SN1, E1, and E2 Reactions of tert-Amyl Compounds: Improved Analysis Using Computational Chemistry and ASAP-HSQC NMR Spectroscopy

A set of inexpensive and pedagogically rich experiments focusing on S(N)1, E1, and E2 reactions have been updated to include modern computational and spectroscopic analyses. The S(N)1 experiment involves treatment of tert-amyl alcohol with hydrochloric acid to generate the corresponding alkyl chloride, which is used as the starting material for the subsequent E2 reaction. The El experiment involves reaction of tert-amyl alcohol with sulfuric acid. Both elimination reactions generate a pair of isomeric methylbutenes, with the ratio being dependent on the reaction mechanism. The combination of computational chemistry and a recently developed fast heteronuclear single-quantum correlation spectroscopy method (ASAP-HSQC), in tandem with H-1 and C-13 NMR and GC-MS analysis, allows the E1 and E2 product mixtures to be fully analyzed by students.