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- 1. Multiple Choice
When preparing terminal alkynes by an elimination reaction, sodium amide (NaNH2) dissolved in liquid ammonia (NH3) is used most frequently. Which of the following statements offers the best explanation for the above statement?
Sodium amide deprotonates the terminal alkyne, driving formation of the alkynide ion
Only sodium amide is a strong enough base to deprotonate a carbon.
The above statement is false; terminal alkynes are not produced under the given conditions.
Terminal alkynes are more stable than the internal alkynes, and are always the favored product.
Steric hindrance favors preparation of the less substituted terminal alkyne.
- 2. Multiple Choice
Consider the list of alkyne addition reactions below, and select all those that involve an enol intermediate.
Hydroboration/oxidation
HgSO4 catalyzed hydration in dilute H2SO4
Hydrohalogenation
Both Hydroboration/oxidation and HgSO4 catalyzed hydration in dilute H2SO4
Both Hydroboration/oxidation and Hydrohalogenation
- 3. Multiple Choice
Which of the following is the acceptable structure for (R)-5-bromohept-2-yne?
V
I
III
IV
II
- 4. Multiple Choice
Which of the following is the structure for 2-hexyne?
III
IV
II
I
- 5. Multiple Choice
Identify the expected major product from the treatment of 1-pentyne with 2 equivalents of HBr.
1,1-dibromopentane
2-bromo-1-pentene
2,2-dibromopentane
1,2-dibromopentane
1-bromo-1-pentene
- 6. Multiple Choice
Identify the final product for the following reaction.
I
V
III
II
IV
- 7. Multiple Choice
For the reaction shown, select the expected major organic product.
V
I
II
IV
III
- 8. Multiple Choice
Provide the IUPAC name for Cl3CCH2CH2CH2C≡CH.
5,5,5-trichloro-1-pentyne
1-heptyne
1,1,1-trichloro-5-hexyne
6,6,6-trichloro-1-hexyne
trichlorobutylacetylene
- 9. Multiple Choice
Why would the following reaction sequence not produce the expected product shown?
NaNH2 is used in the reduction of alkynes to trans alkenes.
Br is not a good enough leaving group.
The terminal alkyne is not acidic enough to be deprotonated.
The reaction sequence is correct and will produce the shown product.
The secondary alkyl halide would undergo an elimination reaction.
- 10. Multiple Choice
What is the major expected product(s) of the reaction shown below?
2,2-dichloropentane
3,3-dichloropentane
2,3-dichloropentane
2,2-dichloropentane and 3,3-dichloropentane
3,3-dichloropentane and 2,3-dichloropentane
- 11. Multiple Choice
What is the IUPAC name for the molecule shown below?
(E)-5-methyl-5-hepten-1-yne
(E)-3-methyl-2-hepten-6-yne
(Z)-3-methyl-2-hepten-6-yne
(E)-2-butynyl-2-butene
(Z)-5-methyl-5-hepten-1-yne
- 12. Multiple Choice
In an acid-catalyzed hydration, which of the following alkynes is expected to produce a single ketone?
2-decyne
3-decyne
4-decyne
5-decyne
All of the above will give a single product
- 13. Multiple Choice
Provide the IUPAC name for the alkyne expected to produce the two compounds listed below upon ozonolysis.
3-octyne
2,2-dimethyl-3-hexyne
1-tert-butyl-1-butyne
5,5-dimethyl-3-hexyne
3,3-dimethyl-2-hexyne
- 14. Multiple Choice
For the reaction below, select the structure of the major organic product.
III
IV
I
II
V
- 15. Multiple Choice
What is the IUPAC name for the molecule shown below?
3-bromo-4-propyl-5-hexyne
4-ethynyl-5-bromo-heptane
3-bromo-4-acetylenylheptane
4-bromo-3-propyl-1-hexyne
3-(1-bromopropyl)-1-hexyne
- 16. Multiple Choice
Which of the compounds shown below would be the most likely product expected from the reaction scheme shown?
IV
I
III
V
II
- 17. Multiple Choice
Provide the IUPAC name for BrCH2CH2C≡CCH2CH3.
6-bromo-4-hexyne
6-bromo-3-hexyne
1-bromo-3-hexyne
1-bromo-2-hexyne
1-bromo-4-hexyne
- 18. Multiple Choice
For the reaction shown below, the expected product will have a stereochemistry of ______.
achiral
racemic
only (S)
meso
only (R)
- 19. Multiple Choice
For the reaction shown, select the expected major organic product.
