The ability to interpret and provide arrow-pushing mechanisms is crucial for students to obtain a deep understanding of organic chemistry. Without this ability, students are often stuck memorizing the details of every reaction individually rather than understanding what is going on in a given transformation. This memorization approach usually proves infeasible as the amount of mechanisms to memorize increases until it reaches an impossible level.<br/>A classic way to teach students how to work out mechanisms is to have them work out what bonds are broken and what bonds are formed. In practice, the most difficult part of the process is mapping the atoms in the starting material(s) to those in the product(s). Using the prime method" students explicitly represent the amount of hydrogens on the carbon atoms (o = 0H, '= 1 H, " = 2H, ''' = 3H). With this method, decisions students need to make regarding mapping atoms are simplified.<br/>Once this mapping is over, students are aided in drawing arrows with the "active atom" method. By drawing correlations between three classes of mechanisms seen often in organic chemistry (nucleophilic/anionic, acidic/cationic, and radical), students are able realize that these three mechanism types have logical similarities and differences.<br/>How to implement these methods will be discussed as well as student outcomes.

Teaching arrow pushing mechanisms in organic chemistry with the prime method and the active atom

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.