workbook to accompany organic chemistry...
TRANSCRIPT
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Workbook to Accompany Organic Chemistry Courses
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Introduction This workbook is designed to train organic students in the art of spectral interpretation. A detailed discussion of the theory of spectroscopy (and spectometry for MS) may be found in most organic textbooks and that material should be studied before attempting the problems. There are tables of data (correlation tables) which are used to interpret aspects of each spectrum. These are included as appendices in the back of the book. Each compound is an “Unknown” and the spectral data are included: infrared (IR); nuclear magnetic resonance (NMR), both proton and 13C. Although not a spectroscopic technique, the low resolution mass spectrum (MS) is also included.
Problem Solving—The Strategy
There are four spectra for each compound:
1) The Mass Spectrum-This is a low resolution spectrum of the fragmentation patterns, resulting
from the electron ionization of the compound. The molecular formula is also included on this page; by
using the index of hydrogen deficiency, it is possible to determine the number of rings and/or double
bonds in the compound.1 The IHD does not distinguish rings from multiple bonds, but does indicate
the total numbers of rings and multiple bonds. The mass spectrum itself, is a listing of the masses for
the fragments, resulting from the ionization of the compound.
2) The Infrared Spectrum-This spectrum shows the vibrational frequencies of different types of
bonding in an organic compound. This data is used to determine the functional groups present in the
compound. There is a table of common vibrational frequencies in reciprocal centimeters (cm-1) in
Appendex B.
3) The 1H NMR-this is used to determine the locations and the types of protons in the structure. The
integration of the proton types is included on the spectra. The integration is the simplest ratio of types
of protons in the structure; always cross check with the molecular formula to be sure that all the
protons have been assigned. There is a correlation table of chemical shift values in Appendix C.
4) The 13C NMR-analogous to proton NMR: this spectrum reveals the different types of carbon in the
compound. These are the standard decoupled 13C NMR spectra; there is also a correlation table of 13C chemical shift data in appendix D.
1 IHD = (#Hs saturated Hydrocarbon) – (#Hs in the compound) / 2
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Suggested Steps: Use the mass spectrum and the molecular formula to determine structural sub-groups. The IR
spectrum is used to determine the functional groups in the compound. On a separate worksheet,
write down the molecular “pieces.” It is also helpful to subtract these atoms from the molecular
formula to determine how much of the structure is left. The 1H NMR is the most valuable for
determining the structure (including isomers). Begin assembling the subgroups and pieces to build a
possible molecule. The NMR will indicate where, and how many protons are possible. At this point,
there will be very few structures which are consistent with the data. The 13C NMR will indicate the
types of carbon atoms (not how many). Combining all the information from all the spectra, propose
(draw) a structure. Go back to each spectra and test for consistency- all the spectral data will be
consistent with the proper structure. The list of all unknowns is included on the last page of the
appendix.
