Chapter Fifteen

Topic: Spectroscopy Section: 15.1 Difficulty Level: Easy 1. A) B) C) D) E) Which of the following is not true about electromagnetic radiation? frequency is directly proportional to wavelength frequency is directly proportional to energy frequency is inversely proportional to wavelength wavelength is inversely proportional to energy none of these Ans: A

Topic: Spectroscopy Section: 15.1 Difficulty Level: Easy 2. A) B) C) D) E) Which of the following electromagnetic radiation has the highest energy? UV X-ray IR microwave visible Ans: B

Topic: Spectroscopy Section: 15.1 Difficulty Level: Easy 3. A) B) C) D) E) Which of the following electromagnetic radiation has the longest wavelength? UV X-ray IR microwave visible Ans: D

Topic: Spectroscopy Section: 15.1 Difficulty Level: Easy

4. A) B) C) D) E)

Which of the following electromagnetic radiation has the highest frequency? UV X-ray IR microwave visible Ans: B

Topic: Spectroscopy Section: 15.1 Difficulty Level: Medium 5. Arrange the following electromagnetic radiation in decreasing (highest to lowest) order of frequency. -rays visible microwave IR UV

A) B) C) D) E)

I V>III>IV>II>I II>V>III>IV>I I>IV>III>V>II V>II>IV>III>I II>IV>V>III>I Ans: B

III

IV

Topic: Spectroscopy Section: 15.1 Difficulty Level: Easy 6. A) B) C) D) E) Which of the following information is primarily obtained from infrared spectroscopy? arrangement of carbon and hydrogen atoms in a compound molecular weight of a compound conjugated system present in a compound functional groups present in a compound all of these Ans: D

Topic: Infrared Spectroscopy Section: 15.2 Difficulty Level: Easy

7. Absorption of _______radiation results in vibrational excitation of the bonds in a compound. A) UV B) Microwave C) IR D) Visible E) x-ray Ans: C Topic: Infrared Spectroscopy Section: 15.2 Difficulty Level: Easy 8. A) B) C) D) E) Which of the following vibrations are observed in IR spectroscopy? stetching rotational bending A&B A&C Ans: E

Topic: Infrared Spectroscopy Section: 15.2 Difficulty Level: Easy 9. Which of the following is currently used to indicate the location of a signal on an IR spectrum? A) wavelength B) wavenumber C) frequency D) A & B E) all of these Ans: B Topic: Infrared Spectroscopy Section: 15.2 Difficulty Level: Easy 10. A) B) C) D) E) Which of the following are units for wavenumber in IR spectroscopy? cm1 cm J.s1 mm none of these Ans: A

Topic: Signal Characteristics Section: 15.3 Difficulty Level: Easy 11. A) B) C) D) E) Which of the following corresponds to the functional group region on an IR spectrum? 1500-4000cm1 400-4000cm1 400-1500cm1 1500-2500cm1 none of these Ans: A

Topic: Signal Characteristics Section: 15.3 Difficulty Level: Easy 12. A) B) C) D) E) Which of the following corresponds to the fingerprint region on an IR spectrum? 1500-4000cm1 400-4000cm1 400-1500cm1 1500-2500cm1 none of these Ans: C

Topic: Signal Characteristics Section: 15.3 Difficulty Level: Medium 13. Which of the following statement(s) is(are) true about the frequency of a stretching vibration according to Hooks law? A) it is directly proportional to strength of the bond & the reduced mass B) it is inversely proportional to strength of the bond & the reduced mass C) it is directly proportional to strength of the bond D) it is inversely proportional to the reduced mass E) C & D Ans: E Topic: Signal Characteristics Section: 15.3 Difficulty Level: Easy

14. Rank the indicated bonds in decreasing (highest to lowest) order of wavenumber.
H H

II
H

III

A) B) C) D) E)

III>II>I I>II>III II>I>III III>I>II none of these Ans: B

Topic: Signal Characteristics Section: 15.3 Difficulty Level: Easy 15. Rank the indicated bonds in decreasing (highest to lowest) order of wavenumber.
H H N O

II
H

III

A) B) C) D) E)

