Organic Chemistry, 9e (Wade)

Chapter 9 Alkynes

1) How many distinct alkynes exist with a molecular formula of C4H6?

A) 0
B) 1
C) 2
D) 3
E) 4
Answer: C
Diff: 1
Section: 9.2
GO: G2

2) How many distinct alkynes exist with a molecular formula of C4H8?

A) 0
B) 1
C) 2
D) 3
E) 4
Answer: A
Diff: 1
Section: 9.2
GO: G2

3) Give the IUPAC name for HC CCH2CH2CH3.

Answer: pent-1-yne
Diff: 1
Section: 9.2
LO: 9.1
MCAT LO: MCAT9.1

4) Draw an acceptable structure for

acetylene. Answer: H—C C—H
Diff: 1
Section: 9.2
LO: 9.1
MCAT LO: MCAT9.1

5) Draw an acceptable structure for hex- 2-yne.

Answer:

Diff: 1
Section: 9.2
LO: 9.1
MCAT LO: MCAT9.1
6) How many distinct terminal alkynes exist with a molecular formula of
A) 1
B) 2
C) 3
D) 4
E) 5
Answer: B
Diff: 2
Section: 9.2
GO: G2

7) How many distinct internal alkynes exist with a molecular formula of

A) 1
B) 2
C) 3
D) 4
E) 5
Answer: C
Diff: 2
Section: 9.2
GO: G2

8) Give the IUPAC name for Cl3CCH2CH2CH2C≡CH.

Answer: 6,6,6-trichlorohex-1-yne
Diff: 2
Section: 9.2
LO: 9.1
MCAT LO: MCAT9.1

9) Provide the IUPAC name for the compound below.

Answer: 3-ethylhex-4-yn-3-ol
Diff: 2
Section: 9.2
LO: 9.1
MCAT LO: MCAT9.1
10) Provide the IUPAC name for Cl3C(CH2)2C≡CH.
Answer: 5,5,5-trichloro-1-pentyne or 5,5,5-trichloropent-1-yne
Diff: 2
Section: 9.2
LO: 9.1
MCAT LO: MCAT9.1

11) Provide the IUPAC name for (CH3)2CHCH2CH(OH)CH2C≡CCH3.

Answer: 2-methyl-6-octyn-4-ol or 2-methyloct-6-yn-4-ol
Diff: 2
Section: 9.2
LO: 9.1
MCAT LO: MCAT9.1

12) Name the compound shown below.

Answer: 6,6-dimethyl-3-heptyne or 6,6-dimethylhept-3-yne

Diff: 2
Section: 9.2
LO: 9.1
MCAT LO: MCAT9.1

13) Draw and name all terminal alkynes with molecular formula C5H8.
Answer: CH3CH2CH2C≡CH, 1-pentyne or pent-1-yne; (CH3)2CHC≡CH, 3-methyl-1-butyne
or 3-methylbut-1-yne
Diff: 2
Section: 9.2
LO: 9.1
MCAT LO: MCAT9.1

14) Provide the IUPAC name for the compound given, including stereochemical designators
as appropriate.

Answer: (E)-hept-4-en-2-yne
Diff: 2
Section: 9.2
LO: 9.1
MCAT LO: MCAT9.1
15) Give the IUPAC name for CH3CH2C CCH(OH)CH3.
Answer: hex-3-yn-2-ol
Diff: 2
Section: 9.2
LO: 9.1
MCAT LO: MCAT9.1

16) Draw an acceptable structure for (R)-5,5-dimethylhept-6-yn-3-ol

Answer:

Diff: 2
Section: 9.2
LO: 9.1
MCAT LO: MCAT9.1

17) Draw an acceptable structure for 3-sec-butylhept-1-yne.

Answer:

Diff: 2
Section: 9.2
LO: 9.1
MCAT LO: MCAT9.1

18) Draw an acceptable structure for (S)-5-phenyloct-2-yne.

Answer:

Diff: 2
Section: 9.2
LO: 9.1
MCAT LO: MCAT9.1

19) Draw an acceptable structure for hepta-3,6-dien-1-yne.

Answer: HC CCH CHCH2CH CH2
Diff: 2
Section: 9.2
LO: 9.1
MCAT LO: MCAT9.1
20) What is the correct IUPAC name for the following structure?

