Question 1

Which of the following statements about carbon radicals is not true?

Accepted Answer

A) Carbon radicals are classified as primary,secondary,tertiary,or quaternary. 
B) A carbon radical is sp2 hybridized. 
C) The geometry of a carbon radical is trigonal planar. 
D) The unhybridized p orbital in a carbon radical contains the unpaired electron. 
A) Carbon radicals are classified as primary,secondary,tertiary,or quaternary. 
B) A carbon radical is sp2 hybridized. 
C) The geometry of a carbon radical is trigonal planar. 
D) The unhybridized p orbital in a carbon radical contains the unpaired electron.

Question 2

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

Accepted Answer

A) Most radicals are unstable. 
B) A radical contains an atom that has an octet of electrons. 
C) Half-headed arrows are used to show the movement of lone electrons. 
D) A radical is formed by homolysis of a covalent bond. 
A) Most radicals are unstable. 
B) A radical contains an atom that has an octet of electrons. 
C) Half-headed arrows are used to show the movement of lone electrons. 
D) A radical is formed by homolysis of a covalent bond.

Question 3

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 4

Which steps are the rate-determining step in the mechanism of radical halogenation?

Accepted Answer

A) Initiation 
B) Propagation 
C) Termination 
D) Initiation and propagation 
A) Initiation 
B) Propagation 
C) Termination 
D) Initiation and propagation

Question 5

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 6

Which of the labeled hydrogens is most easily abstracted in a free radical bromination reaction?

Accepted Answer

A) Ha 
B) Hb 
C) Hc 
D) Hd 
A) Ha 
B) Hb 
C) Hc 
D) Hd

Question 7

A possible reaction of ethane with chlorine is shown below.   This reaction could conceivably occur by the following chain mechanisms [1],[2],and [3].The chain propagating step(s)is (are)________.

Accepted Answer

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

Question 8

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

Question 9

Rank the following radicals in order of decreasing stability,putting the most stable first.

Accepted Answer

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

Question 10

Which of the following statements about radicals is true?

Accepted Answer

A) Cleavage of a stronger bond forms the more stable radical. 
B) The stability of a radical increases as the number of alkyl groups bonded to the radical carbon decreases. 
C) The higher the bond dissociation energy for a C-H bond,the more stable the resulting carbon radical. 
D) Less stable radicals generally do not rearrange to more stable radicals. 
A) Cleavage of a stronger bond forms the more stable radical. 
B) The stability of a radical increases as the number of alkyl groups bonded to the radical carbon decreases. 
C) The higher the bond dissociation energy for a C-H bond,the more stable the resulting carbon radical. 
D) Less stable radicals generally do not rearrange to more stable radicals.

Question 11

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 12

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 13

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 14

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 15

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 16

Which of the following statements about the propagation steps in the chlorination of ethane is true?

Accepted Answer

A) Radical chlorination consists of two propagation steps. 
B) The energy diagram for the propagation steps has three energy barriers. 
C) The first of the propagation steps is rate-determining because its transition state is at lower energy. 
D) The second of the propagation steps is rate-determining because its transition state is at higher energy. 
A) Radical chlorination consists of two propagation steps. 
B) The energy diagram for the propagation steps has three energy barriers. 
C) The first of the propagation steps is rate-determining because its transition state is at lower energy. 
D) The second of the propagation steps is rate-determining because its transition state is at higher energy.

Question 17

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 18

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

Accepted Answer

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

Question 19

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 20

Which of the following is a radical scavenger?

Accepted Answer

A) O3 
B) O2 
C) Vitamin C 
D) CO2 
A) O3 
B) O2 
C) Vitamin C 
D) CO2

Exam 13: Radical Reactions

Which of the following statements about carbon radicals is not true?

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

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

Which steps are the rate-determining step in the mechanism of radical halogenation?

Identify the monomer used to make the following polymer.

Which of the labeled hydrogens is most easily abstracted in a free radical bromination reaction?

A possible reaction of ethane with chlorine is shown below. This reaction could conceivably occur by the following chain mechanisms [1],[2],and [3].The chain propagating step(s)is (are)________.

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

Rank the following radicals in order of decreasing stability,putting the most stable first.

Which of the following statements about radicals is true?

What is the product of the following reaction?

Which of the following statements about bromination is true?

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

Which of the following statements about chlorination is true?

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

Which of the following statements about the propagation steps in the chlorination of ethane is true?

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

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

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

Which of the following is a radical scavenger?

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 Related Compounds

Alkenes and Addition Reactions

Alkynes and Synthesis

Oxidation and Reduction

Conjugation, resonance, and Dienes

Benzene and Aromatic Compounds

Reactions of Aromatic Compounds

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones - Nucleophilic Addition

Carboxylic Acids and the Acidity of the O-H Bond

Carboxylic Acids and Their Derivatives - Nucleophilic Acyl Substitution

Substitution Reactions of Carbonyl Compounds at the a Carbon

Carbonyl Condensation Reactions

Amines

Carbon-Carbon Bond-Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Synthetic Polymers

Lipids

Molecular Ion Peaks and Fragmentation Patterns

Analyzing Molecular Motion and Infrared Spectroscopy

Organic Spectroscopy Concepts

Filters

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 can be formed from the reaction of (CH₃)₃CH with Cl₂ and hn?