III>II>I I>II>III II>I>III III>I>II none of these Ans: D

Topic: Signal Characteristics Section: 15.3 Difficulty Level: Easy

16. Rank the indicated bonds in decreasing (highest to lowest) order of wavenumber.
O

II
H N

III

A) B) C) D) E)

III>II>I I>II>III II>I>III III>I>II none of these Ans: D

Topic: Signal Characteristics Section: 15.3 Difficulty Level: Medium 17. Which one of the following compounds will have the lowest wavenumber for carbonyl absorption?
O O O O O

II

III

IV

A) B) C) D) E)

I II III IV V Ans: D

Topic: Signal Characteristics Section: 15.3 Difficulty Level: Medium

18. Which one of the following compounds will have the lowest wavenumber for carbonyl absorption?
O O O NH2 O O

II

III

IV

A) B) C) D) E)

I II III IV V Ans: C

Topic: Signal Characteristics Section: 15.3 Difficulty Level: Medium 19. Which one of the following compounds will have the highest wavenumber for C=C absorption?

II

III

IV

A) B) C) D) E)

I II III IV V Ans: C

Topic: Signal Characteristics Section: 15.3 Difficulty Level: Hard

20. Which of the following compounds will have the highest wavenumber for carbonyl absorption?
O O O

II

III

A) B) C) D)

I II III II & III Ans: C

Topic: Signal Characteristics Section: 15.3 Difficulty Level: Medium 21. Arrange the indicated bonds in decreasing (highest to lowest) order of wavenumber.
O

I
C N

V
O

III
H

II

IV

A) B) C) D) E)

I>V>II>IV>III IV>II>I>V>III II>I>V>III>IV IV>I>V>II>III IV>II>V>I>III Ans: E

Topic: Signal Characteristics Section: 15.4 Difficulty Level: Medium 22. Which of the following statement(s) is(are) true for an IR-active bond? A) B) C) D) E) the bond must be symmetrical it must change bond length it must change bond angle it must change bond dipole all of these Ans: D

Topic: Signal Characteristics Section: 15.4 Difficulty Level: Medium

23. Which of the following bonds is IR inactive?

CH3CH2

CH2CH3

CH3CH2

III I II

IV

A) B) C) D) E)

I II III I & IV I & III Ans: E

Topic: Signal Characteristics Section: 15.4 Difficulty Level: Medium 24. Which of the following bonds would produce the weakest absorption? A) B) C) D) E) C=C OH C=O sp3CH A&D Ans: A

Topic: Signal Characteristics Section: 15.4 Difficulty Level: Medium 25. Which of the following bonds would produce the strongest absorption? A) B) C) D) E) C=N CC C=O sp2CH CO Ans: C

Topic: Signal Characteristics Section: 15.4 Difficulty Level: Medium

26. 3-hexyne does not show absorption in the range of 2000-2200 cm1, whereas 1-hexyne does. Which of the following explains the reason for this absence of absorption for 3hexyne? A) B) C) D) E) it is a symmetrical compound there is no change in bond dipole there is no bond dipole it is an unsymmetrical compound A, B & C Ans: E

Topic: Signal Characteristics Section: 15.4 Difficulty Level: Medium 27. Which of the following alkene groups will produce the strongest signal?

II

Cl

III

Br

IV

A) B) C) D)

I II III IV Ans: A

Topic: Signal Characteristics Section: 15.5 Difficulty Level: Medium 28. Diluted alcohols show a _____absorption around 3600cm-1, due to _____. A) B) C) D) sharp, hydrogen bonding broad, hydrogen bonding sharp, absence of hydrogen bonding broad, absence of hydrogen bonding Ans: C

Topic: Signal Characteristics Section: 15.5 Difficulty Level: Medium

29. Concentrated alcohols show a _____absorption in the region of 3200-3600cm-1, due to _____. A) B) C) D) sharp, hydrogen bonding broad, hydrogen bonding sharp, polarity broad, polarity Ans: B

Topic: Signal Characteristics Section: 15.5 Difficulty Level: Medium 30. Carboxylic acids show a very broad absorption for the OH compared to alcohols, because they can form a ______. A) B) C) D) dimer polymer trimer tetramer Ans: A

