Question 1

Which of the following alkenes undergoes allylic bromination to form a single monobrominated product?

Accepted Answer

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

Question 2

What is the product of the following reaction?

Accepted Answer

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

Question 3

How many monochlorination products can be formed (constitutional isomers only) from the reaction of CH3CH2CH2CH2CH2CH3 with Cl2 and hF1F1F1S1F1F1F10?

Accepted Answer

A)  3 
B)  4 
C)  5 
D)  6 
A)  3 
B)  4 
C)  5 
D)  6 A

Question 4

Which of the indicated hydrogens is most readily abstracted in a free radical halogenation reaction?

Accepted Answer

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

Question 5

A possible reaction of ethane with chlorine is shown below. $$\mathrm { CH } _ { 3 } \mathrm { CH } _ { 3 } + \mathrm { Cl } _ { 2 } \longrightarrow \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { Cl } + \mathrm { HCl }$$ This reaction could conceivably occur by the following chain mechanisms [1], [2], and [3]. The chain initiating step(s) is (are) _____. [1] $\mathrm { Cl } _ { 2 } \longrightarrow 2 \mathrm { Cl }^*$.
[2] $\mathrm { Cl } ^* + \mathrm { CH } _ { 3 } \mathrm { CH } _ { 3 } \stackrel { \text { slow } } { \longrightarrow } \mathrm { HCl } + \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 }^*$.
[3] $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } ^ { * } + \mathrm { Cl } _ { 2 } \stackrel { \text { fast } } { \longrightarrow } \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { Cl } + \mathrm { Cl }^*$.

Accepted Answer

A)  Only [1] 
B)  Only [2] 
C)  Only [3] 
D)  Only [1] and [2] 
A)  Only [1] 
B)  Only [2] 
C)  Only [3] 
D)  Only [1] and [2]

Question 6

Which of the following statements about bromination is true?

Accepted Answer

A)  The rate-determining step in bromination is exothermic. 
B)  Both radicals are formed. 
C)  A mixture of products results. 
D)  A single radical halogenation product predominates. 
A)  The rate-determining step in bromination is exothermic. 
B)  Both radicals are formed. 
C)  A mixture of products results. 
D)  A single radical halogenation product predominates.

Question 7

How many monochlorination products can be formed from the reaction of (CH3)3CH with Cl2 and hF1F1F1S1F1F1F10?

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4 
A)  1 
B)  2 
C)  3 
D)  4

Question 8

Which of the following statements about radical reactions is not true?

Accepted Answer

A)  Light or heat provides the energy needed for homolytic bond cleavage to form radicals. 
B)  Breaking the weak O-O bond of peroxides initiates radical reactions. 
C)  The diradical O2 removes radicals from a reaction mixture. 
D)  Radicals rearrange. 
A)  Light or heat provides the energy needed for homolytic bond cleavage to form radicals. 
B)  Breaking the weak O-O bond of peroxides initiates radical reactions. 
C)  The diradical O2 removes radicals from a reaction mixture. 
D)  Radicals rearrange.

Question 9

What is the product of the following reaction?

Accepted Answer

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

Question 10

What is the product in the following sequence of reactions?

Accepted Answer

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

Question 11

Which of the following compounds contain secondary (2°) radical carbons?

Accepted Answer

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

Question 12

Which of the following statements about chlorination is true?

Accepted Answer

A)  The rate-determining step in chlorination is endothermic. 
B)  The transition state resembles the product. 
C)  The more stable radical is formed faster. 
D)  A mixture of products results. 
A)  The rate-determining step in chlorination is endothermic. 
B)  The transition state resembles the product. 
C)  The more stable radical is formed faster. 
D)  A mixture of products results.

Question 13

Which of the following compounds contain tertiary (3°) radical carbons?

Accepted Answer

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

Question 14

Identify the monomer used to make the following polymer.

Accepted Answer

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

Question 15

Rank the following radicals in order of increasing stability, putting the least stable first.

Accepted Answer

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

Question 16

What type of reactive intermediate is formed in the reaction of propene with N-bromosuccinimide (NBS) to give 3-bromo-1-propene?

