A new experiment illustrating synthesis, bonding, and structure is proposed for the general chemistry laboratory. This experiment will take advantage of modern instrumental methods of structural determination to present these concepts at a level appropriate for freshmen. Students will run a series of microscale reactions on vanillin, involving oxidation and reduction of the aldehyde, bromination of the aromatic ring, and esterification of the phenol. Both reactants and products will be analyzed by gas chromatography-mass spectrometry and infrared spectrophotometry. This experiment would serve every student in the freshman class by affording a more balanced view of chemistry and providing an alternative entry point into the chemistry major.
