Reduction of Vanillin Isobutyrate: An Infrared Spectroscopy Structure Determination Experiment

Abstract

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.

Highly Reversed Diastereoselective Meerwein–Ponndorf–Verley (MPV) Reductions of Benzoin and Benzoin Pivalate Leading to meso- and dl-Hydrobenzoins: A Collaborative Stereochemical Investigation Using NMR Spectroscopy and Chemical Synthesis

“…The reduction of the carbonyl group in aldehydes and ketones leading to an alcohol is a fundamental transformation discussed in second-year organic chemistry courses and a large number of undergraduate laboratory experiments involving this reaction have been described. 1 Among these reactions, the diastereoselective reduction of α-chiral ketones, particularly those of chiral α-hydroxyketones and their hydroxyl-protected derivatives, has received considerable attention and has long been a subject of interest in modern synthetic organic chemistry. 2 Interestingly, a few related pedagogically engaging and discovery-based under-graduate organic chemistry lab experiments have also appeared in the chemistry education literature.…”