Organic Chemistry 7th Edition Brown

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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 C−C−C 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?

CH3CH2CH2−CC−CH(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)2CHCH2−CC−CH(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

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 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

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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

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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
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?

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 a. (E) 3,4-dibromohexene
b. (Z) 3,4-dibromohexene
c. (E) 2,3-dibromohexene
d. (Z) 2,3-dibromobutene
ANS: A

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

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 ANS: B

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

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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

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

a. 1
b. 2
c. 3
d. 4
ANS: D

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

a. 1
b. 2
c. 3
d. 4
ANS: D

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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 is 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

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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

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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

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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 mol of Br2
b. 2 mol of Br2
c. 1 mol of HBr
d. 2 mol of HBr
ANS: D

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

a. 1 mol of Br2
b. 2 mol of Br2
c. 1 mol of HBr
d. 2 mol of HBr
ANS: A

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

a. H2O; H2SO4
b. 1.) 3 mol 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?

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 a. H2/Lindlar catalyst
b. Na/NH3
c. (sia)2BH; followed by H2O2, NaOH
d. BH3; followed by H2O2, NaOH
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

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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
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

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 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

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

TRUE/FALSE

1. The IUPAC name for the following compound is 2,5-dimethyl-4-ethyl-3-hexene.

ANS: F

2. The triple bond in ethyne is made up of two  bonds, each formed by lateral overlap of two p
orbitals, and a  bond formed by end-on overlap of two sp hybrid orbitals.

ANS: T

3. Acetylene (ethyne) is more acidic and has a shorter carbon to carbon bond than either ethane
or ethene.

ANS: T

4. Consider the following,

the product formed is shown below.

ANS: T

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 5. H2 and Ni would be the required reagents for the following conversion.

ANS: T

6. The following deuteration reaction correctly shows the stereochemistry of the product.

ANS: T

7. The product of the following reaction would be an aldehyde.

ANS: F

8. The key intermediate in the following reaction would be a vinylic carbocation.

ANS: T

9. 2-hexyne will produce a single product upon mercury(II)-catalyzed hydration.

ANS: F

10. The product of the reaction when the following substance is treated with BH3 in THF followed by
H2O2 would be a ketone.

ANS: F

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COMPLETION

1. Addition of H2 to 2-pentyne in the presence of the Lindlar's catalyst will produce ___-2-
pentene.

ANS: cis cis

2. The name of the final product after adding 1 mole of each reactant in the following sequence is
______________________.

ANS: 2-bromo-2-chloropropane

3. Consider an unknown with the molecular formula C4H6. The number of possible alkyne isomers is
_____.

ANS: 2 two

4. Consider an unknown with the molecular formula C4H6. The index of hydrogen deficiency of this
compound is _____.

ANS: 2 two

5. The following species is referred to as a(an)_________________.

ANS: acetylide anion acetylide ion

6. The following species is the conjugate base of _________________.

ANS: Acetylene ethyne

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7. The name of the product of the reaction of the following substance with bromoethane would be
________________.

ANS: 1-butyne but-1-yne

8. ____________________refers to a synthesis developed by examining the structure of the desired

product.

ANS: retrosynthetic analysis retrosynthesis

Select the best reagent or sequence of reagents from the list provided which would best accomplish
each transformation below. Place the letter corresponding to the reagent(s) in the blank to the left of
each reaction. Each transformation requires only one answer.

a. H2SO4, HgSO4 e. 1. Br2,CH2Cl2

b. H2, Lindlar 2. 2 NaNH2, NH3(l)
c. 1. BH3, THF f. 1. HCl
2. H2O2, NaOH 2. NaNH2, NH3(l)
d. 1. NaNH2, NH3(l) g. Li, NH3(l)
2. CH3CH2I h. 1. NaNH2, NH3(l)
2. CH3CH2CH2I

9. _____

ANS: g

10. _____

ANS: a

11. _____

ANS: e

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 12. _____

ANS: h

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

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

ANS:

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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:

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

ANS:

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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:

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

ANS:

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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 synthetic scheme.

ANS:

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

ANS:

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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 synthetic scheme.

ANS:

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

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ANS:

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