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Unknown 1: Mass Spec
MF: C7H8
Interpretation of Spectra
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Unknown 1: IR
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Unknown 1: NMR
Interpretation of Spectra
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Unknown 1: C NMR
Interpretation of Spectra
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Unknown 2: MS
MF: C4H10O
Interpretation of Spectra
1
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Unknown 2: IR
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Unknown 2: NMR
Interpretation of Spectra
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Unknown 2: C NMR
Interpretation of Spectra
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Unknown 3: MS
MF: C3H6O2
Interpretation of Spectra
1
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Unknown 3: IR
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Unknown 3: NMR
Interpretation of Spectra
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Unknown 3: C NMR
Interpretation of Spectra
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Unknown 4: MS
MF: C4H8O2
Interpretation of Spectra
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Unknown 4: IR
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Unknown 4: NMR
Interpretation of Spectra
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Unknown 4: C NMR
Interpretation of Spectra
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Unknown 5: MS
MF: C6H12
Interpretation of Spectra
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Unknown 5: IR
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Unknown 5: NMR
Interpretation of Spectra
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Unknown 5: C NMR
Interpretation of Spectra
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Unknown 6: MS
MF: C7H14
Interpretation of Spectra
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Unknown 6: IR
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Unknown 6: NMR
0123PPM
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Unknown 6: C NMR
Interpretation of Spectra
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Unknown 7: MS
MF: C6H12O2
Interpretation of Spectra
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Unknown 7: IR
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Unknown 7: NMR
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Unknown 7: C NMR
Interpretation of Spectra
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Unknown 8: MS
MF: C5H10O2
Interpretation of Spectra
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Unknown 8: IR
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Unknown 8: NMR
0123456PPM
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Unknown 8: C NMR
Interpretation of Spectra
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Unknown 9: MS
MF: C8H10
Interpretation of Spectra
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Unknown 9: IR
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Unknown 9: NMR
Interpretation of Spectra
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Unknown 9: C NMR
Interpretation of Spectra
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Unknown 10: MS
MF: C9H12
Interpretation of Spectra
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Unknown 10: IR
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Unknown 10: NMR
Interpretation of Spectra
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Unknown 10: C NMR
Interpretation of Spectra
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43
Unknown 11: MS
MF: C2H6O
Interpretation of Spectra
1
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44
Unknown 11: IR
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45
Unknown 11: NMR
Interpretation of Spectra
3
3
2
1
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46
Unknown 11: C NMR
Interpretation of Spectra
4
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47
Unknown 12: MS
MF: C2H4O2
Interpretation of Spectra
1
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48
Unknown 12: IR
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49
Unknown 12: NMR
Interpretation of Spectra
3
3
1
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50
Unknown 12: CNMR
Interpretation of Spectra
4
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51
Unknown 13: MS
MF: C3H6O2
Interpretation of Spectra
1
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52
Unknown 13: IR
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53
Unknown 13: NMR
Interpretation of Spectra
3
3
2
1
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54
Unknown 13: CNMR
Interpretation of Spectra
4
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55
Unknown 14: MS
MF: C4H8O2
Interpretation of Spectra
1
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56
Unknown 14: IR
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57
Unknown 14: NMR
Interpretation of Spectra
3
3
3
2
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58
Unknown 14: CNMR
Interpretation of Spectra
4
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59
Unknown 15: MS
MF: C6H12O2
Interpretation of Spectra
1
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60
Unknown 15: IR
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61
