Question 1

Which of the alkynes below, after undergoing an acid-catalyzed hydration, would be expected to produce two different ketones in nearly equivalent yields?

Accepted Answer

A)  1-hexyne 
B)  2-hexyne 
C)  3-hexyne 
D)  3-methyl-1-pentyne 
E)  4-methyl-1-pentyne 
A)  1-hexyne 
B)  2-hexyne 
C)  3-hexyne 
D)  3-methyl-1-pentyne 
E)  4-methyl-1-pentyne

Question 2

For the reaction shown, which of the compounds below would be the expected enol intermediate?

Accepted Answer

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

Question 3

Which of the reagents below, when reacting with a terminal alkyne, would be expected to produce a ketone as the final major organic product?

Accepted Answer

A)  I and II 
B)  II 
C)  III and IV 
D)  I, II and IV 
E)  I, III and IV 
A)  I and II 
B)  II 
C)  III and IV 
D)  I, II and IV 
E)  I, III and IV

Question 4

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?

Accepted Answer

A)  The above statement is false; terminal alkynes are not produced under the given conditions. 
B)  Sodium amide deprotonates the terminal alkyne, driving formation of the alkynide ion. 
C)  Only sodium amide is a strong enough base to deprotonate a carbon. 
D)  Terminal alkynes are more stable than the internal alkynes, and are always the favored product. 
E)  Steric hindrance favors preparation of the less substituted terminal alkyne. 
A)  The above statement is false; terminal alkynes are not produced under the given conditions. 
B)  Sodium amide deprotonates the terminal alkyne, driving formation of the alkynide ion. 
C)  Only sodium amide is a strong enough base to deprotonate a carbon. 
D)  Terminal alkynes are more stable than the internal alkynes, and are always the favored product. 
E)  Steric hindrance favors preparation of the less substituted terminal alkyne.

Question 5

Provide the IUPAC name for the following compound.

Accepted Answer

4-sec-buty

Question 6

Give the major product from the careful addition of 1 equivalent of Br2 to the alkyne shown below.

Accepted Answer

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

Question 7

What is the IUPAC name for the expected product of the reaction below?

Accepted Answer

A)  propyne 
B)  1-hexyne 
C)  2-hexyne 
D)  3-hexyne 
E)  (
E) -3-hexyne 
A)  propyne 
B)  1-hexyne 
C)  2-hexyne 
D)  3-hexyne 
E)  (
E) -3-hexyne

Question 8

For the reaction below, select the structure of 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 9

What is the IUPAC name for the molecule shown below?

Accepted Answer

A)  (
E) -5-methyl-5-hepten-1-yne 
B)  (Z)-5-methyl-5-hepten-1-yne 
C)  (
E) -3-methyl-2-hepten-6-yne 
D)  (Z)-3-methyl-2-hepten-6-yne 
E)  (
E) -2-butynyl-2-butene 
A)  (
E) -5-methyl-5-hepten-1-yne 
B)  (Z)-5-methyl-5-hepten-1-yne 
C)  (
E) -3-methyl-2-hepten-6-yne 
D)  (Z)-3-methyl-2-hepten-6-yne 
E)  (
E) -2-butynyl-2-butene

Question 10

Select the best reagent to convert 3-heptyne to trans-3-heptene?

Accepted Answer

A)  Na/NH3 
B)  1 eq. NaNH2, NH3 
C)  excess NaNH2, NH3 
D)  H2/Pt 
E)  H2/Lindlar's catalyst 
A)  Na/NH3 
B)  1 eq. NaNH2, NH3 
C)  excess NaNH2, NH3 
D)  H2/Pt 
E)  H2/Lindlar's catalyst

Question 11

What is the expected functional group produced when cyclodecyne is reacted with disiamylborane, followed with treatment of basic hydrogen peroxide?

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 12

What is the IUPAC name for the molecule shown below?