Topic: Signal Characteristics Section: 15.5 Difficulty Level: Medium 31. Primary amines show two medium absorption bands around 3400 cm-1, due to _______. A) B) C) D) symmetric stretching asymmetric stretching both symmetric and asymmetric stretching hydrogen bonding Ans: C

Topic: Signal Characteristics Section: 15.5 Difficulty Level: Medium

32. How can you distinguish between cyclohexanol and cyclohexanecarboxylic acid using IR spectroscopy?
O OH OH

Cyclohexanol

Cyclohexanecarboxylic acid

Ans: The OH absorption for the carboxylic acid is much broader than the alcoholic OH and it will also show absorption for carbonyl group. Topic: Analyzing an IR spectrum Section: 15.6 Difficulty Level: Medium 33. Which of the following compounds will show a broad absorption around 3300 cm-1 and at 1650 cm-1?
OH O O O OH OH

II

III

IV

A) B) C) D) E)

I II III IV V Ans: D

Topic: Analyzing an IR spectrum Section: 15.6 Difficulty Level: Medium

34. Which of the following compounds will show a sharp absorption at 3300 cm-1 and at 2150 cm-1?
C

II

III

IV

A) B) C) D) E)

I II III IV none of these Ans: A

Topic: Analyzing an IR spectrum Section: 15.6 Difficulty Level: Medium 35. Which of the following compounds will show two absorptions at 2600 cm-1 and at 2700 cm-1 along with the carbonyl absorption?
O O O O

NH2

II

III

IV

A) B) C) D) E)

I II III IV none of these Ans: D

Topic: Analyzing an IR spectrum Section: 15.6 Difficulty Level: Medium 36. Which of the following compounds will show absorption at 2250 cm-1?
N NH2 N H C

II

III

IV

A) B) C) D) E)

I II III IV none of these Ans: D

Topic: Analyzing an IR spectrum Section: 15.6 Difficulty Level: Medium 37. Which of the following compounds will have the lowest wavenumber for carbonyl absorption?
O Cl O H O NH2 O OH O O

II

III

IV

A) B) C) D) E)

I II III IV V Ans: C

Topic: Analyzing an IR spectrum Section: 15.6 Difficulty Level: Medium 38. Which of the following is true about the IR spectrum of the following compound?
O

Cl

A) B) C) D) E)

absorptions at 1720 cm-1 & 2150 cm-1 absorptions at 1800 cm-1 & 2150 cm-1 absorptions at 1720 cm-1 & 2250 cm-1 absorptions at 1800 cm-1 & 2250 cm-1 absorptions at 1650 cm-1 & 2150 cm-1 Ans: B

Topic: Analyzing an IR spectrum Section: 15.6 Difficulty Level: Medium

39. Which of the following compounds will show absorptions at 1640 cm-1, 2950 cm-1 and 3050 cm-1 on the IR spectrum?
O

OH

II

III

IV

A) B) C) D) E)

I II III IV V Ans: C

Topic: Analyzing an IR spectrum Section: 15.6 Difficulty Level: Medium 40. A compound with molecular formula C6H10O, shows absorptions at 1720 cm-1 and at 2980 cm-1 on the IR spectrum. Propose a possible structure for this compound. Ans:
O

Topic: Analyzing an IR spectrum Section: 15.6 Difficulty Level: Medium 41. A compound with molecular formula C3H9N, shows absorptions at 3400 cm-1 (two), 2980 cm-1 and at 1100 cm-1 on the IR spectrum. Propose a possible structure for this compound. Ans: CH3CH2CH2NH2 Topic: Analyzing an IR spectrum Section: 15.6 Difficulty Level: Medium

42. A compound with molecular formula C4H8O2, shows absorptions at 2200-3600 cm-1 (broad), 1720 cm-1 and at 1200 cm-1 on the IR spectrum. Propose a possible structure for this compound. Ans:
O

OH

Topic: Analyzing an IR spectrum Section: 15.6 Difficulty Level: Hard 43. Which of the following compounds will have highest wavenumber for carbonyl absorption?
O O O O O O O O

II

III

IV

A) B) C) D)

I II III IV Ans: B

Topic: Analyzing an IR spectrum Section: 15.6 Difficulty Level: Hard 44. Which of the following compounds will have two absorptions at 1820 cm-1 and 1740cm-1?
O O O O O O OH NH2 O Cl

II

III

IV

A) B) C) D) E)

I II III IV V Ans: D

Topic: Analyzing an IR spectrum Section: 15.6 Difficulty Level: Medium 45. Which one of the following compounds is consistent with the following IR spectrum?

