The Synthesis of Isoamyl Acetate (Banana Oil) via an SN2 Reaction

The SN2 reaction between 1-bromo-3-methylbutane and sodium acetate trihydrate takes place smoothly and cleanly in hot DMSO. The product is readily identified as isoamyl acetate by analysis of the resulting IR spectrum, as well as by comparison of the observed IR spectrum to readily available reference spectra. Generally, reasonable yields of product (3793% with an average of 64%) were obtained by students. This laboratory experiment demonstrates the usefulness of the SN2 reaction in the synthesis of a compound of biological interest (a pheromone of the honey bee) as well as of interest to the food industry (as a banana flavoring agent).