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61. Select the best reagent to convert 3-heptyne to trans-3-heptene?
A) Na/NH3
B) 1 eq. NaNH2, NH3
C) xs NaNH2, NH3
D) H2/Pt
E) H2/Lindlar's catalyst
62. Select the reagent(s) expected to accomplish the transformation shown below.
CC
H3CH2C
CH2CH3
C CCH3CH2CH2CH3
?
H
H
A) H2, Pd
B) H2, Lindlar’s catalyst
C) Na, NH3(l)
D) A and B
E) B and C
63. Reaction of 3,4,5-trimethyl-4-hexen-1-yne with H2 and Pd/C will produce which of
the following compounds?
A) 2,3,4-Trimethylhexane
B) 3,4,5-Trimethylhexane
C) 2,3,4-Trimethyl-1-hexene
D) 3,4,5-Trimethyl-1-hexyne
E) 2,3,4-Trimethyl-5-hexyne2
64. Reaction of (3E,5Z)-3-methylhepta-3,5-dien-1-yne with H2 and Pd/C will produce
which of the compounds below?
A) 1-sec-Butylbutane
B) 2-Butylbutane2
C) 3-Methylheptane
D) 3-Methyl-1-heptyne
E) (3E,5Z)-3-Bethyl-1,3,5-heptatriene
65. Of the reaction conditions provided below, which would be expected to convert 1
mole of 4-methyl-1-pentyne into 2-methylpentane?
A) H2, Lindlar’s catalyst
B) Na, NH3(l)
C) 2 moles of HCl
D) 2 moles H2, Pt
E) 1 mole H2, Pt
66. Which reagents shown below would be expected to convert 2-pentyne to (Z)-2-
pentene?
A) H2, Pt
B) Na, NH3
C) H2, Lindlar's catalyst
D) Xs HCl
E) HgSO4, H2O
67. For the reaction shown below, what is the IUPAC name of the expected product?
?
Na
NH3(l)
A) 2-methylhexane
B) (Z)-2-methyl-4-hexene
C) (E)-2-methyl-4-hexene
D) (Z)-5-methyl-2-hexene
E) (E)-5-methyl-2-hexene
68. Select the reagent(s) expected to accomplish the transformation shown below.
C C
CH2CH3
H3CH2C
C CCH3CH2CH2CH3
?HH
A) H2, Ni
B) H2, Ni2B
C) H2, Lindlar’s catalyst
D) A and B
E) B and C
69. What is the expected major organic product from treatment of 4-methyl-2-pentyne
with excess hydrogen in the presence of a platinum catalyst?
A) (E)-4-methyl-2-pentene
B) (Z)-4-methyl-2-pentene
C) 2-methylpentane
D) 4-methylpentane
E) Equal mixture of A and B
70. What is the expected major organic product from treatment of 4-methyl-2-pentyne
with hydrogen in the presence of Lindlar's catalyst?
A) (E)-4-methyl-2-pentene
B) (Z)-4-methyl-2-pentene
C) (E)-2-methyl-2-pentene
D) (Z)-2-methyl-2-pentene
E) 2-methylpentane
71. What is the expected major organic product from treatment of 4-methyl-2-pentyne
with sodium metal in liquid ammonia?
A) (E)-4-methyl-2-pentene
B) (Z)-4-methyl-2-pentene
C) (E)-2-methyl-2-pentene
D) (Z)-2-methyl-2-pentene
E) 2-methylpentane
72. In the reaction between an alkyne and Na metal in liquid ammonia, Na’s role is as
the:
A) Brønsted acid.
B) Brønsted base.
C) reducing agent.
D) catalyst.
E) electrophile.
73. In a dissolving metal reduction of an alkyne, a postulated intermediate is the trans
alkenyl radical, shown below. In which orbital type would the unpaired electron be
located?
R
H R
A) sp
B) sp2
C) sp3
D) p
E) s
74. For the reaction shown below, the resulting stereochemistry of the expected
product is best described as:
H2
Pt
A) only (S)
B) only (R)
C) racemic
D) meso
E) achiral
75. Complete hydrogenation of a mixture of 1-octyne, 2-octyne, and 3-octyne, in the
presence of a palladium catalyst, would produce how many distinct eight-carbon
hydrocarbon products?
A) 1
B) 2
C) 3
D) 6
E) 8
76. For the reaction shown below, the resulting stereochemistry of the expected
product is best described as:
H2
Ni2B (P-2)
A) (R,E)
B) (S,E)
C) (R,Z)
D) (S,Z)
E) only (S)
77. Which of the compounds shown below would be the most likely product expected
from the reaction scheme shown?
xs HCl ?