II
I
V
IV
III
- 20. Multiple Choice
Which sequence of reactions is expected to produce the product below as the final, and major, organic product?
A
B
E
D
C
- 21. Multiple Choice
What is the expected major product of the reaction sequence shown below?
IV
I
II
III
V
- 22. Multiple Choice
Identify the final product for the following reaction.
III
V
IV
I
II
- 23. Multiple Choice
For the reaction sequence below, select the expected major product.
3-methyl-1-hexyne
3-methylhexane
3-methyl-2-hexyne
2-bromo-3-methylhexene
1-bromo-3-methylhexene
- 24. Multiple Choice
Rank the following acids in order of decreasing acidity.
V > I > IV > II > III
V > I > III > II > IV
III > IV > II > I > V
I > IV > V > II > III
IV > I > V > II > III
- 25. Multiple Choice
What is the final major product expected for the following reaction sequence?
2,3-dibromo-3-hexene
(R)-3-bromohexane
meso-3,4-dibromohexane
(±)-3,4-dibromohexane
(S)-3-bromohexane
- 26. Multiple Choice
What is the expected major product of the reaction sequence shown below?
CH≡CH + (CH3)2CHC≡CH
(CH3)2CHCH2C≡CH
(CH3)2CHCHBrC≡CH
CH3CHCH2C≡CCH3
(CH3)2CHC≡CCH3
- 27. Multiple Choice
Provide the IUPAC name for HC≡CCH2CH2CH3.
2-butyne
butyne
1-butyne
pentyne
1-pentyne
- 28. Multiple Choice
Which of the alkyl bromides listed would work as a reagent in step 2 of the reaction sequence shown, with the resulting major product being an internal alkyne?
III, IV, V
I, II, IV
I and III
II, III, V
II and IV
- 29. Multiple Choice
Which of the following is the structure for 3-sec-butyl-1-heptyne?
IV
I
II
V
III
- 30. Multiple Choice
Which of the following is the structure for 2,5,5-trimethylhept-3-yne?
CH3CH2CH(CH3)C≡CCH2CH(CH3)2
CH3CH2C(CH3)2C≡CCH(CH3)2
CH3CH2CH2CH(CH3)C≡CC(CH3)3
(CH3CH2)2C(CH3)C≡CCH2CH3
CH3CH2C(CH3)2C≡CC(CH3)3
- 31. Multiple Choice
Identify the best reagent(s) for this reaction.
NaOCl
H2SO4, HgSO4, H2O
K2Cr2O7, H+
H2, Pd
1. Disiamylborane, 2. HO-, H2O2
- 32. Multiple Choice
Reaction of 3,4,5-trimethyl-4-hexen-1-yne with H2 and Pd/C will produce which of the following compounds?
2,3,4-trimethyl-5-hexyne2
3,4,5-trimethyl-1-hexyne
2,3,4-trimethyl-1-hexene
3,4,5-trimethylhexane
2,3,4-trimethylhexane
- 33. Multiple Choice
A dihalide in which the halogens are attached on the same carbon is called a ________ dihalide.
vicinal
vinylic
cis
allylic
geminal
- 34. Multiple Choice
Which of the alkynes below, after undergoing an acid-catalyzed hydration, would be expected to produce two different ketones in nearly equivalent yields?
1-hexyne
2-hexyne
4-methyl-1-pentyne
3-hexyne
3-methyl-1-pentyne
- 35. Multiple Choice
Which statement below best explains why the Ka of acetylene is greater than that of ethylene?
The electronegativity of sp carbons is greater than that of sp2 carbons.
The 4 π electrons of the acetylide anion better stabilize a negative charge.
Acetylide anions are resonance stabilized.
Acetylene has only two hydrogen atoms while ethylene has four.
The electronegativity of sp carbons is less than that of sp2 carbons.
- 36. Multiple Choice
What is the IUPAC name for diisobutylacetylene?
2,7-dimethyl-4-octyne
2,5-diethyl-3-hexyne
2,2,5,5-tetramethyl-3-hexyne
diisopropylbutyne
3,6-dimethyl-4-octyne
- 37. Multiple Choice
The sigma bond of an alkyne is formed from the overlap of which two orbitals?
sp3-sp3
p-p
sp-sp
sp2-sp2
s-s
- 38. Multiple Choice
What are the products of the reaction shown below?
