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  Home > JCE Print > Journal of Chemical Education > Issues > 2008  > January  >
In the Classroom
A Simple Assignment That Enhances Students' Ability To Solve Organic Chemistry Synthesis Problems and Understand Mechanisms
Jennifer Teixeira and R. W. Holman
Department of Chemistry, Idaho State University, Pocatello, ID 83209-8023
Cover
January 2008
Vol. 85 No. 1
p. 88
Abstract
Organic chemistry students typically struggle with the retrosynthetic approach to solving synthesis problems because most textbooks present the chemistry grouped by "reactions of the functional group". In contrast, the retrosynthetic approach requires the student to envision "reactions that yield the functional group". A second challenge is the inability to visualize the bond-forming and bond-breaking events that allow for predictive chemistry on the basis of reaction mechanism. Here we describe an original, easily implemented approach toward simultaneously addressing both problems. Starting in the middle of the first semester of organic chemistry—where reactions are typically first introduced—students begin to construct a "functional group transformation" notebook, or FGT. As reactions are presented in class, the students log these reactions, including the mechanism, in a reverse context, or a reactions that yield context. By the middle of the second semester of organic chemistry, where the retrosynthetic approach is addressed in full, the students have a notebook organized by functional group formed. The students are, in an ongoing sense, learning to think about organic reactions in both the forward and the reverse (retrosynthetic) sense from the middle of the first semester of organic chemistry through the end of the second semester while also recopying all the mechanistic details associated with each reaction.
Supplement
Three example aspects of the functional group transformation notebook are available. They include: an example index with 15 functional groups sorted by "reactions that yield"; an example functional group category detailing the 12 reactions that yield alkyl halides; and a three-step retrosynthetic problem worked from start to finish highlighting the use of the FGT to aid in the solution process.
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Citation
Teixeira, Jennifer; Holman, Robert W. J. Chem. Educ. 2008, 85, 88.
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Keywords
Mechanisms of Reactions; Organic Chemistry; Second-Year Undergraduate; Student-Centered Learning; Synthesis
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History
Created:
Last Updated:
12/4/2007
12/12/2007
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  Home > JCE Print > Journal of Chemical Education > Issues > 2008  > January  > Page 88


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