SDBS: National Institute of Advanced Industrial Science and Technology

O O OH OH O H

I OH

II

III

IV

OH

OH

A) B) C) D) E)

I II III IV V Ans: D

Topic: Analyzing an IR spectrum Section: 15.6 Difficulty Level: Medium

46. Which one of the following compounds is consistent with the following IR spectrum?

SDBS: National Institute of Advanced Industrial Science and Technology

O O N NH2 N O

N H

I NH 2

II

III

IV

OH

HN

A) B) C) D) E)

I II III IV V Ans: B

Topic: Analyzing an IR spectrum Section: 15.6 Difficulty Level: Medium

47. Which one of the following compounds is consistent with the following IR spectrum?

SDBS: National Institute of Advanced Industrial Science and Technology

OH

OH C

OH

O HO C

II

III

IV

A) B) C) D) E)

I II III IV V Ans: A

Topic: Analyzing an IR spectrum Section: 15.6 Difficulty Level: Medium

48. Which one of the following compounds is consistent with the following IR spectrum?

SDBS: National Institute of Advanced Industrial Science and Technology

OH

II

III

IV

A) B) C) D) E)

I II III IV V Ans: D

Topic: Analyzing an IR spectrum Section: 15.6 Difficulty Level: Medium

49. Which one of the following compounds is consistent with the following IR spectrum?

SDBS: National Institute of Advanced Industrial Science and Technology

OH OH O O OH

II

OH

OH

III

IV

A) B) C) D) E)

I II III IV V Ans: E

Topic: Analyzing an IR spectrum Section: 15.6 Difficulty Level: Medium

50. Which one of the following compounds is consistent with the following IR spectrum?

SDBS: National Institute of Advanced Industrial Science and Technology

NHCH3 CH3 NH2 NH2 N(CH3)2

NH2

CH3

II

III
CH3

IV

A) B) C) D) E)

I II III IV V Ans: B

Topic: Analyzing an IR spectrum Section: 15.6 Difficulty Level: Medium

51. For the following reaction, which of the following is consistent with the IR spectrum of the product?
O CN H

1. DIBAH 2. 3
-1
+

A) absorption at 2250 cm should disappear B) absorption at 3200-3400 cm-1 and 1720cm-1 should appear C) absorption at 2250 cm-1 should disappear, new absorption at 2600-2800 cm-1 and 1720 cm-1 should appear. D) absorption at 2250 cm-1 should disappear and absorption around 3400 cm-1 should appear. E) none of these Ans: C Topic: Analyzing an IR spectrum Section: 15.6 Difficulty Level: Medium 52. For the following reaction, which of the following is consistent with the IR spectrum of the product?
O

H3O+

A) B) C) D) E)

absorption at 2150 cm-1 should disappear absorption at 3300 cm-1 and 2150cm-1 should disappear absorption at 2250 cm-1 should disappear, new absorption at 3300 cm-1 should appear absorption at 1650 cm-1 should disappear and absorption at 3300 cm-1 should appear absorption at 3300 cm-1 and 2150cm-1 should disappear, a new absorption at 1720 cm-1 should appear Ans: E

Topic: Analyzing an IR spectrum Section: 15.6 Difficulty Level: Medium

53. For the following reaction, which of the following is consistent with the IR spectrum of the product?
OH OCH2CH3

1. NaH

A) B) C) D) E)

absorption at 3200-3600 cm-1 should disappear absorption at 3200-3600 cm-1 and 1100 cm-1 should disappear absorption at 1100 cm-1 should disappear and absorption at 3100 cm-1 should appear absorption at 1650 cm-1 should disappear and absorption at 3300 cm-1 should appear. none of these Ans: A

2. CH3CH2Br

Topic: Analyzing an IR spectrum Section: 15.7 Difficulty Level: Hard 54. Predict the product for the following reaction and explain how you will use IR spectroscopy to monitor the progress of the reaction.
1-pentyne 1. NaNH2 2. CH3CH2Br

