There are very few published instructional undergraduate organic chemistry laboratory experiments that require students to explore the different allylic substitution reaction pathways. This poster discusses the development and implementation of an instructional experiment that allows for clear distinction of the different substitution pathways taken by various allylic halides when reacted with acetate nucleophiles. The instructional experiment was initially designed to specifically compare and contrast the SN1 and SN2 reaction pathways, but has since been expanded to become highly amenable to the study of other possible allylic substitution pathways, such as indirect SN2 attack. Upon completion of the standardized synthetic procedures, all products are analyzed by use of gas chromatography under optimized conditions. Students are then asked to rationalize their observed experimental outcomes using commonly understood substitution mechanistic theory.

Novel instructional undergraduate organic chemistry laboratory experiment exploring substitution patterns of various allylic halides

249th National Meeting (2015)

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