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.