Unknown 15: NMR
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62
Unknown 15: CNMR
Interpretation of Spectra
4
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63
Unknown 16: MS
MF: C5H10O2
Interpretation of Spectra
1
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64
Unknown 16: IR
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65
Unknown 16: NMR
Interpretation of Spectra
3
3
32
2
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66
Unknown 16: CNMR
Interpretation of Spectra
4
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67
Unknown 17: MS
MF: C3H8O2
Interpretation of Spectra
1
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68
Unknown 17: IR
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69
Unknown 17: NMR
01234PPM
3
2
2
1
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70
Unknown 17: CNMR
Interpretation of Spectra
4
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71
Unknown 18: MS
MF: C4H10O
Interpretation of Spectra
1
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72
Unknown 18: IR
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73
Unknown 18: NMR
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74
Unknown 18: CNMR
Interpretation of Spectra
4
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75
Unknown 19: MS
MF: C3H7Br
Interpretation of Spectra
1
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76
Unknown 19: IR
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77
Unknown 19: NMR
Interpretation of Spectra
3
2
2
3
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78
Unknown 19: CNMR
Interpretation of Spectra
4
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79
Unknown 20: MS
MF: C3H7Br
Interpretation of Spectra
1
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80
Unknown 20: IR
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81
Unknown 20: NMR
Interpretation of Spectra
3
6
1
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82
Unknown 20: CNMR
Interpretation of Spectra
4
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83
Unknown 21: MS
MF: C3H8O
Interpretation of Spectra
1
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84
Unknown 21: IR
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85
Unknown 21: NMR
Interpretation of Spectra
3
6
1
1
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86
Unknown 21: CNMR
Interpretation of Spectra
4
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87
Unknown 22: MS
MF: C8H8O
Interpretation of Spectra
1
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88
Unknown 22: IR
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89
Unknown 22: NMR
Interpretation of Spectra
3
3
32
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90
Unknown 22: CNMR
Interpretation of Spectra
4
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91
Unknown 23: MS
MF: C7H8O2
Interpretation of Spectra
1
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92
Unknown 23: IR
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93
Unknown 23: NMR
Interpretation of Spectra
3
32
1
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94
Unknown 23: CNMR
Interpretation of Spectra
4
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95
Unknown 24: MS
MF: C7H6O
Interpretation of Spectra
1
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96
Unknown 24: IR
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97
Unknown 24: NMR
Interpretation of Spectra
3
32
1
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98
Unknown 24: CNMR
Interpretation of Spectra
4
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99
Unknown 25: MS
MF: C8H8O2
Interpretation of Spectra
1
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100
Unknown 25: IR
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101
Unknown 25: NMR
Interpretation of Spectra
3
3
32
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102
Unknown 25: CNMR
Interpretation of Spectra
4
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103
Unknown 26: MS
MF: C8H8O2
Interpretation of Spectra
1
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104
Unknown 26: IR
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105
Unknown 26: NMR
Interpretation of Spectr
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106
Unknown 26: CNMR
Interpretation of Spectra
4
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107
Unknown 27: MS
MF: C7H8O
Interpretation of Spectra
1
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108
Unknown 27: IR
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109
Unknown 27: NMR
Interpretation of Spectra
3
3
32
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110
Unknown 27: CNMR
Interpretation of Spectra
4
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111
Unknown 28: MS
MF: C8H8
Interpretation of Spectra
1
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112
Unknown 28: IR
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113
Unknown 28: NMR
Interpretation of Spectra
3
111
32
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114
Unknown 28: CNMR
Interpretation of Spectra
4
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115
Unknown 29: MS
MF: C4H8O
Interpretation of Spectra
1
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116
Unknown 29: IR
