Question 1

Provide the IUPAC name for (CH3)2CHC≡CCH2C(CH3)3.

Accepted Answer

A)  1,1,5,5,5-pentamethyl-2-pentyne 
B)  1,1,1,5,5-pentamethyl-3-pentyne 
C)  2,2,6-trimethyl-4-heptyne 
D)  2,6,6-trimethyl-3-heptyne 
E)  tert-butylisopropylacetylene 
A)  1,1,5,5,5-pentamethyl-2-pentyne 
B)  1,1,1,5,5-pentamethyl-3-pentyne 
C)  2,2,6-trimethyl-4-heptyne 
D)  2,6,6-trimethyl-3-heptyne 
E)  tert-butylisopropylacetylene

Question 2

Which of the compounds listed would be one of the final major products for the following reaction sequence?

Accepted Answer

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

Question 3

Select the reagent(s) expected to accomplish the reaction shown below.

Accepted Answer

A)  H2, Ni 
B)  H2, Ni2B 
C)  Na, NH3(l) 
D)  A or B 
E)  B or C 
A)  H2, Ni 
B)  H2, Ni2B 
C)  Na, NH3(l) 
D)  A or B 
E)  B or C

Question 4

What is the major expected product(s) of the reaction shown below?

Accepted Answer

A)  2,2-dichloropentane 
B)  3,3-dichloropentane 
C)  2,3-dichloropentane 
D)  A and B 
E)  B and C 
A)  2,2-dichloropentane 
B)  3,3-dichloropentane 
C)  2,3-dichloropentane 
D)  A and B 
E)  B and C

Question 5

Which sequence of reagents would be expected to accomplish the synthesis shown?

Accepted Answer

A)  1. HBr; 2. 2 NaNH2 
B)  1. Br2, CCl4 2. 2 NaNH2 
C)  1. Br2, H2O; 2. NaNH2 
D)  1. HBr/ROOR; 2. excess NaNH2 
E)  1. Na, NH3(l) 
A)  1. HBr; 2. 2 NaNH2 
B)  1. Br2, CCl4 2. 2 NaNH2 
C)  1. Br2, H2O; 2. NaNH2 
D)  1. HBr/ROOR; 2. excess NaNH2 
E)  1. Na, NH3(l)

Question 6

Sodium amide (NaNH2, sodamide) reacts with terminal alkynes as a ____.

Accepted Answer

A)  Brønsted acid 
B)  Brønsted base 
C)  reducing agent 
D)  catalyst 
E)  electrophile 
A)  Brønsted acid 
B)  Brønsted base 
C)  reducing agent 
D)  catalyst 
E)  electrophile

Question 7

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.

Accepted Answer

A)  aldehyde 
B)  ketone 
C)  diol 
D)  ether 
E)  carboxylic acid 
A)  aldehyde 
B)  ketone 
C)  diol 
D)  ether 
E)  carboxylic acid

Question 8

Reaction of 3,4,5-trimethyl-4-hexen-1-yne with H2 and Pd/C will produce which of the following compounds?

Accepted Answer

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 
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

Question 9

Draw all constitutional isomers of the molecular formula C6H10 that are terminal alkynes.

Accepted Answer

Question 10

The C≡C bond of an alkyne is composed of which bond types?

Accepted Answer

A)  three anti-bonds 
B)  three σ bonds 
C)  two σ bonds and one π bond 
D)  one σ bond and two π bonds 
E)  three π bonds 
A)  three anti-bonds 
B)  three σ bonds 
C)  two σ bonds and one π bond 
D)  one σ bond and two π bonds 
E)  three π bonds

Question 11

Ozonolysis of one mole of the compound shown is expected to produce how many moles of CO2 upon completion of the reaction?

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4 
E)  8 
A)  1 
B)  2 
C)  3 
D)  4 
E)  8

Question 12

Provide the structure(s) of the expected major organic product(s) from the following reaction:

Accepted Answer

@#IMG-DLM&_TB4454_00

Question 13

Which of the following conditions effectively cleaves all three bonds of a carbon-carbon triple bond?

