Reduction of Vanillin Isobutyrate: An Infrared Spectroscopy Structure Determination Experiment

In this laboratory experiment, first-semester organic chemistry students use mechanistic reasoning to propose possible outcomes for the reaction of vanillin isobutyrate with a hydride source. The students subsequently run the reaction, isolate the product, and acquire its infrared spectrum. The experiment provides students with the opportunity to hone their skills at proposing mechanisms and interpreting IR spectra. It also serves as an introduction to the chemistry of carbonyl-containing functional groups.