Question 1

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 2

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 3

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

Accepted Answer

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

Question 4

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 5

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 6

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 7

How many products, including stereoisomers, are formed when 2-methylpent-2-ene is treated with HBr in presence of peroxides?

Accepted Answer

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

Question 8

Determine the product(s) of the following reaction.

Accepted Answer

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

Question 9

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

Accepted Answer

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

Question 10

Which of the following statements is (are) true about free radical halogenation of alkanes?

Accepted Answer

A) The first of the chain-propagating steps is rate-determining. 
B) The reaction proceeds by way of a flat sp2 hybridized free radical. 
C) The chain-initiating step involves cleavage of a carbon-hydrogen bond to afford a carbon radical and a hydrogen atom. 
D) Statements (The first of the chain-propagating steps is rate-determining) and (The reaction proceeds by way of a flat sp2 hybridized free radical) are both true. 
A) The first of the chain-propagating steps is rate-determining. 
B) The reaction proceeds by way of a flat sp2 hybridized free radical. 
C) The chain-initiating step involves cleavage of a carbon-hydrogen bond to afford a carbon radical and a hydrogen atom. 
D) Statements (The first of the chain-propagating steps is rate-determining) and (The reaction proceeds by way of a flat sp2 hybridized free radical) are both true.

Question 11

A possible reaction of ethane with chlorine is shown below.This reaction could conceivably occur by the following chain mechanisms [1], [2], and [3].Determine DH for step [1].    
Bond dissociation energies (kcal/mol):

Accepted Answer

A) -5 kcal/mol 
B) +58 kcal/mol 
C) -28 kcal/mol 
D) None of the choices are correct. 
A) -5 kcal/mol 
B) +58 kcal/mol 
C) -28 kcal/mol 
D) None of the choices are correct.

Question 12

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 13

How many monochlorination products, including stereoisomers, are formed from (S,S)-1,2-dimethylcyclopropane?

Accepted Answer

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

Question 14

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 15

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 16

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 17

How many products, including stereoisomers, are formed when (R)-2,4-dimethylpent-2-ene is treated with HBr in presence of peroxides?

Accepted Answer

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

Question 18

A possible reaction of ethane with chlorine is shown below.This reaction could conceivably occur by the following chain mechanisms [1], [2], and [3].Determine DH for step [2].Bond dissociation energies (kcal/mol):

Accepted Answer

A) -5 kcal/mol 
B) +58 kcal/mol 
C) -28 kcal/mol 
D) None of the choices are correct. 
A) -5 kcal/mol 
B) +58 kcal/mol 
C) -28 kcal/mol 
D) None of the choices are correct.

Question 19

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 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

Identify the monomer used to make the following polymer.

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

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

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

What is the product in the following sequence of reactions?

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) _______.

How many products, including stereoisomers, are formed when 2-methylpent-2-ene is treated with HBr in presence of peroxides?

Determine the product(s) of the following reaction.

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

Which of the following statements is (are) true about free radical halogenation of alkanes?

A possible reaction of ethane with chlorine is shown below.This reaction could conceivably occur by the following chain mechanisms [1], [2], and [3].Determine DH for step [1]. Bond dissociation energies (kcal/mol):

What is the product in the following sequence of reactions?

How many monochlorination products, including stereoisomers, are formed from (S,S)-1,2-dimethylcyclopropane?

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

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

Which of the following statements about radicals is true?

How many products, including stereoisomers, are formed when (R)-2,4-dimethylpent-2-ene is treated with HBr in presence of peroxides?

A possible reaction of ethane with chlorine is shown below.This reaction could conceivably occur by the following chain mechanisms [1], [2], and [3].Determine DH for step [2].Bond dissociation energies (kcal/mol):

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

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 Related Compounds

Alkenes

Alkynes

Oxidation and Reduction

Mass Spectrometry and Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Conjugation, Resonance, and Dienes

Benzene and Aromatic Compounds

Reactions of Aromatic Compounds

Carboxylic Acids and the Acidity of the O-H Bond

Introduction to Carbonyl Chemistry;

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

Synthetic Polymers

Lipids

Filters

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

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

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