Accepted Answer

A)  Cyclic bromonium ion 
B)  Allylic carbocation 
C)  Allylic carbanion 
D)  Allylic radical 
A)  Cyclic bromonium ion 
B)  Allylic carbocation 
C)  Allylic carbanion 
D)  Allylic radical

Question 17

What is the product in the following sequence of reactions?

Accepted Answer

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

Question 18

Select the route that would most likely produce the desired results from the given starting material.   I. (1) H2SO4 and heat; (2) HBr II. (1) KOH in ethanol; (2) HBr
III) (1) H2SO4 and heat; (2) HBr + peroxides
IV) (1) potassium tert-butoxide in tert-butanol; (2) HBr + peroxides

Accepted Answer

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

Question 19

How many monochlorination products (constitutional isomers and stereoisomers) are formed from the reaction of butane with Cl2 and hF1F1F1S1F1F1F10?

Accepted Answer

A)  2 
B)  3 
C)  4 
D)  5 
A)  2 
B)  3 
C)  4 
D)  5

Question 20

How many allylic halides can be formed when 3-methycyclohexene undergoes allylic halogenation with one equivalent of NBS and light?

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4 
A)  1 
B)  2 
C)  3 
D)  4

Exam 15: Radical Reactions

Which of the following alkenes undergoes allylic bromination to form a single monobrominated product?

What is the product of the following reaction?

How many monochlorination products can be formed (constitutional isomers only) from the reaction of CH3CH2CH2CH2CH2CH3 with Cl2 and h?

Which of the indicated hydrogens is most readily abstracted in a free radical halogenation reaction?

Which of the following statements about bromination is true?

How many monochlorination products can be formed from the reaction of (CH3)3CH with Cl2 and h?

Which of the following statements about radical reactions is not true?

What is the product of the following reaction?

What is the product in the following sequence of reactions?

Which of the following compounds contain secondary (2°) radical carbons?

Which of the following statements about chlorination is true?

Which of the following compounds contain tertiary (3°) radical carbons?

Identify the monomer used to make the following polymer.

Rank the following radicals in order of increasing stability, putting the least stable first.

What type of reactive intermediate is formed in the reaction of propene with N-bromosuccinimide (NBS) to give 3-bromo-1-propene?

What is the product in the following sequence of reactions?

Select the route that would most likely produce the desired results from the given starting material. I. (1) H2SO4 and heat; (2) HBr II. (1) KOH in ethanol; (2) HBr III) (1) H2SO4 and heat; (2) HBr + peroxides IV) (1) potassium tert-butoxide in tert-butanol; (2) HBr + peroxides

How many monochlorination products (constitutional isomers and stereoisomers) are formed from the reaction of butane with Cl2 and h?

How many allylic halides can be formed when 3-methycyclohexene undergoes allylic halogenation with one equivalent of NBS and light?

Structure and Bonding

Acids and Bases

Introduction to Organic Molecules and Functional Groups

Alkanes

Stereochemistry

Understanding Organic Reactions

Alkyl Halides and Nucleophilic Substitution

Alkyl Halides and Elimination Reactions

Alcohols, Ethers and Epoxides

Alkenes

Alkynes

Oxidation and Reduction

Mass Spectrometry and Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Conjugation, Resonance, and Dienes

Benzene and Aromatic Compounds

Electrophilic Aromatic Substitution

Carboxylic Acids and the Acidity of the O-H Bond

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones Nucleophilic Addition

Carboxylic Acids and Derivatives

Substitution Reactions of Carbonyl Compounds at the Alpha-Carbon

Carbonyl Condensation Reactions

Amines

Carbon-Carbon Bond Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Lipids

Synthetic Polymers

Filters

How many monochlorination products can be formed (constitutional isomers only) from the reaction of CH₃CH₂CH₂CH₂CH₂CH₃ with Cl₂ and h?

How many monochlorination products can be formed from the reaction of (CH₃)₃CH with Cl₂ and h?

Select the route that would most likely produce the desired results from the given starting material. I. (1) H₂SO₄ and heat; (2) HBr II. (1) KOH in ethanol; (2) HBr III) (1) H₂SO₄ and heat; (2) HBr + peroxides IV) (1) potassium tert-butoxide in tert-butanol; (2) HBr + peroxides

How many monochlorination products (constitutional isomers and stereoisomers) are formed from the reaction of butane with Cl₂ and h?