posted on 2016-03-10, 18:35authored byNicholas E. Bodé, Alison B. Flynn
Organic synthesis problems require
the solver to integrate knowledge
and skills from many parts of their courses. Without a well-defined,
systematic method for approaching them, even the strongest students
can experience difficulties. Our research goal was to identify the
most successful problem-solving strategies and develop associated
teaching models and learning activities. Specifically we asked: (1)
What problem-solving strategies do undergraduate students use when
solving synthesis-type problems? Are these strategies used correctly/as
intended? (2) What strategies have the highest association with successful
answers? (3) What relationships exist between these strategies? We
analyzed more than 700 responses to synthesis problems from the final
exams of undergraduate organic chemistry courses at a large, research-intensive
institution. We analyzed the data using an open-coding system and
a theoretical framework based on meaningful learning and representational
systems in problem-solving. Our analysis found that successful answers
demonstrated six key strategies: (1) identified newly formed bonds
in the target molecule, (2) identified atoms added to the starting
molecule to form the target, (3) identified key regiochemical relationships,
(4) mapped the atoms of the starting material onto the target, (5)
used a partial or complete retrosynthetic analysis, and (6) drew reaction
mechanisms. The vast majority of successful answers demonstrated the
use of multiple strategies in concert. This higher degree of success
is logical in the context of meaningful learning and of representational
systems in problem-solving. These strategies were often absent from
unsuccessful answers, possibly because students did not know these
strategies, did not believe them to be useful, or did not write them
down. For teaching, our results suggest that students should be taught,
encouraged, and given opportunities to use multiple key strategies;
sample problems are included herein.