Question 1

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 C 
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

Question 2

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

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)  V 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  V

Question 4

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

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  V 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  V

Question 5

Rank the following bases in order of decreasing basicity.

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 > V 
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 > V

Question 6

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

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
A)  I 
B)  II 
C)  III 
D)  IV

Question 7

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/H2SO4 
A)  NaNH2, NH3 
B)  Na, NH3 
C)  H2, Lindlar's catalyst 
D)  H2, Pd/C 
E)  H2O, HgSO4/H2SO4

Question 8

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-heptyne 
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-heptyne

Question 9

Identify the major product.

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  V 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  V

Question 10

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. 
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.

Question 11

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 12

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)  alkene 
A)  aldehyde 
B)  ketone 
C)  diol 
D)  enol 
E)  alkene

Question 13

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-dibromopentane 
A)  1-bromo-1-pentene 
B)  2-bromo-1-pentene 
C)  1,1-dibromopentane 
D)  2,2-dibromopentane 
E)  1,2-dibromopentane

Question 14

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)  8 
A)  1 
B)  2 
C)  3 
D)  6 
E)  8

Question 15

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. 
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.

Question 16

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-hexyne 
A)  3-methylhexane 
B)  1-bromo-3-methylhexene 
C)  2-bromo-3-methylhexene 
D)  3-methyl-1-hexyne 
E)  3-methyl-2-hexyne

Question 17

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 C 
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 C

Question 18

Describe the shape for acetylene.

Accepted Answer

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

Question 19

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

Accepted Answer

A)  BuLi 
B)  NH3 
C)  NaOH 
D)  NaOCH2CH3 
E)  t-BuOK 
A)  BuLi 
B)  NH3 
C)  NaOH 
D)  NaOCH2CH3 
E)  t-BuOK

Question 20

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

Exam 9: Alkynes

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

Provide the IUPAC name for BrCH2CH2C≡CCH2CH3.

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

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

Rank the following bases in order of decreasing basicity.

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

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

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

Identify the major product.

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.

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

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

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

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?

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

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

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

Describe the shape for acetylene.

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

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

A Review of General Chemistry: Electrons, Bonds, and Molecular Properties

Molecular Representations

Acids and Bases

Alkanes and Cycloalkanes

Stereoisomerism

Chemical Reactivity and Mechanisms

Alkyl Halides: Nucleophilic Substitution and Elimination Reactions

Addition Reactions of Alkenes

Radical Reactions

Synthesis

Alcohols and Phenols

Ethers and Epoxides; Thiols and Sulfides

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Conjugated Pi Systems and Pericyclic Reactions

Aromatic Compounds

Aromatic Substitution Reactions

Aldehydes and Ketones

Carboxylic Acids and Their Derivatives

Alpha Carbon Chemistry: Enols and Enolates

Amines

Introduction to Organometallic Compounds

Carbohydrates

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

Provide the IUPAC name for BrCH₂CH₂C≡CCH₂CH₃.

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

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.

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

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