Simulated I spectra Group 1 compounds: Functional group patterns are listed below. Match each structure with one of the 4 simulated I spectra that follow. The wave numbers listed in each spectrum are intended to provide clues as to what the functional group might be. Note your interpretation of what those numbers indicate right on the spectra and write a structure (not a number) in the space provided at the right of each I. Sulfides, tertiary (3o) amines and symmetrical alkynes all lack key diagnostic peaks and can appear similar to one another and similar to simple alkynes. Limited mass spec data is provided to help distinguish these possibilities (M+, M+1, M+2 peaks). Also, watch out for overtone bands (32-34 cm -1 ) in carbonyl compounds (C=). They can be easily mistaken for an amine (N-H) or an alcohol (-H). 1 2 3 H H 4 5 6 7 Cl Cl 8 9 1 NH 2 N H 11 12 13 14 15 N N N H H 16 17 18 19 2 H H 21 22 23 H H H 24 25 26 27 28 29 3 H SH SH SH SH SH S 31 32 NH 2 H N 33 34 35 36 37 38 39 NH 2 N N N 4 H Group 2 compounds: C, H hydrocarbons = alkanyl (=), alkenyl, alkynyl and aromatic. Answer similarly. 1 2 3 4 5 6 7 8 H 9 1 11 12 13 14 15 16 H CH 3 H CH 3 17 18 19 2 y:\files\classes\spectroscopy\i\is simulated from database probs.doc
Group 1 compounds: Functional group patterns are listed above (1-4). To the right of each I draw the structure most consistent with the given I. Provide a minimal interpretation of the I bands (e.g. 1 o NH 2 stretch, C= stretch, para substituted aromatic, monosubstituted alkene, etc.) Watch out for carbonyl (C=) overtone bands. 1 Exact Mass: 11.12 337 329 162 147 138 81 M+ = 11.12 (.%), M+1 = 12.12 (6.9%) 2 296-28 4 3 3 2 2 1 343 36 16 139 146 7 Exact Mass: 1.7 M+ = 1.7 (.%), M+1 = 151.7 (9.9%) 3 4 296-28 172 127 111 7 4 3 3 2 2 1 36 maybe 328 wet C= overtone? 137 126 11 17 297-286 16 143 4 3 3 2 2 1 368 147 138 Exact Mass: 143.13 M+ = 143.13 (.%), M+1 = 144.13 (9.%) Exact Mass: 134.5 M+ = 134.5 (.%), M+1 = 135.5 (6.5%), M+2 = 136.5 (32.2%), M+3 = 137.5 (2.1%) 294-286 18 96 73 44 4 3 3 2 2 1 5 37 16 138 99 Exact Mass: 114.1 M+ = 114.1 (.%), M+1 = 115.11 (7.8%) 296-28 147 1 91 4 3 3 2 2 1 y:\files\classes\spectroscopy\i\is simulated from database probs.doc
6 Exact Mass: 154.2 36 147 138 M+ = 154.2 (.%), M+1 = 155.2 (8.8%), M+2 = 156.2 (32.2%), M+3 = 157.2 (2.8%) 7 294-286 178 82 4 3 3 2 2 1 Exact Mass: 144.12 14 136 18 12 M+ = 144.12 (.%), M+1 = 145.12 (8.9%) 8 9 296-28 174 119 4 3 3 2 2 1 364 298-289 146 13 182 176 14 4 3 3 2 2 1 81 Exact Mass: 158.9 M+ = 158.9 (.%), M+1 = 159.1 (8.9%) Exact Mass: 136.5 M+ = 136.5 (.%), M+1 = 137.6 (8.8%) 37 33-2 1695 129 82 4 3 3 2 2 1 1 138 38 147 69 15 124 overtone Exact Mass: 129.12 M+ = 129.12 (.%), M+1 = 13.12 (7.8%) 33 296-286 16 4 3 3 2 2 1 y:\files\classes\spectroscopy\i\is simulated from database probs.doc
