Students’ Strategies, Struggles, and Successes with Mechanism Problem Solving in Organic Chemistry: A Scoping Review of the Research Literature

Abstract

Solving problems in organic chemistry often requires the consideration of reaction mechanisms. As such, much research has been devoted to the examination of how students consider mechanisms when solving various types of organic chemistry problems, such as predicting the products of a reaction or proposing a synthesis. This article provides a scoping review of this body of research, with a focus on the key themes in the research literature regarding students’ problem solving with organic reaction mechanisms. We first review the literature focused on how students approach mechanism problems in organic chemistry and the common challenges students face with using the electron-pushing formalism. We then identify and synthesize the research findings related to four themes prevalent in the literature about students’ mechanistic problem solving. The first two themes are concerned with common difficulties students demonstrate when solving mechanism problems: (1) solving problems with a product-oriented, rather than process-oriented, approach and (2) focusing on surface features rather than implicit properties of chemical structures and mechanisms. The second two themes involve the particularly challenging aspects of problem solving with reaction mechanisms: the need to (1) consider multiple representations and (2) reason with multiple variables. After discussing these themes, we review the research on how mechanistic problem solving develops through undergraduate and graduate school and then review the literature focused on using and developing authentic problem types to support students’ learning. We conclude by synthesizing implications for teaching and supporting students’ development of problem solving with organic reaction mechanisms.

Class and Exam Modalities’ Impact on Student Exam Scores

“…Exam 1 focuses on fundamental concepts with questions that require recall of rote facts, whereas subsequent exams have a large emphasis on application of concepts to solve more complex problems (e.g., Figure 3), which supports the finding that students tend to score higher on Exam 1 compared to the other exams. 20,21 Additionally, the dip in performance at Exam 2, as can be observed in Figure 4, highlights the change in strategy that students need to employ to answer the applied questions. Exam 2 marks the introduction of stereochemistry and organic reactions, which are typically challenging topics for students.…”

Comparing Student and Generative Artificial Intelligence Chatbot Responses to Organic Chemistry Writing-to-Learn Assignments

“…Recent trends in the chemistry education research literature indicate the value of supporting student reasoning through eliciting written responses to open-ended questions that require engagement with conceptual knowledge. , For example, studies call for the use of writing-to-learn (WTL) assignments, − constructed response items, − or case-comparison activities, − all of which can be used to elicit written responses from students. The pedagogical motivation behind these tasks is to require students to solve problems and engage in reasoning by considering underlying conceptual ideas rather than relying on memorization or other rote learning strategies.…”

CR322: A Web-Based Board Game for Aiding Students in Reviewing Chemical Reactivity

“…Therefore, students’ understanding of Lewis structures and bond-line formulas, electron-pushing formalism (EPF), reaction coordinate diagrams (RCDs), thermochemistry, chemical kinetics, and reactive intermediates are prerequisites for achieving these learning objectives. However, understanding these representations and applying them to problem-solving situations are complex tasks that can be difficult for instructors to teach and for students to learn. , …”

“…However, understanding these representations and applying them to problem-solving situations are complex tasks that can be difficult for instructors to teach and for students to learn. 10,11 In that regard, students struggle to distinguish between comparable intermediates, similar reactions, and similar reagents due to their inability to apply or comprehend the reaction mechanisms, leading to frequently mistaking them. 12 Therefore, it is vital to acknowledge these challenges and to utilize a variety of teaching strategies.…”