1 2425. Review for test 1 (ch12-15). F17. Stafford CHEM 2425. Review for test 1 (ch12-15). F17. Stafford Multiple Choice Identify the choice that best completes the statement or answers the question. ____ 1. What range of wavelengths corresponds to the infrared region of the electromagnetic spectrum? a. 200-400 nm b. 400-700 nm c. 2.5-50 m d. 2-10 mm ____ 2. Which of the following bonds (circled) vibrates at the highest frequency? a. 1 b. 2 c. 3 d. 4 ____ 3. Which of the following combinations of peaks appears in the 1 H NMR spectrum of diethyl ether, CH 3 CH 2 OCH 2 CH 3 ? a. a triplet and a doublet b. a quartet and a sextet c. two singlets d. a triplet and a quartet ____ 4. Which C 4 H 9 Br compound gives a triplet at approximately 3.5 ppm in the 1 H NMR spectrum? a. 1 b. 2 c. 3 d. 4 ____ 5. What is the relative area of the six peaks in a sexet in an 1 H NMR spectrum? a. 1:2:3:3:2:1 b. 1:3:6:6:3:1 c. 1:5:10:10:5:1 d. 1:6:15:15:6:1 ____ 6. Which of the following compounds have enantiotopic protons?
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1 2425. Review for test 1 (ch12-15). F17. Stafford
CHEM 2425. Review for test 1 (ch12-15). F17. Stafford
Multiple Choice
Identify the choice that best completes the statement or answers the question.
____ 1. What range of wavelengths corresponds to the infrared region of the electromagnetic spectrum?
a. 200-400 nm
b. 400-700 nm
c. 2.5-50 m
d. 2-10 mm
____ 2. Which of the following bonds (circled) vibrates at the highest frequency?
a. 1 b. 2 c. 3 d. 4
____ 3. Which of the following combinations of peaks appears in the 1H NMR spectrum of diethyl ether,
CH3CH2OCH2CH3?
a. a triplet and a doublet
b. a quartet and a sextet
c. two singlets
d. a triplet and a quartet
____ 4. Which C4H9Br compound gives a triplet at approximately 3.5 ppm in the 1H NMR spectrum?
a. 1 b. 2 c. 3 d. 4
____ 5. What is the relative area of the six peaks in a sexet in an 1H NMR spectrum?
a. 1:2:3:3:2:1
b. 1:3:6:6:3:1
c. 1:5:10:10:5:1
d. 1:6:15:15:6:1
____ 6. Which of the following compounds have enantiotopic protons?
2 2425. Review for test 1 (ch12-15). F17. Stafford
1. propane
2. butane
3. 2-methylpropane
a. only 1
b. only 2
c. only 1 and 2
d. 1, 2 and 3
____ 7. Which of the following is true for pair of homotropic protons?
1. They will appear at the same chemical shift in an achiral (i.e., nonchiral) environment
2. They will appear at the same chemical shifts in a chiral environment
a. only 1
b. only 2
c. neither 1 nor 2
d. both 1 and 2
____ 8. Which C9H10O compound gives the following 1H NMR spectrum?
3 2425. Review for test 1 (ch12-15). F17. Stafford
a. 1 b. 2 c. 3 d. 4
____ 9. Which of the following gives rise to a prominent peak in the mass spectrum with m/z of 60?
a. 1-hexanol
b. 2-hexanol
c. hexanal
d. hexanoic acid
____ 10. Which of the following arrangements of p atomic orbitals of 1,3-butadiene has the greatest number of nodes?
a. 1 b. 2 c. 3 d. 4
____ 11. What is (are) the major organic product(s) formed in the following reaction?
a. only 1
b. only 1 and 3
c. only 2 and 4
d. only 1 and 4
____ 12. Which of the following is(are) formed upon addition of 1 mol of Br2 to 1,3-cyclohexane?
4 2425. Review for test 1 (ch12-15). F17. Stafford
a. only 2
b. only 1 and 3
c. only 2 and 4
d. 1, 2 and 3
____ 13. What is (are) the major organic product(s) formed in the following reaction?
a. only 1
b. only 3
c. only 1 and 3
d. only 2 and 4
____ 14. What are the units of in ultraviolet-visible spectroscopy?
a. M1cm
1
b. Mcm
c. Jmol1M
1
d. none, is a dimensionless quantity
____ 15. Which of the following laws relates absorbance to the concentration of a sample and the pathlength in
ultraviolet-visible spectroscopy?
