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Organic Chemistry With Biological Applications 2Nd Edition Mcmurry Test Bank Full Chapter PDF
Organic Chemistry With Biological Applications 2Nd Edition Mcmurry Test Bank Full Chapter PDF
Student: ___________________________________________________________________________
1. Instructions: Select the most reasonable formula for the compounds with the following mass spectral data.
2. Instructions: Select the most reasonable formula for the compounds with the following mass spectral data.
3. Loratidine is the active ingredient in the antihistamine Claritin. Mass spectral analysis of loratidine shows M+
at m/z = 382. Loratidine is known to contain nitrogen. What is the minimum number of nitrogens in loratidine?
4. Which of the following statements best describes the base peak in a mass spectrum?
A. The peak from the most stable radical.
B. The peak from the species that has the isotope with the highest atomic number.
C. The peak of highest intensity.
D. The peak from the molecule minus an electron.
E. The M +1 peak
5. What are the masses of the charged fragments produced by alpha cleavage of the following?
6. What are the masses of the charged fragments produced by the dehydration of the following compound?
7. Instructions: Refer to the mass spectrum of 2-methylbutane shown below to answer the following
question(s).
Refer to instructions. Propose structures for fragment ions at m/z = 57, 43, and 29.
10. Below is the mass spectrum of an unknown hydrocarbon. In addition, this hydrocarbon shows characteristic
absorption at 2100 cm-1 in its IR spectrum. Give the structure of this unknown.
11. Which of the following does not involve the interaction of molecules with electromagnetic energy?
A. mass spectrometry
B. infrared spectroscopy
C. ultraviolet spectroscopy
D. nuclear magnetic resonance spectroscopy
12. The amount of energy in electromagnetic radiation is related to the frequency and wavelength of the
radiation. High energy radiation, like gamma rays, is of:
A. low frequency and short wavelength
B. low frequency and long wavelength
C. high frequency and short wavelength
D. high frequency and long wavelength
16. Instructions: Match each of the following groups of bond-types to the region of the infrared spectrum in
which their absorptions occur.
a) How would you use infrared spectroscopy to distinguish between the two compounds?
b) How could the mass spectrum be used to distinguish between the two compounds?
18. Assume you are carrying out the conversion of 1-bromobutane to butan-1-ol. How could you use IR
spectroscopy to determine when the reaction is complete?
19. At what approximate positions might the compound below show IR absorptions?
20. Consider the compound below:
21. Instructions: Match a structure from the list below to the following IR spectra.
A. D.
B. E.
C. F.
1.
22. Which of the following regions in the electromagnetic spectrum corresponds to the radiation with the
highest energy?
A. radio waves
B. ultraviolet
C. infrared
D. visible
23. What are the units for electromagnetic radiation used in infrared spectroscopy?
A. cm
B. cm-1
C. J.mol-1
D. none, wavenumber is a dimensionless quantity
24. Which of the following bonds undergoes stretching at the highest frequency?
A. C=O
B. C-O
C. C=C
D. C-C
25. Which of the following bonds undergoes stretching at the highest frequency?
A. O-H
B. C-H
C. C=O
D. CºC
26. Which of the following compounds gives an infrared spectrum with peaks at 3300 cm-1 (strong, broad peak)
and 1640 cm-1 (sharp, weak peak)?
A.
B.
C.
D.
27. Which of the following compounds gives an infrared spectrum with a peak at strong 1730 cm-1?
A.
B.
C.
D.
28. Which of the following compounds gives an infrared spectrum with peaks at 3300 cm-1 (sharp peak) and
2150 cm-1 (sharp peak)?
A.
B.
C.
D.
29. Which of the following compounds gives an infrared spectrum with no significant peaks at ~3300 cm-1 or
1600-1680 cm-1?
A.
B.
C.
D.
30. Which of the following compounds gives an infrared spectrum with peaks at 3000-3500 cm-1 and ~1750
cm-1?
A.
B.
C.
D.
31. Which of the following compounds gives an infrared spectrum with a peak at ~1750 cm-1, but no significant
peaks at 3000-3500 cm-1 or 1050-1250 cm-1?
A.
B.
C.
D.
32. Which of the following bonds gives rise to a strong absorbance near 1700 cm-1 in the infrared spectrum?
A. C=O
B. C-O
C. C=C
D. C-C
36. Which type of spectroscopy (IR, UV, or MS) will best distinguish between the pair of compounds below?
Give a brief reason.
37. What region of the IR spectrum would be the most useful in distinguishing between the following two
compounds?
38. A 3.42 ´ 10-5 M solution of dibenzalacetone in ethanol produced an absorbance of 0.753 in a 1.00 cm cell.
Based on this data, what is e for this compound?
