Organic Structure Elucidation Workbook

Organic Structure Elucidation

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Problems

EASY MODERATE DIFFICULT

1 2 3 4 5 6 7 8

9 10 11 12 13 14 15 16

17 18 19 20 21 22 23 24

25 26 27 28 29 30 31 32

33 34 35 36 37 38 39 40

41 42 43 44 45 46 47 48

49 50 51 52 53 54 55 56

57 58 59 60 61 62 63 64

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Directory

Problem 1 C3H5BrO2

MW = 152

IR

1H NMR 500 MHz, CDCl3

13C NMR 125 MHz, CDCl3

Mass Spec 70 eV +EI

Problems

Table of Contents

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IR Sample •1•••

Problem 1 - IR spectrum

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Problem 1 H-1 NMR

Problem 1 - 1H NMR spectrum (CDCl3, 500 MHz)

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Problem 1 C-13 NMR

Problem 1 - 13C NMR spectrum (CDCl3, 125 MHz)

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MS Sample •1•••

Problem 1 - positive EI Mass Spectrum

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Directory

Problem 2 C8H14O4

MW = 174

IR



Mass Spec 70 eV +EI

Problems

Table of Contents

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Problem 2 H-1 NMR


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Problem 2 C-13 NMR


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Directory

Problem 3 C9H12

MW = 120

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 3 H-1 NMR



Problem 3 C-13 NMR






Directory

Problem 4 C7H13Br

MW = 176

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 4 H-1 NMR



Problem 4 C-13 NMR






Directory

Problem 5 C5H8O

MW = 84

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 5 H-1 NMR



Problem 5 C-13 NMR






Directory

Problem 6 C9H13NO

MW = 151

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 6 H-1 NMR



Problem 6 C-13 NMR






Directory

Problem 7 C6H10

MW = 82

IR



Mass Spec 70 eV +EI

Problems

Table of Contents

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Problem 7 H-1 NMR


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Problem 7 C-13 NMR


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http://www.nd.edu/~smithgrp/structure/mshtmls/ms7x.html10/28/2010 2:35:33 PM

Directory

Problem 8 C8H11NO

MW = 137

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 8 H-1 NMR



Problem 8 C-13 NMR






Directory

Problem 9 C10BrH7

MW = 206

IR



Mass Spec 70 eV +EI

Problems

Table of Contents


IR Problem •9•••



Problem 9 H-1 NMR



Problem 9 C-13 NMR






Directory

Problem 10 C14H19NO4

MW = 265

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 10 C-13 NMR



Problem 10 H-1 NMR



MS Sample •10••



Directory

Problem 11 C6H12O2

MW = 116

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 11 H-1 NMR



Problem 11 C-13 NMR






Directory

Problem 12 C7H5NO4

MW = 167

IR

1H NMR 500 MHz, DMSO-d6

13C NMR 125 MHz, DMSO-d6

Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 12 H-1 NMR

Problem 12 - 1H NMR spectrum (DMSO-d6, 500 MHz)


Problem 12 C-13 NMR

Problem 12 - 13C NMR spectrum (DMSO-d6, 125 MHz)





