Group 2 compounds: C, H hydrocarbons = alkanyl (=R), alkenyl, alkynyl and aromatic. Answer similarly.

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Osborn Lloyd
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1 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) H H Cl Cl NH 2 N H N N N H H H H H H H H SH SH SH SH SH S NH 2 H N NH 2 N N N 4 H Group 2 compounds: C, H hydrocarbons = alkanyl (=), alkenyl, alkynyl and aromatic. Answer similarly H H CH 3 H CH y:\files\classes\spectroscopy\i\is simulated from database probs.doc

2 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: M+ = (.%), M+1 = (6.9%) Exact Mass: 1.7 M+ = 1.7 (.%), M+1 = (9.9%) maybe 328 wet C= overtone? Exact Mass: M+ = (.%), M+1 = (9.%) Exact Mass: M+ = (.%), M+1 = (6.5%), M+2 = (32.2%), M+3 = (2.1%) Exact Mass: M+ = (.%), M+1 = (7.8%) y:\files\classes\spectroscopy\i\is simulated from database probs.doc

3 6 Exact Mass: M+ = (.%), M+1 = (8.8%), M+2 = (32.2%), M+3 = (2.8%) Exact Mass: M+ = (.%), M+1 = (8.9%) Exact Mass: M+ = (.%), M+1 = (8.9%) Exact Mass: M+ = (.%), M+1 = (8.8%) overtone Exact Mass: M+ = (.%), M+1 = (7.8%) y:\files\classes\spectroscopy\i\is simulated from database probs.doc

4 11 Exact Mass: M+ = 97.9 (.%), M+1 = 98.9 (6.9%) Exact Mass: M+ = (.%), M+1 = (9.8%) Exact Mass: M+ = (.%), M+1 = (9.9%) Exact Mass: M+ = (.%), M+1 = (6.9%) Exact Mass: 16.4 M+ = 16.4 (.%), M+1 = 17.5 (7.7%) y:\files\classes\spectroscopy\i\is simulated from database probs.doc

5 Exact Mass: M+ = (.%), M+1 = (7.8%) Exact Mass: M+ = (.%), M+1 = (9.8%) (wet) Exact Mass: 96.6 M+ = 96.6 (.%), M+1 = 97.6 (6.6%) Exact Mass:.9 M+ =.9 (.%), M+1 = 11.9 (6.5%) Exact Mass:.9 M+ =.9 (.%), M+1 = 11.9 (6.5%) y:\files\classes\spectroscopy\i\is simulated from database probs.doc

6 21 Exact Mass: M+ = (.%), M+1 = (1.7%), M+2 = (4.5%) Exact Mass:.9 M+ =.9 (.%), M+1 = 11.9 (6.5%) Exact Mass: M+ = (.%), M+1 = (9.9%) Exact Mass: M+ = (.%), M+1 = (1.7%), M+2 = (4.5%) Exact Mass: M+ = (.%), M+1 = (9.8%) y:\files\classes\spectroscopy\i\is simulated from database probs.doc

7 26 Exact Mass: M+ = 11.2 (.%), M+1 = (7.3%), M+2 = (4.5%) Exact Mass: M+ = (.%), M+1 = (8.9%) Exact Mass: M+ = (.%), M+1 = (9.5%), M+2 = 14.5 (4.6%) Exact Mass: M+ = (.%), M+1 = (8.8%) Exact Mass: M+ = (.%), M+1 = (1.7%), M+2 = (4.5%) y:\files\classes\spectroscopy\i\is simulated from database probs.doc

8 Exact Mass: M+ = (.%), M+1 = (12.%) Exact Mass: M+ = (.%), M+1 = (1.7%), M+2 = (4.5%) Exact Mass: M+ = (.%), M+1 = (8.9%) Exact Mass: M+ =.13 (.%), M+1 = (7.8%) Exact Mass:.9 M+ =.9 (.%), M+1 = 11.9 (6.5%) y:\files\classes\spectroscopy\i\is simulated from database probs.doc

9 Exact Mass: M+ = (.%), M+1 = (8.9%) Exact Mass: M+ = (.%), M+1 = (5.9%) Exact Mass: M+ = (.%), M+1 = (6.6%) Exact Mass: M+ = (.%), M+1 = (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

10 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.) y:\files\classes\spectroscopy\i\is simulated from database probs.doc

11 para 161 substituted aromatic 1455 overtones y:\files\classes\spectroscopy\i\is simulated from database probs.doc

12 monosubstituted aromatic overtones monosubstituted aromatic overtones meta substituted aromatic overtones y:\files\classes\spectroscopy\i\is simulated from database probs.doc

13 ortho substituted 165 aromatic overtones Exact Mass: 96.9 M+ = 96.9 (.%), M+1 = 97.1 (7.7%) y:\files\classes\spectroscopy\i\is simulated from database probs.doc

14 Formula problem 1 Exact Mass: M+ = (.%), M+1 = (14.5%), M+2 = (97.5%), M+3 = 28.1 (14.2%), M+4 = (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 = (2.8%), M+2 = (38.9%), M+3 = (7.8%), M+4 = (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: M+ = (.%), M+1 = (12.3%), M+2 = (6.%), M+3 = (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

ORGANIC - BROWN 8E CH INFRARED SPECTROSCOPY.

ORGANIC - BROWN 8E CH INFRARED SPECTROSCOPY. !! www.clutchprep.com CONCEPT: PURPOSE OF ANALYTICAL TECHNIQUES Classical Methods (Wet Chemistry): Chemists needed to run dozens of chemical reactions to determine the type of molecules in a compound.