Ans: CH3CH2CH2CCCH2CH3 Absorptions for spC-H around 3300 cm-1 and CC around 2150 cm-1 should disappear from the product IR. Topic: Analyzing an IR spectrum Section: 15.7 Difficulty Level: Hard 55. Predict the product for the following reaction and explain how you will use IR spectroscopy to monitor the progress of the reaction.
O

1. CH3CH2MgBr 2. H2O

Ans:

HO

Absorptions for C=O around 1720 cm-1 would disappear and a new absorption for OH at 3200-3600 cm-1 would appear from the product IR Topic: Mass Spectrometry Section: 15.8 Difficulty Level: Easy

56. A) B) C) D) E)

Mass spectrometry is primarily used to determine: molecular formula of a compound molecular weight of a compound conjugation in a compound A&B A&C Ans: D

Topic: Mass Spectrometry Section: 15.8 Difficulty Level: Easy 57. Which of the following is initially produced when a compound is bombarded with high energy electrons? A) anion B) free radical C) radical cation D) cation E) none of these Ans: C Topic: Mass Spectrometry Section: 15.8 Difficulty Level: Easy 58. A) B) C) D) E) Which of the following is not true about the molecular ion in mass spectrometry? The molecular ion is produced by loss of one electron from the molecule. The mass of the molecular ion is equivalent to the mass of the molecule. The ion is produced by a loss of pair of electrons from the molecule. The molecular ion is often unstable and can undergo fragmentation. none of these Ans: C

Topic: Mass Spectrometry Section: 15.8 Difficulty Level: Easy 59. A) B) C) D) E) Which of the following is always true about the base peak in a mass spectrum? peak corresponding to molecular ion peak corresponding to the most abundant ion peak corresponding to lowest m/z A&C none of these Ans: B

Topic: Mass Spectrometry

Section: 15.8 Difficulty Level: Easy 60. A) B) C) D) E) The separation of ions in the mass spectrometer is done by their ______. electrons to protons ratio mass to neutrons ratio protons to neutrons ratio mass to charge ratio none of these Ans: D

Topic: Analyzing M+ peak Section: 15.9 Difficulty Level: Easy 61. A) B) C) D) E) Which of the following is true about CH3CH3+? it is the parent ion of ethane it is a molecular ion of ethane with m/z =30 it is a fragment of propane A&B none of these Ans: D

Topic: Analyzing M+ peak Section: 15.9 Difficulty Level: Easy 62. Which of the m/z values corresponds to the base peak in the following mass spectrum?

A) B) C) D) E)

45 44 29 15 none of these Ans: C

Topic: Analyzing M+ peak Section: 15.9

Difficulty Level: Easy 63. Which of the m/z values correspond to the molecular ion peak in the following mass spectrum?

A) B) C) D) E)

45 44 29 15 none of these Ans: B

Topic: Analyzing M+ peak Section: 15.9 Difficulty Level: Medium 64. Which of the m/z values correspond to the molecular ion for the following compound?
OH

A) B) C) D) E)

18 82 100 102 103 Ans: D

Topic: Analyzing M+ peak Section: 15.9 Difficulty Level: Medium

65. Which of the following compounds will have odd m/z value for the molecular ion?
O O N H H N N Br

II

III

IV

Br

A) B) C) D) E)

I II III IV none of these Ans: B

Topic: Analyzing M+ peak Section: 15.9 Difficulty Level: Medium 66. Which of the following is true about the molecular weight and the M+-m/z value for the following compound?
Cl NH2

A) B) C) D) E)

odd molecular weight, m/z-115 odd molecular weight, m/z-121 even molecular weight, m/z-96 even molecular weight, m/z-132 none of these Ans: B

Topic: Analyzing (M+1)+ peak Section: 15.10 Difficulty Level: Medium 67. Which of the following is true about the (M+1)+ peak on the mass spectrum of a hydrocarbon? A) B) C) D) E) it is the most abundant peak it is due to the 13C isotope of carbon it has a m/z value lower than the molecular ion it is useful in calculating number of carbon atoms B&D Ans: E