Accepted Answer

A)  HgSO4 and aqueous H2SO4 
B)  1. Disiamylborane 2. H2O2, NaOH 
C)  H2, Lindlar's catalyst 
D)  1. O3 2. H2O 
E)  Na, NH3(l) 
A)  HgSO4 and aqueous H2SO4 
B)  1. Disiamylborane 2. H2O2, NaOH 
C)  H2, Lindlar's catalyst 
D)  1. O3 2. H2O 
E)  Na, NH3(l)

Question 14

What is the expected major organic product from the treatment of 4-methyl-2-pentyne with sodium metal in liquid ammonia?

Accepted Answer

(E)-4-meth

Question 15

What is the IUPAC name for the molecule shown below?

Accepted Answer

A)  1,1-diethyl-2-pentyne 
B)  3-(1-butynyl)pentane 
C)  5-ethyl-3-octyne 
D)  3-ethyl-4-heptyne 
E)  5-ethyl-3-heptyne 
A)  1,1-diethyl-2-pentyne 
B)  3-(1-butynyl)pentane 
C)  5-ethyl-3-octyne 
D)  3-ethyl-4-heptyne 
E)  5-ethyl-3-heptyne

Question 16

In an acid-catalyzed hydration, which of the following alkynes gives a single ketone?

Accepted Answer

A)  2-pentyne 
B)  2-hexyne 
C)  2-heptyne 
D)  3-hexyne 
E)  3-heptyne 
A)  2-pentyne 
B)  2-hexyne 
C)  2-heptyne 
D)  3-hexyne 
E)  3-heptyne

Question 17

Provide the IUPAC name for CH3CH(CH3)C(CH3)2C≡CCH(CH3)2.

Accepted Answer

2,5,5,6-tetramethyl-

Question 18

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 19

For the reaction shown below, select the expected 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 20

Which structure shown below represents (Z)-3,5-dichloro-3-hexen-1-yne?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  I and II are both correct 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  I and II are both correct

Exam 9: Alkynes

Provide the IUPAC name for (CH3)2CHC≡CCH2C(CH3)3.

Which of the compounds listed would be one of the final major products for the following reaction sequence?

Select the reagent(s) expected to accomplish the reaction shown below.

What is the major expected product(s) of the reaction shown below?

Which sequence of reagents would be expected to accomplish the synthesis shown?

Sodium amide (NaNH2, sodamide) reacts with terminal alkynes as a ____.

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.

Reaction of 3,4,5-trimethyl-4-hexen-1-yne with H2 and Pd/C will produce which of the following compounds?

Draw all constitutional isomers of the molecular formula C6H10 that are terminal alkynes.

The C≡C bond of an alkyne is composed of which bond types?

Ozonolysis of one mole of the compound shown is expected to produce how many moles of CO2 upon completion of the reaction?

Provide the structure(s) of the expected major organic product(s) from the following reaction:

Which of the following conditions effectively cleaves all three bonds of a carbon-carbon triple bond?

What is the expected major organic product from the treatment of 4-methyl-2-pentyne with sodium metal in liquid ammonia?

What is the IUPAC name for the molecule shown below?

In an acid-catalyzed hydration, which of the following alkynes gives a single ketone?

Provide the IUPAC name for CH3CH(CH3)C(CH3)2C≡CCH(CH3)2.

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

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

Which structure shown below represents (Z)-3,5-dichloro-3-hexen-1-yne?

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 (CH₃)₂CHC≡CCH₂C(CH₃)₃.

Sodium amide (NaNH₂, sodamide) reacts with terminal alkynes as a ____.

Reaction of 3,4,5-trimethyl-4-hexen-1-yne with H₂and Pd/C will produce which of the following compounds?

Draw all constitutional isomers of the molecular formula C₆H₁₀ that are terminal alkynes.

Ozonolysis of one mole of the compound shown is expected to produce how many moles of CO₂ upon completion of the reaction?

Provide the IUPAC name for CH₃CH(CH₃)C(CH₃)₂C≡CCH(CH₃)₂.