Understanding resonance is essential to predict chemical reactivity and explain reaction mechanisms. Despite its importance in the organic curriculum, few studies have explored students’ difficulties with this concept and faculty’s instructional approaches to teaching it. The goals of this study are to address this gap in the literature by (1) employing an exploratory mixed-methods design to characterize students’ conceptual struggles with resonance and (2) exploring the relationship between students’ struggles and the instructional approach employed. Leveraging the results of a set of interviews with organic chemistry students, we distributed a survey to students in two different sections of a first-semester organic chemistry course at a research-intensive institution. We also conducted postinstruction interviews with the two instructors of the surveyed sections. Analysis of the 180 surveys collected indicates that students tended to focus on the features and processes of recognizing and drawing resonance structures when asked to explain the concept of resonance and mostly did not understand the relationship between resonance structures and the resonance hybrid. A comparison of the two sections showed a significant difference with one section having a better conceptual understanding of resonance than the other. Analysis of the instructional approaches demonstrated that the instructor of the section with higher conceptual understanding focused his instruction on the limitations of chemical representations, while the other instructor focused on the features and processes of recognizing and drawing resonance. This study highlights the need to help students develop metarepresentational competence as well as to better understand instructors’ instructional decisions.

中文翻译：

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探索学生对共鸣的理解及其与教学的关系

了解共振对于预测化学反应性和解释反应机理至关重要。尽管它在有机课程中很重要，但很少有研究探讨这种概念以及教师的教学方法对学生的困难。这项研究的目的是通过（1）采用探索性的混合方法设计来表征学生具有共鸣的概念性挣扎，以及（2）探索学生的挣扎与所采用的教学方法之间的关系，以解决文献中的空白。利用与有机化学专业学生进行的一组访谈的结果，我们向研究密集型机构的第一学期有机化学课程的两个不同部分的学生进行了调查。我们还与被调查部分的两名讲师进行了教学后访谈。对收集到的180个调查的分析表明，当被要求解释共振的概念时，学生倾向于关注识别和绘制共振结构的特征和过程，并且大多不了解共振结构与共振混合体之间的关系。对两个部分的比较显示出显着差异，其中一个部分比其他部分具有更好的共振概念理解。对教学方法的分析表明，具有较高概念理解力的本节讲师将其讲授集中于化学表示法的局限性，而其他讲师则将重点放在识别和吸引共鸣的特征和过程上。