Accepted Answer

A)  (4R,5Z)-4-chlorohept-5-en-2-yne 
B)  (4S,5
E) -4-chlorohept-5-en-2-yne 
C)  (2E,4S)-4-chlorohept-2-en-5-yne 
D)  (2E,4R)-4-chlorohept-2-en-5-yne 
A)  (4R,5Z)-4-chlorohept-5-en-2-yne 
B)  (4S,5
E) -4-chlorohept-5-en-2-yne 
C)  (2E,4S)-4-chlorohept-2-en-5-yne 
D)  (2E,4R)-4-chlorohept-2-en-5-yne

Question 13

The major result of treating 1-butyne with 6M aqueous NaOH would be:

Accepted Answer

A)  the production of the sodium alkynide. 
B)  the production of an alkene. 
C)  the production of an alkane. 
D)  the production of an enol. 
E)  nothing, as the alkyne would not react to an appreciable extent. 
A)  the production of the sodium alkynide. 
B)  the production of an alkene. 
C)  the production of an alkane. 
D)  the production of an enol. 
E)  nothing, as the alkyne would not react to an appreciable extent.

Question 14

What is the IUPAC name for the expected final product of the reaction below?

Accepted Answer

A)  5-decyne 
B)  3-hexyne 
C)  1-octyne 
D)  3-octyne 
E)  5-octyne 
A)  5-decyne 
B)  3-hexyne 
C)  1-octyne 
D)  3-octyne 
E)  5-octyne

Question 15

Which of the compounds shown below would be the most likely product expected from the reaction scheme shown?

Accepted Answer

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

Question 16

Which of the ketones below could not be prepared by an acid-catalyzed hydration of an alkyne?

Accepted Answer

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

Question 17

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 18

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

Accepted Answer

A)  (R)-3-chlorohexane 
B)  (S)-3-chlorohexane 
C)  meso-3,4-dichlorohexane 
D)  (±)-3,4-dichlorohexane 
E)  2,3-dichloro-3-hexene 
A)  (R)-3-chlorohexane 
B)  (S)-3-chlorohexane 
C)  meso-3,4-dichlorohexane 
D)  (±)-3,4-dichlorohexane 
E)  2,3-dichloro-3-hexene

Question 19

Provide the IUPAC name for CH3C≡CC(CH3)2CH(CH2CH3)2.

Accepted Answer

5-ethyl-4,4-dimethyl

Question 20

Which of the circled hydrogen atoms is the least acidic?

Accepted Answer

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

Exam 9: Alkynes

Which of the alkynes below, after undergoing an acid-catalyzed hydration, would be expected to produce two different ketones in nearly equivalent yields?

For the reaction shown, which of the compounds below would be the expected enol intermediate?

Which of the reagents below, when reacting with a terminal alkyne, would be expected to produce a ketone as the final major organic product?

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?

Provide the IUPAC name for the following compound.

Give the major product from the careful addition of 1 equivalent of Br2 to the alkyne shown below.

What is the IUPAC name for the expected product of the reaction below?

For the reaction below, select the structure of the expected major organic product.

What is the IUPAC name for the molecule shown below?

Select the best reagent to convert 3-heptyne to trans-3-heptene?

What is the expected functional group produced when cyclodecyne is reacted with disiamylborane, followed with treatment of basic hydrogen peroxide?

What is the IUPAC name for the molecule shown below?

The major result of treating 1-butyne with 6M aqueous NaOH would be:

What is the IUPAC name for the expected final product of the reaction below?

Which of the compounds shown below would be the most likely product expected from the reaction scheme shown?

Which of the ketones below could not be prepared by an acid-catalyzed hydration of an alkyne?

Identify the major product.

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

Provide the IUPAC name for CH3C≡CC(CH3)2CH(CH2CH3)2.

Which of the circled hydrogen atoms is the least acidic?

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

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?

Give the major product from the careful addition of 1 equivalent of Br₂ to the alkyne shown below.

Provide the IUPAC name for CH₃C≡CC(CH₃)₂CH(CH₂CH₃)₂.