A) (Z) 1-cyclopentyl-3,6-dimethylhept-3-en-1-yne
B) (E) 1-cyclopentyl-3,6-dimethylhept-1-yn-3-ene
C) (Z) 1-cyclopentyl-4,7-dimethylhept-4-en-2-yne
D) (E) 1-cyclopentyl-3,6-dimethylhept-3-en-1-yne
Answer: D
Diff: 2
Section: 9.2
LO: 9.1
MCAT LO: MCAT9.1

21) Provide the IUPAC name for the compound below.

A) 1-chloro-4-methylpent-2-yne
B) 5-chloro-2-methylpent-3-yne
C) sec-butylchloromethylacetylene
D) 1-chloro-4,4-dimethylbut-2-yne
Answer: A
Diff: 2
Section: 9.2
LO: 9.1
MCAT LO: MCAT9.1

22) The correct IUPAC name for the following structure is .

A) (Z) 4-isopropyl-4-hepten-2-yne
B) (E) 4-isopropyl-3-hepten-5-yne
C) (E) 4-isopropyl-4-hepten-2-yne
D) (Z) 4-isopropyl-3-hepten-5-yne
Answer: C
Diff: 3
Section: 9.2
LO: 9.1
MCAT LO: MCAT9.1
23) What is the correct IUPAC name for the following compound?

A) 4-(1-bromopropyl)-1-hexen-5-yne
B) 4-allyl-5-bromo-1-hexyne
C) 3-(1-bromopropyl)-5-hexen-1-yne
D) 5-bromo-4-ethynyl-1-heptene
Answer: C
Diff: 3
Section: 9.2
LO: 9.1
MCAT LO: MCAT9.1

24) Give the IUPAC name for CH3CH CHCH CHC

CCH3. Answer: octa-2,4-dien-6-yne
Diff: 3
Section: 9.2
LO: 9.1
MCAT LO: MCAT9.1

25) Which of the following improperly describes the physical properties of an alkyne?
A) relatively nonpolar
B) nearly insoluble in water
C) less dense than water
D) insoluble in most organic solvents
E) boiling point nearly the same as an alkane with similar carbon
skeleton Answer: D
Diff: 2
Section: 9.3
LO: 2.5
MCAT LO: MCAT2.5

26) Which of the following alkynes has the lowest boiling point?
A) 3,3-dimethyl-1-butyne
B) 1-hexyne
C) 2-heptyne
D) 3-hexyne
E) 1-decyne
Answer: A
Diff: 2
Section: 9.3
LO: 2.5
MCAT LO: MCAT2.5
27) The pi bond of an alkyne is and than the pi bond of an alkene.
A) shorter; stronger
B) shorter; weaker
C) longer; stronger
D) longer; weaker
Answer: B
Diff: 2
Section: 9.5
MCAT LO: MCAT9.3

28) How many moles of oxygen are required in the complete combustion of 1 mole of acetylene?
A) 1
B) 1.5
C) 2
D) 2.5
E) 3
Answer: D
Diff: 2
Section: 9.4
LO: 9.5
MCAT LO: MCAT9.2

29) Write the complete, balanced equation for the combustion of 2-pentyne.
Answer: CH3C CCH2CH3 + 7O2 → 5CO2 + 4 H2O
Diff: 2
Section: 9.4
LO: 9.5
MCAT LO: MCAT9.2

30) How many moles of water are produced when one mole of propyne undergoes
complete combustion?
A) 1
B) 2
C) 3
D) 4
Answer: B
Diff: 2
Section: 9.4
LO: 9.5
MCAT LO: MCAT9.2
31) The carbon-carbon triple bond of an alkyne is composed of .
A) three σ bonds
B) three π bonds
C) two σ bonds and one π bond
D) one σ bond and two π bonds
Answer: D
Diff: 1
Section: 9.5
LO: 9.1
MCAT LO: MCAT9.3

32) In trans-hept-4-en-2-yne the shortest carbon-carbon bond is between carbons .

A) 1 and 2
B) 2 and 3
C) 3 and 4
D) 4 and 5
E) 6 and 7
Answer: B
Diff: 1
Section: 9.5
LO: 9.1
MCAT LO: MCAT9.1

33) Circle the shortest bond in the compound below.