CH3OC≡CH + Na+CH3-
CH3C≡CCH3 + Na+OH-
CH3C≡CH + CH3O-Na+
no reaction
CH3C≡COCH3 + Na+OH-
- 39. Multiple Choice
Identify the major product.
II
IV
I
III
V
- 40. Multiple Choice
What is the IUPAC name for the molecule shown below?
1,1-diethyl-2-pentyne
5-ethyl-3-octyne
5-ethyl-3-heptyne
3-(1-butynyl)pentane
3-ethyl-4-heptyne
- 41. Multiple Choice
Which sequence of reactions is expected to produce the product below as the final, and major, organic product?
I
V
IV
II
III
- 42. Multiple Choice
Rank the following carbanions in order of increasing base strength.
I < II < III
II < III < I
III < I < II
III < II < I
II < I < III
- 43. Multiple Choice
What is the IUPAC name for the molecule shown below?
5-tert-butyl-1-hexyne
5,6,6-trimethyl-1-heptyne
sec-butyl-tert-butylacetylene
2,2,3-(3-butynyl)butane
2,2,3-trimethyl-6-heptyne
- 44. Multiple Choice
Which of the following statements is true about propyne, H-C≡C-CH3?
The C≡C-C bond angle is 180°.
It contains a total of three pi bonds.
It contains a total of three sigma bonds.
All carbon-carbon bonds are of equal length.
The H-C≡C bond angle is about 109.5°.
- 45. Multiple Choice
What is the IUPAC name for the molecule shown below?
6-bromo-6,6-dimethyl-3-hexyne
6-bromo-3-octyne
6-bromo-6-methyl-3-heptyne
2-bromo-2-methyl-4-heptyne
2-bromo-4-octyne
- 46. Multiple Choice
For the reaction below, select the structure of the expected major organic product.
II
IV
III
I
V
- 47. Multiple Choice
Which sequence of reactions is expected to produce cis-3-octene as the final, and major, organic product?
V
IV
III
I
II
- 48. Multiple Choice
What is the IUPAC name for the molecule shown below?
(E)-5-isopropyloct-5-en-3-yne
(E)-4-isopropyloct-3-en-5-yne
(Z)-5-isopropyloct-5-en-3-yne
(E)-4-(2-methylethyl)oct-3-en-5-yne
(Z)-4-isopropyloct-3-en-5-yne
- 49. Multiple Choice
For the reaction shown, select the expected major organic product.
IV
III
I
V
II
- 50. Multiple Choice
Which of the compounds shown below would be the most likely product expected from the reaction scheme shown?
IV
I
V
II
III
- 51. Multiple Choice
Which sequence of reactions is expected to produce the product below as the final, and major, organic product?
B
E
A
D
C
- 52. Multiple Choice
Identify the functional group that would be expected to be found in the final product upon completion of the reaction between 1-hexyne and a mixture of mercuric sulfate and aqueous sulfuric acid.
diol
ketone
ether
carboxylic acid
aldehyde
- 53. Multiple Choice
In the reaction between an alkyne and Na metal in liquid ammonia, the role of Na is an a(n) ___________.
catalyst
Brønsted acid
reducing agent
electrophile
Brønsted base
- 54. Multiple Choice
Provide the IUPAC name for (CH3)2CHC≡CCH2C(CH3)3.
1,1,5,5,5-pentamethyl-2-pentyne
1,1,1,5,5-pentamethyl-3-pentyne
2,6,6-trimethyl-3-heptyne
2,2,6-trimethyl-4-heptyne
tert-butylisopropylacetylene
- 55. Multiple Choice
Identify the final product for the following reaction.
II
IV
III
I
V
- 56. Multiple Choice
What mechanistic intermediate is used to explain the preference for addition of the Br atom, of HBr, to the internal carbon of a terminal alkyne?
Formation of an intermediate with partial positive charge on a secondary carbon
Addition of H, from HBr, to the least hindered carbon.
Steric hindrance for the approach of the Br atom to the primary carbon.
Formation of an intermediate with partial positive charge on a primary carbon
Addition of the H atom to the carbon already with an H.
- 57. Multiple Choice
Of the reaction conditions provided below, which would be expected to convert 1 mole of 4-methyl-1-pentyne into 2-methylpentane?
H2, Lindlar's catalyst
2 moles of HCl
Na, NH3(I)
2 moles H2, Pt
1 mole H2, Pt
- 58. Multiple Choice
For the reaction shown below, the resulting stereochemistry of the expected product is best described as:
only (S)
(S,Z)
(S,E)
(R,Z)
(R,E)
- 59. Multiple Choice
Select the expected major product(s) from the treatment of 1-pentyne with 1 equivalent of Br2.
