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A) I B) II C) III D) I and II
A) I B) II C) III D) I and II
A) I B) II C) III D) IV
4. What is the approximate bond angle of the substituents around a nitrogen atom in
amines?
A) 90° B) 109.5° C) 120° D) 180°
5. Although an amine nitrogen atom containing an electron pair and bonded to three
different groups is technically a stereogenic center, the chirality of the amine nitrogen is
often ignored. Why is that?
A) Because four bonds are needed to define a stereogenic center.
B) Because chirality only exists with the tetrahedral carbon atoms.
C) Because there is usually slow interconversion between the two isomeric forms at
room temperature.
D) Because there is usually rapid interconversion between the two isomeric forms at
room temperature.
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6. Why should the chirality of an ammonium salt with four different groups on the
nitrogen atom not be ignored?
A) Because there is rapid interconversion between the two isomeric forms at room
temperature.
B) Because interconversion cannot occur between the two isomeric forms at room
temperature.
C) Because the compound would be a meso compound.
D) Because the compound would be a racemic mixture.
A) isopropylamine C) 2-methyl-1-propanamine
B) sec-butylamine D) isobutylamine
A) isopropylamine
B) sec-butylamine
C) isobutylamine
D) tert-butylamine
A) isopropylamine C) tert-butylamine
B) 2-methyl-2-propanamine D) isobutylamine
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A) diisopropylamine
B) dipropylamine
C) diisopropanamine
D) dibutylamine
A) dimethylisobutylamine C) N,N-dimethylbutanamine
B) butyldimethylamine D) sec-butyldimethylamine
A) N-propylhexanamine C) N-ethylcyclohexylamine
B) N-propylaniline D) N-propylcyclohexanamine
A) N-ethyl-N-methylpentylamine C) N-methyl-3-octanamine
B) N-ethyl-N-methyl-1-pentanamine D) N-ethyl-2-heptanamine
A) 3-methyl-1-hexanamine C) 4-methyl-1-hexanamine
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B) 4-methyl-1-hexylamine D) 3-methyl-6-hexylamine
A) N-ethyl-N-methylcyclopentanamine C) N-methyl-N-ethylcyclopentylamine
B) N-cyclopentyl-N-methylethanamine D) N-ethyl-N-methylpentanamine
A) 1-methyl-N-propyl-1-propanamine C) 2-propyl-3-hexanamine
B) 4-methyl-4-heptanamine D) N-propyl-2-pentanamine
A) (S)-methyl-4-hexanamine C) (R)-2-methyl-4-hexanamine
B) (S)-5-methyl-3-hexanamine D) (R)-5-methyl-3-hexanamine
A) (Z)-4-hexen-1-amine C) (E)-2-hexen-6-amine
B) (E)-4-hexen-1-amine D) (Z)-2-hexen-6-amine
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19. What is the correct assignment of the names of the following aromatic amines?
20. Arrange the following compounds in order of decreasing boiling point, putting the
compound with the highest boiling point first.
A) I > II > III B) I > III > II C) III > I > II D) III > II > I
21. Arrange the following compounds in order of increasing boiling point, putting the
compound with the least boiling point first.
A) I < II < III B) II < I < III C) I < III < II D) II < III < I
22. Arrange the following amines in order of decreasing water solubility, putting the most
soluble amine first.
A) I > II > III B) II > I > III C) III > I > II D) II > III > I
23. The mass spectrum of an amine shows a parent peak with an odd mass for the molecular
ion. What does this tell you about the amine?
A) The amine is a primary amine.
B) The amine is a secondary amine.
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25. A compound with molecular formula C6H15N exhibits a singlet at 0.9 (1H), a triplet at
1.10 (3H), a singlet at 1.15 (9H), and a quartet at 2.6 (2H) in its 1HNMR spectrum.
Its IR spectrum shows one medium absorption band near 3400 cm-1. What is the
structure of this compound?
A) I B) II C) III D) IV
26. What is the name given to naturally occurring amines derived from plant sources?
A) Enamines B) Imines C) Alkaloids D) Alkamines
27. Why is direct nucleophilic substitution of an alkyl halide with NH3 not a very useful
method for preparing primary amines?
A) NH3 is not a nucleophile.
B) Elimination will occur.
C) NH3 is too bulky to act as a nucleophile.
D) Polyalkylation of the amine will result in multiple products.
28. In the preparation of primary amines, how can direct nucleophilic substitution between
NH3 and alkyl halide be made more practical than reacting NH3 and the alkyl halide in a
1:1 ratio?
A) Use a large excess of NH3.
B) Use a large excess of alkyl halide.
C) Use a limited amount of NH3.
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30. Which of the following alkyl halides cannot be used to prepare primary amines by the
Gabriel synthesis?
A) 2-bromo-2-methylbutane C) 2-bromo-3-methylbutane
B) 1-bromo-2-methylbutane D) 1-bromo-3-methylbutane
32. What is the major organic product obtained in the following reaction?
A) I B) II C) III D) IV
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33. What is the major organic product obtained in the following reaction?
A) I B) II C) III D) IV
34. What is the major organic product obtained in the following reaction?
A) I B) II C) III D) IV
35. What is the major organic product obtained in the following reaction?
A) I B) II C) III D) IV
36. Why are 1°, 2°, and 3° alkylamines more basic than ammonia (NH3)?
A) Because of the electron-withdrawing inductive effect of the alkyl groups.
B) Because of the steric hindrance of the alkyl groups.
C) Because of the resonance delocalization of the alkyl groups.
D) Because of electron-donating inductive effect of the alkyl groups.
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38. Rank the following compounds in order of increasing basicity, putting the least basic
compound first.
39. Rank the following compounds in order of decreasing basicity, putting the most basic
compound first.
40. Rank the following compounds in order of increasing basicity, putting the least basic
first.
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41. Rank the following compounds in order of decreasing basicity, putting the most basic
first.
44. Rank the following compounds in increasing order of basicity, putting the least basic
first.
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45. Rank the nitrogen atoms in chloroquine, shown below, in order of decreasing basicity,
putting the most basic nitrogen atom first.
A) I B) II C) III D) IV
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A) I B) II C) III D) IV
A) I B) II C) III D) IV
A) I B) II C) III D) IV
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A) I B) II C) III D) IV
A) I B) II C) III D) IV
A) NaI B) (1) NaNO2, HCl; (2) NaI C) (1) NaNO2, HCl; (2) I2 D) I2
A) NaF B) (1) NaNO2, HCl; (2) F2 C) (1) NaNO2, HCl; (2) HBF4 D) F2
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A) I B) II C) III D) IV
A) I B) II C) III D) IV
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58. What starting materials are required to synthesize the following azo compound?
A) I B) II C) III D) IV
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Answer Key
1. D
2. C
3. B
4. B
5. D
6. B
7. D
8. B
9. C
10. A
11. D
12. D
13. B
14. C
15. A
16. D
17. B
18. B
19. D
20. C
21. D
22. B
23. D
24. C
25. B
26. C
27. D
28. A
29. B
30. A
31. B
32. D
33. B
34. A
35. B
36. D
37. A
38. A
39. C
40. B
41. D
42. B
43. D
44. B
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45. C
46. A
47. B
48. D
49. A
50. D
51. A
52. B
53. B
54. C
55. D
56. A
57. D
58. B
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