Question 1

For the reaction shown, which of the compounds listed 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 2

For the reaction below, which of the alkynes listed would be expected to produce the product under the conditions shown?

Accepted Answer

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

Question 3

Identify the final product for the following reaction.

Accepted Answer

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

Question 4

What is the major product of the reaction shown below?

Accepted Answer

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 
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

Question 5

What is the IUPAC name for the molecule shown below?

Accepted Answer

A)  5,6,6-trimethyl-1-heptyne 
B)  5-tert-butyl-1-hexyne 
C)  2,2,3-trimethyl-6-heptyne 
D)  2,2,3-(3-butynyl)butane 
E)  sec-butyl-tert-butylacetylene 
A)  5,6,6-trimethyl-1-heptyne 
B)  5-tert-butyl-1-hexyne 
C)  2,2,3-trimethyl-6-heptyne 
D)  2,2,3-(3-butynyl)butane 
E)  sec-butyl-tert-butylacetylene

Question 6

A dihalide in which the halogens are attached on adjacent carbons is called a _______________ dihalide.

Accepted Answer

A)  vicinal 
B)  geminal 
C)  vinylic 
D)  allylic 
E)  cis 
A)  vicinal 
B)  geminal 
C)  vinylic 
D)  allylic 
E)  cis

Question 7

What is the IUPAC name for the molecule shown below?

Accepted Answer

A)  6-bromo-3-octyne 
B)  6-bromo-6-methyl-3-heptyne 
C)  2-bromo-2-methyl-4-heptyne 
D)  6-bromo-6,6-dimethyl-3-hexyne 
E)  2-bromo-4-octyne 
A)  6-bromo-3-octyne 
B)  6-bromo-6-methyl-3-heptyne 
C)  2-bromo-2-methyl-4-heptyne 
D)  6-bromo-6,6-dimethyl-3-hexyne 
E)  2-bromo-4-octyne

Question 8

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 9

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 10

What is the expected major final product of the reaction sequence shown below?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  None of the shown products will be produced. 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  None of the shown products will be produced.

Question 11

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 12

Of the reaction conditions provided below, which would be expected to convert 1 mole of 4-methyl-1-pentyne into 2-methylpentane?

Accepted Answer

A)  H2, Lindlar's catalyst 
B)  Na, NH3(l) 
C)  2 moles of HCl 
D)  2 moles H2, Pt 
E)  1 mole H2, Pt 
A)  H2, Lindlar's catalyst 
B)  Na, NH3(l) 
C)  2 moles of HCl 
D)  2 moles H2, Pt 
E)  1 mole H2, Pt

Question 13

Rank the following carbanions in order of increasing base strength.

Accepted Answer

A)  I < II < III 
B)  II < III < I 
C)  III < II < I 
D)  III < I < II 
E)  II < I < III 
A)  I < II < III 
B)  II < III < I 
C)  III < II < I 
D)  III < I < II 
E)  II < I < III

Question 14

For the reaction shown below, the resulting stereochemistry of the expected product is best described as:

Accepted Answer

A)  (R,
E)  
B)  (S,
E)  
C)  (R,Z) 
D)  (S,Z) 
E)  only (S) 
A)  (R,
E)  
B)  (S,
E)  
C)  (R,Z) 
D)  (S,Z) 
E)  only (S)

Question 15

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 16

Which statement below best explains why the Ka of acetylene is greater than that of ethylene?

Accepted Answer

A)  Acetylide anions are resonance stabilized. 
B)  The 4 $\pi$ electrons of the acetylide anion better stabilize a negative charge. 
C)  The electronegativity of sp carbons is greater than that of sp2 carbons. 
D)  The electronegativity of sp carbons is less than that of sp2 carbons. 
E)  Acetylene has only two hydrogen atoms while ethylene has four. 
A)  Acetylide anions are resonance stabilized. 
B)  The 4 $\pi$ electrons of the acetylide anion better stabilize a negative charge. 
C)  The electronegativity of sp carbons is greater than that of sp2 carbons. 
D)  The electronegativity of sp carbons is less than that of sp2 carbons. 
E)  Acetylene has only two hydrogen atoms while ethylene has four.

Question 17

What is the expected major final product of the reaction sequence 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 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

What is the IUPAC name for the molecule shown below?

Accepted Answer

A)  (
E) -4-isopropyloct-3-en-5-yne 
B)  (Z)-4-isopropyloct-3-en-5-yne 
C)  (
E) -5-isopropyloct-5-en-3-yne 
D)  (Z)-5-isopropyloct-5-en-3-yne 
E)  (
E) -4-(2-methylethyl)oct-3-en-5-yne 
A)  (
E) -4-isopropyloct-3-en-5-yne 
B)  (Z)-4-isopropyloct-3-en-5-yne 
C)  (
E) -5-isopropyloct-5-en-3-yne 
D)  (Z)-5-isopropyloct-5-en-3-yne 
E)  (
E) -4-(2-methylethyl)oct-3-en-5-yne

Question 20

Determine which compound will react with sodium in liquid ammonia to form trans-3-hexene.

Accepted Answer

A)  cis-3-hexene 
B)  trans-2-hexene 
C)  3-hexyne 
D)  2-hexyne 
E)  cis-2-hexene 
A)  cis-3-hexene 
B)  trans-2-hexene 
C)  3-hexyne 
D)  2-hexyne 
E)  cis-2-hexene

Exam 9: Alkynes

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

For the reaction below, which of the alkynes listed would be expected to produce the product under the conditions shown?

Identify the final product for the following reaction.

What is the major product of the reaction shown below?

What is the IUPAC name for the molecule shown below?

A dihalide in which the halogens are attached on adjacent carbons is called a _______________ dihalide.

What is the IUPAC name for the molecule shown below?

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

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

What is the expected major final product of the reaction sequence shown below?

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

Of the reaction conditions provided below, which would be expected to convert 1 mole of 4-methyl-1-pentyne into 2-methylpentane?

Rank the following carbanions in order of increasing base strength.

For the reaction shown below, the resulting stereochemistry of the expected product is best described as:

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

Which statement below best explains why the Ka of acetylene is greater than that of ethylene?

What is the expected major final product of the reaction sequence shown below?

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

What is the IUPAC name for the molecule shown below?

Determine which compound will react with sodium in liquid ammonia to form trans-3-hexene.

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

Which statement below best explains why the K_a of acetylene is greater than that of ethylene?