A. 2.57 ´ 105
B. 2.20 ´ 104
C. 4.54 ´ 10-5
D. 2.92 ´ 104
39. Which of the following compounds would have the longest lmax in the UV region of the electromagnetic
spectrum?
A B C
A. A
B. B
C. C
D. All would have the same lmax.
40. Circle any of the following compounds that would be a candidate to produce a UV absorption spectrum.
1. Instructions: Select the most reasonable formula for the compounds with the following mass spectral data.
2. Instructions: Select the most reasonable formula for the compounds with the following mass spectral data.
3. Loratidine is the active ingredient in the antihistamine Claritin. Mass spectral analysis of loratidine shows M+
at m/z = 382. Loratidine is known to contain nitrogen. What is the minimum number of nitrogens in loratidine?
Since the molecular ions are even numbers, loratidine must have an even number of nitrogen atoms. Therefore,
the minimum number of nitrogen atoms in loratidine is two.
4. Which of the following statements best describes the base peak in a mass spectrum?
A. The peak from the most stable radical.
B. The peak from the species that has the isotope with the highest atomic number.
C. The peak of highest intensity.
D. The peak from the molecule minus an electron.
E. The M +1 peak
5. What are the masses of the charged fragments produced by alpha cleavage of the following?
This compound, phenylacetone, has the formula C9H10O and a nominal mass of 134. Alpha cleavage will result
in charged fragments at m/z = 43 and m/z = 119.
6. What are the masses of the charged fragments produced by the dehydration of the following compound?
This compound has the formula C9H20O and a mass of 144. Dehydration will result in the loss of H2O
producing a charged fragment at m/z = 126, 18 mass units less than M+.
7. Instructions: Refer to the mass spectrum of 2-methylbutane shown below to answer the following
question(s).
Refer to instructions. Propose structures for fragment ions at m/z = 57, 43, and 29.
m/z structure
57
43
29
10. Below is the mass spectrum of an unknown hydrocarbon. In addition, this hydrocarbon shows characteristic
absorption at 2100 cm-1 in its IR spectrum. Give the structure of this unknown.
The formula weight of 54 corresponds to a molecular formula of C4H6, which has two degrees of unsaturation.
Possible structures for this formula are:
11. Which of the following does not involve the interaction of molecules with electromagnetic energy?
A. mass spectrometry
B. infrared spectroscopy
C. ultraviolet spectroscopy
D. nuclear magnetic resonance spectroscopy
12. The amount of energy in electromagnetic radiation is related to the frequency and wavelength of the
radiation. High energy radiation, like gamma rays, is of:
A. low frequency and short wavelength
B. low frequency and long wavelength
C. high frequency and short wavelength
D. high frequency and long wavelength
A=B<D<C
16. Instructions: Match each of the following groups of bond-types to the region of the infrared spectrum in
which their absorptions occur.
1. N-H, C-H, and O-H stretching and bending motions. below 1500 cm-1 3
2. triple bond stretching vibrations. 2000 to 1500 cm-1 4
3. C-C, C-O, C-N, and C-X single-bond vibrations. 4000 to 2500 cm-1 1
4. C=O, C=N, and C=C bond absorptions. 2500 to 2000 cm-1 2
17. Cyclohexene and hex-2-yne both have the molecular formula, C6H10.
a) How would you use infrared spectroscopy to distinguish between the two compounds?
b) How could the mass spectrum be used to distinguish between the two compounds?
a) To use IR spectroscopy to distinguish between
isomers, find a strong IR absorption present in
one isomer that is absent in the other isomer.
b) Although the M+ peak (82) for both would be the same, the fragmentation pattern would be different.
18. Assume you are carrying out the conversion of 1-bromobutane to butan-1-ol. How could you use IR
spectroscopy to determine when the reaction is complete?
The infrared spectrum of the starting bromide contains only alkyl C-H absorptions which appear in the
2850-2960 cm-1 region. As the reaction progresses, a broad absorption at 3400-3640 cm-1, due to the O-H
stretch, should develop. When the relative intensity of this band no longer increases, the reaction is complete.
19. At what approximate positions might the compound below show IR absorptions?
This compound should show a medium absorption at 2210-2260 cm-1 for the nitrile, and a strong absorption at
about 1735 cm-1 for the ester carbonyl.
20. Consider the compound below:
a) This compound should show a characteristic broad absorption above 3400 cm-1 due to the -OH group and absorptions at about 3030, 1500
and 1600 cm-1 for the aromatic ring.
b)
The aromatic absorptions would not be present but a strong absorption at 2850-2960 cm-1 due to alkane -C-H would be present.
