The text Organic Structures from 2D NMR Spectra contains a graded set of structural problems employing 2D-NMR spectroscopy. The Instructors Guide and Solutions Manual to Organic Structures from 2D NMR Spectra is a set of step-by-step worked solutions to every problem in Organic Structures from 2D NMR Spectra. While it is absolutely clear that there are many ways to get to the correct solution of any of the problems, the instructors guide contains at least one complete pathway to every one of the questions. In addition, the instructors guide carefully rationalises every peak in every spectrum in relation to the correct structure. The Instructors Guide and Solutions Manual to Organic Structures from 2D NMR Spectra: Is a complete set of worked solutions to the problems contained in Organic Structures from 2D NMR Spectra. Provides a step-by-step description of the process to derive structures from spectra as well as annotated 2D spectra indicating the origin of every cross peak. Highlights common artefacts and re-enforces the important characteristics of the most common techniques 2D NMR techniques including COSY, NOESY, HMBC, TOCSY, CH-Correlation and multiplicity-edited C-H Correlation. This guide is an essential aid to those teachers, lecturers and instructors who use Organic Structures from 2D NMR as a text to teach students of Chemistry, Pharmacy, Biochemistry and those taking courses in Organic Chemistry.

L. D. Field is the author of Instructor's Guide and Solutions Manual to Organic Structures from 2D NMR Spectra, published by Wiley. A. M. Magill is the author of Instructor's Guide and Solutions Manual to Organic Structures from 2D NMR Spectra, published by Wiley.

Preface ix

Solutions Summary 1

Problem 1 (1-iodopropane) 7

Problem 2 (2-butanone) 11

Problem 3 (2-hexanone) 15

Problem 4 (ethyl propionate) 19

Problem 5 (ethyl 3-ethoxypropionate) 23

Problem 6 (4-acetylbutyric acid) 28

Problem 7 (3-ethoxypropionyl chloride) 32

Problem 8 (ethyl 3-chloropropionate) 36

Problem 9 (isoamyl acetate) 40

Problem 10 (trans-4-hexen-3-one) 45

Problem 11 (trans-2-octen-4-one) 50

Problem 12 (3-nitrobenzaldehyde) 55

Problem 13 (3-iodotoluene) 61

Problem 14 (8-hydroxy-5-nitroquinoline) 64

Problem 15 (2-bromo-3-picoline) 69

Problem 16 (trans-anethole) 72

Problem 17 (cis-2-pentene) 75

Problem 18 (p-tolyl benzoate) 79

Problem 19 (phenyl p-toluate) 86

Problem 20 (4-biphenylyl acetate) 93

Problem 21 (4'-phenoxyacetophenone) 99

Problem 22 (4'-tert-butylacetophenone) 106

Problem 23 (2,2,4'-trimethylpropiophenone) 110

Problem 24 (trans-2-methyl-3-phenyl-2-propen-1-ol) 114

Problem 25 (methyl 4-ethoxybenzoate) 119

Problem 26 (methyl 3-(p-tolyl)propionate) 123

Problem 27 (4-(4'-methoxyphenyl)-2-butanone) 127

Problem 28 (ethyl 6-bromohexanoate) 132

Problem 29 (piperonal) 135

Problem 30 (cis-3-hexenyl benzoate) 139

Problem 31 (trans-2,cis-6-nonadienal) 146

Problem 32 (allyl glycidyl ether) 155

Problem 33 (3,4-epoxy-4-methyl-2-pentanone) 159

Problem 34 (dl-methionine) 162

Problem 35 (N-acetyl-l-leucine) 165

Problem 36 (isoamyl valerate) 170

Problem 37 ((E)-4-methyl-4'-nitrostilbene) 173

Problem 38 (2-tert-butyl-6-methylphenol) 181

Problem 39 (2-allyl-6-methylphenol) 186

Problem 40 (2-hydroxy-4-methoxybenzaldehyde) 194

Problem 41 (2'-hydroxy-5'-methylacetophenone) 198

Problem 42 (3'-fluoro-4'-methoxyacetophenone) 203

Problem 43 (trans-ferulic acid) 209

Problem 44 (sec-butyl 3-hydroxycinnamate) 215

Problem 45 (1-benzosuberone) 221

Problem 46 (dimethyl (3-bromopropyl)phosphonate) 228

Problem 47 (caffeine) 233

Problem 48 (benzyloxypropionitrile) 238

Problem 49 (cineole) 242

Problem 50 (thymoquinone) 246

Problem 51 (4-bromo-1-indanol) 251

Problem 52 (1-bromo-4-methylnaphthalene) 257

Problem 53 (carvacrol) 264

Problem 54 (acetoacetanilide) 272

Problem 55 (ethyl acetamidocyanoacetate) 277

Problem 56 (α-humulene) 283

Problem 57 (3,4-dihydro-2H-benzopyran-3-carboxylic acid) 289

Problem 58 (quinidine) 296

Problem 59 (salbutamol) 312

Problem 60 (2-hydroxy-1-naphthaldehyde) 322

Problem 61 (6-methyl-4-chromanone) 329

Problem 62 (citronellal) 336

Problem 63 ((+)-cis-2-oxabicyclo-[3.3.0]oct-6-en-3-one) 344

Problem 64 (melatonin) 349

Problem 65 (carvone) 362

Problem 66 (haloperidol) 370