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117
Unknown 29: NMR
Interpretation of Spectra
3
3
22
1
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118
Unknown 29: CNMR
Interpretation of Spectra
4
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119
Unknown 30: MS
MF: C4H8O
Interpretation of Spectra
1
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120
Unknown 30: IR
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121
Unknown 30: NMR
Interpretation of Spectra
3
6
1
1
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122
Unknown 30: CNMR
Interpretation of Spectra
4
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123
Unknown 31: MS
MF: C4H8O
Interpretation of Spectra
1
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124
Unknown 31: IR
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125
Unknown 31: NMR
Interpretation of Spectra
3
3
3
2
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126
Unknown 31: CNMR
Interpretation of Spectra
4
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127
Unknown 32: MS
MF: C6H10
Interpretation of Spectra
1
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128
Unknown 32: IR
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129
Unknown 32: NMR
Interpretation of Spectra
3
4 42
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130
Unknown 32: CNMR
Interpretation of Spectra
4
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131
Unknown 33: MS
MF: C5H10O
Interpretation of Spectra
1
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132
Unknown 33: IR
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133
Unknown 33: NMR
Interpretation of Spectra
3
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134
Unknown 33: CNMR
Interpretation of Spectra
4
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135
Unknown 34: MS
MF: C6H12O2
Interpretation of Spectra
1
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136
Unknown 34: IR
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137
Unknown 34: NMR
Interpretation of Spectra
3
9
2
1
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138
Unknown 34: CNMR
Interpretation of Spectra
4
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139
Unknown 35: MS
MF: C6H10O
Interpretation of Spectra
1
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140
Unknown 35: IR
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141
Unknown 35: NMR
Interpretation of Spectra
3
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142
Unknown 35: CNMR
Interpretation of Spectra
4
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143
Unknown 36: MS
MF: C5H11Cl
Interpretation of Spectra
1
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144
Unknown 36: IR
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145
Unknown 36: NMR
Interpretation of Spectra
3
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146
Unknown 36: CNMR
Interpretation of Spectra
4
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147
Unknown 37: MS
MF: C5H10O
Interpretation of Spectra
1
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148
Unknown 37: IR
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149
Unknown 37: NMR
Interpretation of Spectra
3
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150
Unknown 37: CNMR
Interpretation of Spectra
4
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151
Unknown 38: MS
MF: C6H10
Interpretation of Spectra
1
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152
Unknown 38: IR
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153
Unknown 38: NMR
Interpretation of Spectra
3
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154
Unknown 38: CNMR
Interpretation of Spectra
4
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155
Unknown 39: MS
MF: C9H12
Interpretation of Spectra
1
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156
Unknown 39: IR
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157
Unknown 39: NMR
Interpretation of Spectra
3
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158
Unknown 39: CNMR
Interpretation of Spectra
4
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159
Unknown 40: MS
MF: C6H12O
Interpretation of Spectra
1
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160
Unknown 40: IR
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161
Unknown 40: NMR
Interpretation of Spectra
3
1
1
6
2
2
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162
Unknown 40: CNMR
Interpretation of Spectra
4
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163
Unknown 41: MS
MF: C10H14O
Interpretation of Spectra
1
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164
Unknown 41: IR
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165
Unknown 41: NMR
Interpretation of Spectra
3
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166
Unknown 41: CNMR
Interpretation of Spectra
4
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167
Unknown 42: MS
MF: C6H12O
Interpretation of Spectra
1
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168
Unknown 42: IR
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169
Unknown 42: NMR
Interpretation of Spectra
3
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170
Unknown 42: CNMR
Interpretation of Spectra
4
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171
Unknown 43: MS
MF: C6H5Br
