This article describes the successful implementation of an oral examination format in the organic chemistry curriculum at the University of Toronto. Oral examinations are used to replace traditional written midterm examinations in several courses. In an introductory organic class, each student is allotted 15 min to individually discuss one pre-selected "named" reaction with the course instructors. To stimulate further learning, students must choose a particular reaction that has not been presented during lecture or performed in the laboratory. In upper-level courses, students review selected literature syntheses of either a drug molecule or natural product. The oral examination format provides a dynamic assessment approach that can be individualized to facilitate an in-depth analysis of student comprehension. (Contains 2 tables and 1 figure.)