alkyne
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Brown Organic Chemistry 6e Test Bank 1
CHAPTER 7—ALKYNES
MULTIPLE CHOICE
1. Approximately how long is a carbon-carbon triple bond of an alkyne?
a. 110 pm
b. 121 pm
c. 135 pm
d. 156 pm
ANS: B
2. What is the approximate CCC bond angle in propyne?
a. 90
b. 109
c. 120
d. 180
ANS: D
3. How many alkynes are there with the molecular formula C6H10?
a. 4
b. 5
c. 6
d. 7
ANS: D
4. How many terminal alkynes are there with the molecular formula C7H12?
a. 5
b. 7
c. 8
d. 9
ANS: C
5. Which atomic orbitals overlap to form the carbon-carbon triple bond of an alkyne?
a. 2s + 2s; sp + sp; 2p + 2p
b. sp + sp; sp + sp; 2p + 2p
c. sp + sp; 2p + 2p; 2p + 2p
d. sp2 + sp
2; sp + sp; 2p + 2p
ANS: C
6. Which atomic orbitals overlap to form the carbon-carbon single bond of 1-propyne?
a. 2s + sp
b. sp + sp2
c. sp + sp3
d. sp2 + sp
3
ANS: C
Brown Organic Chemistry 6e Test Bank 2
7. What is the smallest cycloalkyne that is stable at room temperature?
a. cyclohexyne
b. cyclononyne
c. cyclododecyne
d. cycloeicosyne
ANS: B
8. What is the IUPAC name of the following compound?
CH3CH2CH2CCCH(CH3)2
a. 1-isopropyl-1-pentyne
b. 2-methyl-3-heptyne
c. 6-methyl-4-heptyne
d. isopropyl propyl ethyne
ANS: B
9. What is the IUPAC name of the following compound?
(CH3)2CHCH2CCCH(CH3)2
a. 2,6-dimethyl-3-heptyne
b. 2,6-dimethyl-4-heptyne
c. 1,1,5,5-tetramethyl-2-pentyne
d. 4-nonyne
ANS: A
10. What is the IUPAC name of the following compound?
a. 3,4-dimethyl-1-hexen-5-yne
b. 4-ethynyl-2-vinylbutane
c. 3-methyl-4-vinyl-1-pentyne
d. 4-ethynyl-3-methyl-1-pentyne
ANS: A
11. What is the IUPAC name of the following compound
a. vinylcyclohexane
b. allylcyclohexane
c. ethynylcyclohexane
d. acetylcyclohexane
Brown Organic Chemistry 6e Test Bank 3
ANS: C
12. What is the IUPAC name of the following compound?
a. (R)-4-methyl-2-hexyne
b. (S)-4-methyl-2-hexyne
c. (R)-3-methyl-4-hexyne
d. (S)-3-methyl-4-hexyne
ANS: B
13. What is the IUPAC name for the following compound?
a. (R)-3-methyl-1-penten-4-yne
b. (S)-3-methyl-1-penten-4-yne
c. (R)-4-methyl-4-penten-1-yne
d. (S)-4-methyl-4-penten-1-yne
ANS: A
14. Which of the following is the strongest acid?
a. propane
b. cyclopropane
c. propene
d. propyne
ANS: D
15. Which of the following has the lowest pKa?
a. butane
b. 1-butene
c. 1-butyne
d. 2-butyne
ANS: C
Brown Organic Chemistry 6e Test Bank 4
16. What is the correct assignment of the acid, base, conjugate acid and conjugate base in the following
equilibrium?
