Question 1

Which of the following chlorobenzenes does not undergo nucleophilic aromatic substitution upon treatment with NaNH2?

Accepted Answer

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

Question 2

Which of the following reactions or sequences will provide 1-propylbenzene as the major product?

Accepted Answer

A) treatment of benzene with isopropyl alcohol and HF 
B) treatment of benzene with propanoyl chloride and AlCl3; followed by reaction with Zn(Hg) and HCl 
C) treatment of benzene with 1-chloropropane and AlCl3 
D) treatment of benzene with 1-propene and HF 
A) treatment of benzene with isopropyl alcohol and HF 
B) treatment of benzene with propanoyl chloride and AlCl3; followed by reaction with Zn(Hg) and HCl 
C) treatment of benzene with 1-chloropropane and AlCl3 
D) treatment of benzene with 1-propene and HF

Question 3

What is the electrophile in the reaction of benzene with tert-butyl chloride and AlCl3?

Accepted Answer

A) CH3+ 
B) Cl+ 
C) (CH3)C+ 
D) benzene 
A) CH3+ 
B) Cl+ 
C) (CH3)C+ 
D) benzene

Question 4

The predominant intermediate in the electrophilic nitration of benzenesulfonic acid is shown below.

Accepted Answer

A) True 
 B)False

Question 5

What is the major organic product obtained from the following reaction?

Accepted Answer

The answer of What is the major organic product obtained...

Question 6

Which of the following substituents is ortho/para directing and deactivating in electrophilic aromatic substitution reactions?

Accepted Answer

A) OH 
B) Cl 
C) CH3 
D) NO2 
A) OH 
B) Cl 
C) CH3 
D) NO2

Question 7

What is the major organic product obtained from the following reaction (assume that mixtures of ortho and para disubstituted compounds can be separated; continue the synthesis with either one)?

Accepted Answer

@#IMG-DLM&_TB1813_00

Question 8

Which of the following compounds undergoes the most rapid nucleophilic substitution with hydroxide ion?

Accepted Answer

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

Question 9

The compound shown below is (nitromethyl)benzene. One would expect this compound to more reactive than toluene toward electrophilic substitution.

Accepted Answer

A) True 
 B)False

Question 10

Provide the structure (a single resonance contributor) of the key intermediate in the electrophilic aromatic nitration of chlorobenzene.

Accepted Answer

The answer of Provide the structure (a single resonance contributor)...

Question 11

Which of the following sets of substituents are all meta directing in electrophilic aromatic substitution reactions?

Accepted Answer

A) CH3, OH, Br 
B) Cl, NH2, CN 
C) COCH3, NO2, COOH 
D) NH2, COCH3, OH 
A) CH3, OH, Br 
B) Cl, NH2, CN 
C) COCH3, NO2, COOH 
D) NH2, COCH3, OH

Question 12

What is the major organic product obtained from the following reaction?

Accepted Answer

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

Question 13

Which of the following sets of substituents are all meta directing in electrophilic aromatic substitution reactions?

Accepted Answer

A) CN, NO2, COCH3 
B) CH3, OCH3, COCH3 
C) Cl, NH2, CH3 
D) CH3, NH3, OCH3 
A) CN, NO2, COCH3 
B) CH3, OCH3, COCH3 
C) Cl, NH2, CH3 
D) CH3, NH3, OCH3

Question 14

Which of the following sets of substituents are all ortho/para directing in electrophilic aromatic substitution reactions?

Accepted Answer

A) Br, CH3, NO2 
B) CH3, NH2, Br 
C) Cl, OCH3, COCH3 
D) NO2, COCH3, COOH 
A) Br, CH3, NO2 
B) CH3, NH2, Br 
C) Cl, OCH3, COCH3 
D) NO2, COCH3, COOH

Question 15

Which mechanism accounts for the reaction of chlorobenzene with acetyl chloride and AlCl3 to form 4-chloroacetophenone?

Accepted Answer

A) Bimolecular nucleophilic substitution (SN2) 
B) Nucleophilic aromatic substitution by elimination-addition 
C) Nucleophilic aromatic substitution by addition-elimination 
D) Electrophilic aromatic substitution 
A) Bimolecular nucleophilic substitution (SN2) 
B) Nucleophilic aromatic substitution by elimination-addition 
C) Nucleophilic aromatic substitution by addition-elimination 
D) Electrophilic aromatic substitution

Question 16

Which of the following is the structure of the complex of Br2 with FeBr3 involved in the electrophilic bromination of benzene?

