OPE: An organic chemistry practice environment

Over 70,000 students take organic chemistry each year in the USA, but attrition rates approach 50% in some cases.  The obstacles to success in organic chemistry are both the large amount of material that students are required to learn and more importantly, the unfamiliar style of problem solving and assessment.  Although students may be able to rote memorize reagents and basic reaction patterns, especially if they diligently use the computer-based flashcards and practice environments available today, they often struggle to solve higher-order multi-step synthesis and nuanced mechanism problems. These students fail to understand the fundamental concepts that underlie and integrate the hundreds of reactions that they must learn. 

Co-PI Ian Gould has developed a method of instruction based on problem solving from fundamental principles (e.g., Lewis acid/base theory; retrosynthetic analysis).  Prof. Gould's sections of CHM 233 and CHM 234 are grounded in constructivist pedagogy, wherein students construct an understanding in a strongly guided setting by applying principles to explain reactions or derive synthesis paths.  By all available measures, the courses are a success, earning Prof. Gould numerous awards for teaching including the prestigious President’s Professorship.  Although his materials are used by other organic chemistry instructors, they are passive (html and pdf files).  A pilot project developed a tutoring system for multi-step retrosynthesis, one of the most difficult and complex part of intro organic chemistry.  It was used throughout spring semester 2011 and was successful, according to surveys and focus group reports from students. 

Nonetheless, student reports often suggest even though they think they are studying effectively, they are actually using ineffective methods especially for studying the passive problem sets, which still comprise 95% of the coursework.  Their illusion is consistent with studies of meta-cognitive and self-regulated learning.  The students’ deficit appears not to be a lack of familiarity with good learning strategies, because they seem to already know about solving problems from first principles, drawing molecular structures on paper, etc.  Nor is it a lack of overall motivation, as most make organic chemistry their highest priority course. It seems instead that they do not fully appreciate the benefits of these more effortful methods of learning in specific situations. The same phenomenon has been observed in recent fine-grained studies of students using tutoring systems and other educational and therapeutic systems. 

A technique that has been successful in those other systems is software (called a meta-cognitive coach) that closely monitors students’ problems solving so that it can offer unsolicited advice at just the right moments to motivate students to use specific, more effective learning strategies. For instance, the coach might convince a student to study a problem 2 or 3 times deeply rather than 20 or 30 times shallowly.  We propose to develop and evaluate an organic chemistry practice system that (1) explicitly supports problem solving from fundamental principles and (2) includes a meta-cognitive coach to urge students to use this approach and other effective learning strategies as well. 

The Intellectual Merit of this research is testing whether problem-solving from fundamental principles will indeed increase learning, and whether the meta-cognitive coach will  motivate students to use this form of studying.  A random-assignment experiment will test these hypotheses in Dr. Gould’s class.

The Broad Impact of this research is the development of an online practice system that may significantly improve organic chemistry students’ learning, which may reduce attrition and ultimately increase the flow of a diversity of students through this critical scientific pipeline.


Last updated April 5, 2013.