Answer:

Diff: 2
Section: 9.5
MCAT LO: MCAT9.4
34) Which of the species below is less basic than acetylide?
A) CH3Li
B) CH3ONa
C) CH3MgBr
D) both A and C
E) all of the above
Answer: B
Diff: 2
Section: 9.6
LO: 9.2
GO: G2

35) Among the compounds water, but-1-yne, but-2-yne, and ethane, which are stronger
acids than ammonia?
A) but-1-yne and ethane
B) water and but-1-yne
C) water and ethane
D) but-1-yne and but-2-yne
Answer: B
Diff: 2
Section: 9.6
LO: 9.2
GO: G2

36) To a solution of propyne in diethyl ether, one molar equivalent of CH3Li was added and the
resulting mixture was stirred for 0.5 hour. After this time, an excess of D2O was added.
Describe the major organic product(s) of this reaction.
A) CH3C CD + CH4
B) CH3C CCH3
C) CD3C CD3
D) CH3C CCD3
E) CH3C CD +
CH3D Answer: A
Diff: 2
Section: 9.6
LO: 9.2, 9.5
MCAT LO: MCAT9.2
37) What is the pKa of a terminal alkyne?
A) 4
B) 10
C) 16
D) 25
E) 44
Answer: D
Diff: 2
Section: 9.6
LO: 9.2
MCAT LO: MCAT9.4

38) Explain why the synthetic route shown below would be unsuccessful.

H—C C:- Na+ H3CH2C—C C—CH2CH3

3. CH3CH2I

Answer: Sodium methoxide is not a sufficiently strong base to deprotonate the intermediate
terminal alkyne.
Diff: 2
Section: 9.6
LO: 9.2
GO: G2

39) Provide the major organic product of the reaction below.

Answer: (CH3)2CHCH2CH2C≡CD
Diff: 2
Section: 9.6
LO: 9.5
MCAT LO: MCAT9.2

40) Why are terminal alkynes more acidic then other hydrocarbons?
Answer: The carbanion which results upon deprotonation of a terminal alkyne has the lone pair
of electrons in an sp hybrid orbital. The greater % s character of this orbital gives this orbital a
significantly lower energy.
Diff: 2
Section: 9.6
LO: 9.2
MCAT LO: MCAT9.4
41) Provide the structure of the major organic product(s) in the reaction below.

Answer:

Diff: 2
Section: 9.6
LO: 9.2

42) Using pKa values, determine whether or not the following reaction will proceed
to completion.

Answer:

Yes, this reaction will go to completion because methane is a weaker acid.

Diff: 2
Section: 9.6
LO: 9.2
GO: G2
MCAT LO: MCAT9.4

43) Using pKa values, determine whether or not the following reaction will proceed
to completion.

Answer: No, this reaction will not go to completion. The pKa of the alkyne is 25, while
methanol is ~15.
Diff: 2
Section: 9.6
LO: 9.2
MCAT LO: MCAT9.4
44) Using pKa values, determine whether or not the following reaction will proceed
to completion.

Answer:

Yes, this reaction will go to completion because hydrogen is a weaker acid.

Diff: 2
Section: 9.6
LO: 9.2
MCAT LO: MCAT9.4

45) Which of the following bases are sufficiently strong to deprotonate a terminal alkyne with
an equilibrium constant greater than 1?

1) sodium methoxide 3) n-butyl lithium

2) lithium diisopropyl amide 4) phenylmagnesium bromide

A) 1, 2, and 3
B) 2, 3 and 4
C) 2 and 3
D) 3 and 4
E) 1, 2, 3 and 4
Answer: B
Diff: 3
Section: 9.6
LO: 9.2
MCAT LO: MCAT9.4

46) Provide the structure of the major organic product(s) in the reaction sequence below.

CH3CH2C CH →
Answer: CH3CH2C CCH2Ph
Diff: 1
Section: 9.7
47) Describe a sequence of reactions by which hept-3-yne can be straightforwardly
prepared from acetylene.
Answer:
1) NaNH2
2) CH3CH2Br
3) NaNH2
4) CH3CH2CH2Br
Diff: 1
Section: 9.7
LO: 9.4

48) Describe a sequence of reactions by which butylbenzene can be straightforwardly

prepared from phenylacetylene.
Answer:
1) NaNH2
2) CH3CH2Br
3) H2, Pt
Diff: 1
Section: 9.7
LO: 9.4, 9.5
GO: G2
MCAT LO: MCAT9.2

49) Explain why the synthetic route shown below would be unsuccessful.