21. Instructions: Match a structure from the list below to the following IR spectra.
A. D.
B. E.
C. F.
1.
22. Which of the following regions in the electromagnetic spectrum corresponds to the radiation with the
highest energy?
A. radio waves
B. ultraviolet
C. infrared
D. visible
23. What are the units for electromagnetic radiation used in infrared spectroscopy?
A. cm
B. cm-1
C. J.mol-1
D. none, wavenumber is a dimensionless quantity
24. Which of the following bonds undergoes stretching at the highest frequency?
A. C=O
B. C-O
C. C=C
D. C-C
25. Which of the following bonds undergoes stretching at the highest frequency?
A. O-H
B. C-H
C. C=O
D. CºC
26. Which of the following compounds gives an infrared spectrum with peaks at 3300 cm-1 (strong, broad peak)
and 1640 cm-1 (sharp, weak peak)?
A.
B.
C.
D.
27. Which of the following compounds gives an infrared spectrum with a peak at strong 1730 cm-1?
A.
B.
C.
D.
28. Which of the following compounds gives an infrared spectrum with peaks at 3300 cm-1 (sharp peak) and
2150 cm-1 (sharp peak)?
A.
B.
C.
D.
29. Which of the following compounds gives an infrared spectrum with no significant peaks at ~3300 cm-1 or
1600-1680 cm-1?
A.
B.
C.
D.
30. Which of the following compounds gives an infrared spectrum with peaks at 3000-3500 cm-1 and ~1750
cm-1?
A.
B.
C.
D.
31. Which of the following compounds gives an infrared spectrum with a peak at ~1750 cm-1, but no significant
peaks at 3000-3500 cm-1 or 1050-1250 cm-1?
A.
B.
C.
D.
32. Which of the following bonds gives rise to a strong absorbance near 1700 cm-1 in the infrared spectrum?
A. C=O
B. C-O
C. C=C
D. C-C
36. Which type of spectroscopy (IR, UV, or MS) will best distinguish between the pair of compounds below?
Give a brief reason.
37. What region of the IR spectrum would be the most useful in distinguishing between the following two
compounds?
38. A 3.42 ´ 10-5 M solution of dibenzalacetone in ethanol produced an absorbance of 0.753 in a 1.00 cm cell.
Based on this data, what is e for this compound?
A. 2.57 ´ 105
B. 2.20 ´ 104
C. 4.54 ´ 10-5
D. 2.92 ´ 104
39. Which of the following compounds would have the longest lmax in the UV region of the electromagnetic
spectrum?
A B C
A. A
B. B
C. C
D. All would have the same lmax.
40. Circle any of the following compounds that would be a candidate to produce a UV absorption spectrum.
Percentage on
Original Substance.
Zinc, calculated as zinc chloride 19·53
Copper, calculated as copper chloride 1·77
Lead, calculated as lead chloride 0·19
Tin and arsenic were both absent, and the chlorine present closely corresponded with the proportion
of chloride shown above.
The portion of the substance which was insoluble in water was found to contain the following metallic
substances:
Percentage on
Original Substance.
Tin, calculated as tin oxide 6·09
Lead, calculated as lead oxide 1·33
Copper, calculated as copper oxide 0·57
Zinc, calculated as zinc oxide 0·20
This portion of the sample was also free from arsenic.
China,
Furniture
Jet and and
Earthen- Rocking- Electrical
China. ware. Tiles. Majolica. ham. Fittings. Sanitary. Totals
1900 M. 11 21 62 23 12 22 3 30 5
F. 10 42 67 60 15 27 2 18 —
1901 M. 7 13 37 13 9 16 — — 3
F. 2 8 28 25 7 12 2 18 1
1902[A] M. 3 6 30 11 6 11 — — —
F. 2 8 33 29 5 9 2 18 1
1903 M. 1 2 29 11 8 14 1 10 3
F. 6 25 32 29 9 16 6 55 —
1904[B] M. 2 4 31 11 6 11 — — —
F. 1 4 41 37 19 34 1 9 1
1905 M. 4 8 25 9 4 7 — — —
F. 3 13 23 20 14 25 4 36 2
1906 M. 5 8 34 12 7 15 — — —
F. 2 7 41 37 10 21 3 18 —
1907 M. 6 10 38 13 4 8 — — 1
F. 7 23 33 30 6 12 1 6 —
1908 M. 4 6 45 16 3 6 — — 1
F. 1 3 42 38 8 16 1 6 —
1909 M. 2 3 22 8 4 8 — — —
F. 1 3 17 15 7 14 — — 2