This research paper examines the intricacies of problem-solving (PS) in organic chemistry (OC), exploring the internal and external factors that influence students’ success in this demanding discipline. Data was collected through a questionnaire administered to 128 City College of New York students during Spring and Fall semesters of 2022. The study revealed that students face challenges learning OC, which include memorization, understanding underlying concepts, and effective PS. Notably, there is a gap between students’ professed beliefs about effective PS strategies and their actual practices. While students acknowledge the importance of techniques such as annotation, trial and error, and questioning, they inconsistently apply these strategies in practice. Annotation emerged as a valuable tool, enabling students to externalize complex thought processes and reduce reliance on memorization. Trial and error, coupled with exposure to expert PS techniques, proved effective. The role of confidence in PS was highlighted, and the need to balance memorization of reactions and rules such as naming with a profound understanding of OC concepts was emphasized. Resonance as a justification for answers underscored the importance of understanding and applying principles rather than relying solely on memorization. The data highlights the importance of aligning beliefs with actions in the learning process and the need for a balanced approach that combines knowledge with effective PS techniques. The findings offer valuable implications for educators and students seeking to enhance their performance in OC.