NMR Spectroscopy in the Undergraduate Curriculum: First Year and

Subject Index

Downloaded by 80.82.77.83 on October 28, 2017 | http://pubs.acs.org Publication Date (Web): September 15, 2016 | doi: 10.1021/bk-2016-1221.ix002

B Benchtop NMR, undergraduate organic courses determining sample purity, 110 ethyl acetate and dimethylformamide, 1H NMR spectrum, 111f natural product identification, 116 limonene and correlating picoSpin spectrum, extraction scheme, 117f small molecule, identification, 109 n-propanol using the picoSpin 45, 1H NMR spectrum, 110f synthesized product, analysis, 111 cyclohexanone from cyclohexanol, reaction scheme, 115f methyl salicylate, synthetic scheme and picoSpin 45 NMR, 113f produce 1,2-dibromocyclohexane from cyclohexanol, two-step reaction scheme, 114f R-carvone and picoSpin spectrum, reaction scheme for the reduction, 116f R-carvone to carvacrol, reaction scheme for oxidation, 115f synthetic scheme and picoSpin 45 1H NMR spectrum, 112f

F Free radical chlorination experimental procedure, 86 introduction, 81 1-chloro- and 2-chloropropane, free radical reaction, 83f 1-chlorobutane, free radical chlorination, 82f free radical chlorination reactions, factors that affect the reactivity, 84t primary and secondary hydrogen atom, chlorine radical abstraction, 83f total correlation spectroscopy (TOCSY) NMR experiment, 85 results and discussion, 86 1D 1H NMR spectrum, stacked spectra, 94f

1D 1H NMR spectrum of the reaction product 1-chlorobutane, stacked spectra, 95f 1D TOCSY NMR spectroscopy, structural analysis, 93 free radical chlorination, 1H NMR spectrum, 87f free radical chlorination of 1-chlorobutane, 1H NMR spectrum, 90f free radical chlorination of 2-methylbutane, 1H NMR spectrum, 88f free radical chlorination of propylbenzene, 1H NMR spectrum, 89f hexane, student calculation table, 90t multiple substrates, relative reactivity values, 92t relative reactivity values, 92f substrates, normalized relative reactivity values, 91t

M 4-Methylanisole, diacylation Friedel-Crafts acylation reactions, 138 reactions involved, summary, 138s NMR background, 139 ethanol, HSQC NMR spectrum, 139f nomenclature, 140 products of the diacylation, identification at 80 °C, 146 4-hydroxy-3,5-dipropionyltoluene, NMR data from 1:3 mixture, 148t 1:3 mixture of 4-hydroxy3,5-dipropionyltoluene:4hydroxy-3-propionytoluene, 1H NMR, 147f products of the diacylation, identification at room temperature, 144 HMBC spectrum of 4-hydroxy-3-propionyltoluene, expanded part, 146f 4-hydroxy-3-propionyltoluene, NMR data, 145t 1:2 mixture of 4-hydroxy3-propionyltoluene:4methoxy-3-propionyltoluene, 1H NMR, 144f

179 Soulsby et al.; NMR Spectroscopy in the Undergraduate Curriculum: First Year and Organic Chemistry Courses Volume 2 ACS Symposium Series; American Chemical Society: Washington, DC, 2016.


standard acylation reaction, identification of the product, 141 4-methoxy-3-propionyltoluene, expanded HMBC spectrum, 144f 4-methoxy-3-propionyltoluene, 1H NMR spectrum, 142f 4-methoxy-3-propionyltoluene, NMR data, 143t 1-Methylcyclohexanol, dehydration introduction, 99 1-methylcyclohexanol, dehydration, 100s 2-methylcyclohexanol, dehydration, 100s 4-methylcyclohexanol, dehydration, 100s results and discussion, 102 distillate (1-methylcyclohexene), 13C NMR spectrum, 103f distillate (1-methylcyclohexene), DEPT spectra, 104f formation values, calculated heat, 103s

N NMR spectroscopy, undergraduate curriculum acquisition, 6 advanced 1D and 2D NMR experiments, 5 basic 1D NMR spectroscopy, 3 basic 2D NMR spectroscopy, 4 data analysis, 6

O Organic chemistry, interweaving and scaffolded learning conclusions, 56 curriculum, implementation of spectroscopy addition of HBr to 2-methylbut-2-ene, potential products, 49f carbon-carbon and carbon-hydrogen bonds, IR stretching frequencies, 47f case study, hybridization, 46 chemical shift data, comparison, 47f exams and group activities, sample integrative questions, 48f fundamental organic chemistry concepts and examples of

