Question 1

Which mechanism accounts for the reaction of 4-bromotoluene with sodium amide to form a mixture of 3- and 4-aminotoluene?

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 B

Question 2

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 B

Question 3

What is the electrophile in the reaction of benzene with acetyl chloride, CH3COCl, and AlCl3?

Accepted Answer

A)  CH3CºO+ 
B)  CH3+ 
C)  CH3CO2- 
D)  benzene 
A)  CH3CºO+ 
B)  CH3+ 
C)  CH3CO2- 
D)  benzene A

Question 4

Which of the following undergoes the most rapid sulfonation upon treatment with fuming sulfuric acid?

Accepted Answer

A)  benzene 
B)  benzoic acid 
C)  benzonitrile 
D)  nitrobenzene 
A)  benzene 
B)  benzoic acid 
C)  benzonitrile 
D)  nitrobenzene

Question 5

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 6

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 7

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 8

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 9

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 10

Which of the following is the reactive intermediate in the nucleophilic substitution of 4-bromo-1-toluene with sodium amide?

Accepted Answer

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

Question 11

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

Accepted Answer

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

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

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 14

What type of intermediate is formed in the reaction between bromobenzene and sodium amide to give aniline?

Accepted Answer

A)  Meisenheimer complex 
B)  benzyne 
C)  cyclohexadienyl cation 
D)  benzyl radical 
A)  Meisenheimer complex 
B)  benzyne 
C)  cyclohexadienyl cation 
D)  benzyl radical

Question 15

Which of the following is the reactive intermediate formed in the electrophilic Friedel-Crafts acylation of toluene with CH3COCl and AlCl3?

Accepted Answer

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

Question 16

Provide the structure (a single resonance contributor) of the key intermediate in the following reaction.

Accepted Answer

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

Question 17

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 18

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

Accepted Answer

A)  COCH3 
B)  NH3 
C)  Br 
D)  CH2CH3 
A)  COCH3 
B)  NH3 
C)  Br 
D)  CH2CH3

Question 19

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 20

What type of intermediate is formed in the reaction between chlorobenzene and tert-butyl chloride and AlCl3 to give 4-chloro-1-tert-butylbenzene?

Accepted Answer

A)  Meisenheimer complex 
B)  benzyne 
C)  cyclohexadienyl cation 
D)  benzyl radical 
A)  Meisenheimer complex 
B)  benzyne 
C)  cyclohexadienyl cation 
D)  benzyl radical

Exam 22: Reactions of Benzene and Its Derivatives

Which mechanism accounts for the reaction of 4-bromotoluene with sodium amide to form a mixture of 3- and 4-aminotoluene?

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

What is the electrophile in the reaction of benzene with acetyl chloride, CH3COCl, and AlCl3?

Which of the following undergoes the most rapid sulfonation upon treatment with fuming sulfuric acid?

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

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

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

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

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

Which of the following is the reactive intermediate in the nucleophilic substitution of 4-bromo-1-toluene with sodium amide?

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

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

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

What type of intermediate is formed in the reaction between bromobenzene and sodium amide to give aniline?

Which of the following is the reactive intermediate formed in the electrophilic Friedel-Crafts acylation of toluene with CH3COCl and AlCl3?

Provide the structure (a single resonance contributor) of the key intermediate in the following reaction.

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

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

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

What type of intermediate is formed in the reaction between chlorobenzene and tert-butyl chloride and AlCl3 to give 4-chloro-1-tert-butylbenzene?

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

Filters

What is the electrophile in the reaction of benzene with acetyl chloride, CH₃COCl, and AlCl₃?

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

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

Which of the following is the reactive intermediate formed in the electrophilic Friedel-Crafts acylation of toluene with CH₃COCl and AlCl₃?

What type of intermediate is formed in the reaction between chlorobenzene and tert-butyl chloride and AlCl₃ to give 4-chloro-1-tert-butylbenzene?