Topic: Analyzing (M+1)+ peak Section: 15.10 Difficulty Level: Medium

68. Which molecular formula is consistent with the following mass spectrum data? M+ at m/z= 84, relative height=10.0% (M+1)+ at m/z= 85, relative height=0.56% A) B) C) D) E) C5H10O C5H8O C5H24 C6H12 C4H6O2 Ans: B

Topic: Analyzing (M+1)+ peak Section: 15.10 Difficulty Level: Medium 69. Which molecular formula is consistent with the following mass spectrum data? M+ at m/z= 72, relative height=73.0% (M+1)+ at m/z= 73, relative height=3.3% A) B) C) D) E) C4H10O C4H9N C5H12 C4H8O none of these Ans: D

Topic: Analyzing (M+1)+ peak Section: 15.10 Difficulty Level: Medium 70. Provide a molecular formula that is consistent with the following mass spectrum data. M+ at m/z= 73, relative height=86.1% (M+1)+ at m/z= 74, relative height=3.2% Ans: C3H7NO Topic: Analyzing (M+1)+ peak Section: 15.10 Difficulty Level: Hard 71. Provide a molecular formula that is consistent with the following mass spectrum data. M+ at m/z= 136, relative height=65.6% (M+1)+ at m/z= 137, relative height=6.2% Ans: C9H12O

Topic: Analyzing (M+1)+ peak Section: 15.10 Difficulty Level: Hard 72. Provide a molecular formula that is consistent with the following mass spectrum data. M+ at m/z= 167, relative height=50.0% (M+1)+ at m/z= 168, relative height=4.4% Ans: C8H9NO3 Topic: Analyzing (M+2)+ peak Section: 15.11 Difficulty Level: Medium 73. Compounds containing chlorine or bromine usually show a strong _____peak. A) B) C) D) E) molecular ion base M+1 M+2 all of these Ans: D

Topic: Analyzing (M+2)+ peak Section: 15.11 Difficulty Level: Medium 74. Which of the following will produce M+ and (M+2)+ peaks of equal intensity? A) B) C) D) E) nitrogen chlorine bromine oxygen B&C Ans: C

Topic: Analyzing (M+2)+ peak Section: 15.11 Difficulty Level: Medium

75. Presence of bromine produces M+ and (M+2)+ peaks of equal intensity on a mass spectrum because: A) B) C) D) 81Br isotope has higher natural abundance than 79Br isotope 79Br and 81Br isotopes have almost equal natural abundance 79Br isotope has higher natural abundance than 81Br isotope none of these Ans: B

Topic: Analyzing (M+2)+ peak Section: 15.11 Difficulty Level: Medium 76. Which molecular formula is consistent with the following mass spectrum data? M+ at m/z= 78, relative height=23.5% (M+1)+ at m/z= 79, relative height=0.78% (M+2)+ at m/z= 80, relative height=7.5% A) B) C) D) E) C6H6 C3H7Cl C6H8 C6H9Cl none of these Ans: B

Topic: Analyzing (M+2)+ peak Section: 15.11 Difficulty Level: Medium 77. Which molecular formula is consistent with the following mass spectrum data? M+ at m/z= 108, relative height=61.5% (M+1)+ at m/z= 109, relative height=1.5% (M+2)+ at m/z= 110, relative height=61.3% A) B) C) D) E) C2H5Br C5H12Cl C8H12 C2H7Br none of these Ans: A

Topic: Analyzing (M+2)+ peak Section: 15.11 Difficulty Level: Medium

78. For which of the following compounds will the (M+2)+ peak intensity be around 25% of the intensity of the molecular ion peak? A) B) C) D) E) CH3CH2CH2Br CH3CH2CH2OH CH3CH2CH2Cl CH3CH2CH2NH2 none of these Ans: C

Topic: Analyzing (M+2)+ peak Section: 15.11 Difficulty Level: Medium 79. Which of the following mass spectra shows the presence of bromine in a compound?