Cl
CH3CH2C CH
Cl Cl Cl
Cl
I II III IV V
Cl
Cl
Cl
A) I
B) II
C) III
D) IV
E) V
78. The expected major product from treatment of 1-pentyne with excess HBr in the
presence of peroxides is:
A) 1-bromo-1-pentene
B) 2-bromo-1-pentene
C) 1,1-dibromopentane
D) 2,2-dibromopentane
E) 1,2-dibromopentane
79. The expected major product from the treatment of 1-pentyne with 1 equivalent of
HBr is:
A) 1-bromo-1-pentene
B) 2-bromo-1-pentene
C) 1,1-dibromopentane
D) 2,2-dibromopentane
E) 1,2-dibromopentane
80. The expected major product from the treatment of 1-pentyne with 2 equivalents of
HBr is:
A) 1-bromo-1-pentene
B) 2-bromo-1-pentene
C) 1,1-dibromopentane
D) 2,2-dibromopentane
E) 1,2-dibromopentane
81. For the reaction below, select the structure of the expected major organic product.
1 eq HCl
?
I II III IV V
Cl
Cl
Cl Cl
Cl
A) I
B) II
C) III
D) IV
E) V
82. What is the major expected product(s) of the reaction shown below?
C CCH3CH2CH3
HCl ?
A) 2,2-Dichloropentane
B) 3,3-Dichloropentane
C) 2,3-Dichloropentane
D) A and B
E) B and C
83. For the reaction shown, select the expected major organic product.
1) 1 eq HCl
2) 1 eq HBr
?
I II III IV V
Br
Cl
Cl
Br
Br
Cl Br
Cl
Br
Cl
Cl
Br
A) I
B) II
C) III
D) IV
E) V
84. Which of the compounds shown below would be the most likely product expected
from the reaction scheme shown?
HBr
ROOR ?
(CH3)2CHCH2C CH
Br
Br
Br
Br
Br Br
I II III IV
A) I and II
B) III and IV
C) II and III
D) II and IV
E) I and IV
85. Select the expected major product(s) from the treatment of 1-pentyne with
1 equivalent of HBr in the presence of peroxides.
A) 2-Bromo-1-pentene
B) (E)-1-Bromo-1-pentene
C) (Z)-1-Bromo-1-pentene
D) A and B
E) B and C
86. 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?
A) Formation of a more stable primary vinylic carbocation.
B) Formation of a more stable secondary vinylic carbocation.
C) Addition of the H atom to the carbon already with an H.
D) Addition of H, from HBr, to the least hindered carbon.
E) Steric hindrance for the approach of the Br atom to the primary carbon.
87. For the transformation shown, select the most appropriate reagent(s) to effect the
change.
?(CH3)2CHCH2CCH3
O
(CH3)2CHCH2C CH
A) H2SO4, HgSO4
B) 1. Disiamylborane, 2. HO–, H2O, H2O2
C) K2Cr2O7, H+
D) NaOCl
E) H2, Pd
88. For the transformation shown, select the most appropriate reagent(s) to effect the
change.
?(CH3)2CHCH2CH2CH
(CH3)2CHCH2C CH
O
A) H2SO4, HgSO4
B) 1. Disiamylborane, 2. HO–, H2O, H2O2
C) K2Cr2O7, H+
D) NaOCl
E) H2, Pd
89. For the reaction shown, which of the compounds below would be the expected
major, and final, organic product?
CH3CH2CH(CH3)C CH HgSO4
?
+H2OH2SO4
I II III IV V
O
OOH
OOH
A) I
B) II
C) III
D) IV
E) V
90. For the reaction shown, which of the compounds listed would be the expected
major, and final, organic product?
H2O, H2SO4
HgSO4
?
I II III IV V
O
O
O
OH
OH
A) I
B) II
C) III
D) IV
E) V
91. For the reaction shown, which of the compounds below would be the expected
major organic product?
H2O, H2SO4
HgSO4
OH OH
OH
OO
O
HO OH
I II III IV V
?
A) I
B) II
C) III
D) IV
E) V
92. For the reaction shown, which of the compounds below would be the expected
major, and final, organic product?
?
I II III IV V
O
O
O
OH
OH
1) BH3•THF
2) H2O2, NaOH
A) I
B) II
C) III
D) IV
E) V
93. For the reaction shown, which of the compounds below would be the expected
major, and final, organic product?
OH
III III IV V
?
O
OH O
OH
OH
1) BH3•THF
2) H2O2, NaOH
A) I
B) II
C) III
D) IV
E) V
94. For the reaction shown, which of the compounds listed would be the expected
major, and final, organic product?
?
I II III IV V
1) Disiamylborane
2) H2O2, NaOH
O
O
OH
OH OH
OH
A) I
B) II
C) III
D) IV
E) V
95. For the reaction shown, which of the compounds listed would be the expected
major, and final, organic product?
CH3CH2C(CH3)2C CH
I II III IV V
O
O OH
OOH
?
