Question 1

Draw the major product(s) of the following reaction. Is the product optically active? Explain.

Accepted Answer

@#IMG-DLM&_TB4454_00 The produ

Question 2

Which monomer is used for the synthesis of poly(vinyl chloride)?

Accepted Answer

A)  1-chloroethene 
B)  1-chloroethane 
C)  1,2-dichloroethene 
D)  1-chloro-1-propene 
A)  1-chloroethene 
B)  1-chloroethane 
C)  1,2-dichloroethene 
D)  1-chloro-1-propene

Question 3

Compound A has molecular formula C9H20. Compound A produces exactly three constitutional isomers upon monochlorination, and one major constitutional isomer upon monobromination. Which of the following are possible structures of compound A?

Accepted Answer

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

Question 4

Draw all of the reasonable resonance structures for the radical shown below.

Accepted Answer

The answer of Draw all of the reasonable resonance structures...

Question 5

Which of the following is the rate-determining step in the free-radical bromination of methane?

Accepted Answer

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

Question 6

Which of the following shows the initiation step of monochlorination of methane?

Accepted Answer

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

Question 7

Predict the major product obtained upon radical bromination of t-butylcyclohexane.

Accepted Answer

A)  1-bromo-1-tert-butylcyclohexane 
B)  2-bromo-1-tert-butylcyclohexane 
C)  3-bromo-1-tert-butylcyclohexane 
D)  4-bromo-1-tert-butylcyclohexane 
E)  1-bromo-1,1-dimethylethylcyclohexane 
A)  1-bromo-1-tert-butylcyclohexane 
B)  2-bromo-1-tert-butylcyclohexane 
C)  3-bromo-1-tert-butylcyclohexane 
D)  4-bromo-1-tert-butylcyclohexane 
E)  1-bromo-1,1-dimethylethylcyclohexane

Question 8

Give arrows to show a homolytic bond cleavage of ethane to produce two methyl radicals.

Accepted Answer

The answer of Give arrows to show a homolytic bond...

Question 9

Give the arrows to show the propagation steps for the autooxidation of diethyl ether.

Accepted Answer

The answer of Give the arrows to show the propagation...

Question 10

Propose a sequence of reactions to accomplish the following synthesis.

Accepted Answer

The answer of Propose a sequence of reactions to accomplish...

Question 11

Identify an example of initiation.

Accepted Answer

A)  homolytic cleavage 
B)  heterolytic cleavage 
C)  hydrogen abstraction 
D)  coupling 
E)  hydrogen addition 
A)  homolytic cleavage 
B)  heterolytic cleavage 
C)  hydrogen abstraction 
D)  coupling 
E)  hydrogen addition

Question 12

Which of the labeled C-H bonds is the weakest?

Accepted Answer

A)  C-Ha 
B)  C-Hb 
C)  C-Hc 
D)  C-Hd 
E)  C-He 
A)  C-Ha 
B)  C-Hb 
C)  C-Hc 
D)  C-Hd 
E)  C-He

Question 13

Which of the following is most reactive towards chlorination?

Accepted Answer

A)  methane 
B)  chloromethane 
C)  dichloromethane 
D)  chloroform 
E)  ethane 
A)  methane 
B)  chloromethane 
C)  dichloromethane 
D)  chloroform 
E)  ethane

Question 14

Draw arrows to show termination by coupling of two growing poly(vinyl chloride) chains.

Accepted Answer

The answer of Draw arrows to show termination by coupling...

Question 15

Which term most accurately describes the process shown below?

Accepted Answer

A)  coupling 
B)  hydrogen abstraction 
C)  halogen abstraction 
D)  homolytic cleavage 
E)  addition to a π bond 
A)  coupling 
B)  hydrogen abstraction 
C)  halogen abstraction 
D)  homolytic cleavage 
E)  addition to a π bond

Question 16

Methylenecyclopentane can be exposed to allylic bromination conditions to give multiple regioisomeric compounds, including Compound X. Compound X can then be hydrogenated to give Compound Y, which has only 4 distinct resonances in the proton-decoupled 13C NMR spectrum. What are the structures of compounds X and Y?

Accepted Answer

Question 17

Upon treatment with NBS and irradiation with UV light, 2-methyl-2-butene reacts to produce exactly six monobrominated compounds. Draw the products of this reaction.

Accepted Answer

The answer of Upon treatment with NBS and irradiation with...

Question 18

Which of the following would you expect to function as an initiator at the lowest temperature?

Accepted Answer

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

Question 19

Cyclic compound A has molecular formula C5H10 and undergoes monochlorination to yield exactly three different constitutional isomers. Identify compound A and show the monochlorination products.

Accepted Answer

Question 20

Poly(methyl methacrylate) (PMMA) is a light, shatter-resistant plastic prepared by the free-radical polymerization of methyl methacrylate (shown below). What is the repeat unit of PMMA?

Accepted Answer

A)   
B)   
C)   
D)   
A)   
B)   
C)   
D)

Exam 10: Radical Reactions

Draw the major product(s) of the following reaction. Is the product optically active? Explain.

Which monomer is used for the synthesis of poly(vinyl chloride)?

Compound A has molecular formula C9H20. Compound A produces exactly three constitutional isomers upon monochlorination, and one major constitutional isomer upon monobromination. Which of the following are possible structures of compound A?

Draw all of the reasonable resonance structures for the radical shown below.

Which of the following is the rate-determining step in the free-radical bromination of methane?

Which of the following shows the initiation step of monochlorination of methane?

Predict the major product obtained upon radical bromination of t-butylcyclohexane.

Give arrows to show a homolytic bond cleavage of ethane to produce two methyl radicals.

Give the arrows to show the propagation steps for the autooxidation of diethyl ether.

Propose a sequence of reactions to accomplish the following synthesis.

Identify an example of initiation.

Which of the labeled C-H bonds is the weakest?

Which of the following is most reactive towards chlorination?

Draw arrows to show termination by coupling of two growing poly(vinyl chloride) chains.

Which term most accurately describes the process shown below?

Upon treatment with NBS and irradiation with UV light, 2-methyl-2-butene reacts to produce exactly six monobrominated compounds. Draw the products of this reaction.

Which of the following would you expect to function as an initiator at the lowest temperature?

Cyclic compound A has molecular formula C5H10 and undergoes monochlorination to yield exactly three different constitutional isomers. Identify compound A and show the monochlorination products.

Poly(methyl methacrylate) (PMMA) is a light, shatter-resistant plastic prepared by the free-radical polymerization of methyl methacrylate (shown below). What is the repeat unit of PMMA?

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

Alkynes

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

Compound A has molecular formula C₉H₂₀. Compound A produces exactly three constitutional isomers upon monochlorination, and one major constitutional isomer upon monobromination. Which of the following are possible structures of compound A?

Cyclic compound A has molecular formula C₅H₁₀ and undergoes monochlorination to yield exactly three different constitutional isomers. Identify compound A and show the monochlorination products.