Workbook to Accompany Organic Chemistry...

0

Workbook to Accompany Organic Chemistry Courses

1

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

2

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.

3

Unknown 1: Mass Spec

MF: C7H8

Interpretation of Spectra

1

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4

Unknown 1: IR

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5

Unknown 1: NMR


3

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3 5

6

Unknown 1: C NMR


4

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7

Unknown 2: MS

MF: C4H10O


1

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8

Unknown 2: IR

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9

Unknown 2: NMR


3

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3

2

10

Unknown 2: C NMR


4

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11

Unknown 3: MS

MF: C3H6O2


1

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12

Unknown 3: IR

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13

Unknown 3: NMR


3

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1 1

14

Unknown 3: C NMR


4

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15

Unknown 4: MS

MF: C4H8O2


1

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16

Unknown 4: IR

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17

Unknown 4: NMR


3

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3

3

2

18

Unknown 4: C NMR


4

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19

Unknown 5: MS

MF: C6H12


1

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20

Unknown 5: IR

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21

Unknown 5: NMR


3

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22

Unknown 5: C NMR


4

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23

Unknown 6: MS

MF: C7H14


1

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24

Unknown 6: IR

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25

Unknown 6: NMR

0123PPM

311

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26

Unknown 6: C NMR


4

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27

Unknown 7: MS

MF: C6H12O2


1

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28

Unknown 7: IR

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29

Unknown 7: NMR

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30

Unknown 7: C NMR


4

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31

Unknown 8: MS

MF: C5H10O2


1

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32

Unknown 8: IR

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33

Unknown 8: NMR

0123456PPM

6

3

1

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34

Unknown 8: C NMR


4

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35

Unknown 9: MS

MF: C8H10


1

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36

Unknown 9: IR

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37

Unknown 9: NMR


3

3

2

5

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38

Unknown 9: C NMR


4

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39

Unknown 10: MS

MF: C9H12


1

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40

Unknown 10: IR

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41

Unknown 10: NMR


3

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6

1

5

42

Unknown 10: C NMR


4

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43

Unknown 11: MS

MF: C2H6O


1

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44

Unknown 11: IR

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45

Unknown 11: NMR


3

3

2

1

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46

Unknown 11: C NMR


4

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47

Unknown 12: MS

MF: C2H4O2


1

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48

Unknown 12: IR

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49

Unknown 12: NMR


3

3

1

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50

Unknown 12: CNMR


4

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51

Unknown 13: MS

MF: C3H6O2


1

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52

Unknown 13: IR

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53

Unknown 13: NMR


3

3

2

1

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54

Unknown 13: CNMR


4

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55

Unknown 14: MS

MF: C4H8O2


1

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56

Unknown 14: IR

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57

Unknown 14: NMR


3

3

3

2

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58

Unknown 14: CNMR


4

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59

Unknown 15: MS

MF: C6H12O2


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


4

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63

Unknown 16: MS

MF: C5H10O2


1

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64

Unknown 16: IR

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65

Unknown 16: NMR


3

3

32

2

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66

Unknown 16: CNMR


4

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67

Unknown 17: MS

MF: C3H8O2


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


4

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71

Unknown 18: MS

MF: C4H10O


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


4

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75

Unknown 19: MS

MF: C3H7Br


1

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76

Unknown 19: IR

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77

Unknown 19: NMR


3

2

2

3

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78

Unknown 19: CNMR


4

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79

Unknown 20: MS

MF: C3H7Br


1

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80

Unknown 20: IR

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81

Unknown 20: NMR


3

6

1

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82

Unknown 20: CNMR


4

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83

Unknown 21: MS

MF: C3H8O


1

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84

Unknown 21: IR

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85

Unknown 21: NMR


3

6

1

1

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86

Unknown 21: CNMR


4

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87

Unknown 22: MS

MF: C8H8O


1

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88

Unknown 22: IR

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89

Unknown 22: NMR


3

3

32

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90

Unknown 22: CNMR


4

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91

Unknown 23: MS

MF: C7H8O2


1

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92

Unknown 23: IR

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93

Unknown 23: NMR


3

32

1

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94

Unknown 23: CNMR


4

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95

Unknown 24: MS

MF: C7H6O


1

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96

Unknown 24: IR

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97

Unknown 24: NMR


3

32

1

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98

Unknown 24: CNMR


4

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99

Unknown 25: MS

MF: C8H8O2


1

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100

Unknown 25: IR

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101

Unknown 25: NMR


3

3

32

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102

Unknown 25: CNMR


4

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103

Unknown 26: MS

MF: C8H8O2


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


4

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107

Unknown 27: MS

MF: C7H8O


1

________________________________________________________________________________

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108

Unknown 27: IR

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109

Unknown 27: NMR


3

3

32

________________________________________________________________________________

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____________________________________________________________

