳香族化合物 \"取代基对反应活性和取向的影响 \"教学法","authors":"Chao-Tun Cao, and , Chenzhong Cao*, ","doi":"10.1021/acs.jchemed.4c0083210.1021/acs.jchemed.4c00832","DOIUrl":null,"url":null,"abstract":"<p >The effect of substituents on the reactivity and orientation is important for aromatic compounds in organic chemistry. The “telling style” is used in traditional teaching methods and does not make a deep impression of the learned content in students. The lack of a clear criterion causes a vague understanding of the orientation of the substituted groups. This study developed a new method termed the “nuclear magnetic resonance (NMR)-based method (NBM)” to teach the “effect of substituents on reactivity and orientation”, which changed the “telling style” teaching method to a “discussing style” teaching method. A normalized method was used to correct the scale of <sup>1</sup>H NMR chemical shift change to that of <sup>13</sup>C NMR chemical shift change. The sum of the <sup>1</sup>H and <sup>13</sup>C NMR chemical shift changes was used to discuss the following issues: (i) verifying the activating or deactivating groups, (ii) determining the <i>ortho–para</i> or <i>meta</i> directors, and (iii) predicting the orientation of an incoming group in disubstituted benzene. The NBM presented in this paper is intuitive and simple, which can help students to understand the “effect of substituents on reactivity and orientation” in electrophilic aromatic substitution and cultivate the ability of students to analyze problems using NMR.</p>","PeriodicalId":43,"journal":{"name":"Journal of Chemical Education","volume":"101 12","pages":"5306–5312 5306–5312"},"PeriodicalIF":2.5000,"publicationDate":"2024-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Nuclear Magnetic Resonance-Based Method to Teach the “Effect of Substituents on the Reactivity and Orientation” of Aromatic Compounds\",\"authors\":\"Chao-Tun Cao, and , Chenzhong Cao*, \",\"doi\":\"10.1021/acs.jchemed.4c0083210.1021/acs.jchemed.4c00832\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >The effect of substituents on the reactivity and orientation is important for aromatic compounds in organic chemistry. The “telling style” is used in traditional teaching methods and does not make a deep impression of the learned content in students. The lack of a clear criterion causes a vague understanding of the orientation of the substituted groups. This study developed a new method termed the “nuclear magnetic resonance (NMR)-based method (NBM)” to teach the “effect of substituents on reactivity and orientation”, which changed the “telling style” teaching method to a “discussing style” teaching method. A normalized method was used to correct the scale of <sup>1</sup>H NMR chemical shift change to that of <sup>13</sup>C NMR chemical shift change. The sum of the <sup>1</sup>H and <sup>13</sup>C NMR chemical shift changes was used to discuss the following issues: (i) verifying the activating or deactivating groups, (ii) determining the <i>ortho–para</i> or <i>meta</i> directors, and (iii) predicting the orientation of an incoming group in disubstituted benzene. The NBM presented in this paper is intuitive and simple, which can help students to understand the “effect of substituents on reactivity and orientation” in electrophilic aromatic substitution and cultivate the ability of students to analyze problems using NMR.</p>\",\"PeriodicalId\":43,\"journal\":{\"name\":\"Journal of Chemical Education\",\"volume\":\"101 12\",\"pages\":\"5306–5312 5306–5312\"},\"PeriodicalIF\":2.5000,\"publicationDate\":\"2024-11-13\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Chemical Education\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acs.jchemed.4c00832\",\"RegionNum\":3,\"RegionCategory\":\"教育学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Chemical Education","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.jchemed.4c00832","RegionNum":3,"RegionCategory":"教育学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Nuclear Magnetic Resonance-Based Method to Teach the “Effect of Substituents on the Reactivity and Orientation” of Aromatic Compounds
The effect of substituents on the reactivity and orientation is important for aromatic compounds in organic chemistry. The “telling style” is used in traditional teaching methods and does not make a deep impression of the learned content in students. The lack of a clear criterion causes a vague understanding of the orientation of the substituted groups. This study developed a new method termed the “nuclear magnetic resonance (NMR)-based method (NBM)” to teach the “effect of substituents on reactivity and orientation”, which changed the “telling style” teaching method to a “discussing style” teaching method. A normalized method was used to correct the scale of 1H NMR chemical shift change to that of 13C NMR chemical shift change. The sum of the 1H and 13C NMR chemical shift changes was used to discuss the following issues: (i) verifying the activating or deactivating groups, (ii) determining the ortho–para or meta directors, and (iii) predicting the orientation of an incoming group in disubstituted benzene. The NBM presented in this paper is intuitive and simple, which can help students to understand the “effect of substituents on reactivity and orientation” in electrophilic aromatic substitution and cultivate the ability of students to analyze problems using NMR.
期刊介绍:
The Journal of Chemical Education is the official journal of the Division of Chemical Education of the American Chemical Society, co-published with the American Chemical Society Publications Division. Launched in 1924, the Journal of Chemical Education is the world’s premier chemical education journal. The Journal publishes peer-reviewed articles and related information as a resource to those in the field of chemical education and to those institutions that serve them. JCE typically addresses chemical content, activities, laboratory experiments, instructional methods, and pedagogies. The Journal serves as a means of communication among people across the world who are interested in the teaching and learning of chemistry. This includes instructors of chemistry from middle school through graduate school, professional staff who support these teaching activities, as well as some scientists in commerce, industry, and government.