Utilizing the Imine Condensation in Organic Chemistry Teaching Laboratories to Reinforce Steric Effects, Electronic Effects, and Green Chemistry Principles

Abstract

The imine condensation reaction is commonly addressed in second semester organic chemistry classrooms as imines and their derivatives are found in many pharmaceutical scaffolds and biological and catalytic processes. Despite this, imine condensations are still absent from many organic chemistry laboratory curriculums. The work discussed here focuses on comparing the reactivity of the imine condensation with methyl t-butyl ether versus dichloromethane as the solvent as a way to better understand green chemistry along with analyzing steric and electronic effects on reaction. Three primary butyl amines with differing levels of steric hindrance are reacted with a wide variety of substituted aromatic aldehydes that range from electron donating to electron withdrawing. The products are analyzed using 1H NMR spectroscopy, and the percent conversion for each reaction is determined. The results of this work and strategies for implementation of an imine condensation project in second semester organic chemistry laboratory are presented.