A question of pattern recognition: investigating the impact of structure variation on students’ proficiency in deciding about resonance stabilization

The ability to reason with representations is pivotal for successful learning in Organic Chemistry and is closely linked to representational competence. Given the visual nature of this discipline, this comprises competency in extracting and processing relevant visual information. With regard to the resonance concept, proficiency in identifying whether electron delocalization applies in a molecule is an essential prerequisite to using this concept in problem-solving. However, prior research shows that students struggle to recognize whether molecules profit from electron delocalization, and seldom use this concept in problem-solving. As it remains unclear how the variation of structural features affects students’ consideration of resonance, this quantitative study seeks to identify characteristics regarding students’ perception of electron delocalization. To this end, undergraduate students enrolled in an Organic Chemistry I course (N = 699) completed an online survey in which they had to decide on resonance stabilization for molecular structures with varying structural features. K-means cluster analysis was performed to explore patterns in students’ proficiency in discerning resonance stabilization and how they relate to other performance variables (e.g., time-on-task). The results suggest pattern recognition approaches with students’ attention being guided by singular structural features or structures’ visual similarity to familiar patterns (i.e., allylic carbocations), with less attention to implicit features.