H—C C:- Na+ (H3C)3C—C C—CH2CH3

3. (CH3)3CBr

Answer: The tert-butyl bromide would not undergo SN2 when treated with the intermediate
alkynide because the steric hinderance in the halide is too great. Instead, the alkynide
would deprotonate the tertiary bromide via an E2 mechanism.
Diff: 2
Section: 9.7
LO: 9.4
GO: G2
MCAT LO: MCAT9.2
50) Provide the major organic product of the reaction shown below.

Answer:

Diff: 2
Section: 9.7
LO: 9.4
MCAT LO: MCAT9.2

51) What's the problem with the synthetic approach shown below?

Answer: The bromide is tertiary and therefore too hindered to undergo SN2. An E2 reaction
would occur instead.
Diff: 2
Section: 9.7
LO: 9.4
MCAT LO: MCAT9.2

52) Fill in the missing reagent.

Answer:

Diff: 2
Section: 9.7
LO: 9.4
GO: G2
MCAT LO: MCAT9.2
53) Provide the structure of the major organic product(s) in the reaction below.

Answer:

Diff: 2
Section: 9.7
LO: 9.4
MCAT LO: MCAT9.2

54) Provide the structure of the major organic product(s) in the reaction sequence below.

Answer:

Diff: 2
Section: 9.7
LO: 9.4
MCAT LO: MCAT9.2

55) Provide the structure of the major organic product(s) in the reaction below.

Answer:

Diff: 2
Section: 9.7
LO: 9.4
GO: G2
MCAT LO: MCAT9.2
56) Describe a sequence of reactions by which 1-propylcyclohexan-1-ol can be straightforwardly
prepared from propyne.
Answer:
1) NaNH2
2) cyclohexanone
3) H+, H2O
4) H2, Pt
Diff: 2
Section: 9.7
LO: 9.6
GO: G2

57) Describe a sequence of reactions by which the compound shown below can be
straightforwardly prepared from acetylene.

Answer:
1) NaNH2
2) CH3CH2Br
3) NaNH2
4) cyclopentanone
5) H+, H2O
Diff: 2
Section: 9.7
LO: 9.4
GO: G2

58) Name the product which results when CH3C CLi reacts with CH3CH2COCH2CH3
followed by addition of water.
Answer: 3-ethylhex-4-yn-3-ol
Diff: 3
Section: 9.7
LO: 9.4
GO: G2
MCAT LO: MCAT9.2
59) What conditions could be used to isomerize hept-2-yne to hept-1-yne?
Answer:
1) NaNH2, 150°C
2) H2O
Diff: 3
Section: 9.7
LO: 9.4
GO: G2
MCAT LO: MCAT9.2

60) Provide a correct structure for the product of the following reaction.

Answer:

Diff: 3
Section: 9.7
LO: 9.4

61) Complete the short synthesis below by providing the necessary reagents.

Answer:
1) Br2 2) CH3C≡CNa 3) Na / NH3
Diff: 3
Section: 9.9
LO: 9.6
62) Describe a sequence of reactions by which (E)-5-bromopent-2-ene can be straightforwardly
prepared from propyne.
Answer:
1) NaNH2
2) ethylene oxide (oxirane)
3) H+, H2O
4) Na, NH3
5) PBr3
Diff: 3
Section: 9.7
LO: 9.6

63) Why is a terminal alkyne favored when sodium amide (NaNH2) is used in an elimination
reaction with 2,3-dichlorohexane?
A) The strong base deprotonates the terminal alkyne and removes it from the equilibrium.
B) The resonance favors the formation of the terminal rather than internal alkyne.
C) The positions of the Cl atoms induce the net formation of the terminal alkyne.
D) The terminal alkyne is more stable than the internal alkyne and is naturally the
favored product.
E) The terminal alkyne is not favored in this reaction.
Answer: A
Diff: 2
Section: 9.8
LO: 9.5
MCAT LO: MCAT9.2

64) Provide the major organic product of the reaction below.