II

III A) B) C) D) E) I II III IV none of these Ans: A

IV

Four spectra above: courtesy of SDBS: National Institute of Advanced Industrial Science and Technology

Topic: Analyzing the fragments Section: 15.12 Difficulty Level: Medium 80. Which of the following compounds will produce a prominent (M-18) peak in the mass spectrum? A) B) C) D) E) 2-methylheptane 1-heptanol heptanamine heptanal none of these Ans: B

Topic: Analyzing the fragments Section: 15.12 Difficulty Level: Medium 81. Which of the following compounds will produce a prominent (M-15) peak in the mass spectrum? A) B) C) D) E) 2-methylheptane 1-heptanol heptanamine 1-chloroheptane none of these Ans: A

Topic: Analyzing the fragments Section: 15.12 Difficulty Level: Medium 82. Which of the following is not a prominent peak in the mass spectrum of 2-methyl-2pentanol? A) B) C) D) E) (M-15) (M-18) (M-29) (M-16) none of these Ans: D

Topic: Analyzing the fragments Section: 15.12 Difficulty Level: Medium

83. Which of the following compounds will have a prominent peak at (M-127)? A) B) C) D) E) CH3CH2CH2I (CH3CH2)3CCH2Cl (CH3)3CCH2CH2Br (CH3)2CHCH(CH3)2 none of these Ans: A

Topic: Analyzing the fragments Section: 15.12 Difficulty Level: Medium 84. Which of the following compounds will have a base peak at m/z=43? A) B) C) D) E) CH3CH2CH2CH2CH2CH3 (CH3CH2)2CHCH3 (CH3)3CCH2CH3 (CH3)2CHCH(CH3)2 none of these Ans: D

Topic: Analyzing the fragments Section: 15.12 Difficulty Level: Medium 85. Which of the following is the base peak in the mass spectrum of 2,2,4-trimethylpentane? A) B) C) D) E) 114 57 42 29 none of these Ans: B

Topic: Analyzing the fragments Section: 15.12 Difficulty Level: Medium

86. Which of the following is expected to be the base peak in the mass spectrum of CH3(CH2)4OH? A) B) C) D) E) 88 55 42 31 none of these Ans: C

Topic: Analyzing the fragments Section: 15.12 Difficulty Level: Medium 87. Which of the following is expected to be the base peak in the mass spectrum of 2methyl-2-butanol? A) B) C) D) E) 73 55 43 31 59 Ans: E

Topic: Analyzing the fragments Section: 15.12 Difficulty Level: Medium 88. Which of the following is expected to be the base peak in the mass spectrum of CH3CH2NH2? A) B) C) D) E) 15 28 30 45 none of these Ans: C

Topic: Analyzing the fragments Section: 15.12 Difficulty Level: Medium

89. Provide the structures of the fragments that result when the molecular ion of 2heptanone undergoes fragmentation via McLafferty rearrangement. Ans:
+
H O

Topic: Analyzing the fragments Section: 15.12 Difficulty Level: Medium 90. Provide the structure of the major fragment that results when the molecular ion of (CH3)2CHCH2CH2NH2 undergoes fragmentation. Ans:
H N H

Topic: Analyzing the fragments Section: 15.12 Difficulty Level: Medium 91. Provide the structure of the major fragment that results when the molecular ion of CH3CH2CH2CH2OH undergoes fragmentation via alpha cleavage. Ans:
O H

Topic: Analyzing the fragments Section: 15.12 Difficulty Level: Medium 92. Which of the following is expected to be the base peak in the mass spectrum of pentanal?
O

CH3CH2CH2CH2CH pentanal A) B) C) D) E) 29 41 44 58 86 Ans: C

Topic: Analyzing the fragments Section: 15.12 Difficulty Level: Medium 93. Which one of the following compounds is consistent with the mass spectrum below?

SDBS: National Institute of Advanced Industrial Science and Technology

A) B) C) D) E)

CH3CH2CH(CH3)2 CH3CHOHCH2CH3 CH3CH2OCH2CH3 CH3CH2NHCH2CH3 none of these Ans: D

Topic: Analyzing the fragments Section: 15.12 Difficulty Level: Medium

94. Which one of the following compounds is consistent with the mass spectrum below?

SDBS: National Institute of Advanced Industrial Science and Technology

A) B) C) D) E)

CH3CH2CH(CH3)2 CH3CHOHCH2CH3 CH3CH2OCH2CH3 CH3CH2NHCH2CH3 none of these Ans: B

Topic: Analyzing the fragments Section: 15.12 Difficulty Level: Medium 95. Which one of the following compounds is consistent with the mass spectrum below?

