Journal:
Journal of Chemical Education
Abstract:
Once faced with structure–reactivity relationships in the context of nucleophilic substitution at sp3 carbon, introductoryorganic chemistry students must compare and contrast the various attributes and ramifications of SN2 versus SN1 reactionpathways. The dramatic (even melodramatic) way in which some students ask such comparative questions inspired aparody of Hamlet’s famous to be or not to be soliloquy. Herein, Hamlet (the son of an organic chemist of Denmark) is thesurrogate of any and every student as he uses a thoroughly Shakespearian approach to sorting out some of the keydistinguishing features of SN2 versus SN1 reactions.