Answer: CH3(CH2)5C≡CH
Diff: 2
Section: 9.8
LO: 9.4
65) When 2,2-dibromobutane is heated at 150°C in the presence of molten KOH, what is
the major organic product?
A) 1-bromobut-1-yne
B) 1-bromobut-2-yne
C) but-1-yne
D) but-2-yne
E) but-1-ene
Answer: D
Diff: 3
Section: 9.8
LO: 9.4

66) Describe a sequence of reactions by which hept-1-yne can be straightforwardly

prepared from hept-1-ene.
Answer:
1) Br2
2) NaNH2, heat
Diff: 3
Section: 9.8
LO: 9.4

67) Treatment of hex-2-yne with mercuric sulfate in dilute sulfuric acid yields a mixture of two
ketones. Similar treatment of hex-3-yne produces a single ketone instead of a mixture. Explain.
Answer: The two carbons of the triple bond in hex-3-yne are equivalent, and only 3-hexanone
results. In the case of hex-2-yne, the two carbons of the triple bond are not equivalent, and a
mixture of 2- and 3-hexanone results.
Diff: 1
Section: 9.9
LO: 9.5
MCAT LO: MCAT9.2

68) Which of the following describes an unsymmetrical addition reaction?

A) propyne with 1 mole H2, Ni and heat
B) propyne with 2 moles Cl2 in CCl4
C) propyne with 1 mole Br2 in CCl4
D) propyne with Na/NH3
E) propyne with 1 mole
HBr Answer: E
Diff: 1
Section: 9.9
LO: 9.5
MCAT LO: MCAT9.2
69) Which of the following reagents will convert 1 mole of 3-methylpent-1-yne into 3-
methylpentane?
A) 1 mole of Br2 in CCl4
B) 2 moles of Cl2 in CCl4
C) 2 moles of HCl
D) 2 moles H2, Ni and heat
E) 1 mole H2, Ni and heat
Answer: D
Diff: 1
Section: 9.9
LO: 9.5
MCAT LO: MCAT9.2

70) Give the product of the following reaction:

Answer:

Diff: 1
Section: 9.9
LO: 9.5
MCAT LO: MCAT9.2

71) Describe a sequence of reactions by which trans-pent-2-ene can be straightforwardly

prepared from propyne.
Answer:
1) NaNH2
2) CH3CH2Br
3) Na, NH3
Diff: 1
Section: 9.9
LO: 9.6
72) Which of the following reagents should be used to convert to
A) H2, Pt
B) Na, NH3
C) H2, Lindlar's catalyst
D) H2SO4, H2O
E) HgSO4, H2O
Answer: B
Diff: 2
Section: 9.9
LO: 9.6
GO: G2

73) Which of the following reagents should be used to convert to

A) H2, Pt
B) Na, NH3
C) H2, Lindlar's catalyst
D) H2SO4, H2O
E) HgSO4, H2O
Answer: C
Diff: 2
Section: 9.9
LO: 9.6
GO: G2

74) A mixture of hept-1-yne, hept-2-yne, and hept-3-yne was hydrogenated in the presence of a
platinum catalyst until hydrogen uptake ceased. If one assumes that the hydrogenation went to
completion, how many different seven-carbon hydrocarbons were produced?
A) 1
B) 2
C) 3
D) 6
E) 8
Answer: A
Diff: 2
Section: 9.9
LO: 9.5
MCAT LO: MCAT9.2
75) is produced when 1 equivalent of HBr is added to hex-1-yne in the presence of
peroxides.
A) 2-Bromohex-1-ene
B) E-1-Bromohex-1-ene
C) Z-1-Bromohex-1-ene
D) A mixture of E and Z isomers of 1-bromohex-1-ene
E) E-2-Bromohex-2-ene
Answer: D
Diff: 2
Section: 9.9
LO: 9.5
MCAT LO: MCAT9.2

76) Which of the alkyne addition reactions below involve(s) an enol intermediate?
A) hydroboration/oxidation
B) treatment with HgSO4 in dilute H2SO4
C) hydrogenation
D) both A and B
E) none of the above
Answer: D
Diff: 2
Section: 9.9
LO: 9.3