a. 1 = acid; 2 = base; 3 = conjugate acid; 4 = conjugate base
b. 1 = acid; 2 = base; 3 = conjugate base; 4 = conjugate acid
c. 1 = base; 2 = acid; 3 = conjugate acid; 4 = conjugate base
d. 1 = base; 2 = acid; 3 = conjugate base; 4 = conjugate acid
ANS: B
17. What is the major organic product obtained from the following reaction?
a. cyclohexyne
b. 1,3-cyclohexadiene
c. cyclohexene
d. 1,2-diaminocyclohexane
ANS: B
18. What is the major organic product obtained from the following reaction?
a. (E) 2-butene
b. (Z) 2-butene
c. 2-butyne
d. 1-butyne
ANS: C
19. Which sequence of reactions can be used to convert 1-pentene to 1-pentyne
a. Treatment with HBr; followed by treatment with NaOH
b. Treatment with Br2; followed by treatment with NaNH2
c. Treatment with Br2; followed by treatment with H2SO4
d. Treatment with Br2, H2O; followed by treatment with NaOH
ANS: B
20. Which sequence of reactions can be used to convert (Z) 2-pentene to 2-pentyne
a. Treatment with Br2; followed by treatment with NaNH2
b. Treatment with Br2, H2O; followed by treatment with NaOH
c. Treatment with Br2; followed by treatment with H2SO4
d. Treatment with HBr; followed by treatment with NaOH
Brown Organic Chemistry 6e Test Bank 5
ANS: A
21. What is the major organic product obtained from the following reaction?
a. 2-methyl-3-hexene
b. 2-methyl-3-heptyne
c. 2-bromo-3-methylbutane
d. 2-methyl-2-butene
ANS: B
22. What is the major organic product obtained from the following reaction?
a. 1-methyl-4-nonyne
b. 2-methyl-4-nonyne
c. 2-methyl-3-nonyne
d. 3-methyl-4-nonyne
ANS: D
23. What is the major organic product obtained from the following reaction?
a. (E) 1,2-dibromobutene
b. (Z) 1,2-dibromobutene
c. (E) 2,3-dibromobutene
d. (Z) 2,3-dibromobutene
ANS: C
24. What is the major organic product obtained from the following reaction?
a. (E) 3,4-dibromohexene
b. (Z) 3,4-dibromohexene
c. (E) 2,3-dibromohexene
d. (Z) 2,3-dibromobutene
ANS: A
Brown Organic Chemistry 6e Test Bank 6
25. What is the major organic product obtained from the following reaction?
a. 2,3-dibromobutane
b. 2,2,3,3-tetrabromobutane
c. 2,3-dibromobutene
d. 2,2-dibromobutane
ANS: B
26. What is the major organic product obtained from the following reaction?
a. 3,4-dibromohexane
b. 3,3-dibromohexane
c. (Z) 3,4-dibromohexene
d. 3,3,4,4-tetrabromohexane
ANS: D
27. What is the major organic product obtained from the following reaction?
a. 2,3-dibromobutane
b. 2,2,3,3-tetrabromobutane
c. 2,3-dibromobutene
d. 2,2-dibromobutane
ANS: D
28. What is the major organic product obtained from the following reaction?
a. 3,4-dibromohexane
b. 3,3-dibromohexane
c. (E) 3,4-dibromohexene
d. 3,3,4,4-tetrabromohexane
ANS: B
Brown Organic Chemistry 6e Test Bank 7
29. What is the major organic product obtained from the following reaction?
a. butanal
b. cis-2-butene
c. 2-butanol
d. butanone
ANS: A
30. What is the major organic product obtained from the following reaction?
a. 2-hexanone
b. hexanal
c. 2-hexanol
d. cis-2-hexene
ANS: B
31. What is the major organic product obtained from the following reaction?
a. butanal
b. cis-2-butene
c. 2-butanol
d. butanone
ANS: A
32. What is the major organic product obtained from the following reaction?
a. 2-hexanone
b. hexanal
c. 2-hexanol
d. cis-2-hexene
ANS: B
Brown Organic Chemistry 6e Test Bank 8
33. What is the major organic product obtained from the following reaction?
a. 1 b. 2 c. 3 d. 4
ANS: A
34. What is the major organic product obtained from the following reaction?
a. 1 b. 2 c. 3 d. 4
ANS: D
Brown Organic Chemistry 6e Test Bank 9
35. What is the major organic product obtained from the following reaction?
a. 1 b. 2 c. 3 d. 4
ANS: D
Brown Organic Chemistry 6e Test Bank 10
37. What is the major organic product obtained from the following reaction?
a. 1 b. 2 c. 3 d. 4
ANS: B
38. What type of intermediate s formed in the Hg2
catalyzed hydration of an alkyne??
