In the field of chemistry, representations serve an essential function in conveying and communicating knowledge about the chemical world. While experts are traditionally adept at identifying, interpreting, and manipulating these visualizations, novices often are not. To address the concern of promoting representational competence in novice populations, the series of studies presented in this dissertation utilizes a mixed-methods approach to examine the relationship between students' use of concrete models and their performance, specifically, on representational translation tasks (RTTs) in Organic Chemistry. Students' perceptions of modeling and faculty perceptions of and uses of models in classroom contexts are also examined. While results indicated significant increases in performance on RTTs for students who made effective use of concrete models to complete these tasks, students' proclivity for using models was found to be negatively influenced, at times, by perceived practical constraints of the learning environment -modeling being too time-consuming of a task, no engagement in modeling practices in the classroom or directed instruction on how to build and use models, etc. In addition, while faculty were generally found to view models in a positive light, classroom observation data revealed that their use of models during instruction was often inconsistent with promoting representational competence. Together, these data suggest that attention to both cognitive and contextual factors need be taken into consideration when attempting to create a holistic account of how novices come to develop representational competence in the domain.