Investigation of Intramolecular Hydrogen Bonds using 1H NMR Spectroscopy: An Organic Chemistry Laboratory for Life-Science Majors

TCE

The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 20 (2015) pp 254-255

Investigation of Intramolecular Hydrogen Bonds using ¹H NMR Spectroscopy: An Organic Chemistry Laboratory for Life-Science Majors

Lindsey O. Davis*

Department of Chemistry, Berry College, P.O. Box 495016, Mount Berry, GA 30149, ldavis@berry.edu
Received July 27, 2015. Accepted September 16, 2015.

Published: 25 September 2015

Abstract. We present a laboratory experiment that covers the concepts of synthesis, NMR, and hydrogen bonding for a second-semester organic chemistry class for life-science majors. Two imines are synthesized from the addition of para-toluidine to either ortho- or para-vanillin through a solvent-less reaction. Students use their acquired ¹H NMR spectra of each imine to determine which imine possesses an intramolecular hydrogen bond. This experiment helps provide a clear connection between organic chemistry and biological sciences.

Key Words: Laboratories and Demonstrations; organic chemistry; NMR; life-science majors

(*) Corresponding author. (E-mail: ldavis@berry.edu )

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Supporting Materials:

Student handout for the laboratory including pre-laboratory and laboratory report questions, copies of ¹H NMR spectra of imines 1 and 2, and notes to the instructor are available. (78 KB)