practiceexam1_answ_S20

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Old Dominion University *

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213

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Chemistry

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Apr 3, 2024

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pdf

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6

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1 CHEM 213 Practice Exam #1 Answer Key 1. Examining the infrared spectrum of a compound allows us to: a. determine the types of functional groups present in the compound b. determine the carbon-hydrogen framework of the compound c. determine the molecular weight of the compound d. determine the nature of the conjugated pi electron system in the compound 2. What IR absorption bands are consistent with this structure? a. 3100, 1700, 3300 cm –1 b. 3300, 3050, 2900 cm –1 c. 3300, 1700, 750 cm –1 d. 3300, 2900, 2250 cm –1 3. The amount of energy in infrared light corresponds to the amount of energy needed to… a. … promote one electron from a bonding to an antibonding molecular orbital. b. … "flip" the spin of a 13 C or 1 H nucleus. c. … strip a molecule of one electron to generate a cation radical. d. … increase the vibrational motions of organic molecules. 4. Which of the following bonds undergoes stretching at the highest ENERGY? a. C—H b. C—O c. C C d. C—C 5. 13 C NMR DEPT spectroscopy… a. …is based on molecular vibrations. b. …can tell you how many H’s are bonded to each carbon. c. …can tell you how many H’s are on neighboring carbons. d. …is only useful for very simple molecules. 6. What type of electromagnetic radiation is used in NMR a. gamma rays b. radio waves c. visible light d. X-rays 7. How does the presence of electrons effect the chemical shift of a proton compared to a "bare" proton (i.e. a proton with no orbiting electrons)? a. The presence of electrons has no effect on the chemical shift of a proton. b. Electrons cause a proton to absorb at a higher frequency than a bare proton. c. Electrons will shift a proton's absorption upfield from that of a bare proton. d. Chemical shift applies to IR not NMR. OH
2 8. Circle all of the following IR bands that you would expect to see in the IR spectrum of caffeine. 3400 cm –1 1710 cm –1 1650 cm –1 3100 cm –1 9. List the 4 of the 5 IR peaks (range and vibration) you expect to see in the following molecule (i.e. 3300-3500 cm -1 , N-H stretch). (8 pts.) a.__O-H stretch, 3200-3600 cm -1 _ c._ Csp 2 -H stretch, 3000-3100 cm -1 _ b._ Csp 3 -H stretch, 3000-2850 cm -1 __ d.__ C N stretch, 2210-2260 cm -1 _ e. _ C=C stretch, 1620-1680 cm -1 __ 10. For each of the compounds below tell how many signals you would expect the molecule to have in its 13 C NMR spectrum without splitting. (10pts) 11. For each of the compounds below tell how many signals you would expect the molecule to have in its 1 H NMR spectra ignoring splitting. (10pts) 12. Predict the splitting patterns you would expect for the proton(s) attached to the carbon indicated by the arrow. a.) b.) H 3 C C H 2 OH H C Cl H doublet of doublets quartet of triplets or triplet of quartests a b b c c d b b a a e e c
3 13. Rank (1-5) the chemical shifts of the indicated hydrogens from the highest (1) to the lowest (5). 14. Based on the carbon NMR below, provide a structure for the following molecular formula: C 5 H 8 O 3 . Label each peak in the spectrum with a letter and label the corresponding carbons in your structure with the appropriate letter. Show all your work for partial credit. DU = [(5*2)+2-8]/2=2 C C CH 3 CH 3 CH 2 O O O b d e c a b d e a c
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