The Tragedy of Hamlet, Son of an Organic Chemist of Denmark

Once faced with structure–reactivity relationships in the context of nucleophilic substitution at sp3 carbon, introductory

organic chemistry students must compare and contrast the various attributes and ramifications of SN2 versus SN1 reaction

pathways. The dramatic (even melodramatic) way in which some students ask such comparative questions inspired a

parody of Hamlet’s famous to be or not to be soliloquy. Herein, Hamlet (the son of an organic chemist of Denmark) is the

surrogate of any and every student as he uses a thoroughly Shakespearian approach to sorting out some of the key

distinguishing features of SN2 versus SN1 reactions.