11 Exact Mass: 97.9 22 147 138 73 M+ = 97.9 (.%), M+1 = 98.9 (6.9%) 12 297-28 4 3 3 2 2 1 37 164 138 331 Exact Mass: 136.9 M+ = 136.9 (.%), M+1 = 137.9 (9.8%) 13 296-28 147 17 7 4 3 3 2 2 1 341 36 282 274 16 146 14 Exact Mass: 134.7 M+ = 134.7 (.%), M+1 = 135.8 (9.9%) 14 296-28 17 83 4 3 3 2 2 1 Exact Mass: 115.1 M+ = 115.1 (.%), M+1 = 116.1 (6.9%) 142 138 64 15 364 296-286 336 166 163 4 3 3 2 2 1 341 282 274 36 16 146 296-28 17 83 7 4 3 3 2 2 1 14 68 6 Exact Mass: 16.4 M+ = 16.4 (.%), M+1 = 17.5 (7.7%) y:\files\classes\spectroscopy\i\is simulated from database probs.doc
16 341 112 Exact Mass: 114.1 M+ = 114.1 (.%), M+1 = 115.11 (7.8%) 1 296-28 172 4 3 3 2 2 1 17 37 29-287 161 151 141 Exact Mass: 131.7 M+ = 131.7 (.%), M+1 = 132.8 (9.8%) 18 223 82 5 4 3 3 2 2 1 3 (wet) 33 162 Exact Mass: 96.6 M+ = 96.6 (.%), M+1 = 97.6 (6.6%) 19 1685 296-28 4 3 3 2 2 1 341 286 272 147 139 112 73 Exact Mass:.9 M+ =.9 (.%), M+1 = 11.9 (6.5%) 2 296-28 173 4 3 3 2 2 1 138 66 334 Exact Mass:.9 M+ =.9 (.%), M+1 = 11.9 (6.5%) 296-28 147 1 4 3 3 2 2 1 y:\files\classes\spectroscopy\i\is simulated from database probs.doc
21 Exact Mass: 152.7 37 29-287 256 16 151 141 8 76 M+ = 152.7 (.%), M+1 = 153.7 (1.7%), M+2 = 154.6 (4.5%) 22 7 4 3 3 2 2 1 37 164 138 332 Exact Mass:.9 M+ =.9 (.%), M+1 = 11.9 (6.5%) 23 296-28 147 17 89 4 3 3 2 2 1 339 36 33 166-2 Exact Mass: 134.7 M+ = 134.7 (.%), M+1 = 135.8 (9.9%) 296-28 169 122 7 69 4 3 3 2 2 1 24 Exact Mass: 152.7 37 29-287 256 16 151 141 76 M+ = 152.7 (.%), M+1 = 153.7 (1.7%), M+2 = 154.6 (4.5%) 7 4 3 3 2 2 1 25 36 34 Exact Mass: 136.9 M+ = 136.9 (.%), M+1 = 137.9 (9.8%) 296-28 137 16 1 1 7 1245 4 3 3 2 2 1 y:\files\classes\spectroscopy\i\is simulated from database probs.doc
26 Exact Mass: 11.2 37 258 141 161 151 76 M+ = 11.2 (.%), M+1 = 111.2 (7.3%), M+2 = 112.1 (4.5%) 27 69 4 3 3 2 2 1 138 147 Exact Mass: 129.15 M+ = 129.15 (.%), M+1 = 13.16 (8.9%) 296-28 4 3 3 2 2 1 28 Exact Mass: 138.5 37 29-287 256 161 141 151 M+ = 138.5 (.%), M+1 = 139.5 (9.5%), M+2 = 14.5 (4.6%) 29 3 81 5 4 3 3 2 2 1 16 292 33 325 1515 124 815 4 3 3 2 2 1 37 141 159 151 76 Exact Mass: 122.7 M+ = 122.7 (.%), M+1 = 123.8 (8.8%) Exact Mass: 152.7 M+ = 152.7 (.%), M+1 = 153.7 (1.7%), M+2 = 154.6 (4.5%) 296-28 69 4 3 3 2 2 1 y:\files\classes\spectroscopy\i\is simulated from database probs.doc
31 32 3 114 296-28 1765 12 69 4 3 3 2 2 1 37 29-287 262 16 159 147 138 141 76 Exact Mass: 178.1 M+ = 178.1 (.%), M+1 = 179.1 (12.%) Exact Mass: 152.7 M+ = 152.7 (.%), M+1 = 153.7 (1.7%), M+2 = 154.6 (4.5%) 33 74 4 3 3 2 2 1 Exact Mass: 129.15 329 147 138 138 725 M+ = 129.15 (.%), M+1 = 13.16 (8.9%) 296-28 4 3 3 2 2 1 34 Exact Mass:.13 137 72 M+ =.13 (.%), M+1 = 11.13 (7.8%) 35 296-28 14 4 3 3 2 2 1 37 164 138 66 334 99 Exact Mass:.9 M+ =.9 (.%), M+1 = 11.9 (6.5%) 296-28 147 16 91 4 3 3 2 2 1 y:\files\classes\spectroscopy\i\is simulated from database probs.doc
36 138 Exact Mass: 13.14 M+ = 13.14 (.%), M+1 = 131.14 (8.9%) 296-28 146 112 4 3 3 2 2 1 37 Exact Mass: 117.8 M+ = 117.8 (.%), M+1 = 118.8 (5.9%) 294-298 138 156 4 3 3 2 2 1 38 Exact Mass: 123.3 38 286 162 M+ = 123.3 (.%), M+1 = 124.4 (6.6%) 152 13 71 68 4 3 3 2 2 1 39 4 33-2 141 129 12 297 286 171 4 3 3 2 2 1 343 336 38 34 1 138 162 142 159 7 4 3 3 2 2 1 94 7 Exact Mass: 116.8 M+ = 116.8 (.%), M+1 = 117.9 (6.7%) Exact Mass: 93.6 M+ = 93.6 (.%), M+1 = 94.6 (6.6%) y:\files\classes\spectroscopy\i\is simulated from database probs.doc
