Question 1

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

Accepted Answer

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

Question 2

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 3

Draw all possible monochlorination products of 3,3-dimethylpentane, including stereoisomers.

Accepted Answer

The answer of Draw all possible monochlorination products of 3,3-dimethylpentane,...

Question 4

Predict the major product of the following reaction.

Accepted Answer

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

Question 5

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

Accepted Answer

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

Question 6

When 2-methyl-1-propene is exposed to NBS and UV light, only one major product is obtained. How many distinct resonances in the proton-decoupled 13C NMR spectrum are observed in the product?

Accepted Answer

Question 7

Which of the following is expected to be a major product for the reaction shown below?

Accepted Answer

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

Question 8

Which of the following is an example of initiation?

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 9

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

Question 10

Identify an example of propagation.

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 11

Which of the following correctly describes the nature of the transition state of the rate-determining step of the free-radical bromination of methane?

Accepted Answer

A)  the transition state resembles the reactants more than the products 
B)  the transition state resembles the products more than the reactants 
C)  the transition state equally resembles products and reactants 
A)  the transition state resembles the reactants more than the products 
B)  the transition state resembles the products more than the reactants 
C)  the transition state equally resembles products and reactants

Question 12

Identify the intermediate leads to the major product for the reaction of 2-methyl-2-butene with hydrogen bromide in the presence of peroxide.

Accepted Answer

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

Question 13

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 14

Azobisisobutyronitrile (AIBN) is commonly used as a radical initiator. Draw arrows to show this process.

Accepted Answer

The answer of Azobisisobutyronitrile (AIBN) is commonly used as a...

Question 15

Give the arrows to show the propagation steps for the following reaction.

Accepted Answer

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

Question 16

Identify the 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 17

Predict the product(s) of the following reaction.

Accepted Answer

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

Question 18

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

Question 19

Draw the arrows to show the propagation steps in the chlorination of propane to produce 2-chloropropane.

Accepted Answer

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

Question 20

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

Exam 10: Radical Reactions

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

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

Draw all possible monochlorination products of 3,3-dimethylpentane, including stereoisomers.

Predict the major product of the following reaction.

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

When 2-methyl-1-propene is exposed to NBS and UV light, only one major product is obtained. How many distinct resonances in the proton-decoupled 13C NMR spectrum are observed in the product?

Which of the following is expected to be a major product for the reaction shown below?

Which of the following is an example of initiation?

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

Identify an example of propagation.

Which of the following correctly describes the nature of the transition state of the rate-determining step of the free-radical bromination of methane?

Identify the intermediate leads to the major product for the reaction of 2-methyl-2-butene with hydrogen bromide in the presence of peroxide.

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

Azobisisobutyronitrile (AIBN) is commonly used as a radical initiator. Draw arrows to show this process.

Give the arrows to show the propagation steps for the following reaction.

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

Predict the product(s) of the following reaction.

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

Draw the arrows to show the propagation steps in the chlorination of propane to produce 2-chloropropane.

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

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

When 2-methyl-1-propene is exposed to NBS and UV light, only one major product is obtained. How many distinct resonances in the proton-decoupled ¹³C NMR spectrum are observed in the product?