Vivian T. Lee, Jordan Kellenberger, Katherine Borton and Shawn D. Montag*,
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A Citrus Serenade: An Improved Procedure for the Imine Condensation Reaction in Undergraduate Laboratories
The imine condensation reaction is commonly addressed in second semester organic chemistry classrooms. With recent pushes toward green chemistry and developing safer reactions, there is a growing interest in attempting organic reactions in the presence of water or aqueous solvents. The work discussed here provides an important update to a previously reported laboratory experiment that utilizes freshly squeezed fruit juices and water as the reaction solvents to compare the reactivity of the imine condensation with respect to steric, electronic, and pH effects. Five different aromatic benzaldehyde derivatives are reacted with n-butylamine, sec-butylamine, and tert-butylamine in the presence of an aqueous solvent. Students from multiple sections were able to successfully perform the updated reaction and analyze the products with 1H NMR spectroscopy, calculate the percent conversion for each reaction, and analyze reaction trends. The conversion rates for this imine condensation laboratory experiment greatly exceed those from our previously reported study which utilized organic solvents ( J. Chem. Educ.2023, 100 (11), 4456). Strategies for implementation of this updated imine condensation project are presented.
期刊介绍:
The Journal of Chemical Education is the official journal of the Division of Chemical Education of the American Chemical Society, co-published with the American Chemical Society Publications Division. Launched in 1924, the Journal of Chemical Education is the world’s premier chemical education journal. The Journal publishes peer-reviewed articles and related information as a resource to those in the field of chemical education and to those institutions that serve them. JCE typically addresses chemical content, activities, laboratory experiments, instructional methods, and pedagogies. The Journal serves as a means of communication among people across the world who are interested in the teaching and learning of chemistry. This includes instructors of chemistry from middle school through graduate school, professional staff who support these teaching activities, as well as some scientists in commerce, industry, and government.