CHEM213exam1S24_key

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1 CHEM 213 Organic Chemistry Spring 2024 Exam 1 Answer Key 1) Why do C C bonds vibrate at a higher frequency than C=C bonds? a. The triple bond is the stronger “spring” due to its stronger bond. b. Since the C C atoms are bonded to less atoms, they have a smaller mass than the C=C atoms. c. Vibrations break the bonds and the triple bond wants to be broken less than the double bond. d. Actually, C=C bonds vibrate at a higher frequency. 2) The peaks in an infrared spectrum correspond to… a. …the IR lightwaves that cause the molecule to slow down. b. …the IR lightwaves transmitted by the sample. c. …the IR lightwaves with frequencies that match vibrations in the molecule. d. IR lightwaves have nothing to do with the peaks. 3) What IR absorption bands are consistent with this structure? a. …3400, 3050, 2900 cm -1 b. …2900, 1650, 3400 cm -1 c. …3400, 1650, 1600 cm -1 d. …3400, 2900, 2250 cm -1 4) B eff , the magnetic field felt by a nucleus, is determined by… a. … only the applied magnetic field. b. … the applied magnetic field plus electron shielding. c. … the applied magnetic field, electron shielding and any nearby magnetic fields, such as the magnetic field induced by benzene ring current. d. … the applied magnetic field, electron shielding, nearby magnetic fields and the vibrations of the nucleus 5) 13 C NMR can tell you… a. …about functional groups present and how shielded some carbons are. b. …the number of non-equivalent carbons in the molecule. c. …whether or not your compound has an alkyl ring. d. …all of the above. e. …only a and b. f. …only a and c. 6) How many carbon atoms does a molecule contain if in its mass spectrum the relative abundance of the M+ peak is 50.1% and of the M+1 peak is 5.5%. a. 10 b. 9 c. 8 d. 7
2 7) List 4 of the 5 non-fingerprint region IR peaks ( range and vibration ) you expect to see for the following molecule. (16 pts.) a. C N, 2260-2210 cm -1 c. Csp 3 -H, 3000-2800 cm -1 b. C=C, 1620-1680 cm -1 d. Csp 2 -H, 3100-3000 cm -1 e. O-H, 3600-3200 cm -1 8) For each of the following compounds below tell how many signals you would expect the molecule to have in its proton NMR specturm (ignoring splitting) (12 pts.) 9) Predict the splitting patterns for the protons indicated by the arrow. (12 pts.) quartet singlet triplet of triplets triplet 10) For each of the compounds below tell how many signals you would expect the molecule to have in its normal, broadband decoupled 13 C NMR spectra. (6 pts.)
3 11) Rank (1-4) the chemical shifts of the indicated hydrogens from highest (1) to lowest (4). (8 pts.) 12) Label all non-fingerprint peaks in the IR below. Based on these peaks, make a separate list of the functional group(s) most likely in the molecule that made this spectrum. (10 pts.) Possible functional groups: alcohol, alkene 13) Provide a molecular formula for the compound with the following mass spectrum. (8 pts.) 77 112 114 C 6 H 5 Cl 3:1 ratio of M+ peak and M+2 peak indicates Cl (35 amu) 112 – 35 = 77 (benzene cation peak) Rule of 13: 77/13 = 5.9 ~ 6 12 x 6 = 72 77 – 72 = 5 = # of H’s ignore this peak O-H Csp 3 -H C=C Csp 2 -H
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