110

Unknown 27: CNMR


4

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

____________________________________________________________

111

Unknown 28: MS

MF: C8H8


1

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

____________________________________________________________

112

Unknown 28: IR

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

____________________________________________________________

113

Unknown 28: NMR


3

111

32

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

____________________________________________________________

114

Unknown 28: CNMR


4

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

____________________________________________________________

115

Unknown 29: MS

MF: C4H8O


1

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

____________________________________________________________

116

Unknown 29: IR

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

____________________________________________________________

117

Unknown 29: NMR


3

3

22

1

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

118

Unknown 29: CNMR


4

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

____________________________________________________________

119

Unknown 30: MS

MF: C4H8O


1

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

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____________________________________________________________

120

Unknown 30: IR

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

____________________________________________________________

121

Unknown 30: NMR


3

6

1

1

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

____________________________________________________________

122

Unknown 30: CNMR


4

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

____________________________________________________________

123

Unknown 31: MS

MF: C4H8O


1

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

124

Unknown 31: IR

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

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________________________________________________________________________________

________________________________________________________________________________

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________________________________________________________________________________

________________________________________________________________________________

____________________________________________________________

125

Unknown 31: NMR


3

3

3

2

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

____________________________________________________________

126

Unknown 31: CNMR


4

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

____________________________________________________________

127

Unknown 32: MS

MF: C6H10


1

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

____________________________________________________________

128

Unknown 32: IR

________________________________________________________________________________

________________________________________________________________________________

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________________________________________________________________________________

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________________________________________________________________________________

________________________________________________________________________________

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________________________________________________________________________________

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129

Unknown 32: NMR


3

4 42

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

____________________________________________________________

130

Unknown 32: CNMR


4

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

____________________________________________________________

131

Unknown 33: MS

MF: C5H10O


1

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

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________________________________________________________________________________

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____________________________________________________________

132

Unknown 33: IR

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

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________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

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133

Unknown 33: NMR


3

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

134

Unknown 33: CNMR


4

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

____________________________________________________________

135

Unknown 34: MS

MF: C6H12O2


1

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

____________________________________________________________

136

Unknown 34: IR

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

____________________________________________________________

137

Unknown 34: NMR


3

9

2

1

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

____________________________________________________________

138

Unknown 34: CNMR


4

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

____________________________________________________________

139

Unknown 35: MS

MF: C6H10O


1

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

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____________________________________________________________

140

Unknown 35: IR

________________________________________________________________________________

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________________________________________________________________________________

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____________________________________________________________

141

Unknown 35: NMR


3

________________________________________________________________________________

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________________________________________________________________________________

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________________________________________________________________________________

________________________________________________________________________________

____________________________________________________________

142

Unknown 35: CNMR


4

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

____________________________________________________________

143

Unknown 36: MS

MF: C5H11Cl


1

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

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____________________________________________________________

144

Unknown 36: IR

________________________________________________________________________________

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________________________________________________________________________________

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____________________________________________________________

145

Unknown 36: NMR


3

________________________________________________________________________________

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________________________________________________________________________________

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________________________________________________________________________________

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________________________________________________________________________________

________________________________________________________________________________

____________________________________________________________

146

Unknown 36: CNMR


4

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

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________________________________________________________________________________

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________________________________________________________________________________

________________________________________________________________________________

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____________________________________________________________

147

Unknown 37: MS

MF: C5H10O


1

________________________________________________________________________________

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________________________________________________________________________________

________________________________________________________________________________

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148

Unknown 37: IR

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149

Unknown 37: NMR


3

________________________________________________________________________________

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150

Unknown 37: CNMR


4

________________________________________________________________________________

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____________________________________________________________

151

Unknown 38: MS

MF: C6H10


1

________________________________________________________________________________

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152

Unknown 38: IR

________________________________________________________________________________

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153

Unknown 38: NMR


3

________________________________________________________________________________

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154

Unknown 38: CNMR


4

________________________________________________________________________________

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________________________________________________________________________________

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____________________________________________________________

