NMR Spectroscopy in the Undergraduate Curriculum, Volume 4 In-Person and Distance Learning Approaches

Strategies to integrate NMR spectroscopy in-person and virtually

Nuclear magnetic resonance spectroscopy has grown to be an important part of the undergraduate curriculum; however, lack of access to chemical instrumentation and experiential learning has introduced a difficult challenge for educators. This work expands on topics covered in the first three volumes (1128, 1221, and 1225), including a new focus on approaches to incorporate NMR spectrometers into the curriculum for in-person and distance learning. Chapters explore the characterization of organic molecules and synthetic products using NMR, quantitative and computational methods employing NMR, and novel applications of multinuclear and multidimensional NMR.

Laura J. Anna earned her B.S. in chemistry from Indiana University of Pennsylvania, where she had her first introduction to NMR spectroscopy on a 60 MHz instrument. She obtained her Ph.D. in organic chemistry from the University of Michigan investigating applications of chiral vinyl sulfoxides in
the asymmetric synthesis of natural products with Dr. Joseph P.Marino. She began her academic career at Millersville University, Millersville, PA, where she was a professor of chemistry for 14 years working with 200 MHz and 400 MHz high-field NMR instruments. She transitioned to Montgomery College,
Rockville, MD in 2011, where she is now professor of chemistry and department chair. Her current curriculum efforts continue to focus on the integration of NMR spectroscopy in the organic chemistry curriculum using benchtop and 90MHz instruments and the initiation of an undergraduate research
program at Montgomery College.

David Soulsby earned his B.Sc. degree in chemistry from the University of Lancaster, England. He then attended the University of Colorado Boulder, obtaining a Ph.D. in organic chemistry. His research involved the development of ferrocenyl oxazoline catalysts for use in the Heck reaction with Dr.
Tarek Sammakia. He began his academic career at the University of Redlands, Redlands, CA in 2001, where he is a professor of chemistry. He served as department chair from 2011-2014. He continues to teach organic chemistry, developing new laboratory experiments that highlight group data collection
and analysis with NMR spectroscopy. Working alongside undergraduate students, his research focuses on the incorporation of NMR spectroscopy into the undergraduate curriculum, quantitative NMR, and novel ozonolysis reactions.

Anton (Tony) S.Wallner earned his B.S. degree in chemistry from the University of Wisconsin-Milwaukee. He then attended the University of Michigan (M.S. in analytical chemistry) and obtained a Ph.D. in physical chemistry from Case Western Reserve University, where he studied magnetic resonance
imaging of ceramics and polymers with Dr. Bill Ritchey. He conducted research at the Naval Air Warfare Center on MRI of rocket propellants and explosives and took a sabbatical at Monash University in Melbourne, Australia investigating the degradation of creatine followed by NMR. He began his
academic career at Missouri Western State University. He moved to Barry University as chair and professor of chemistry in the Department of Physical Sciences. He then became Associate Dean of Undergraduate Programs at Barry University. Since 2017, he has served as Dean of the College of Arts and
Sciences at Webster University. His research, with active participation from undergraduates, focuses on the synthesis, characterization, and degradation of novel creatine salts followed by NMR.

Preface

Characterization of Organic Molecules and Synthetic Products Using NMR

Chapter 1: Application of Benchtop Nuclear Magnetic Resonance for Structure Elucidation in a Multi-Outcome Experiment: Microwave-Promoted Reduction of Unknown Aldehydes and Ketones, Mengqi Zhang and Richard W. Morrison
Chapter 2: 13C NMR with Proton Coupling Allows Teaching of Hybridization of C-H Bonds on an Experimental Basis, Donald D. Clarke
Chapter 3: Scaffolding NMR Teaching and Learning at an Undergraduate Program in a Virtual World, Susan M. Schelble, William Cole Cronk, and John Buckner
Chapter 4: Synthesis and NMR Spectroscopic Characterization of 1H-1,2,3-Triazoles, Christopher R. Butler, Loren J. Taylor, and Allen M. Schoffstall
Chapter 5: An Inquiry-Based Approach to Electrophilic Aromatic Substitution: Quantifying and Identifying Nitration Products by ¹H NMR, Nanette M. Wachter, Nicole Wedad Khouryawad, and Haley E. Tarbox

Quantitative and Computational Methods Employing NMR

Chapter 6: Physical Chemistry Laboratory Projects Using Vapor Phase NMR, Thomas C. DeVore and Jun Yin
Chapter 7: Synergy between Spectroscopy and Computation: Determining the Major Conformer of an Unexpected Diels-Alder Reaction Product, John E. Hanson and Luc Boisvert
Chapter 8: Quantitative NMR in Undergraduate Labs, Juan F. Araneda, Michael A. Bernstein, Terry Chu, Matthew C. Leclerc, and Susanne D. Riegel
Chapter 9: Using Internet-Based Approaches to Enhance the Teaching of NMR Spectroscopy across the Undergraduate Curriculum, David P. Soulsby
Chapter 10: Kinetic Investigations of Acid-Catalyzed Enolization of Acetophenones by ¹H NMR: Analyzing the Effect of Substituents on the Rate of Deuterium Exchange, Nanette M. Wachter and Haley E. Tarbox

Novel Applications of Multinuclear and Multidimensional NMR

Chapter 11: Using 19F NMR Spectra to Enhance Undergraduate Organic Teaching and Research Labs, Melvin Druelinger and David Dillon
Chapter 12: Using the HSQC Experiment to Teach 2D NMR Spectroscopy in Physical Chemistry, Teresa Longin
Chapter 13: Heteronuclear NMR Spectroscopy in the Undergraduate Curriculum: Direct and Indirect Effects, Sara S. Rocks and Robert A. Stockland
Chapter 14: Synthesis and NMR Characterization of a Dihydropyrazine, a Tetrahydroquinoxaline, and a Tetrahydrooxadiazolopyrazine, MacKinnly Knoerzer, Gavin R. Hoffman, Hannah K.Maben, Andrew T.McGrath, Andrew D. Outlaw, Brett Mayer, and Allen M. Schoffstall
Chapter 15: Teaching Multidimensional Heteronuclear NMR Analysis to Undergraduate Students, Nathan T. Wright and C. Jackson White

Editors' Biographies
Author Index
Subject Index