SDBS: National Institute of Advanced Industrial Science and Technology

A) B) C) D) E)

CH3CH2CH(CH3)2 CH3CHOHCH2CH3 CH3CH2OCH2CH3 CH3CH2NHCH2CH3 none of these Ans: A

Topic: High-resolution mass spectrometry Section: 15.13 Difficulty Level: Easy 96. High-resolution mass spectrometry is used to determine the _____ of a compound. A) B) C) D) E) degree of unsaturation molecular formula molecular weight B&C none of these Ans: B

Topic: High-resolution mass spectrometry Section: 15.13 Difficulty Level: Medium 97. How will you distinguish between the following compounds using high-resolution mass spectrometry?
O Cl

II

Ans: Compound I: m/z at 102.0678 Compound II: m/z at 102.0235 Topic: High-resolution mass spectrometry Section: 15.13 Difficulty Level: Medium 98. How will you distinguish between the following compounds using high-resolution mass spectrometry?
OH

II

Ans: Compound I: m/z at 98.0729 Compound II: m/z at 98.1092 Topic: Gas chromatography-mass spectrometry Section: 15.14 Difficulty Level: Medium

99. GC-mass spectrometry is used to find the _________ of each compound in a __________. A) B) C) D) E) molecular formula, mixture of alkanes molecular weight, mixture of compounds molecular formula, mixture of compounds B&C none of these Ans: B

Topic: High-resolution mass spectrometry Section: 15.15 Difficulty Level: Medium 100. Electrospray ionization is used to obtain mass spectra of proteins because: A) B) C) D) it allows for faster fragmentation of molecular ion the molecular ion usually does not undergo fragmentation it allows for slow fragmentation of molecular ion none of these Ans: B

Topic: Hydrogen deficiency index Section: 15.16 Difficulty Level: Easy 101. Calculate the degree of unsaturation for C9H11N. A) B) C) D) E) 4 6 2 5 none of these Ans: D

Topic: Hydrogen deficiency index Section: 15.16 Difficulty Level: Easy

102. Calculate the degree of unsaturation for C14H14N2O. A) B) C) D) E) 4 6 8 10 9 Ans: E

Topic: Hydrogen deficiency index Section: 15.16 Difficulty Level: Easy 103. Calculate the degree of unsaturation for C11H8ClBrO. A) B) C) D) E) 4 6 7 8 10 Ans: C

Topic: Hydrogen deficiency index Section: 15.16 Difficulty Level: Medium 104. Calculate the degree of unsaturation for C5H5Br2NO. A) B) C) D) E) 4 6 2 3 7 Ans: D

Topic: Hydrogen deficiency index Section: 15.16 Difficulty Level: Medium

105. Which of the following compounds have the same degree of unsaturation? C5H5Br2NO C6H5Br C8H10BrIO C9H11NO A) B) C) D) E)
I I & II I & III III & IV II & III none of these Ans: B II III IV

Topic: Hydrogen deficiency index Section: 15.16 Difficulty Level: Medium 106. Propose a possible structure for a compound with molecular formula C6H5Br Ans:
Br

Topic: Hydrogen deficiency index Section: 15.16 Difficulty Level: Medium 107. Propose all possible structures for a compound with molecular formula C4H9N that shows two medium absorptions at 3400 cm-1 and no absorption in the range of 16001800 cm-1 in its IR spectrum. NH2 Ans: NH2

Topic: Hydrogen deficiency index Section: 15.16 Difficulty Level: Medium 108. Propose possible structure(s) for a compound with molecular formula C4H7N that shows absorption at 2250 cm-1 in its IR spectrum. Ans: CH3CH2CH2CN Topic: Hydrogen deficiency index Section: 15.16 Difficulty Level: Medium

109. Propose a possible structure for a compound with molecular formula C5H8O2 that shows absorption at 1720 cm-1 and no absorption in the range of 1500-1700 cm-1 or 2600-2800 cm-1 in its IR spectrum. Ans:
O O