1) Disiamylborane
2) H2O2, NaOH
A) I
B) II
C) III
D) IV
E) V
96. For the reaction shown, which of the compounds listed would be the expected enol
intermediate?
H2O, H2SO4
HgSO4
OH
III III IV V
?
OH O
OH OH
OH
OH
A) I
B) II
C) III
D) IV
E) V
97. For the reaction shown, which of the compounds below would be the expected enol
intermediate?
OH
III III IV V
OH O
OH OH OH
OH
?
1) BH3•THF
2) H2O2, NaOH
A) I
B) II
C) III
D) IV
E) V
98. Which of the ketones below could not be prepared by an acid-catalyzed hydration
of an alkyne?
O OOO O
I II III IV V
A) I
B) II
C) III
D) IV
E) V
99. Consider the list of alkyne addition reactions below, and select all those that
involve an enol intermediate.
A) Hydroboration/oxidation
B) HgSO4 catalyzed hydration in dilute H2SO4
C) Hydrohalogenation
D) Both A and B
E) Both A and C
100. In an acid-catalyzed hydration, which of the following alkynes is expected to
produce a single ketone?
A) 2-decyne
B) 3-decyne
C) 4-decyne
D) 5-decyne
E) All of the above will give a single product
101. In an acid-catalyzed hydration, which of the following alkynes gives a single
ketone?
A) 2-pentyne
B) 2-hexyne
C) 2-heptyne
D) 3-hexyne
E) 3-heptyne
102. For the reaction below, how many different organic products would be expected?
H2O, H2SO4
HgSO4
?
A) one
B) two
C) three
D) four
E) five
103. Which of the following alkynes would give a single product under hydroboration-
oxidation conditions?
A) 1-hexyne
B) 2-hexyne
C) 3-hexyne
D) A and B would each give a single product
E) A and C would each give a single product
104. Which of the alkynes below, after undergoing an acid-catalyzed hydration, would
be expected to produce two different ketones in nearly equivalent yields?
A) 1-hexyne
B) 2-hexyne
C) 3-hexyne
D) 3-methyl-1-pentyne
E) 4-methyl-1-pentyne
105. For the reaction shown, which of the compounds listed below would be the
expected major, and final, organic product?
?
I II III IV V
1) 9-BBN
2) H2O2, NaOH
OO
OH
OH
OH
OH
A) I
B) II
C) III
D) IV
E) V
106. For the reaction below, which of the alkynes listed would be expected to produce
the product under the conditions shown?
I II III IV V
1) 9-BBN
2) H2O2, NaOH
?O
A) I
B) II
C) III
D) IV
E) V
107. What functional group would be expected to be found in the major, and final,
organic product upon completion of the reaction between 1-hexyne and a mixture
of mercuric sulfate and aqueous sulfuric acid?
A) aldehyde
B) ketone
C) diol
D) ether
E) carboxylic acid
108. What functional group would be expected to be found in the major, and final,
organic product upon completion of the reaction below.
?
1) 9-BBN
2) H2O2, NaOH
A) aldehyde
B) ketone
C) diol
D) enol
E) alkene
109. What is the expected functional group produced when cyclooctyne is reacted with
disiamylborane, followed with treatment of basic hydrogen peroxide?
A) aldehyde
B) ketone
C) diol
D) ether
E) carboxylic acid
110. Which of the reagents below, upon completion of reaction with a terminal alkyne,
would be expected to produce an aldehyde as the final major organic product?
1) Disiamylborane
2) H2O2, NaOH
1) 9-BBN
2) H2O2, NaOH
1) BH3•THF
2) H2O2, NaOH
H2O, H2SO4
HgSO4
III III IV
A) I and II
B) II and III
C) III and IV
D) I, II and IV
E) I, III and IV
111. What is the major product of the reaction shown below?
C CCH3CH2CH2CH3
excess Cl2?
CCl4
A) (E)-2,3-Dichloro-2-hexene
B) (Z)-2,3-Dichloro-2-hexene
C) 2,2-Dichlorohexane
D) 3,3-Dichlorohexane
E) 2,2,3,3-Tetrachlorohexane
112. Which of the compounds shown below would be the most likely product expected
from the reaction scheme shown?
xs Cl2?
Cl
CH3CH2C CH
Cl Cl Cl
Cl
I II III IV V
Cl
Cl
Cl
Cl
Cl Cl
Cl
A) I
B) II
C) III
D) IV
E) V
113. Careful addition of 1 equivalent of Br2 to the alkyne shown below would be
expected to produce which of the following as the major organic product?
1 eq Br2?
I II III IV V
Br
Br
Br
H
Br
Br
Br
Br
CCl4
HBr
Br Br Br Br
A) I
B) II
C) III
D) IV
E) V
