Question 1

The electrophilic bromination or chlorination of benzene requires ______ along with the halogen.

Accepted Answer

A)  UV light 
B)  a Brønsted base 
C)  a Lewis base 
D)  a Lewis acid 
E)  none of these 
A)  UV light 
B)  a Brønsted base 
C)  a Lewis base 
D)  a Lewis acid 
E)  none of these

Question 2

Aryl and vinyl halides cannot be used in the Friedel-Crafts alkylation reaction, because they do not __________.

Accepted Answer

form stabl

Question 3

Which one of the following substituents will not direct the incoming group to the meta position during electrophilic aromatic substitution?

Accepted Answer

A)  -NO2 
B)  -C$\equiv$N 
C)  -OCH3 
D)  -COOH 
E)  all of these 
A)  -NO2 
B)  -C$\equiv$N 
C)  -OCH3 
D)  -COOH 
E)  all of these

Question 4

Give the preferred products from the nitration of bromobenzene.

Accepted Answer

The answer of Give the preferred products from the nitration...

Question 5

Identify the rate-determining step in the electrophilic aromatic substitution of benzene.

Accepted Answer

A)  Formation of an electrophile 
B)  Formation of a sigma complex. 
C)  Loss of a proton from the sigma complex. 
D)  Addition of an electrophile & loss of a proton 
E)  None of these 
A)  Formation of an electrophile 
B)  Formation of a sigma complex. 
C)  Loss of a proton from the sigma complex. 
D)  Addition of an electrophile & loss of a proton 
E)  None of these

Question 6

Predict the major product for the following reaction.

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  V 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  V

Question 7

Identify the electrophile in the sulfonation reaction of benzene.

Accepted Answer

A)  SO2+ 
B)  H2SO4 
C)  SO3+ 
D)  H2SO3 
E)  SO3 
A)  SO2+ 
B)  H2SO4 
C)  SO3+ 
D)  H2SO3 
E)  SO3

Question 8

Which one of the following compounds does not undergo a Friedel-Crafts reaction?

Accepted Answer

A)  benzene 
B)  chlorobenzene 
C)  nitrobenzene 
D)  toluene 
E)  t-butylbenzene 
A)  benzene 
B)  chlorobenzene 
C)  nitrobenzene 
D)  toluene 
E)  t-butylbenzene

Question 9

Provide the reagent(s) necessary to carry out the following conversion.

Accepted Answer

The answer of Provide the reagent(s) necessary to carry out...

Question 10

Provide the structures of the major resonance contributors when nitrobenzene reacts with an electrophile in electrophilic aromatic substitution at the meta position.

Accepted Answer

The answer of Provide the structures of the major resonance...

Question 11

Which one of the following compounds will be least reactive towards a Friedel-Crafts reaction?

Accepted Answer

A)  nitrobenzene 
B)  anisole 
C)  phenol 
D)  benzene 
E)  chlorobenzene 
A)  nitrobenzene 
B)  anisole 
C)  phenol 
D)  benzene 
E)  chlorobenzene

Question 12

Which one of the following substituents will direct the incoming group to the meta position during electrophilic aromatic substitution?

Accepted Answer

A)  -NO2 
B)  -C$\equiv$N 
C)  -CCl3 
D)  -COOH 
E)  all of these 
A)  -NO2 
B)  -C$\equiv$N 
C)  -CCl3 
D)  -COOH 
E)  all of these

Question 13

Which one of the following compounds would be least reactive toward electrophilic aromatic substitution?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  V 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  V

Question 14

Identify the reagents used to carry out the chlorination of benzene.

Accepted Answer

A)  Cl2/CCl4 
B)  Cl2/FeCl3 
C)  Cl2/AlCl3 
D)  NaCl/Fe 
E)  both B and C 
A)  Cl2/CCl4 
B)  Cl2/FeCl3 
C)  Cl2/AlCl3 
D)  NaCl/Fe 
E)  both B and C

Question 15

In a Clemmensen reduction, an aryl ketone is reduced to _____________.

Accepted Answer

A)  an aryl aldehyde 
B)  an aryl alkane 
C)  an aryl carboxylic acid 
D)  an aryl ester 
E)  an aryl anhydride 
A)  an aryl aldehyde 
B)  an aryl alkane 
C)  an aryl carboxylic acid 
D)  an aryl ester 
E)  an aryl anhydride

Question 16

Provide all resonance structures of the sigma complex when aniline reacts with an electrophile (E+) to yield the para-substituted product.

Accepted Answer

Question 17

Provide the reagents necessary to carry out the following conversion.

Accepted Answer

1. CH₃CH₂Cl/

Question 18

List the three steps involved in an electrophilic aromatic substitution reaction.

Accepted Answer

1. Formation of an electrophil

Question 19

Predict the major product for the following reaction.

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  V 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  V

Question 20

Provide the structures of the major intermediate and products in the following reaction sequence.

Accepted Answer

The answer of Provide the structures of the major intermediate...

Exam 18: Aromatic Substitution Reactions

The electrophilic bromination or chlorination of benzene requires ______ along with the halogen.

Aryl and vinyl halides cannot be used in the Friedel-Crafts alkylation reaction, because they do not __________.

Which one of the following substituents will not direct the incoming group to the meta position during electrophilic aromatic substitution?

Give the preferred products from the nitration of bromobenzene.

Identify the rate-determining step in the electrophilic aromatic substitution of benzene.

Predict the major product for the following reaction.

Identify the electrophile in the sulfonation reaction of benzene.

Which one of the following compounds does not undergo a Friedel-Crafts reaction?

Provide the reagent(s) necessary to carry out the following conversion.

Provide the structures of the major resonance contributors when nitrobenzene reacts with an electrophile in electrophilic aromatic substitution at the meta position.

Which one of the following compounds will be least reactive towards a Friedel-Crafts reaction?

Which one of the following substituents will direct the incoming group to the meta position during electrophilic aromatic substitution?

Which one of the following compounds would be least reactive toward electrophilic aromatic substitution?

Identify the reagents used to carry out the chlorination of benzene.

In a Clemmensen reduction, an aryl ketone is reduced to _____________.

Provide all resonance structures of the sigma complex when aniline reacts with an electrophile (E+) to yield the para-substituted product.

Provide the reagents necessary to carry out the following conversion.

List the three steps involved in an electrophilic aromatic substitution reaction.

Predict the major product for the following reaction.

Provide the structures of the major intermediate and products in the following reaction sequence.

A Review of General Chemistry: Electrons, Bonds, and Molecular Properties

Molecular Representations

Acids and Bases

Alkanes and Cycloalkanes

Stereoisomerism

Chemical Reactivity and Mechanisms

Alkyl Halides: Nucleophilic Substitution and Elimination Reactions

Addition Reactions of Alkenes

Alkynes

Radical Reactions

Synthesis

Alcohols and Phenols

Ethers and Epoxides; Thiols and Sulfides

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Conjugated Pi Systems and Pericyclic Reactions

Aromatic Compounds

Aldehydes and Ketones

Carboxylic Acids and Their Derivatives

Alpha Carbon Chemistry: Enols and Enolates

Amines

Introduction to Organometallic Compounds

Carbohydrates

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

Provide all resonance structures of the sigma complex when aniline reacts with an electrophile (E⁺) to yield the para-substituted product.