Student perceptions of partial charges and nucleophilicity/electrophilicity when provided with either a bond-line, ball-and-stick, or electrostatic potential map for molecular representation

Abstract

Education in organic chemistry is highly reliant on molecular representations. Students abstract information from representations to make sense of submicroscopic interactions. This study investigates relationships between differing representations: bond-line structures, ball-and-stick, or electrostatic potential maps (EPMs), and predicting partial charges, nucleophiles, and electrophiles. The study makes use of students’ answers in hot-spot question format, where they select partially charged atoms on the image of a molecule and explanations. Analysis showed no significant difference among students when predicting a partially positive atom with each representation; however, more students with EPMs were able to correctly predict the partially negative atom. No difference was observed across representations in students predicting electrophilic character; while representations did influence students identifying nucleophilic character. The affordance of EPMs was that they cued more students to cite relative electronegativity indicating that such students were able to recognize the cause for electron rich/poor areas. This recognition is central to rationalizing mechanisms in organic chemistry. This study offers implications on incorporating EPMs during instruction and provides evidence-based support in how EPMs could be useful in promoting learning on topics that relate to an uneven charge distribution.