Note: Intro -- NMR Spectroscopy in the Undergraduate Curriculum, Volume 4: In-Person and Distance Learning Approaches -- ACS Symposium Series1376 -- NMR Spectroscopy in the Undergraduate Curriculum, Volume 4: In-Person and Distance Learning Approaches -- Library of Congress Cataloging-in-Publication Data -- Foreword -- Preface -- Characterization of Organic Molecules and Synthetic Products Using NMR -- Characterization of Organic Molecules and Synthetic Products Using NMR -- Application of Benchtop Nuclear Magnetic Resonance for Structure Elucidation in a Multi-Outcome Experiment: Microwave-Promoted Reduction of Unknown Aldehydes and Ketones -- 13C NMR with Proton Coupling Allows Teaching of Hybridization of C-H Bonds on an Experimental Basis -- Scaffolding NMR Teaching and Learning at an Undergraduate Program in a Virtual World -- Synthesis and NMR Spectroscopic Characterization of 1H-1,2,3-Triazoles -- An Inquiry-Based Approach to Electrophilic Aromatic Substitution: Quantifying and Identifying Nitration Products by 1H NMR -- Quantitative and Computational Methods Employing NMR -- Quantitative and Computational Methods Employing NMR -- Physical Chemistry Laboratory Projects Using Vapor Phase NMR -- Synergy between Spectroscopy and Computation: Determining the Major Conformer of an Unexpected Diels-Alder Reaction Product -- Quantitative NMR in Undergraduate Labs -- Using Internet-Based Approaches to Enhance the Teaching of NMR Spectroscopy across the Undergraduate Curriculum -- Kinetic Investigations of Acid-Catalyzed Enolization of Acetophenones by 1H NMR: Analyzing the Effect of Substituents on the Rate of Deuterium Exchange -- Novel Applications of Multinuclear and Multidimensional NMR -- Novel Applications of Multinuclear and Multidimensional NMR -- Using 19F NMR Spectra to Enhance Undergraduate Organic Teaching and Research Labs. , Using the HSQC Experiment to Teach 2D NMR Spectroscopy in Physical Chemistry -- Heteronuclear NMR Spectroscopy in the Undergraduate Curriculum: Direct and Indirect Effects -- Synthesis and NMR Characterization of a Dihydropyrazine, a Tetrahydroquinoxaline and a Tetrahydrooxadiazolopyrazine -- Teaching Multidimensional Heteronuclear NMR Analysis to Undergraduate Students -- Editors' Biographies -- Indexes -- Indexes -- Author Index -- Subject Index -- Preface -- Characterization of Organic Molecules and Synthetic Products Using NMR -- 1 -- Application of Benchtop Nuclear Magnetic Resonance for Structure Elucidation in a Multi-Outcome Experiment: Microwave-Promoted Reduction of Unknown Aldehydes and Ketones -- Introduction -- Fourier-Transform Infrared Spectroscopy and Nuclear Magnetic Resonance Spectroscopy in Introductory Organic Chemistry Courses and the Integrated Laboratory Course at UGA -- The Utility of Benchtop NMR at UGA -- Microwave Promotion and Its Application at UGA -- Experimental Section -- Benchtop NMR Spectrometer Parameters and Sample Preparation -- Figure 1. Nine unknown starting aldehyde and ketone candidates. Numerical assignments for the nine unknown aldehydes and ketones are shown for reference. -- Figure 2. A screenshot of benchtop NMR interface (picoSpin model) and parameter as reference. Water was injected as the test run sample. Eight scans took ~ 30 seconds and provided quality spectra. "Tx frequency" varied daily based on the shimming result. -- Spectral Analysis -- Figure 3. a) Visual comparison of the nine starting aldehydes and ketones candidates. b) Visual comparison of the nine alcohol products. Numerical assignments for the nine unknowns were listed in Figure 1. Both photos were taken by the author prior to and after the reaction with white paper as background. , Figure 4. FTIR spectrum of 4-ethoxybenzaldehyde (4) reduction product collected from student data in 2018 fall. The presence of O-H bond stretch around 3400 cm-1 and disappearance of carbonyl bond stretch around 1700 cm-1 indicated reaction completion. -- Figure 5. FTIR spectrum of propiophenone (8) reduction product collected from student data in 2018 fall. The presence of O-H bond stretch around 3400 cm-1 and the disappearance of the carbonyl bond stretch around 1700 cm-1 indicated reaction completion. -- Figure 6. 1H NMR spectrum of 4-ethoxybenzaldehyde (4) reduction product with peak assignments. The peak at 5.07 ppm corresponds to residual dichloromethane solvent. The tetramethylsilane (TMS) reference signal was set to 0.0 ppm. -- Figure 7. 