77) What is the major organic product that results when 3-heptyne is hydrogenated in
the presence of Lindlar's catalyst?
A) 2-heptyne
B) (Z)-2-heptene
C) (Z)-3-heptene
D) (E)-3-heptene
E) heptane
Answer: C
Diff: 2
Section: 9.9
LO: 9.5
GO: G7
MCAT LO: MCAT9.2
78) What is the major organic product that results when 3-heptyne is subjected to
excess hydrogen and a platinum catalyst?
A) 2-heptyne
B) (Z)-2-heptene
C) (Z)-3-heptene
D) (E)-3-heptene
E) heptane
Answer: E
Diff: 2
Section: 9.9
LO: 9.5
MCAT LO: MCAT9.2

79) What is the major organic product that results when 3-heptyne is treated with sodium
metal in ammonia?
A) 2-heptyne
B) (Z)-2-heptene
C) (Z)-3-heptene
D) (E)-3-heptene
E) heptane
Answer: D
Diff: 2
Section: 9.9
LO: 9.5
MCAT LO: MCAT9.2

80) What is the major organic product that results when 1-heptyne is treated with 2
equivalents of HBr?
A) 2,3-dibromo-1-heptene
B) 2,3-dibromo-2-heptene
C) 1,2-dibromoheptane
D) 2,2-dibromoheptane
E) 1,1-dibromoheptane
Answer: D
Diff: 2
Section: 9.9
LO: 9.5
MCAT LO: MCAT9.2
81) What class of organic product results when 1-heptyne is treated with a mixture of mercuric
acetate in aqueous sulfuric acid?
A) aldehyde
B) ketone
C) diol
D) ether
E) carboxylic acid
Answer: B
Diff: 2
Section: 9.9
LO: 9.5
MCAT LO: MCAT9.2

82) What class of organic product results when 1-heptyne is reacted with
disiamylborane followed by treatment with basic hydrogen peroxide?
A) aldehyde
B) ketone
C) diol
D) ether
E) carboxylic acid
Answer: A
Diff: 2
Section: 9.9
LO: 9.5
MCAT LO: MCAT9.2

83) What major organic product results when 1-octyne is treated with sodium metal in liquid
ammonia?
A) (E)-1-octene
B) (Z)-1-octene
C) 1-octene, you can't call it E or Z
D) 1-octyne
E) octane
Answer: C
Diff: 3
Section: 9.9
LO: 9.5
GO: G2
MCAT LO: MCAT9.2

84) Name the compound which results when pent-1-yne is treated with sodium in liquid
ammonia.
Answer: pent-1-ene
Diff: 2
Section: 9.9
LO: 9.5
MCAT LO: MCAT9.2
85) Provide the major organic product of the reaction shown below.

Answer:

Diff: 2
Section: 9.9
LO: 9.5
MCAT LO: MCAT9.2

86) Provide the major organic product of the reaction shown below.

Answer:

Diff: 2
Section: 9.9
LO: 9.5
MCAT LO: MCAT9.2
87) Provide the major organic product of the reaction shown below.

Answer:

Diff: 2
Section: 9.9
LO: 9.5
MCAT LO: MCAT9.2

88) Provide the major organic product of the reaction below.

Answer:

Diff: 2
Section: 9.9
LO: 9.5
MCAT LO: MCAT9.2

89) Provide the major organic product of the reaction below.

Answer: (CH3)2CHCH2CH2CH=CH2
Diff: 2
Section: 9.9
LO: 9.5
MCAT LO: MCAT9.2
90) Provide the major organic product of the reaction below.

Answer: (CH3)2CHCH2CH2CH2CHO
Diff: 2
Section: 9.9
LO: 9.5
MCAT LO: MCAT9.2

91) Provide the structure of the major organic product(s) in the reaction below.

Answer:

Diff: 2
Section: 9.9
LO: 9.5
MCAT LO: MCAT9.2

92) Provide the structure of the major organic product(s) in the reaction below.

Answer:

Diff: 2
Section: 9.9
LO: 9.5
MCAT LO: MCAT9.2
93) Provide the structure of the major organic product(s) in the reaction below.

Answer:

Diff: 2
Section: 9.9
LO: 9.5
MCAT LO: MCAT9.2

94) Provide the structure of the major organic product(s) in the reaction below.

Ph—C C—Ph →
Answer:

Diff: 2
Section: 9.9
LO: 9.5
MCAT LO: MCAT9.2

95) Provide the major organic product of the reaction shown below.

