Date of Award


Document Type


Degree Name

Doctor of Philosophy (PhD)



First Advisor

Ronald G. Good


Because stereochemistry is an important part of both high school and college chemistry curricula, a study of difficulties experienced by students in the learning of stereochemistry was undertaken in a one-semester college organic chemistry course. This study, conducted over the course of two semesters with more than two hundred students, utilized clinical interviews, concept maps, and student journals to identify these difficulties, which were then tabulated and categorized. Although student journals were not a productive source of information, the types of difficulties that emerged from the concept maps were compared and contrasted with those that emerged from the clinical interviews. Data from the concept maps were analyzed using Kendall's W, a nonparametric statistic that was deemed appropriate for determining concordance between individual concept maps. The correlation between values of Kendall's W for sets of concept maps and multiple choice questions designed to evaluate the content of these same maps was determined, with values of Pearson's r of .8093 (p = .051) and .7191 (p = .044) for the Fall, 1997 and Spring, 1998 semesters, respectively. These data were used to estimate the occurrence of critical junctures in the learning of stereochemistry, or points at which students must possess a certain framework of understanding of previous concepts in order to master new material (Trowbridge & Wandersee, 1994). One critical juncture was identified that occurred when the topics of enantiorners, absolute configuration, and inversion of configuration were introduced. Among the more important conclusions of this study to the learning of stereochemistry are the following. Both concept maps and interviews provided useful information regarding difficulties in the learning of stereochemistry; this information was complementary in some aspects and similar in others. Concept maps were useful in diagnosing difficulties in application of terms and definitions, whereas interviews were useful when seeking information about difficulties in the manipulation of chemical structures. Both concept maps and interviews were superior to student journals as tools to probe student difficulties in the learning of stereochemistry.