Interpretation of Spectra
1
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172
Unknown 43: IR
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173
Unknown 43: NMR
Interpretation of Spectra
3
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174
Unknown 43: CNMR
Interpretation of Spectra
4
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175
Unknown 44: MS
MF: C6H12O
Interpretation of Spectra
1
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176
Unknown 44: IR
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177
Unknown 44: NMR
Interpretation of Spectra
3
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178
Unknown 44: CNMR
Interpretation of Spectra
4
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179
Unknown 45: MS
MF: C7H7Br
Interpretation of Spectra
1
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Unknown 45: IR
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Unknown 45: NMR
Interpretation of Spectra
3
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2
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Unknown 45: CNMR
Interpretation of Spectra
4
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183
Unknown 46: MS
MF: C6H6O
Interpretation of Spectra
1
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184
Unknown 46: IR
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185
Unknown 46: NMR
Interpretation of Spectra
3
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3
1
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186
Unknown 46: CNMR
Interpretation of Spectra
4
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187
Unknown 47: MS
MF: C6H4BrNO2
Interpretation of Spectra
1
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188
Unknown 47: IR
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189
Unknown 47: NMR
Interpretation of Spectra
3
1 1
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190
Unknown 47: CNMR
Interpretation of Spectra
4
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191
Unknown 48: MS
MF: C6H4BrNO2
Interpretation of Spectra
1
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192
Unknown 48: IR
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193
Unknown 48: NMR
Interpretation of Spectra
3
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194
Unknown 48: CNMR
Interpretation of Spectra
4
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195
Unknown 49: MS
MF: C6H5NO2
Interpretation of Spectra
1
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196
Unknown 49: IR
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197
Unknown 49: NMR
Interpretation of Spectra
3
2
2 1
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198
Unknown 49: CNMR
Interpretation of Spectra
4
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199
Unknown 50: MS
MF: C7H5NO4
Interpretation of Spectra
1
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Unknown 50: IR
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Unknown 50: NMR
Interpretation of Spectra
3
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Unknown 50: CNMR
Interpretation of Spectra
4
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Appendices
A. Natural Abundance of Isotopes for selected Elements
Element Symbol Nominal Mass Exact Mass Abundance
H 1 1.00783 99.99 Hydrogen D or 2H 2 2.0141 0.01
12C 12 12 98.91 Carbon 13C 13 13.0034 1.09
14N 14 14.0031 99.6 Nitrogen 15N 15 15.0001 0.37
16O 16 15.9949 99.76 17O 17 16.9991 0.037
Oxygen 18O 18 17.9992 0.2 Fluorine F 19 18.9984 100
28Si 28 27.9769 92.28 29Si 29 28.9765 4.7
Silicon 30Si 30 29.9738 3.02 Phosphorus P 31 30.9738 100
32S 32 31.9721 95.02 33S 33 32.9715 0.74
Sulphur 34S 34 33.9679 4.22 35Cl 35 34.9689 75.77
Chlorine 37Cl 37 36.9659 24.23 79Br 79 78.9183 50.5
Bromine 81Br 81 80.9163 49.5 Iodine I 127 126.9045 100
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B. Characteristic Absorptions for various Functional Groups in IR Spectra
Functional Group Absorption(s) (cm-1) Comments Alkyl C-H Stretch 2950 - 2850 (m or s) Alkane C-H bonds are common and
are not usually diagnostic; however, the demarkation of 3000 cm-1 should be noted: aliphatic C--H are below this value.
Alkenyl C-H Stretch 3100 - 3010 (m) Absorption peaks above 3000 cm-1 are frequently diagnostic of unsaturation
Alkenyl C=C Stretch 1680 - 1620 (v) Alkynyl C-H Stretch ~3300 (s) Alkynyl C=C Stretch 2260 - 2100 (v) Aromatic C-H Stretch ~3030 (v) Absorption peaks above 3000 cm-1 Aromatic C-H Bending 860 - 680 (s) Aromatic C=C Bending 1700 - 1500 (m,m)
Alcohol/Phenol O-H Stretch
3550 - 3200 (broad, s) Hydrogen-Bonded Hydroxyl display an intese, broad "U" shaped appearance.
Carboxylic Acid O-H Stretch
3000 - 2500 (broad, v) This OH stretch paired with a C=O ~ 1780-1710 cm-1
Amine N-H Stretch 3500 - 3300 (m) Primary amines produce two N-H stretch absorptions, secondary amides only one, and tetriary none.
Nitrile C=N Stretch 2260 - 2220 (m) Aldehyde C=O Stretch 1740 - 1690 (s)
Ketone C=O Stretch 1750 - 1680 (s) Ester C=O Stretch 1750 - 1735 (s)
Carboxylic Acid C=O Stretch
1780 - 1710 (s)
Amide C=O Stretch 1690 - 1630 (s)
The carbonyl stretching absorption is usually one of the strongest in the spectrum. It is also one of the most common.
Amide N-H Stretch 3700 - 3500 (m) As with amines, an amide produces zero to two N-H absorptions depending on its type.