a. an alcohol
b. an enol
c. a 1,2-diene
d. an epoxide
ANS: B
39. What is the major organic product obtained from the following reaction?
a. 1 b. 2 c. 3 d. 4
ANS: C
Brown Organic Chemistry 6e Test Bank 11
40. What is the major organic product obtained from the following reaction?
a. 1 b. 2 c. 3 d. 4
ANS: D
41. What is the major organic product obtained from the following reaction?
a. butane
b. 1-butene
c. cis-2-butene
d. trans-2-butene
ANS: D
42. What is the major organic product obtained from the following reaction?
a. 1 b. 2 c. 3 d. 4
ANS: B
Brown Organic Chemistry 6e Test Bank 12
43. What is the major organic product obtained from the following reaction?
a. butane
b. 1-butene
c. cis-2-butene
d. trans-2-butene
ANS: C
44. What is the major organic product obtained from the following reaction?
a. 1 b. 2 c. 3 d. 4
ANS: A
45. What is the major organic product obtained from the following reaction?
a. butane
b. 1-butene
c. cis-2-butene
d. trans-2-butene
ANS: C
Brown Organic Chemistry 6e Test Bank 13
46. What is the major organic product obtained from the following reaction?
a. 1 b. 2 c. 3 d. 4
ANS: A
47. What is the best choice of reagent(s) to perform the following transformation?
a. 1 mole of Br2
b. 2 moles of Br2
c. 1 mole of HBr
d. 2 moles of HBr
ANS: D
48. What is the best choice of reagent(s) to perform the following transformation?
a. 1 mole of Br2
b. 2 moles of Br2
c. 1 mole of HBr
d. 2 moles of HBr
ANS: A
Brown Organic Chemistry 6e Test Bank 14
49. What is the best choice of reagent(s) to perform the following transformation?
a. H2O; H2SO4
b. 1. 3 moles of NaNH2; 2. H3O+
c. KMnO4, NaOH, H2O
d. Zn
ANS: B
50. What is the best choice of reagent(s) to perform the following transformation?
a. H2/Pt
b. H2/Lindlar catalyst
c. Na/NH3
d. BH3; followed by H2O2, NaOH
ANS: C
51. What is the best choice of reagent(s) to perform the following transformation?
a. H2/Pt
b. H2/Lindlar catalyst
c. Na/NH3
d. BH3; followed by H2O2, NaOH
ANS: B
52. What is the best choice of reagent(s) to perform the following transformation?
a. H2/Lindlar catalyst
b. Na/NH3
c. (sia)2BH; followed by H2O2, NaOH
d. BH3; followed by H2O2, NaOH
Brown Organic Chemistry 6e Test Bank 15
ANS: C
53. What is the best choice of reagent(s) to perform the following transformation?
a. H2/Lindlar catalyst
b. Na/NH3
c. (sia)2BH; followed by H2O2, NaOH
d. BH3; followed by H2O2, NaOH
ANS: D
54. What is the major organic product obtained from the following series of reactions?
a. 1 b. 2 c. 3 d. 4
ANS: A
55. What is the major organic product obtained from the following series of reactions?
a. propanal, CH3CH2CHO
b. 1-propanol, CH3CH2CH2OH
c. butanal, CH3CH2CH2CHO
d. butanone, CH3COCH2CH3
Brown Organic Chemistry 6e Test Bank 16
ANS: D
56. What is the major organic product obtained from the following series of reactions?
a. (E)-5-phenyl-2-pentene
b. 6-phenyl-1-hexene
c. (Z)-6-phenyl-2-hexene
d. (E)-6-methyl-3-heptene
ANS: C
57. What is the major organic product obtained from the following series of reactions?
a. (Z)-2-heptene
b. (Z)-1,5-heptene
c. 1-heptene
d. heptane
ANS: D
58. What is the major organic product obtained from the following series of reactions?
a. (Z)-2-heptene
b. (E)-2-heptene
c. 1-heptene
d. heptane
ANS: B
59. Which of the following reagents react with 2-butyne to form (Z)-2-butene
1. H2/Lindlar catalyst
2. (sia)2BH followed by CH3COOH
3. Na/NH3
a. only 1
b. only 2
c. only 3
d. only 1 and 2
ANS: D
Brown Organic Chemistry 6e Test Bank 17
60. Which of the following reagents react with 2-butyne to form butane
a. H2/Lindlar catalyst
b. H2/Pd
c. (sia)2BH followed by CH3COOH
d. Na/NH3
ANS: B
PROBLEM
1. What is IUPAC name of the following compound?
ANS:
(R)-4-chloro-2-pentyne
2. What is IUPAC name of the following compound?
ANS:
(S)-2-chloro-3-hexyne
3. What is IUPAC name of the following compound?
ANS:
1,5-heptadiyne
4. What is IUPAC name of the following compound?
ANS:
2,5-octadiyne
Brown Organic Chemistry 6e Test Bank 18
5. What is the major organic product obtained from the following reaction?
ANS:
6. What is the major organic product obtained from the following reaction?
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7. What is the major organic product obtained from the following reaction?
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8. What is the major organic product obtained from the following reaction?
ANS:
Brown Organic Chemistry 6e Test Bank 19
9. What is the major organic product obtained from the following reaction?
ANS:
10. What is the major organic product obtained from the following reaction?
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11. What is the major organic product obtained from the following reaction?
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12. What is the major organic product obtained from the following reaction?
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13. What is the major organic product obtained from the following reaction?
ANS:
Brown Organic Chemistry 6e Test Bank 20
14. What is the major organic product obtained from the following reaction?
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15. What is the major organic product obtained from the following reaction?
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16. Outline how one might achieve the following transformation, showing reagents and the isolated
intermediates in the synthesitc scheme.
ANS:
17. Outline how one might achieve the following transformation, showing reagents and the isolated
intermediates in the synthesitc scheme.
Brown Organic Chemistry 6e Test Bank 21
ANS:
18. Outline how one might achieve the following transformation, showing reagents and the isolated
intermediates in the synthetic scheme.
ANS:
19. Outline how one might achieve the following transformation, showing reagents and the isolated
intermediates in the synthesitc scheme.
Brown Organic Chemistry 6e Test Bank 22
ANS:
20. Outline how one might achieve the following transformation, showing reagents and the isolated
intermediates in the synthetic scheme.
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