Understanding of the nature of science is key to the development of new curricular materials that mirror the practice of science. Three problem types (project level, synthetic planning, and day-to-day) in synthetic organic chemistry emerged during a thematic content analysis of the research experiences of eight practising synthetic organic chemists. Project-level problems include the overarching purpose of synthesizing target molecules. Synthetic planning problems include both the retrosynthetic analysis of target molecules and subsequent development of synthetic pathway proposals. Day-to-day problems include the "hurdles" faced in research laboratories while attempting to realize proposed synthetic pathways. Recommendations are made as to how understanding of the three problem types impact undergraduate-level organic chemistry instruction. (Contains 2 schemes and 2 figures.)