a. Buzz-Beer law
b. Beer-Lambert law
c. Duff-Beer law
d. Christopher-Lambert law
____ 16. What is the IUPAC name of the following compound?
5 2425. Review for test 1 (ch12-15). F17. Stafford
a. 2,4-dibromotoluene
b. 2,4-dibromophenol
c. 2,4-dibromohydroxybenzene
d. 4,6-dibromophenol
____ 17. Which of the following represents the energy levels of the molecular orbitals of benzene?
a. 1 b. 2 c. 3 d. 4
____ 18. What is the correct assignment of the names of the following heterocycles?
a. 1 = pyrrole; 2 = thiophene; 3 = pyridine
b. 1 = thiophene; 2 = furan; 3 = pyrrole
c. 1 = pyridine; 2 = thiophene; 3 = furan
d. 1 = pyridine; 2 = thiophene; 3 = pyrrole
6 2425. Review for test 1 (ch12-15). F17. Stafford
____ 19. What is the hybridization of the nitrogen atom of pyridine?
a. s
b. sp
c. sp2
d. sp3
____ 20. Which of the following compounds is antiaromatic?
a. ethane
b. cyclobutadiene
c. benzene
d. cyclooctatetraene
____ 21. Which of the following compounds undergoes heterolytic carbon-halogen bond cleavage to form a stable
organic cation?
a. 1 b. 2 c. 3 d. 4
____ 22. Which of the following has the compounds shown in the correct order of decreasing acidity (i.e., more
acidic > less acidic)?
a. 1 > 2 > 3
b. 2 > 3 > 1
c. 3 > 2 > 1
d. 1 > 3 > 2
____ 23. What is the major organic product obtained from the following reaction?
7 2425. Review for test 1 (ch12-15). F17. Stafford
a. 1 b. 2 c. 3 d. 4
____ 24. What is the major organic product obtained from the following reaction?
a. 1 b. 2 c. 3 d. 4
____ 25. Which of the following represents the energy levels of the molecular orbitals of cyclobutadiene?
8 2425. Review for test 1 (ch12-15). F17. Stafford
a. 1 b. 2 c. 3 d. 4
____ 26. What are the relative positions of the substituents in the following structure?
a. anti
b. meta
c. ortho
d. para
____ 27. What are the relative positions of the substituents in the following structure?
9 2425. Review for test 1 (ch12-15). F17. Stafford
a. anti
b. meta
c. ortho
d. para
____ 28. Which of the following is true about [10]annulene?
a. [10]annulene is planar
b. [10]annulene is nonaromatic
c. [10]annulene undergoes addition reactions similar to simple alkenes
d. [10]annulene has 10 pi electrons
____ 29. Which of the following is not true about [the bridged [10]annulene shown below?
a. all of the carbon atoms of bridged [10]annulene are all in the same plane
b. bridged [10]annulene is aromatic
c. bridged [10]annulene undergoes substitution reactions similar to benzene
d. bridged [10]annulene has 10 pi electrons
____ 30. Which of the following does not undergo oxidation in the presence of H2CrO4?
a. 1 b. 2 c. 3 d. 4
Completion
Complete each statement.
10 2425. Review for test 1 (ch12-15). F17. Stafford
MATCH each of the following groups of bond-types to the region of the infrared spectrum in which their
absorptions occur. Place the letter of the region in the blank to the left of the bond-type.
a. 4000 to 2500 cm1
b. 2500 to 2000 cm1
c. 2000 to 1500 cm1
d. below 1500 cm1
1. _____ CC, CO, CN, and CX single-bond vibrations.
2. _____ C=O, C=N, and C=C bond absorptions.
3. _____ NH, CH, and OH stretching and bending motions.
4. _____ triple bond stretching vibrations.
MATCH a structure from the list below to the following IR spectra. Place the letter of the structure in the
blank provided.
5. _____
11 2425. Review for test 1 (ch12-15). F17. Stafford