155

Unknown 39: MS

MF: C9H12


1

________________________________________________________________________________

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156

Unknown 39: IR

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157

Unknown 39: NMR


3

________________________________________________________________________________

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158

Unknown 39: CNMR


4

________________________________________________________________________________

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________________________________________________________________________________

________________________________________________________________________________

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________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

____________________________________________________________

159

Unknown 40: MS

MF: C6H12O


1

________________________________________________________________________________

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160

Unknown 40: IR

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161

Unknown 40: NMR


3

1

1

6

2

2

________________________________________________________________________________

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162

Unknown 40: CNMR


4

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

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________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

____________________________________________________________

163

Unknown 41: MS

MF: C10H14O


1

________________________________________________________________________________

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164

Unknown 41: IR

________________________________________________________________________________

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165

Unknown 41: NMR


3

________________________________________________________________________________

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________________________________________________________________________________

166

Unknown 41: CNMR


4

________________________________________________________________________________

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________________________________________________________________________________

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________________________________________________________________________________

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____________________________________________________________

167

Unknown 42: MS

MF: C6H12O


1

________________________________________________________________________________

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________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

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________________________________________________________________________________

168

Unknown 42: IR

________________________________________________________________________________

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169

Unknown 42: NMR


3

________________________________________________________________________________

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____________________________________________________________

170

Unknown 42: CNMR


4

________________________________________________________________________________

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________________________________________________________________________________

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____________________________________________________________

171

Unknown 43: MS

MF: C6H5Br


1

________________________________________________________________________________

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172

Unknown 43: IR

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173

Unknown 43: NMR


3

________________________________________________________________________________

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174

Unknown 43: CNMR


4

________________________________________________________________________________

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________________________________________________________________________________

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________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

____________________________________________________________

175

Unknown 44: MS

MF: C6H12O


1

________________________________________________________________________________

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176

Unknown 44: IR

________________________________________________________________________________

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177

Unknown 44: NMR


3

________________________________________________________________________________

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178

Unknown 44: CNMR


4

________________________________________________________________________________

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________________________________________________________________________________

________________________________________________________________________________

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________________________________________________________________________________

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____________________________________________________________

179

Unknown 45: MS

MF: C7H7Br


1

________________________________________________________________________________

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180

Unknown 45: IR

________________________________________________________________________________

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181

Unknown 45: NMR


3

________________________________________________________________________________

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________________________________________________________________________________

________________________________________________________________________________

____________________________________________________________

5

2

182

Unknown 45: CNMR


4

________________________________________________________________________________

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________________________________________________________________________________

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________________________________________________________________________________

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____________________________________________________________

183

Unknown 46: MS

MF: C6H6O


1

________________________________________________________________________________

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184

Unknown 46: IR

________________________________________________________________________________

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185

Unknown 46: NMR


3

________________________________________________________________________________

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________________________________________________________________________________

________________________________________________________________________________

____________________________________________________________

3

1

2

186

Unknown 46: CNMR


4

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

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________________________________________________________________________________

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________________________________________________________________________________

________________________________________________________________________________

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____________________________________________________________

187

Unknown 47: MS

MF: C6H4BrNO2


1

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

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188

Unknown 47: IR

________________________________________________________________________________

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189

Unknown 47: NMR


3

1 1

________________________________________________________________________________

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190

Unknown 47: CNMR


4

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

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________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

____________________________________________________________

191

Unknown 48: MS

MF: C6H4BrNO2


1

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

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192

Unknown 48: IR

________________________________________________________________________________

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193

Unknown 48: NMR


3

________________________________________________________________________________

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194

Unknown 48: CNMR


4

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

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________________________________________________________________________________

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________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

____________________________________________________________

195

Unknown 49: MS

MF: C6H5NO2


1

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

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196

Unknown 49: IR

________________________________________________________________________________

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197

Unknown 49: NMR


3

2

2 1

________________________________________________________________________________

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198

Unknown 49: CNMR


4

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

____________________________________________________________

199

Unknown 50: MS

MF: C7H5NO4


1

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

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____________________________________________________________

200

Unknown 50: IR

________________________________________________________________________________

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________________________________________________________________________________

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________________________________________________________________________________

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____________________________________________________________

201

Unknown 50: NMR


3

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

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________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

________________________________________________________________________________

____________________________________________________________

202

Unknown 50: CNMR


4

________________________________________________________________________________

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203

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

204

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.

205

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

206

D. Chemical Shifts for 13C NMR

207

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

Workbook to Accompany Organic Chemistry...

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