UC Berkeley

Organic Chemistry is considered by many to be the quintessential “weeder course”, widely identified in the premed and STEM persistence literature as a gatekeeper to students interested in STEM or health fields (Barr, Gonzalez, & Wanat, 2008; Lovecchio & Dundes, 2002). There has therefore been considerable interest in determining ways to improve students’ outcomes in organic chemistry courses. While redesigning curriculum and developing interventions is an important step in this process, it is also important to better understand what helps students to do well in organic chemistry.

In this dissertation I utilize a mixed-methods study design to explore how students’ study behaviors and problem-solving strategies are associated with student performance in a second-semester organic chemistry course for non-majors, Organic Chemistry 2. This dissertation begins by exploring how study behaviors are associated with overall performance but then interrogates differences in the relationships between different types of questions (mechanism and predict-the-product) and between questions with different relationships to the curriculum (problem-type and exercise-type questions). It finally conducts a more detailed exploration on the differences between student problem-solving strategies on problem-type and exercise-type questions. In order to explore these issues, the goal of data collection was to provide a comprehensive understanding of the entire course. A survey based on the resources available in Organic Chemistry 2 and students’ study behaviors associated with them was developed and utilized. In-class observations, student exams, course materials, and exam scores were also collected. A subset of students was also interviewed using a think-aloud protocol based on questions from their exams.

Survey results were analyzed using hierarchical linear modeling and multiple linear regression. Results showed that students’ overall exams scores were positively associated with studying more than 10 hours, active note-taking, and testing their understanding when working on practice problems. Exam scores were negatively associated with passive engagement in group-work. However subsequent analyses showed that different categories of questions (mechanism and predict-the-product) are associated with very different strategies from each other and overall exam scores. Notable differences were also seen between problem-type and exercise-type questions even within the same category of question. All these results indicate that determining what study behaviors are associated with higher scores in Organic Chemistry is more complicated than might be initially expected and that advice to students on how to study should consider the type of questions that students are struggling with. It also indicates that instructors should think critically about more than just the content being tested when designing exam questions.

Interviews were analyzed using thematic coding centered on student decision making and reasoning strategies. Results from initial thematic coding were finalized into activity logs which were then tabulated to better compare the reasoning strategies used in the problem-type and exercise-type questions and their outcomes. Results showed that problem-type and exercise-type questions are associated with different approaches and reasoning strategies. In particular the use of chemical reasoning seems to be important for performance on problem-type questions but other reasoning strategies can be just as effective in exercises. This chapter then discusses how chemical reasoning is undervalued by students and how exercise-type questions may not measure students understanding of chemical concepts.