Research has shown that within a traditional organic chemistry curriculum, organic chemistry students struggle to develop deep conceptual understanding of reactions and attribute little meaning to the electron-pushing formalism. At the University of Ottawa, a new curriculum was developed for organic chemistry in which students are taught the language of the electron-pushing formalism prior to learning about specific reactions. Reactions are then organized by governing pattern of mechanism rather than by functional group and are taught in a gradient of complexity. To investigate how students are making connections across reactions within the new curriculum, a card sort task was developed. The card sort task consisted of 25 cards, each depicting the reactants and solvent for a reaction taught during the two-semester organic chemistry sequence. The first part of the task asked participants to sort 15 of 25 cards into categories. Then, participants were given the 10 remaining cards to incorporate into categories with the previous 15. Participants were asked to explain the characteristics of each category and their sorting process. Students (N= 16) in an organic chemistry course were interviewed while enrolled in the second semester course. We analyzed the students’ sorts based on which cards were sorted frequently together, the underlying characteristics used to form the categories, and the participants’ sorting processes. Participants created categories based on different levels of interpreting the reactions on the cards, with levels ranging from recognizing identical structural features to identifying similar types of mechanisms. Based on this study, if we want students to develop mechanistic thinking, we think students need to be more explicitly directed to the patterns present in organic reaction mechanisms and given opportunities to uncover and identify patterns on their own, during both summative and formative assessments.

To explore the differences between how organic chemistry students and organic chemistry professors think about organic chemistry reactions, we administered a card sort task to participants with a range of knowledge and experience levels. Beginning students created a variety of categories ranging from structural similarities to process oriented categories. Professors and more experienced graduate students created their categories only for process oriented reasons. Professors discussed different features of the reactions than the students did, suggesting that students need guidance and opportunities to develop skills to identify mechanistically relevant features in a reaction. More specifically, at the University of Ottawa, a transformed organic chemistry curriculum has been designed and implemented where students are first taught the language of mechanisms before learning about specific reactions. Then, students are taught reactions in order of their governing pattern of mechanism, rather than by functional group. We developed a card sort task to investigate how students perceive the organization of the reactions in the curriculum as well as to explore how graduate students and professors think about organic chemistry reactions. There were 25 cards designed with reactants and reagents for reactions taught within the first two semesters of organic chemistry. The card sort task is composed of two parts: first, participants are asked to sort 15 cards into categories; second, the participants are given 10 additional cards and asked to incorporate them into their existing categories. During the fall 2017 semester, second semester organic chemistry students (N = 16), organic chemistry graduate students (N = 10), and professors who either teach and/or conduct research in organic chemistry (N = 7) were interviewed using the card sort task. We analyzed the participants' categories for cards that were frequently sorted together and the reasons they gave for creating the categories and then compared the findings across the different participant groups.

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