Question 1

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 2

Identify a limitation of the Friedel-Crafts alkylation of benzene.

Accepted Answer

A)  Acylium ion does not undergo rearrangement. 
B)  A benzene ring with electron-withdrawing groups can undergo alkylation under normal reaction conditions. 
C)  The alkylated products are less reactive than benzene. 
D)  Alkyl carbocation formed during a reaction can rearrange to a more stable carbocation. 
A)  Acylium ion does not undergo rearrangement. 
B)  A benzene ring with electron-withdrawing groups can undergo alkylation under normal reaction conditions. 
C)  The alkylated products are less reactive than benzene. 
D)  Alkyl carbocation formed during a reaction can rearrange to a more stable carbocation.

Question 3

What type of intermediate is formed upon treatment of 1-chloro-2,4-dinitrobenzene with sodium hydroxide to give 2,4-dinitrophenol?

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 4

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 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 is the reactive intermediate formed in the electrophilic bromination of toluene with Br2, FeBr3?

Accepted Answer

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

Question 7

Consider the reaction below to answer the following question(s).   Fill in the blank with the appropriate letter or response.
-The Lewis acid catalyst in the reaction is _____.

Accepted Answer

The answer of Consider the reaction below to answer the...

Question 8

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 9

Consider the reaction below to answer the following question(s).   Fill in the blank with the appropriate letter or response.
-This reaction proceeds _____ (faster or slower) than when benzene is used.

Accepted Answer

The answer of Consider the reaction below to answer the...

Question 10

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 11

The name of the expected product from the following reaction is ___________________.

Accepted Answer

4-ethyl-1,

Question 12

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

Accepted Answer

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

Question 13

What is the role of AlCl3 in Friedel Crafts acylations using acid chlorides?

Accepted Answer

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

Question 14

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 15

Which of the following cannot be prepared from benzene in two synthetic steps?

Accepted Answer

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

Question 16

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

Accepted Answer

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

Question 17

The product of the following reaction would be 2-nitrotoluene.

Accepted Answer

A) True 
 B)False

Question 18

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 19

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

Accepted Answer

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

Question 20

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

Exam 22: Reactions of Benzene and Its Derivatives

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

Identify a limitation of the Friedel-Crafts alkylation of benzene.

What type of intermediate is formed upon treatment of 1-chloro-2,4-dinitrobenzene with sodium hydroxide to give 2,4-dinitrophenol?

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?

Which of the following is the reactive intermediate formed in the electrophilic bromination of toluene with Br2, FeBr3?

Consider the reaction below to answer the following question(s). Fill in the blank with the appropriate letter or response. -The Lewis acid catalyst in the reaction is _____.

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

Consider the reaction below to answer the following question(s). Fill in the blank with the appropriate letter or response. -This reaction proceeds _____ (faster or slower) than when benzene is used.

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

The name of the expected product from the following reaction is ___________________.

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

What is the role of AlCl3 in Friedel Crafts acylations using acid chlorides?

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

Which of the following cannot be prepared from benzene in two synthetic steps?

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

The product of the following reaction would be 2-nitrotoluene.

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

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

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

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 is the reactive intermediate formed in the electrophilic bromination of toluene with Br₂, FeBr₃?

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

What is the role of AlCl₃ in Friedel Crafts acylations using acid chlorides?

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