1H NMR spectrum of propiophenone (8) reduction product with peak assignments. The peak at 5.07 ppm corresponds to residual dichloromethane solvent. The tetramethylsilane (TMS) reference signal was set to 0.0 ppm. -- Figure 8. Flow chart illustrating the identification process for the unknown starting material candidate based on 1H NMR spectrum. This chart was not provided to students. -- Student Feedback in Post-Lab Online Survey -- Virtual Practice for Multi-Outcome Experiments -- Conclusions -- Acknowledgments -- References -- 2 -- 13C NMR with Proton Coupling Allows Teaching of Hybridization of C-H Bonds on an Experimental Basis -- Introduction -- Calibrating the Relationship of 1JCH and Percent s Character of a C-H Bond -- Relationship between 1JCH and 1JCD -- C-H and C-Cl Bond Hybridization in Chlorinated Methane Compounds -- Hybridization in Cyclic Hydrocarbons -- Figure 1. Structure of cyclooctatetraene. -- Relationship between Hybridization and pKa -- Relationship between Hybridization and Hyperconjugation -- Hybridizations with n Values of Less than One -- Other Hybridization Misconceptions. , Integration into the Curriculum -- Example: Practical Uses of One-Bond Coupling 1JCH - Assignment of Close Chemical Shift Carbon Signals -- Figure 2. Structure of imidazo[1,2-a]pyridine. -- Figure 3. 1H coupled 13C spectrum of imidazo[1,2-a]pyridine. -- Conclusions -- Acknowledgments -- References -- 3 -- Scaffolding NMR Teaching and Learning at an Undergraduate Program in a Virtual World -- Introduction -- Planning with Short Notice -- Pre-pandemic Teaching and Learning -- Virtual Adaptations of Teaching and Learning -- Specifics for Lecture, Laboratory and Advanced Organic -- Introduction of NMR Spectroscopy in First-Semester Organic Chemistry Laboratory -- Figure 1. Screenshot from NMR teaching video. -- Figure 2. Overview of SN2 mechanism. -- Teaching NMR Spectroscopy in Organic Chemistry Lecture Courses -- Expanding on NMR Spectroscopy for Second-Semester Organic Chemistry Laboratory -- Changing the Advanced Molecular Identification Course from F2F to Virtual -- Results -- Student Learning Outcomes-First-Semester Organic Chemistry Laboratory Course -- Figure 3. 1H NMR spectra of the starting material (left) and the recovered product (right) from the SN1 reaction of tert-amyl chloride with hydrochloric acid. -- Figure 4. 1H NMR spectrum of incomplete SN1 reaction product mixture. Labeled signals P1-P3 are from product protons -- R1-R4 from reactant protons. -- Student Learning Outcomes-Second-Semester Organic Chemistry Laboratory Course -- Figure 5. 13C NMR spectrum (top) and 1H NMR spectrum (bottom, with expanded insets) of p-hydroxybenzaldehyde. -- Figure 6. 1H NMR spectrum of impure curcumin extracted from turmeric. -- Student Learning Outcomes-Senior-Level Spectroscopy Identification Course -- Figure 7. 1H NMR spectra of isobutanol C4H10O at 60MHz (top) and 300 MHz (bottom). -- Figure 8. Probing anomalies in C8H8O3 isomers. , Assessment of Goal Achievements -- Summary and Future -- Acknowledgments -- References -- 4 -- Synthesis and NMR Spectroscopic Characterization of 1H-1,2,3-Triazoles -- Introduction -- Synthetic Methods -- Figure 1. Structures of 1,2,3-triazoles 1-6 synthesized in this chapter. -- Scheme 1. Synthesis of Bis-triazole 1 -- NMR Spectroscopy -- NMR Spectra of Bis-triazole 1 -- Figure 2. The 1H NMR spectrum of compound 1. -- Figure 3. The 13C NMR spectrum of compound 1. -- Figure 4. The HSQC spectrum of compound 1. -- Figure 5. The HMBC spectrum of compound 1. -- NMR Spectra of Triazole 2 -- Figure 6. The 1H NMR spectrum of compound 2. -- Figure 7. The 13C NMR spectrum of compound 2. -- Figure 8. The HSQC spectrum of compound 2. -- Figure 9. The HMBC spectrum of compound 2. -- NMR Spectra of Triazole 3 -- Figure 10. The 1H NMR spectrum of compound 3. -- Figure 11. The 13C NMR spectrum of compound 3. -- Figure 12. The HSQC spectrum of compound 3. -- Figure 13. The HMBC spectrum of compound 3. -- NMR Spectra of Triazole 4 -- Figure 14. The 1H NMR spectrum of compound 4. -- Figure 15. The 13C NMR spectrum (aromatic region) of compound 4. -- Figure 16. The HSQC spectrum of compound 4. -- Figure 17. The scale expanded HMBC spectrum of compound 4. -- NMR Spectra of Triazole 5 -- Figure 18. 1H NMR spectrum of compound 5. -- Figure 19. The 13C NMR spectrum of compound 5. -- Figure 20. The HSQC of compound 5. -- Figure 21. The HMBC spectrum of compound 5. -- NMR Spectra of Triazole 6 -- Figure 22. The 1H NMR spectrum of compound 6. -- Figure 23. The 13C NMR spectrum of compound 6. -- Figure 24. The HSQC NMR spectrum of compound 6. -- Figure 25. The HMBC NMR spectrum of compound 6. -- Experimental NMR Spectroscopy -- Experimental Synthetic Procedures -- Dimethyl 1,1′-(benzene-1,4-diyldimethanediyl)bis(1H-1,2,3-triazole-4-carboxylate) (1) 24. , Methyl 1-(2-oxopropyl)-1H-1,2,3-triazole-5-carboxylate (2).