the spectroscopic evidence, connections, 45t other topics, applying spectroscopy, 44 promoting higher-level thinking, 48 pedagogical motivation course philosophy, connections, 44 setting classroom culture, 43 structural perspective, interconnected knowledge and skills, 43f structure, interweaving knowledge, 42 spectroscopy first, opportunities and challenges first-semester organic laboratory project, synthetic scheme, 50f future learning, connections, 51 good study habits, 51 IR spectroscopy, condensed roadmap, 53t longitudinal development, 55 NMR spectroscopy, condensed roadmap, 54t potential drawbacks, 52 spectroscopy theory, 49 Organic chemistry laboratory, utilizing NMR, 119 background, 120 Studying of molecular structure, esters as a template 18 commercially available esters, 123f ethyl isobutanoate, 1H NMR spectrum and corresponding structure, 124f laboratory details, 121 materials and instrumentation, 122 student feedback and outcomes, 125 study of keto-enol equilibrium, proton NMR 1,3-dicarbonyl compounds, 129t instructor notes, 132 Ke/k, impact of steric bulk, 130 keto form of methyl 3-oxobutanoate, resonance stabilization, 131f pentane-2,4-dione (1) to 4-hydroxypent-3-en-2-one (R = R’ = -CH3), tautomerization, 126f pentane-2,4-dione with peak assignments, 1H NMR spectrum, 129f

S Soft drinks, measurement of phosphates experimental details, 33


U

free induction decay 250ppm phosphorous, 34f ppm versus integrated peak intensity, concentration of phosphorous, 35f processed spectrum, comparison, 34f soft drinks, concentration of phosphorous using NMR, 35t soft drinks, concentration of phosphorous using UV/VIS, 36t


T Teaching 1H NMR spectroscopy, 61 constructivism, 64 neural scaffolding, 65 multiplicity for SI peer leaders, completed table, 67t SI peer leader packet, information given, 67t SI sessions, portion of aromatic problem set, 69f SI sessions, problems that contained oxygen, 68f SI sessions, sample problems, 66f C7H6O, 1H NMR spectrum, 74f C6H5OBr, comparison of the results, 75f C6H5OBr, 1H NMR spectrum, 75f comparison of the results, 74f data gathering and statistical methods, 69 diethyl ether CH2 protons, question about splitting pattern, 71f drawing structure for C7H6O from 1H NMR spectrum, question, 73f ethyl acetate spectrum, question about number of signals, 70f number of signals expected, comparison of the results, 70f pre-test to post-test, percentage improvement, 71f propyl acetate spectrum, question about number of signals, 71f qualitative data, 76 quantitative data, 70 SI and non-SI groups, comparison of the results, 73f splitting pattern expected, comparison of the results, 72f structure for C4H8O2 from 1H NMR spectrum, question, 72f supplemental instruction, 62 SI Peer Leaders, 62

Unequivocal proof, NMR spectroscopy in an organic laboratory project, 151 discussion, 152 2-azido-1-phenylethanone, preparation, 155 reduction of (1) to (2), formation of a possible intermediate (5), 154f synthetic procedures, 154 triazole derivatives, synthesis, 153f experimental NMR spectroscopy, 156 spectral interpretation, 158 compound 1, 13C NMR spectrum, 159f compound 1, HMBC spectrum, 161f compound 1, 1H NMR spectrum, 159f compound 1, HSQC spectrum, 160f compound 2, 13C NMR spectrum, 163f compound 2, 2D HMBC spectrum, 164f compound 2, 2D HSQC spectrum, 164f compound 2, 1H NMR spectrum, 162f compound 3, 13C NMR spectrum, 166f compound 3, 2D HMBC spectrum, 167f compound 3, 2D HSQC spectrum, 166f compound 3, 1H NMR spectrum, 165f compound 4, 13C NMR spectrum, 169f compound 4, 2D HMBC spectrum, 170f compound 4, 2D HSQC spectrum, 170f compound 4, 1H NMR spectrum, 168f 2D-COSY spectrum of compound 2, selected regions, 162f 2D COSY spectrum of compound 4, selected regions, 168f University of Technology Sydney, first-year chemistry, 13 demonstrator feedback, 25 identify unknown samples, NMR flow chart, 26f design, 18 first-year chemistry, 14 UTS Superlab, 15f isoamyl acetate, preparation and characterization in experiment 4, 23 isoamyl acetate synthesis scheme, 24f synthesis product isoamyl acetate, 1H NMR spectrum, 24f organic reactions, experiment 2, 19 butanal, FTIR spectrum, 20f butanal, 1H NMR spectrum, 21f butanone, FTIR spectrum, 21f


butanone, 1H NMR spectrum, 22f 2-methyl-2-butanol, FTIR spectrum, 20f 2-methyl-2-butanol, 1H NMR spectrum, 22f 1-propanol, FTIR spectrum, 21f 1-propanol, 1H NMR spectrum, 23f unknown samples, experiment 2 chemical formulas, 20f student experience, project assessment, 26


Advanced Chemistry 2 student survey, section, 27f Likert ASCIv2 student survey results, 28f NMR quiz results, advanced chemistry, 27f UTS instrumentation, 15 completed run, Picospin-45 NMR software, 17f FID, Picospin-45 NMR software, 18f UTS picoSpin-45 NMR, 16f


NMR Spectroscopy in the Undergraduate Curriculum: First Year and

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