In this study we explore the strategies that undergraduate and graduate chemistry students use when engaged in classification tasks involving symbolic and microscopic (particulate) representations of different chemical reactions. We were specifically interested in characterizing the basic features to which students pay attention when classifying chemical reactions at the symbolic and microscopic levels. We identified the categories that students create when classifying chemical reactions, and compared the performance in simple classification tasks of students with different levels of preparation in the discipline. Our results suggest that advanced levels of expertise in chemical classification do not necessarily evolve in a linear and continuous way with academic training; a significant proportion of undergraduate students, regardless of their level of preparation in chemistry, based their classification schemes on the identification of surface features and failed to create chemically meaningful classes. Students' ability to identify chemically meaningful groups was strongly influenced by their recent learning experiences and their graduate work in chemistry. The level of expertise and the type of chemical representation influenced the number and types of categories created, the nature of the features used to build a class, and the role that these features played during the classification process. Although all of the participants in our study expressed similar levels of unfamiliarity with the microscopic images of chemical reactions, advanced students were more adept at using the available representational features to build chemical meaning. (Contains 5 tables and 7 figures.)