Answer:

Diff: 2
Section: 9.9
LO: 9.5
MCAT LO: MCAT9.2
96) Provide the major organic product of the reaction shown below.

Answer:

Diff: 2
Section: 9.9
LO: 9.5
MCAT LO: MCAT9.2

97) Provide the major organic product of the reaction shown below.

Answer:

Diff: 2
Section: 9.10
LO: 9.5
MCAT LO: MCAT9.2

98) Provide the major organic product of the reaction shown below.

Answer:

Diff: 2
Section: 9.10
LO: 9.5
MCAT LO: MCAT9.2
99) Provide the major organic product of the reaction shown below.

Answer:

Diff: 2
Section: 9.10
LO: 9.5
MCAT LO: MCAT9.2

100) Provide the major organic product of the reaction shown below.

Answer:

Diff: 2
Section: 9.9
LO: 9.5
MCAT LO: MCAT9.2

101) Provide the major organic product of the reaction shown below.

Answer:

Diff: 2
Section: 9.9
LO: 9.5
MCAT LO: MCAT9.2
102) Provide the major organic product of the reaction shown below.

Answer:

Diff: 2
Section: 9.9
LO: 9.4, 9.5
GO: G2
MCAT LO: MCAT9.2

103) Describe a sequence of reactions by which racemic 2,3-dibromobutane can be

straightforwardly prepared from propyne.
Answer:
1) NaNH2
2) CH3I
3) H2, Lindlar's catalyst
4) Br2,
CCl4 Diff: 2
Section: 9.9
LO: 9.6
GO: G2

104) Describe a sequence of reactions by which hexan-2-ol can be straightforwardly prepared

from hex-1-yne.
Answer:
1) HgSO4, H2O, H2SO4
2) NaBH4
Diff: 2
Section: 9.9
LO: 9.6
GO: G2
105) What is the major product of the following acid/catalyzed hydration reaction?

A)

B)

C)

D)

E)

Answer: C
Diff: 3
Section: 9.9
LO: 9.5
MCAT LO: MCAT9.2
106) Complete the following reaction sequences below by filling-in the missing reagents
or structures.

Answer:

Diff: 3
Section: 9.9
LO: 9.4, 9.5
GO: G7
MCAT LO: MCAT9.2

107) Provide the structure of the major organic product(s) in the reaction below.

Answer:

Diff: 3
Section: 9.9
LO: 9.5
MCAT LO: MCAT9.2

108) Provide the structure of the major organic product(s) in the reaction sequence below.

Answer:

Diff: 3
Section: 9.9
LO: 9.5
MCAT LO: MCAT9.2
109) In the reduction of alkynes using sodium in liquid ammonia, which of the species below
is not thought to be an intermediate in the commonly accepted mechanism?
A) vinyl anion
B) vinyl radical
C) radical anion
D) vinyl cation
Answer: D
Diff: 3
Section: 9.9
LO: 9.3

110) In the addition of hydrogen bromide to alkynes in the absence of peroxides, which of
the following species is thought to be an intermediate?
A) vinyl anion
B) vinyl cation
C) vinyl radical
D) carbene
E) none of the above
Answer: B
Diff: 3
Section: 9.9
LO: 9.3
111) Complete the transformation below by indicating the necessary sequence of reagents.

A) 1) DBr 2) BD3 3) H2O2 / NaOH

B) 1) D2 / Pd, BaSO4, quinoline 2) Br2 / H2O
C) 1) Na / ND3 2) Br23) H2O
D) 1) Na / ND3 2) Br2 / H2O
E) 1) Br2 / H2O 2) D2 / Pd, BaSO4, quinoline
Answer: B
Diff: 3
Section: 9.9
LO: 9.6
GO: G2

112) Complete the synthesis below by providing all necessary reagents and show all
intermediate structures.

