CHAPTER 7ALKYNES

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 + sp2; 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 + sp3
ANS: C

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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.
b.
c.
d.

3,4-dimethyl-1-hexen-5-yne
4-ethynyl-2-vinylbutane
3-methyl-4-vinyl-1-pentyne
4-ethynyl-3-methyl-1-pentyne

ANS: A
11. What is the IUPAC name of the following compound

a.
b.
c.
d.

vinylcyclohexane
allylcyclohexane
ethynylcyclohexane
acetylcyclohexane

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ANS: C
12. What is the IUPAC name of the following compound?

a.
b.
c.
d.

(R)-4-methyl-2-hexyne
(S)-4-methyl-2-hexyne
(R)-3-methyl-4-hexyne
(S)-3-methyl-4-hexyne

ANS: B
13. What is the IUPAC name for the following compound?

a.
b.
c.
d.

(R)-3-methyl-1-penten-4-yne
(S)-3-methyl-1-penten-4-yne
(R)-4-methyl-4-penten-1-yne
(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

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16. What is the correct assignment of the acid, base, conjugate acid and conjugate base in the following
equilibrium?

a.
b.
c.
d.

1 = acid; 2 = base; 3 = conjugate acid; 4 = conjugate base

1 = acid; 2 = base; 3 = conjugate base; 4 = conjugate acid
1 = base; 2 = acid; 3 = conjugate acid; 4 = conjugate base
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.
b.
c.
d.

cyclohexyne
1,3-cyclohexadiene
cyclohexene
1,2-diaminocyclohexane

ANS: B
18. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

(E) 2-butene
(Z) 2-butene
2-butyne
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

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ANS: A
21. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

2-methyl-3-hexene
2-methyl-3-heptyne
2-bromo-3-methylbutane
2-methyl-2-butene

ANS: B
22. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1-methyl-4-nonyne
2-methyl-4-nonyne
2-methyl-3-nonyne
3-methyl-4-nonyne

ANS: D
23. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

(E) 1,2-dibromobutene
(Z) 1,2-dibromobutene
(E) 2,3-dibromobutene
(Z) 2,3-dibromobutene

ANS: C
24. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

(E) 3,4-dibromohexene
(Z) 3,4-dibromohexene
(E) 2,3-dibromohexene
(Z) 2,3-dibromobutene

ANS: A

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25. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

2,3-dibromobutane
2,2,3,3-tetrabromobutane
2,3-dibromobutene
2,2-dibromobutane

ANS: B
26. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

3,4-dibromohexane
3,3-dibromohexane
(Z) 3,4-dibromohexene
3,3,4,4-tetrabromohexane

ANS: D
27. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

2,3-dibromobutane
2,2,3,3-tetrabromobutane
2,3-dibromobutene
2,2-dibromobutane

ANS: D
28. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

3,4-dibromohexane
3,3-dibromohexane
(E) 3,4-dibromohexene
3,3,4,4-tetrabromohexane

ANS: B

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29. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

butanal
cis-2-butene
2-butanol
butanone

ANS: A
30. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

2-hexanone
hexanal
2-hexanol
cis-2-hexene

ANS: B
31. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

butanal
cis-2-butene
2-butanol
butanone

ANS: A
32. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

2-hexanone
hexanal
2-hexanol
cis-2-hexene

ANS: B

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33. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ANS: A
34. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ANS: D

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35. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ANS: D

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37.

a.
b.
c.
d.

What is the major organic product obtained from the following reaction?

1
2
3
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.
b.
c.
d.

1
2
3
4

ANS: C

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40. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ANS: D
41. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

butane
1-butene
cis-2-butene
trans-2-butene

ANS: D
42. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ANS: B

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43. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

butane
1-butene
cis-2-butene
trans-2-butene

ANS: C
44. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ANS: A
45. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

butane
1-butene
cis-2-butene
trans-2-butene

ANS: C

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46. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ANS: A
47. What is the best choice of reagent(s) to perform the following transformation?

a.
b.
c.
d.

1 mole of Br2
2 moles of Br2
1 mole of HBr
2 moles of HBr

ANS: D
48. What is the best choice of reagent(s) to perform the following transformation?

a.
b.
c.
d.

1 mole of Br2
2 moles of Br2
1 mole of HBr
2 moles of HBr

ANS: A

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49. What is the best choice of reagent(s) to perform the following transformation?

a.
b.
c.
d.

H2O; H2SO4
1. 3 moles of NaNH2; 2. H3O+
KMnO4, NaOH, H2O
Zn

ANS: B
50. What is the best choice of reagent(s) to perform the following transformation?

a.
b.
c.
d.

H2/Pt
H2/Lindlar catalyst
Na/NH3
BH3; followed by H2O2, NaOH

ANS: C
51. What is the best choice of reagent(s) to perform the following transformation?

a.
b.
c.
d.

H2/Pt
H2/Lindlar catalyst
Na/NH3
BH3; followed by H2O2, NaOH

ANS: B
52. What is the best choice of reagent(s) to perform the following transformation?

a.
b.
c.
d.

H2/Lindlar catalyst
Na/NH3
(sia)2BH; followed by H2O2, NaOH
BH3; followed by H2O2, NaOH

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ANS: C
53. What is the best choice of reagent(s) to perform the following transformation?

a.
b.
c.
d.

H2/Lindlar catalyst
Na/NH3
(sia)2BH; followed by H2O2, NaOH
BH3; followed by H2O2, NaOH

ANS: D
54. What is the major organic product obtained from the following series of reactions?

a.
b.
c.
d.

1
2
3
4

ANS: A
55. What is the major organic product obtained from the following series of reactions?

a.
b.
c.
d.

propanal, CH3CH2CHO
1-propanol, CH3CH2CH2OH
butanal, CH3CH2CH2CHO
butanone, CH3COCH2CH3

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ANS: D
56. What is the major organic product obtained from the following series of reactions?

a.
b.
c.
d.

(E)-5-phenyl-2-pentene
6-phenyl-1-hexene
(Z)-6-phenyl-2-hexene
(E)-6-methyl-3-heptene

ANS: C
57. What is the major organic product obtained from the following series of reactions?

a.
b.
c.
d.

(Z)-2-heptene
(Z)-1,5-heptene
1-heptene
heptane

ANS: D
58. What is the major organic product obtained from the following series of reactions?

a.
b.
c.
d.

(Z)-2-heptene
(E)-2-heptene
1-heptene
heptane

ANS: B
59. Which of the following reagents react with 2-butyne to form (Z)-2-butene
1.
2.
3.
a.
b.
c.
d.

H2/Lindlar catalyst
(sia)2BH followed by CH3COOH
Na/NH3
only 1
only 2
only 3
only 1 and 2

ANS: D

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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

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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?

ANS:

7. What is the major organic product obtained from the following reaction?

ANS:

8. What is the major organic product obtained from the following reaction?

ANS:

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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?

ANS:

11. What is the major organic product obtained from the following reaction?

ANS:

12. What is the major organic product obtained from the following reaction?

ANS:

13. What is the major organic product obtained from the following reaction?

ANS:

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14. What is the major organic product obtained from the following reaction?

ANS:

15. What is the major organic product obtained from the following reaction?

ANS:

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.

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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.

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ANS:

20. Outline how one might achieve the following transformation, showing reagents and the isolated
intermediates in the synthetic scheme.

ANS:

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