Group 2 compounds: C, H hydrocarbons = alkanyl (=), alkenyl, alkynyl and aromatic patterns are listed above (1-2). To the right of each I draw the structure most consistent with the given I. Provide a minimal interpretation of the I bands (e.g. para substituted aromatic, monosubstituted alkene, etc.) 1 16 212 76 33 3 147 69 62 2 296-28 4 3 3 2 2 1 38 1646 147 89 73 3 296-28 4 3 3 2 2 1 3 16 2 147 7 69 296-28 4 3 3 2 2 1 4 31 1665 147 71 5 296-28 4 3 3 2 2 1 16 39 3 147 67 4 3 3 2 2 1 y:\files\classes\spectroscopy\i\is simulated from database probs.doc
6 1675 147 296-28 4 3 3 2 2 1 7 137 72 296-28 14 4 3 3 2 2 1 8 2 147 725 9 296-28 6 4 3 3 2 2 1 3 32 para 161 substituted aromatic 1455 overtones 16 545 296-28 1515 83 4 3 3 2 2 1 1 38 164 147 995 91 725 296-28 4 3 3 2 2 1 y:\files\classes\spectroscopy\i\is simulated from database probs.doc
11 331 212 147 725 296-28 6 4 3 3 2 2 1 12 168 137 147 84 13 296-28 4 3 3 2 2 1 39 33 monosubstituted aromatic overtones 164 147 73 296-28 7 4 3 3 2 2 1 14 39 33 monosubstituted aromatic overtones 164 147 15 296-28 76 96 69 4 3 3 2 2 1 3 32 meta substituted aromatic overtones 161 149 132 16 89 296-28 1455 795 7 4 3 3 2 2 1 y:\files\classes\spectroscopy\i\is simulated from database probs.doc
16 3 32 ortho substituted 165 aromatic overtones 16 149 296-28 14 7 4 3 3 2 2 1 17 296 28 38 33 164 16 149 995 91 74 18 7 4 3 3 2 2 1 38 74 146 138 97 19 296-28 4 3 3 2 2 1 147 Exact Mass: 96.9 M+ = 96.9 (.%), M+1 = 97.1 (7.7%) 2 296-28 6 4 3 3 2 2 1 296 28 36 33 166 16 149 74 89 7 4 3 3 2 2 1 y:\files\classes\spectroscopy\i\is simulated from database probs.doc
Formula problem 1 Exact Mass: 277.1 M+ = 277.1 (.%), M+1 = 278.1 (14.5%), M+2 = 279.1 (97.5%), M+3 = 28.1 (14.2%), M+4 = 281.1 (1.1%) Hints: 1. What does the odd mass tell you? 2. What does the M+1 tell you? 3. What does the M+2 tell you? 4. There are 12 H in the proton NM. 5. There are 13 C in the C-13 NM. 6. There are 5 pi bonds in the C-13 NM. Questions: What is the molecular formula? How many degrees of unsaturation are there? How many rings and pi bonds are there? Formula problem 2 Exact Mass: 33.8 M+ = 33.8 (.%), M+1 = 331.9 (2.8%), M+2 = 332.8 (38.9%), M+3 = 333.8 (7.8%), M+4 = 334.8 (1.5%) Hints: 1. What does the even mass tell you? 2. What does the M+1 tell you? 3. What does the M+2 tell you? 4. There are 19 H in the proton NM. 5. There are 19 C in the C-13 NM. 6. There are 6 pi bonds in the C-13 NM. Questions: What is the molecular formula? How many degrees of unsaturation are there? How many rings and pi bonds are there? Formula problem 3 Exact Mass: 262.14 M+ = 262.14 (.%), M+1 = 263.14 (12.3%), M+2 = 264.13 (6.%), M+3 = 263.13 (1.5%), Hints: 1. What does the even mass tell you? 2. What does the M+1 tell you? 3. What does the M+2 tell you? 4. There are 22 H in the proton NM. 5. There are 11 C in the C-13 NM. 6. There is 1 pi bonds in the C-13 NM. Questions: What is the molecular formula? How many degrees of unsaturation are there? How many rings and pi bonds are there? y:\files\classes\spectroscopy\i\is simulated from database probs.doc