Ozonolysis Problems That Promote Student Reasoning

Abstract

The structural features inherent in acyclic monoterpenes that follow the isoprene rule often lead to unique sets of ozonolysis products from which their structures, excluding stereochemistry, can be determined from molecular formulas only. This article shows with three examples how students may elucidate the structures of these compounds by analysis of the oxidative and reductive workup products. The oxidative and reductive workup products of 66 compounds that follow the isoprene rule are provided in the Supplemental Material. Fifty of them give a unique set of products from which a single structure can be elucidated by the techniques exemplified in the article. The remaining 16 compounds give products that satisfy two structures. The problems vary in difficulty, affording instructors of beginning organic or qualitative organic analysis courses a set of degradation problems that complement spectral and synthetic problems in engaging students to apply their knowledge and enhance their reasoning skills whil...