1,1-dibromo-1-pentene
(E)-1,2-dibromo-1-pentene
(Z)-1-bromo-1-pentene
1,1-dibromo-1-pentene and (E)-1,2-dibromo-1-pentene
(E)-1,2-dibromo-1-pentene and (Z)-1-bromo-1-pentene
- 60. Multiple Choice
Identify the final product for the following reaction.
I
V
III
II
IV
- 61. Multiple Choice
For the reaction below, which of the alkynes listed would be expected to produce the product under the conditions shown?
II
III
I
V
IV
- 62. Multiple Choice
Which of the following is the structure for (2E,4E)-octa-2,4-dien-6-yne?
V
II
IV
I
III
- 63. Multiple Choice
What is the final major product expected for the following reaction sequence?
2,3-dichloro-3-hexene
(±)-3,4-dichlorohexane
meso-3,4-dichlorohexane
(S)-3-chlorohexane
(R)-3-chlorohexane
- 64. Multiple Choice
What is the expected major final product of the reaction sequence shown below?
I
IV
None of the shown products will be produced
II
III
- 65. Multiple Choice
Which of the circled hydrogen atoms is the most acidic?
II
V
I
III
IV
- 66. Multiple Choice
Provide the IUPAC name for Cl3C(CH2)4C≡CH.
7,7,7-trichloro-1-heptyne
4,4,4-trichloro-1-butyne
6,6,6-trichloro-1-hexyne
1,1,1-trichloro-5-heptyne
1,1,1-trichloro-6-heptyne
- 67. Multiple Choice
What is the IUPAC name for the molecule shown below?
(2E,4R)-4-chlorohept-2-en-5-yne
(2E,4S)-4-chlorohept-2-en-5-yne
(4S,5E)-4-chlorohept-5-en-2-yne
(4R,5Z)-4-chlorohept-5-en-2-yne
- 68. Multiple Choice
Which reagents shown below would be expected to convert 2-pentyne to (Z)-2-pentene?
HgSO4, H2O
excess HCl
H2, Lindlar's catalyst
Na, NH3
H2, Pt
- 69. Multiple Choice
Which structure shown below represents (Z)-3,5-dichloro-3-hexen-1-yne?
IV
I and II are both correct
II
III
I
- 70. Multiple Choice
Which of the circled hydrogen atoms is the least acidic?
V
IV
I
III
II
- 71. Multiple Choice
Predict the major organic products of the reaction below.
I and II
II and IV
I and III
I and IV
II and III
- 72. Multiple Choice
A dihalide in which the halogens are attached on adjacent carbons is called a ______ dihalide.
Geminal
Vinylic
Vicinal
Allylic
Cis
- 73. Multiple Choice
For the reaction below, how many different organic products would be expected?
Three
One
Two
Four
Five
- 74. Multiple Choice
Which of the compounds shown below would be the most likely product expected from the reaction scheme shown?
I
IV
V
II
III
- 75. Multiple Choice
For 2-pentyne, which of the following describes the orbital overlap of the C2-C3 sigma bond?
sp3-sp3
p-p
sp3-sp
sp2-sp2
sp-sp
- 76. Multiple Choice
What is the IUPAC name for the expected product of the reaction below?
(E)-3-hexyne
1-hexyne
2-hexyne
3-hexyne
propyne
- 77. Multiple Choice
Which sequence of reactions is expected to produce the product below as the final, and major, organic product?
B
A
C
E
D
- 78. Multiple Choice
Select the reagent(s) expected to accomplish the reaction shown below.
H2, Pd
H2, Lindlar's catalyst
Na, NH3(l)
H2, Pd and H2, Lindlar's catalyst
H2, Lindlar's catalyst and Na, NH3(l)
- 79. Multiple Choice
What is the IUPAC name for the molecule shown below?
4-tert-butyl-2-pentyne
2,2,3-trimethyl-4-hexyne
4,5,5-trimethyl-2-hexyne
2,2-dimethyl-3-(1-propynyl)butane
4,5,5,5-tetramethyl-2-pentyne
- 80. Multiple Choice
Identify the product of the reaction of an alkyne with sodium and ammonia.
alkane
diene
cis alkene
trans alkene
alkyne
- 81. Multiple Choice
For the reaction shown, select the expected major organic product.