Accepted Answer

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

Question 17

What is the role of FeBr3 in electrophilic aromatic bromination of benzene using Br2?

Accepted Answer

A) nucleophile 
B) electrophile 
C) Lewis acid 
D) base 
A) nucleophile 
B) electrophile 
C) Lewis acid 
D) base

Question 18

What is the major organic product obtained from the following reaction?

Accepted Answer

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

Question 19

What is the major organic product obtained from the following sequence of reactions?

Accepted Answer

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

Question 20

Which of the following sets of substituents are all activating groups in electrophilic aromatic substitution reactions?

Accepted Answer

A) Br, NH2, CH3 
B) CH3, NH2, OCH3 
C) OH, COCH3, CH3, 
D) Br, CN, NO2 
A) Br, NH2, CH3 
B) CH3, NH2, OCH3 
C) OH, COCH3, CH3, 
D) Br, CN, NO2

Exam 22: Reactions of Benzene and Its Derivatives

Which of the following chlorobenzenes does not undergo nucleophilic aromatic substitution upon treatment with NaNH2?

Which of the following reactions or sequences will provide 1-propylbenzene as the major product?

What is the electrophile in the reaction of benzene with tert-butyl chloride and AlCl3?

The predominant intermediate in the electrophilic nitration of benzenesulfonic acid is shown below.

What is the major organic product obtained from the following reaction?

Which of the following substituents is ortho/para directing and deactivating in electrophilic aromatic substitution reactions?

What is the major organic product obtained from the following reaction (assume that mixtures of ortho and para disubstituted compounds can be separated; continue the synthesis with either one)?

Which of the following compounds undergoes the most rapid nucleophilic substitution with hydroxide ion?

The compound shown below is (nitromethyl)benzene. One would expect this compound to more reactive than toluene toward electrophilic substitution.

Provide the structure (a single resonance contributor) of the key intermediate in the electrophilic aromatic nitration of chlorobenzene.

Which of the following sets of substituents are all meta directing in electrophilic aromatic substitution reactions?

What is the major organic product obtained from the following reaction?

Which of the following sets of substituents are all meta directing in electrophilic aromatic substitution reactions?

Which of the following sets of substituents are all ortho/para directing in electrophilic aromatic substitution reactions?

Which mechanism accounts for the reaction of chlorobenzene with acetyl chloride and AlCl3 to form 4-chloroacetophenone?

Which of the following is the structure of the complex of Br2 with FeBr3 involved in the electrophilic bromination of benzene?

What is the role of FeBr3 in electrophilic aromatic bromination of benzene using Br2?

What is the major organic product obtained from the following reaction?

What is the major organic product obtained from the following sequence of reactions?

Which of the following sets of substituents are all activating groups in electrophilic aromatic substitution reactions?

Covalent Bonding and Shapes of Molecules

Alkanes and Cycloalkanes

Stereoisomerism and Chirality

Acids and Bases

Alkenes: Bonding, Nomenclature, and Properties

Reactions of Alkenes

Alkynes

Haloalkanes, Halogenation, and Radical Reactions

Nucleophilic Substitution and Beta-Elimination

Alcohols

Ethers, Epoxides, and Sulfides

Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Mass Spectrometry

An Introduction to Organometallic Compounds

Aldehydes and Ketones

Carboxylic Acids

Functional Derivatives of Carboxylic Acids

Enolate Anions and Enamines

Dienes, Conjugated Systems, and Pericyclic Reactions

Benzene and the Concept of Aromaticity

Amines

Catalytic Carbon-Carbon Bond Formation

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids

Organic Polymer Chemistry

Filters

Which of the following chlorobenzenes does not undergo nucleophilic aromatic substitution upon treatment with NaNH₂?

What is the electrophile in the reaction of benzene with tert-butyl chloride and AlCl₃?

Which mechanism accounts for the reaction of chlorobenzene with acetyl chloride and AlCl₃ to form 4-chloroacetophenone?

Which of the following is the structure of the complex of Br₂ with FeBr₃ involved in the electrophilic bromination of benzene?

What is the role of FeBr₃ in electrophilic aromatic bromination of benzene using Br₂?