Question 1

Which of the following are major products of the reaction shown?

Accepted Answer

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

Question 2

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 A

Question 3

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

Accepted Answer

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

Question 4

How many constitutional isomers are possible if propane is dichlorinated? Draw them.

Accepted Answer

The answer of How many constitutional isomers are possible if...

Question 5

Use correct arrow formalism to show the mechanism of the following radical process:

Accepted Answer

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

Question 6

In the molecule shown below, determine which of the highlighted C-H bonds (from a to e) is expected to have the lowest bond dissociation energy.

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 7

Which term most accurately describes the process shown below?

Accepted Answer

A)  hydrogen abstraction 
B)  halogen abstraction 
C)  homolytic cleavage 
D)  coupling 
E)  elimination 
A)  hydrogen abstraction 
B)  halogen abstraction 
C)  homolytic cleavage 
D)  coupling 
E)  elimination

Question 8

Propose an efficient synthesis of 3,4-dimethyl-2-pentanol using 2-methyl-2-butene and ethanol as your sources of carbon.

Accepted Answer

The answer of Propose an efficient synthesis of 3,4-dimethyl-2-pentanol using...

Question 9

Which of the following compounds would be expected to be least destructive to the ozone layer?

Accepted Answer

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

Question 10

Which of the following is expected to function as an antioxidant?

Accepted Answer

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

Question 11

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

Accepted Answer

@#IMG-DLM& The product is not

Question 12

Use correct arrow formalism to draw all of the reasonable resonance structures for the radical shown below.

Accepted Answer

The answer of Use correct arrow formalism to draw all...

Question 13

Propylene (propene) undergoes free radical polymerization with benzoyl peroxide, but does not produce very long chains. Provide a reasonable explanation for this result.

Accepted Answer

There are C-H bonds at allylic positions

Question 14

Which of the following represents a propagation step in the monochlorination of methylene chloride (CH2Cl2)?

Accepted Answer

A)    
B) Cl2 
C)    
D)    
A)    
B) Cl2 
C)    
D)

Question 15

Which term best describes the process shown below?

Accepted Answer

A)  neutralization 
B)  propagation 
C)  termination 
D)  initiation 
E)  elimination 
A)  neutralization 
B)  propagation 
C)  termination 
D)  initiation 
E)  elimination

Question 16

Free radical chlorination of ethane can produce higher halogenation products (dichlorinated, trichlorinated, etc…) in addition to chloroethane. How could the production of higher halogenated products be minimized?

Accepted Answer

A)  Use an excess of chlorine 
B)  Use an excess of ethane 
C)  Use equimolar chlorine and ethane 
D)  It is not possible to minimize the production of higher halogenated products 
A)  Use an excess of chlorine 
B)  Use an excess of ethane 
C)  Use equimolar chlorine and ethane 
D)  It is not possible to minimize the production of higher halogenated products

Question 17

Which of the following is the most stable radical?

Accepted Answer

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

Question 18

Upon treatment with NBS and irradiation with UV light, 1-ethyl-4-methylbenzene produces exactly three monobrominated compounds (including stereoisomers). Draw the products of this reaction.

Accepted Answer

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

Question 19

Rank the following radicals in order of decreasing stability (most stable to least stable).

Accepted Answer

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

Question 20

Which of the following processes is responsible for the fact that free radical bromination of methane is slower than free radical chlorination?

Accepted Answer

A)  initiation 
B)  hydrogen abstraction 
C)  halogen abstraction 
D)  termination 
E)  entropy 
A)  initiation 
B)  hydrogen abstraction 
C)  halogen abstraction 
D)  termination 
E)  entropy

Exam 11: Radical Reactions

Which of the following are major products of the reaction shown?

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

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

How many constitutional isomers are possible if propane is dichlorinated? Draw them.

Use correct arrow formalism to show the mechanism of the following radical process:

In the molecule shown below, determine which of the highlighted C-H bonds (from a to e) is expected to have the lowest bond dissociation energy.

Which term most accurately describes the process shown below?

Propose an efficient synthesis of 3,4-dimethyl-2-pentanol using 2-methyl-2-butene and ethanol as your sources of carbon.

Which of the following compounds would be expected to be least destructive to the ozone layer?

Which of the following is expected to function as an antioxidant?

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

Use correct arrow formalism to draw all of the reasonable resonance structures for the radical shown below.

Propylene (propene) undergoes free radical polymerization with benzoyl peroxide, but does not produce very long chains. Provide a reasonable explanation for this result.

Which of the following represents a propagation step in the monochlorination of methylene chloride (CH2Cl2)?

Which term best describes the process shown below?

Free radical chlorination of ethane can produce higher halogenation products (dichlorinated, trichlorinated, etc…) in addition to chloroethane. How could the production of higher halogenated products be minimized?

Which of the following is the most stable radical?

Upon treatment with NBS and irradiation with UV light, 1-ethyl-4-methylbenzene produces exactly three monobrominated compounds (including stereoisomers). Draw the products of this reaction.

Rank the following radicals in order of decreasing stability (most stable to least stable).

Which of the following processes is responsible for the fact that free radical bromination of methane is slower than free radical chlorination?

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

Which of the following represents a propagation step in the monochlorination of methylene chloride (CH₂Cl₂)?