Answer:
1) NaNH2, 2) bromoethane, 3) Na / NH3
Diff: 3
Section: 9.9
LO: 9.6

113) Describe a sequence of reactions by which meso-2,3-dibromobutane can be

straightforwardly prepared from propyne.
Answer:
1) NaNH2
2) CH3Br
3) Na, NH3
4) Br2,
CCl4 Diff: 3
Section: 9.9
LO: 9.6
114) Describe a sequence of reactions by which meso-hexane-3,4-diol can be straightforwardly
prepared from hex-3-yne.
Answer:
1) H2, Lindlar's catalyst
2) OsO4, H2O2 or cold, dilute KMnO4, -OH
or
1) Na, NH3
2) PhCO3H
3) H3O+ or -
OH Diff: 3
Section: 9.9
LO: 9.6

115) Describe a sequence of reactions by which (Z)-hex-3-en-1-ol can be straightforwardly

prepared from but-1-yne.
Answer:
1) NaNH2
2) ethylene oxide (oxirane)
3) H+, H2O
4) H2, Lindlar's
catalyst Diff: 3
Section: 9.9
LO: 9.6

116) Describe a sequence of reactions by which the compound shown below can be
straightforwardly prepared from acetylene.

Answer:
1) NaNH2
2) CH3I
3) NaNH2
4) CH3I
5) Na, NH3
6) PhCO3H
Diff: 3
Section: 9.9
LO: 9.6
GO: G2
117) Complete the following reaction by filling in the necessary reagents.

Answer:
1) NaNH2, 2) n-PrBr, 3) H2 / Lindlar's cat., 4) Br2
Diff: 3
Section: 9.9
LO: 9.6
GO: G2

118) Which of the following reagents should be used to convert an internal alkyne to an

A) KMnO4, H2O, neutral

B) O3 then H2O
C) Sia2BH then H2O2
D) Na, NH3
E) HgSO4, H2SO4
Answer: A
Diff: 2
Section: 9.10
LO: 9.6
GO: G2

119) What two organic compounds result when 3-heptyne is heated in basic aqueous KMnO4?
Answer: CH3CH2CO2- and CH3CH2CH2CO2-
Diff: 2
Section: 9.10
LO: 9.5
MCAT LO: MCAT9.2

120) What two organic compounds result when 3-heptyne is treated with ozone followed by
hydrolysis?
Answer: CH3CH2CO2H and CH3CH2CH2CO2H
Diff: 2
Section: 9.10
LO: 9.5
MCAT LO: MCAT9.2
121) Provide the structure of the major organic product(s) in the reaction below.

CH3CH2CH2CH2CH2—C C—CH2CH3 →
Answer: CH3CH2CH2CH2CH2CO2H + CH3CH2CO2H
Diff: 2
Section: 9.10
LO: 9.5
MCAT LO: MCAT9.2

122) Draw the products which result when oct-3-yne is heated in basic potassium permanganate
solution.
Answer: CH3CH2CO2- K+ + CH3CH2CH2CH2CO2- K+
Diff: 2
Section: 9.10
LO: 9.5
MCAT LO: MCAT9.2

123) Describe a sequence of reactions by which CH3CH2CH2COCH2CH3 can be

straightforwardly prepared from but-1-yne.
Answer:
1) NaNH2
2) CH3CH2Br
3) HgSO4, H2O, H2SO4
Diff: 2
Section: 9.10
LO: 9.6

124) Predict the necessary starting material for the reaction below.

Answer: 3-methyl-2-hepten-5-yne
Diff: 3
Section: 9.10
LO: 9.6
125) Provide the structure of the major organic product(s) in the reaction below.

Answer:

Diff: 3
Section: 9.10
LO: 9.5
MCAT LO: MCAT9.2

126) An unknown alkyne with a molecular formula of C7H12 give the following products upon
ozonolysis. What is the structure of the starting material?

A) CH3CH2CH2C CCH2CH3
B) (CH3)2CHC CCH2(CH3)2
C) (CH3)2CHC CCH2CH3
D) CH3CH2C
CCH2CH3 Answer: C
Diff: 3
Section: 9.10
LO: 9.7
GO: G2
127) An unknown alkyne with a molecular formula of C6H10 gives only one product
upon ozonolysis, which is shown below. What is the structure of the starting material?

A) CH3CH2C CCH2CH3
B) CH3CH2C CH
C) CH3CH2C CCH3
D) The structure can't be determined with the information
given. Answer: A
Diff: 3
Section: 9.10
LO: 9.7
GO: G2

128) Provide a mechanism for the reaction shown below.

Answer:
Diff: 3
Section: 9.9
LO: 9.3