Directory

Problem 13 C5H10O4

MW = 134

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 13 C-13 NMR



Problem 13 H-1 NMR






Directory

Problem 14 C8H6O2

MW = 134

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 14 H-1 NMR



Problem 14 C-13 NMR






Directory

Problem 15 C13H10O3

MW = 214

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 15 H-1 NMR



Problem 15 C-13 NMR






Directory

Problem 16 C7H6O2

MW = 122

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 16 H-1 NMR



Problem 16 C-13 NMR






Directory

Problem 17 C9H10O3

MW = 166

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 17 H-1 NMR



Problem 17 C-13 NMR






Directory

Problem 18 C7H10O4

MW = 158

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 18 H-1 NMR



Problem 18 C-13 NMR






Directory

Problem 19 C9H7NO4

MW = 193

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 19 H-1 NMR



Problem 19 C-13 NMR






Directory

Problem 20 C8H9NO2

MW = 151

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 20 H-1 NMR



Problem 20 C-13 NMR






Directory

Problem 21 C9H12O3

MW = 168

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 21 H-1 NMR



Problem 21 C-13 NMR






Directory

Problem 22 C9H12N2O

MW = 164

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 22 H-1 NMR



Problem 22 C-13 NMR






Directory

Problem 23 C9H10O3

MW = 166

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 23 H-1 NMR



Problem 23 C-13 NMR






Directory

Problem 24 C9H10O3

MW = 166

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 24 H-1 NMR



Problem 24 C-13 NMR






Directory

Problem 25 C14H14O2

MW = 214

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 25 H-1 NMR



Problem 25 C-13 NMR






Directory

Problem 26 C7H11O4Br

MW = 238

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 26 H-1 NMR



Problem 26 C-13 NMR






Directory

Problem 27 C8H19N

MW = 129

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 27 H-1 NMR



Problem 27 C-13 NMR






Directory

Problem 28 C6H12O2Cl2

MW = 186

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 28 H-1 NMR



Problem 28 C-13 NMR






Directory

Problem 29 C3H7OCl

MW = 94

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 29 H-1 NMR



Problem 29 C-13 NMR






Directory

Problem 30 C6H6O2

MW = 110

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 30 H-1 NMR



Problem 30 C-13 NMR






Directory

Problem 31 C6H7NO

MW = 109

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 31 H-1 NMR



Problem 31 C-13 NMR






Directory

Problem 32 C7H6NF3

MW = 161

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 32 H-1 NMR



Problem 32 C-13 NMR






Directory

Problem 33 C6H4Cl2

MW = 146

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 33 H-1 NMR



Problem 33 C-13 NMR






Directory

Problem 34 C6H5NO3

MW = 139

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 34 H-1 NMR



Problem 34 C-13 NMR






Directory

Problem 35 C6H5NO3

MW = 139

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 35 H-1 NMR



Problem 35 C-13 NMR



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Directory

Problem 36 C4H4N2

MW = 80

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 36 H-1 NMR



Problem 36 C-13 NMR






Directory

Problem 37 C6H7PO3

MW = 158

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 37 H-1 NMR



Problem 37 C-13 NMR






Directory

Problem 38 C9H8N2

MW = 144

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 38 H-1 NMR



Problem 38 C-13 NMR






Directory

Problem 39 C5H6O3

MW = 114

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 39 H-1 NMR



Problem 39 C-13 NMR






Directory

Problem 40 C16H35N

MW = 241

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 40 H-1 NMR



Problem 40 C-13 NMR






Directory

Problem 41 C6H12O5

MW = 164

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 41 H-1 NMR



Problem 41 C-13 NMR






Directory

Problem 42 C13H9NO3

MW = 227

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 42 H-1 NMR



Problem 42 C-13 NMR






Directory

Problem 43 C7H6BrF

MW = 188

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 43 H-1 NMR



Problem 43 C-13 NMR






Directory

Problem 44 C13H10

MW = 166

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 44 H-1 NMR



Problem 44 C-13 NMR






Directory

Problem 45 C10H11NO2

MW = 177

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 45 H-1 NMR



Problem 45 C-13 NMR






Directory

Problem 46 C5H12O2

MW = 104

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 46 H-1 NMR



Problem 46 C-13 NMR






Directory

Problem 47 C6H12O3

MW = 132

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 47 H-1 NMR



Problem 47 C-13 NMR






Directory

Problem 48 C10H20O

MW = 156

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 48 H-1 NMR



Problem 48 C-13 NMR






Directory

Problem 49 C9H16O5

MW = 204

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 49 H-1 NMR



Problem 49 C-13 NMR






Directory

Problem 50 C3H7OCl

MW = 94

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 50 H-1 NMR



Problem 50 C-13 NMR






Directory

Problem 51 C8H6O3

MW = 150

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 51 H-1 NMR



Problem 51 C-13 NMR






Directory

Problem 52 C9H10O2

MW = 150

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 52 H-1 NMR



Problem 52 C-13 NMR






Directory

Problem 53 C6H8O2

MW = 112

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 53 H-1 NMR



Problem 53 C-13 NMR






Directory

Problem 54 C5H7NO3

MW = 129

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 54 H-1 NMR



Problem 54 C-13 NMR






Directory

Problem 55 C8H8O2

MW = 136

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 55 H-1 NMR



Problem 55 C-13 NMR






Directory

Problem 56 C7H11NO2

MW = 141

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 56 H-1 NMR



Problem 56 C-13 NMR






Directory

Problem 57 C6H5O2SCl

MW = 176

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 57 H-1 NMR



Problem 57 C-13 NMR






Directory

Problem 58 C10H13N5O4

MW = 267

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 58 H-1 NMR



Problem 58 C-13 NMR






Directory

Problem 59 C14H12O2

MW = 212

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 59 H-1 NMR



Problem 59 C-13 NMR






Directory

Problem 60 C4HO3Br

MW = 176

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 60 H-1 NMR



Problem 60 C-13 NMR






Directory

Problem 61 C8H14O3

MW = 158

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 61 H-1 NMR



Problem 61 C-13 NMR






Directory

Problem 62 C6H11O2Br

MW = 194

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 62 H-1 NMR



Problem 62 C-13 NMR






Directory

Problem 63 C14H12O2

MW = 212

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 63 H-1 NMR



Problem 63 C-13 NMR






Directory

Problem 64 C10H12O

MW = 148

IR



Mass Spec 70 eV +EI

Problems

Table of Contents





Problem 64 H-1 NMR



Problem 64 C-13 NMR






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Organic Structure Elucidation Workbook