Question 1

Which of the following statements about the stereochemistry of halogenation reactions is true?

Accepted Answer

A) An achiral starting material always gives an achiral product only. 
B) An achiral starting material always gives a racemic product only. 
C) The configuration at a stereogenic center of a product must change even if a reaction does not occur at a stereogenic center. 
D) An achiral starting material always gives either an achiral or a racemic product. 
A) An achiral starting material always gives an achiral product only. 
B) An achiral starting material always gives a racemic product only. 
C) The configuration at a stereogenic center of a product must change even if a reaction does not occur at a stereogenic center. 
D) An achiral starting material always gives either an achiral or a racemic product. D

Question 2

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 3

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 B

Question 4

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 5

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 6

Which of the following compounds contain primary (1°) 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 7

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 8

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 9

How many monochlorination products can be formed (constitutional isomers only) from the reaction of (CH3)2CHCH2CH3 with Cl2 and hn?

Accepted Answer

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

Question 10

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 11

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 12

Determine the monochlorination product(s).

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 13

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 14

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 initiating step(s) is (are) _____.

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 15

Determine 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 16

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 17

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 18

Which of the following statements about chlorination and bromination is true?

Accepted Answer

A) Bromination is unselective, yielding a mixture of products. 
B) Chlorination is often selective, yielding one major product. 
C) Chlorination is faster than bromination. 
D) Bromination is faster than chlorination. 
A) Bromination is unselective, yielding a mixture of products. 
B) Chlorination is often selective, yielding one major product. 
C) Chlorination is faster than bromination. 
D) Bromination is faster than chlorination.

Question 19

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

Accepted Answer

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

Question 20

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.

Exam 15: Radical Reactions

Which of the following statements about the stereochemistry of halogenation reactions is true?

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

Which of the following is a radical scavenger?

Which of the following statements about chlorination is true?

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

Which of the following compounds contain primary (1°) radical carbons?

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

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

How many monochlorination products can be formed (constitutional isomers only) from the reaction of (CH3)2CHCH2CH3 with Cl2 and hn?

Identify the monomer used to make the following polymer.

Identify the monomer used to make the following polymer.

Determine the monochlorination product(s).

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

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 initiating step(s) is (are) _____.

Determine the product of the following reaction.

Which of the following statements about bromination is true?

What is the product of the following reaction?

Which of the following statements about chlorination and bromination is true?

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

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

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 (CH₃)₂CHCH₂CH₃ with Cl₂ and hn?

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