Question 1

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?

Accepted Answer

A)   1
B)   2
C)   3
D)   6
E)   8F) C) and D)
G) B) and E)

Question 2

Provide the IUPAC name for Cl3C(CH2) 4C≡CH.

Accepted Answer

A)   4,4,4-trichloro-1-butyne
B)   1,1,1-trichloro-6-heptyne
C)   1,1,1-trichloro-5-heptyne
D)   6,6,6-trichloro-1-hexyne
E)   7,7,7-trichloro-1-heptyneF) A) and B)
G) B) and D)

Question 3

Which sequence of reactions is expected to produce cis-3-octene as the final, and major, organic product?

Accepted Answer

A)   I
B)   II
C)   III
D)   IV
E)   VF) B) and E)
G) All of the above

Question 4

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.

Accepted Answer

A)   Sodium amide is not a strong enough base to deprotonate the alkyne.
B)   Sodium amide in methanol reduces alkynes to alkenes.
C)   Methanol is a poor solvent for dissolving alkynes.
D)   Methanol is more acidic than the alkyne and will be deprotonated instead.
E)   Methanol is toxic, and should be avoided when possible.F) C) and E)
G) C) and D)

Question 5

Which of the bases below would quantitatively deprotonate a terminal alkyne?

Accepted Answer

A)   BuLi
B)   NH3
C)   NaOH
D)   NaOCH2CH3
E)   t-BuOKF) C) and D)
G) A) and E)

Question 6

Identify the functional group would be expected to be found in the final product in the reaction below.

Accepted Answer

A)   aldehyde
B)   ketone
C)   diol
D)   enol
E)   alkeneF) B) and C)
G) A) and C)

Question 7

Identify the major product.

Accepted Answer

A)   I
B)   II
C)   III
D)   IV
E)   VF) A) and E)
G) B) and C)

Question 8

Which of the following statements is true about propyne, H-C≡C-CH3?

Accepted Answer

A)   It contains a total of three sigma bonds.
B)   It contains a total of three pi bonds.
C)   The H-C≡C bond angle is about 109.5°.
D)   The C≡C-C bond angle is 180°.
E)   All carbon-carbon bonds are of equal length.F) C) and D)
G) A) and E)

Question 9

Which of the following is the structure for 2-hexyne?

Accepted Answer

A)   I
B)   II
C)   III
D)   IVE) B) and D)
F) C) and D)

Question 10

Rank the following bases in order of decreasing basicity.  I > V > II > IV B)  III > V > IV > I> II C)  V > I > III > II > IV D)  III > IV > II > V > I E)  IV > II > I > III > V" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   III > I > V > II > IV
B)   III > V > IV > I> II
C)   V > I > III > II > IV
D)   III > IV > II > V > I
E)   IV > II > I > III > VF) A) and E)
G) B) and D)

Question 11

For the reaction shown, select the expected major organic product.

Accepted Answer

A)   I
B)   II
C)   III
D)   IV
E)   VF) B) and E)
G) B) and C)

Question 12

Describe the shape for acetylene.

Accepted Answer

The answer of Describe the shape for acetylene....

Question 13

What is the final major product expected for the following reaction sequence?

Accepted Answer

The answer of What is the final major product expected...

Question 14

Select the expected major product(s)  from the treatment of 1-pentyne with 1 equivalent of HBr in the presence of peroxides.

Accepted Answer

A)   2-bromo-1-pentene
B)   (
E)  -1-bromo-1-pentene
C)   (Z) -1-bromo-1-pentene
D)   A and B
E)   B and CF) None of the above
G) A) and B)

Question 15

Which of the reagents below would convert 2-pentyne to trans-2-pentene?

Accepted Answer

A)   NaNH2, NH3
B)   Na, NH3
C)   H2, Lindlar's catalyst
D)   H2, Pd/C
E)   H2O, HgSO4/H2SO4F) A) and E)
G) None of the above

Question 16

Select the expected major product(s)  from the treatment of 1-pentyne with 1 equivalent of Br2.

Accepted Answer

A)   1,1-dibromo-1-pentene
B)   (
E)  -1,2-dibromo-1-pentene
C)   (Z) -1-bromo-1-pentene
D)   A and B
E)   B and CF) B) and C)
G) D) and E)

Question 17

Provide the IUPAC name for BrCH2CH2C≡CCH2CH3.

Accepted Answer

A)   1-bromo-3-hexyne
B)   6-bromo-3-hexyne
C)   1-bromo-2-hexyne
D)   6-bromo-4-hexyne
E)   1-bromo-4-hexyneF) A) and B)
G) A) and C)

Question 18

Of the species listed below, select those less basic than acetylide.

Accepted Answer

A)   BuLi
B)   NaNH2
C)   NaOCH3
D)   both A and C
E)   both B and CF) A) and D)
G) A) and C)

Question 19

Identify the expected major product from the treatment of 1-pentyne with 2 equivalents of HBr.

Accepted Answer

A)   1-bromo-1-pentene
B)   2-bromo-1-pentene
C)   1,1-dibromopentane
D)   2,2-dibromopentane
E)   1,2-dibromopentaneF) All of the above
G) C) and D)

Question 20

For the reaction sequence below, select the expected major product.

Accepted Answer

A)   3-methylhexane
B)   1-bromo-3-methylhexene
C)   2-bromo-3-methylhexene
D)   3-methyl-1-hexyne
E)   3-methyl-2-hexyneF) None of the above
G) C) and D)

Exam 9: Alkynes

Identify the expected major product from the treatment of 1-pentyne with 2 equivalents of HBr.

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Which of the reagents below would convert 2-pentyne to trans-2-pentene?

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Which of the following statements is true about propyne, H-C≡C-CH3?

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Identify the major product.

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Select the expected major product(s) from the treatment of 1-pentyne with 1 equivalent of Br2.

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Which of the bases below would quantitatively deprotonate a terminal alkyne?

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Which of the following is the structure for 2-hexyne?

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What is the final major product expected for the following reaction sequence?

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Which sequence of reactions is expected to produce cis-3-octene as the final, and major, organic product?

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Of the species listed below, select those less basic than acetylide.

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Provide the IUPAC name for BrCH2CH2C≡CCH2CH3.

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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?

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Rank the following bases in order of decreasing basicity.

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Identify the functional group would be expected to be found in the final product in the reaction below.

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For the reaction sequence below, select the expected major product.

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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.

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Select the expected major product(s) from the treatment of 1-pentyne with 1 equivalent of HBr in the presence of peroxides.

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Describe the shape for acetylene.

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For the reaction shown, select the expected major organic product.

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Provide the IUPAC name for Cl3C(CH2) 4C≡CH.

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Which of the following statements is true about propyne, H-C≡C-CH₃?

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Select the expected major product(s) from the treatment of 1-pentyne with 1 equivalent of Br₂.

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Provide the IUPAC name for BrCH₂CH₂C≡CCH₂CH₃.

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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.

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Provide the IUPAC name for Cl₃C(CH₂) ₄C≡CH.

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