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C. Chemical Shifts for 1H NMR
RCH2OR
(CH3 )4Si
ArCH3
RCH3
RC CH
RCCH3
ROHRCH2OH
ArCH2R
O
O
RCH2RR3CH
R2NH
RCCH2R
R2C=CRCHR2
R2C=CHR
RCH
O
RCOH
O
RCH2ClRCH2BrRCH2I
RCH2F
ArHO
O
R2C=CH2
RCOCH3
RCOCH2R
ArOH
9.5-10.1
3.7-3.9
3.4-3.6
Type ofHydrogen
0 (by definition)
Type ofHydrogen
ChemicalShift (δ)
1.6-2.62.0-3.0
0.8-1.01.2-1.41.4-1.7
2.1-2.3
0.5-6.0
2.2-2.6
3.4-4.0
ChemicalShift (δ)
3.3-4.0
2.2-2.52.3-2.8
0.5-5.0
4.6-5.05.0-5.7
10-13
4.1-4.73.1-3.3
3.6-3.84.4-4.5
6.5-8.5
4.5-4.7
RCH2ORRCH2OR
(CH3 )4Si(CH3 )4Si
ArCH3ArCH3
RCH3RCH3
RCRC CHCH
RCCH3RCCH3
ROHROHRCH2OHRCH2OH
ArCH2RArCH2R
O
O
RCH2RRCH2RR3CHR3CH
R2NHR2NH
RCCH2RRCCH2R
R2C=CRCHR2R2C=CRCHR2
R2C=CHRR2C=CHR
RCHRCH
O
RCOHRCOH
O
RCH2ClRCH2ClRCH2BrRCH2BrRCH2IRCH2I
RCH2FRCH2F
ArHArHO
O
R2C=CH2R2C=CH2
RCOCH3RCOCH3
RCOCH2RRCOCH2R
ArOHArOH
9.5-10.19.5-10.1
3.7-3.93.7-3.9
3.4-3.63.4-3.6
Type ofHydrogenType ofHydrogen
0 (by definition)0 (by definition)
Type ofHydrogenType ofHydrogen
ChemicalShift (δ)ChemicalShift (δ)
1.6-2.61.6-2.62.0-3.02.0-3.0
0.8-1.00.8-1.01.2-1.41.2-1.41.4-1.71.4-1.7
2.1-2.32.1-2.3
0.5-6.00.5-6.0
2.2-2.62.2-2.6
3.4-4.03.4-4.0
ChemicalShift (δ)ChemicalShift (δ)
3.3-4.03.3-4.0
2.2-2.52.2-2.52.3-2.82.3-2.8
0.5-5.00.5-5.0
4.6-5.04.6-5.05.0-5.75.0-5.7
10-1310-13
4.1-4.74.1-4.73.1-3.33.1-3.3
3.6-3.83.6-3.84.4-4.54.4-4.5
6.5-8.56.5-8.5
4.5-4.74.5-4.7
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D. Chemical Shifts for 13C NMR
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D. Index of Unknowns
Unknown # NAME Page Unknown # NAME Page1 Toluene 3 26 Phenyl Acetate 103 2 Diethyl Ether 7 27 Methyl Phenyl Ether (anisole) 107 3 Methyl Acetate 11 28 Phenyl Ethylene (styrene) 111 4 Ethyl Acetate 15 29 n-butyraldehyde 115 5 Cyclohexane 19 30 iso-butyraldehyde 119 6 Methylcyclohexane 23 31 2-butanone 123 7 Isobutyl Acetate 27 32 cyclohexene 127 8 Isopropyl Acetate 31 33 3-pentanone 131 9 Ethyl Benzene 35 34 3,3-Dimethylbutyric Acid 135 10 Isopropyl Benzene (cumene) 39 35 Cyclohexanone 139 11 Ethanol 43 36 1-chloropentane 143 12 Acetic Acid 47 37 3-methyl-2-butanone 147 13 Propionic Acid 51 38 1-methyl-1-cyclopentene 151 14 Methyl Propionate 55 39 m-Ethyltoluene 155 15 n-Propyl Propionate 59 40 Cyclohexanol 159 16 n-Propyl Acetate 63 41 2-Phenyl-2-butanol 163 17 1-Propanol 67 42 1-Methylcyclopentanol 167 18 2-Butanol 71 43 Bromobenzene 171 19 1-Bromopropane 75 44 3-hexanone 175 20 2-Bromopropane 79 45 Benzyl Bromide 179 21 2-Propanol 83 46 Phenol 183 22 Acetophenone 87 47 p-Bromonitrobenzene 187 23 Benzoic Acid 91 48 m-Bromonitrobenzene 191 24 Benzaldehyde 95 49 Nitrobenzene 195 25 Methyl Benzoate 99 50 m-Nitrobenzoic Acid 199