V
IV
II
III
I
- 82. Multiple Choice
Give the hybridization for the carbanion in the acetylide ion.
s2p2
sp3
sp
sp2
s2p
- 83. Multiple Choice
For the reaction shown below, select the expected major product.
II
V
I
III
IV
- 84. Multiple Choice
Which sequence of reagents would be expected to accomplish the synthesis of 1-butyne shown below?
C
E
B
A
D
- 85. Multiple Choice
Identify the final product for the following reaction.
III
IV
V
II
I
- 86. Multiple Choice
What is the IUPAC name for the molecule shown below?
5,5,5-trichloro-2-pentyne
1,1,1-trichloro-4-hexyne
6,6,6-trichloro-2-hexyne
4,4,4-trichloro-1-butyne
1,1,1-trichloro-2-butyne
- 87. Multiple Choice
What is the hybridization of the carbon atoms numbered 1 and 2 respectively in the following structure?
sp3, sp2
sp, sp
sp2, sp
sp, sp2
sp2, sp2
- 88. Multiple Choice
Determine which compound will react with sodium in liquid ammonia to form trans-3-hexene.
2-hexyne
cis-2-hexene
cis-3-hexene
trans-2-hexene
3-hexyne
- 89. Multiple Choice
What is the expected functional group produced when cyclodecyne is reacted with disiamylborane, followed with treatment of basic hydrogen peroxide?
aldehyde
ether
carboxylic acid
diol
ketone
- 90. Multiple Choice
Select the best explanation for why methanol, CH3OH, cannot be used as a solvent for the deprotonation of a terminal alkyne by sodium amide, NaNH2.
Methanol is more acidic than the alkyne and will be deprotonated instead.
Sodium amide is not a strong enough base to deprotonate the alkyne.
Sodium amide in methanol reduces alkynes to alkenes.
Methanol is toxic, and should be avoided when possible.
Methanol is a poor solvent for dissolving alkynes.
- 91. Multiple Choice
Identify the expected major product from the treatment of 1-pentyne with 1 equivalent of HBr.
2,2-dibromopentane
2-bromo-1-pentene
1,2-dibromopentane
1-bromo-1-pentene
1,1-dibromopentane
- 92. Multiple Choice
Sodium amide (NaNH2, sodamide) reacts with terminal alkynes as a ____.
Brønsted acid
Brønsted base
reducing agent
electrophile
catalyst
- 93. Multiple Choice
What is the IUPAC name for the molecule shown below?
5-ethyl-2-methyl-3-octyne
1-isopropyl-3-ethyl-1-hexyne
2-methyl-5-propyl-3-heptyne
6-methyl-3-propyl-4-heptyne
4-ethyl-7-methyl-5-octyne
- 94. Multiple Choice
For the reaction shown, select the expected major organic product.
II
I
IV
III
V
- 95. Multiple Choice
Which of the reagents below would convert 2-pentyne to trans-2-pentene?
NaNH2, NH3
H2, Lindlar's catalyst
H2, Pd/C
H2O, HgSO4/H2SO4
Na, NH3
- 96. Multiple Choice
How many distinct eight-carbon hydrocarbon products would be formed in the complete hydrogenation of a mixture of 1-octyne, 2-octyne, and 3-octyne, in the presence of a palladium catalyst?
2
3
6
8
1
- 97. Multiple Choice
For 2,4-hexadiyne, which of the following describes the orbital overlap of the C3-C4 sigma bond?
sp2-sp2
sp3-sp3
sp3-sp
sp-sp
p-p
- 98. Multiple Choice
How many moles of hydrogen are required for the complete reduction of 1 mole of (3E,5Z)-3-methylhepta-3,5-dien-1-yne?
5
4
2
3
1
- 99. Multiple Choice
The major result of treating 1-butyne with 6M aqueous NaOH would be:
nothing, as the alkyne would not react to an appreciable extent.
the production of an enol.
the production of an alkene.
the production of an alkane.
the production of the sodium alkynide.
- 100. Multiple Choice
Which of the following statements best describes the general reactivity of alkynes?
Alkynes fail to undergo electrophilic addition reactions, unlike alkenes.
An alkyne reacts as an electrophile and is therefore electron rich.
An alkyne reacts as a nucleophile and is therefore electron poor.
An alkyne reacts as an electrophile and is therefore electron poor.
An alkyne reacts as a nucleophile and is therefore electron rich.
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