Question 1

Which of the following are possible termination steps in the chlorination of methane?

Accepted Answer

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

Question 2

Use correct arrow formalism to show the second propagation step for the reaction of a chlorine radical with ozone.

Accepted Answer

The answer of Use correct arrow formalism to show the...

Question 3

Methylenecyclopentane (below) 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 4

Predict the major product of the following reaction:

Accepted Answer

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

Question 5

Use correct arrow formalism to show a homolytic bond cleavage of ethane to produce two methyl radicals.

Accepted Answer

The answer of Use correct arrow formalism to show a...

Question 6

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

Accepted Answer

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

Question 7

Which intermediate leads to the major product for the reaction of 2-methyl-2-butene with hydrogen bromide?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  None of the above 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  None of the above

Question 8

Compound A, C6H12 reacts with HBr/ROOR to give compound B, C6H13Br. Compound C, C6H14, reacts with bromine and light to produce compound B, C6H13Br. Suggest structures for compounds A, B, and C.

Accepted Answer

Question 9

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

Question 10

Which of the following is an example of initiation?

Accepted Answer

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

Question 11

Your textbook mentions that the free radical polymerization of ethylene can produce branches. Although branches of various lengths are possible, butyl branches are very common. Suggest an explanation for this fact.

Accepted Answer

As the chain grows, the motion of the en

Question 12

Propose an efficient sequence of reactions to accomplish the following transformation.

Accepted Answer

1. Br₂, light 2. pota

Question 13

Upon treatment with NBS and irradiation with UV light, 2-propyl-1-pentene produces exactly four monobrominated compounds (including stereoisomers). Draw and name the products of this reaction.

Accepted Answer

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

Question 14

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 15

Which intermediate leads to the major product for the reaction of 2-methyl-2-butene with hydrogen bromide and hydrogen peroxide?

Accepted Answer

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

Question 16

Which monomer is used for the synthesis of Teflon?

Accepted Answer

A)  1,1-difluoroethene 
B)  1,1,2,2-tetrafluoropropene 
C)  1,1,2,2-tetrafluoroethene 
D)  tetrafluoromethane 
A)  1,1-difluoroethene 
B)  1,1,2,2-tetrafluoropropene 
C)  1,1,2,2-tetrafluoroethene 
D)  tetrafluoromethane

Question 17

Predict the major product(s) of the reaction shown below:

Accepted Answer

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

Question 18

Which of the following is (are) the likely major product(s) of the reaction shown?

Accepted Answer

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

Question 19

Predict the major product(s) of the following reaction.

Accepted Answer

The answer of Predict the major product(s) of the following...

Question 20

A bromine radical can add to the  $\pi$ bond of 2-methylpropene. Use correct arrow formalism to show this process and the expected result.

Accepted Answer

@#IMG-DLM& Br adds to the least substitu

Exam 11: Radical Reactions

Which of the following are possible termination steps in the chlorination of methane?

Use correct arrow formalism to show the second propagation step for the reaction of a chlorine radical with ozone.

Predict the major product of the following reaction:

Use correct arrow formalism to show a homolytic bond cleavage of ethane to produce two methyl radicals.

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

Which intermediate leads to the major product for the reaction of 2-methyl-2-butene with hydrogen bromide?

Compound A, C6H12 reacts with HBr/ROOR to give compound B, C6H13Br. Compound C, C6H14, reacts with bromine and light to produce compound B, C6H13Br. Suggest structures for compounds A, B, and C.

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?

Which of the following is an example of initiation?

Your textbook mentions that the free radical polymerization of ethylene can produce branches. Although branches of various lengths are possible, butyl branches are very common. Suggest an explanation for this fact.

Propose an efficient sequence of reactions to accomplish the following transformation.

Upon treatment with NBS and irradiation with UV light, 2-propyl-1-pentene produces exactly four monobrominated compounds (including stereoisomers). Draw and name the products of this reaction.

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

Which intermediate leads to the major product for the reaction of 2-methyl-2-butene with hydrogen bromide and hydrogen peroxide?

Which monomer is used for the synthesis of Teflon?

Predict the major product(s) of the reaction shown below:

Which of the following is (are) the likely major product(s) of the reaction shown?

Predict the major product(s) of the following reaction.

A bromine radical can add to the π\piπ bond of 2-methylpropene. Use correct arrow formalism to show this process and the expected result.

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

Molecular Representations

Acids and Bases

Alkanes and Cycloalkanes

Stereoisomerism

Chemical Reactivity and Mechanisms

Substitution Reactions

Alkenes: Structure and Preparation Via 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

Carbohydrates

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

Compound A, C₆H₁₂ reacts with HBr/ROOR to give compound B, C₆H₁₃Br. Compound C, C₆H₁₄, reacts with bromine and light to produce compound B, C₆H₁₃Br. Suggest structures for compounds A, B, and C.

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?

A bromine radical can add to the $\pi$ bond of 2-methylpropene. Use correct arrow formalism to show this process and the expected result.