Science educators strive to teach students how to be well-rounded scientists with the ability to problem solve, anticipate errors, and adapt to unexpected roadblocks. Traditional organic chemistry experiments seldom teach these skills, no matter how novel or contemporary the subject material. This paper reports on the success of a quarter-long organic chemistry laboratory experiment that takes the form of a research project designed to teach these real-life skills. Students took a three-step synthetic sequence from a literature source, and changed parameters to improve the yield. This involved library research and two levels of proposals, followed by a written report and a poster presentation. The goal was to simulate the different aspects of a research lab, from literature searches to problem solving to presenting results. The students experienced unexpected difficulties and were graded on how they overcame these obstacles, rather than on how much they improved the yields.