Deck 18: Aromatic Substitution Reactions

Question 1

Predict the product for the following reaction.

Answer 1

Question 2

Identify the electrophile in the chlorination of benzene.

A) Cl₂
B)
C) AlCl₃
D) AlCl₂
E)

Answer 2

Question 3

Identify the mechanism by which benzene reacts with bromine.

Answer 3

electrophilic aromatic substitution

Question 4

Predict the product for the following reaction.

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

Question 5

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

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

Question 6

Identify the electrophile in the nitration of benzene.

A) sulfonium ion
B) nitrogen dioxide
C) nitronium ion
D) nitrous oxide
E) Nitrogen dioxide

Question 7

Provide a stepwise curved arrow mechanism for the chlorination of benzene in the presence of FeCl₃.

Question 8

Identify the electrophile in the bromination of benzene.

A) Br₂
B)
C) FeBr₃
D) FeBr₂
E)

Question 9

Predict the product for the following reaction.

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

Question 10

Cyclohexene undergoes an addition reaction with bromine, but benzene does not. Instead, benzene undergoes a substitution reaction with bromine. Explain why.

Question 11

Predict the product for the following reaction.

Question 12

Which of the following reagents would you use as the basis for a simple chemical test that would distinguish between ethylbenzene and styrene?

A) NaI/acetone
B) Br₂/CCl₄
C) NaOH/H₂O
D) NaBH₄/CH₃OH
E) HCl/H₂O

Question 13

Identify the electrophile in the iodination of benzene.

A) I₂
B)
C) CuI₃
D) CuI₂
E)

Question 14

Draw all of the resonance structures of the sigma complex which is formed when benzene reacts with an electrophile (E⁺).

Question 15

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

A) I₂/CCl₄
B) I₂/FeCl₃
C) I₂/AlCl₃
D) I₂/CuCl₂
E) NaI/Acetone

Question 16

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

Question 17

Identify the electrophile in the nitration of benzene.

A) NO₂⁺
B) HNO₃
C) NO₃⁺
D) H₂SO₄
E) NO₂

Question 18

Identify the electrophile in the sulfonation reaction of benzene.

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

Question 19

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

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

Question 20

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

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 21

Predict the major product for the reaction between benzene and 2-chlorobutane in the presence of AlCl₃.

A) chlorobenzene
B) sec-butylbenzene
C) ethylbenzene
D) isopropylbenzene
E) t-butylbenzene

Question 22

Predict the major product for the following reaction and provide a stepwise, curved arrow mechanism for the formation of the product.

Question 23

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

Question 24

Provide the curved arrow mechanism for the following reaction.

Question 25

Which one of the following reactions is most likely to give a polysubstituted product?

A) Friedel-Crafts alkylation
B) Friedel-Crafts acylation
C) nitration
D) sulfonation
E) halogenation

Question 26

Predict the structure of the major product for the following reaction.

Question 27

Predict the major product for the following reaction.

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

Question 28

Which of the following reactions would produce isopropylbenzene as the major product?

A) I
B) II
C) III
D) IV
E) all of these

Question 29

Predict the major product for the following reaction.

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

Question 30

Predict the major product for the following reaction.

A) I
B) II
C) III
D) IV
E) none of these

Question 31

Which of the following reactions would produce t-butylbenzene as the major product?

A) I
B) II
C) III
D) IV
E) all of these

Question 32

Predict the major product for the following reaction.

Question 33

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

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

Question 34

Provide a stepwise, curved arrow mechanism for the following reaction.

Question 35

Predict the major product for the following reaction.

Question 36

Which of the following halides cannot be used for a Friedel-Crafts alkylation reaction?

A) bromobenzene
B) vinylchloride
C) 2-chloropropane
D) chloroethane
E) both A and B

Question 37

Identify the electrophile in a Friedel-Crafts alkylation.

A) aluminum chloride
B) carbocation
C) aluminum tetrachloride ion
D) carbanion
E) radical

Question 38

Identify the product from the reaction of nitrobenzene with iron and hydrochloric acid, followed with base.

A) nitrobenzene
B) benzene
C) aniline
D) 1,3-dinitrobenzene
E) 1,4-dinitrobenzene

Question 39

Predict the major product for the following reaction.

Question 40

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

Question 41

Which of the following substituents will not direct the incoming group to the ortho/para position during electrophilic aromatic substitution?

A) -CH₂CH₃
B) -CF₃
C) -OCH₃
D) -NHCH₃
E) -Br

Question 42

Which of the following substituents will direct the incoming group to the ortho/para position during electrophilic aromatic substitution?

A) -CH₂CH₃
B) -CF₃
C) -OCH₃
D) -COOCH₃
E) both A and C

Question 43

Predict the structure of the major product for the following reaction.

Question 44

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

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

Question 45

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

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

Question 46

Predict the structure of the product for the following reaction.

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

Question 47

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

Question 48

Provide the reagents necessary to carry out the following conversion.

Question 49

An alkyl group ___________ the benzene ring to make it __________ reactive than benzene.

Question 50

Predict the structure of the major product for the following reaction.

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

Question 51

Predict the structure of the product for the following reaction.

Question 52

Provide the structure of the major products formed in each step of the following reaction sequence.

Question 53

Predict the structure of the product for the following reaction.

Question 54

A nitro group ___________ the benzene ring to make it __________ reactive than benzene.

Question 55

Which one of the following compounds will be most reactive towards an electrophilic aromatic bromination reaction?

A) nitrobenzene
B) anisole
C) acetanilide
D) benzene
E) benzaldehyde

Question 56

Predict the structure of the major product for the following reaction.

Question 57

Which of the following compounds will yield the ortho substituted compound as the major product for a nitration reaction?

A) toluene
B) ethylbenzene
C) cumene
D) t-butylbenzene
E) none of these

Question 58

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

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

Question 59

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

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

Question 60

Identify the electrophile for the Friedel-Crafts acylation of benzene.

A) aluminum tetrachloride anion
B) aluminum chloride
C) acylium ion
D) carbocation
E) carbanion

Question 61

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

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

Question 62

Predict the major product for the following reaction.

Question 63

Predict the major product for the following reaction.

Question 64

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

Question 65

Arrange the following compounds in order of decreasing reactivity towards electrophilic aromatic substitution.

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

Question 66

Predict the major product for the following reaction.

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

Question 67

Predict the major product for the following reaction.

Question 68

A halogen ___________ the benzene ring; the ring is __________ reactive than benzene.

Question 69

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

Question 70

Predict the major product for the following reaction.

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

Question 71

Which of the following substituents will direct the incoming group to the ortho/para position during electrophilic aromatic substitution?

A) -NO₂
B) -CF₃
C) -Br
D) -COOCH₃
E) none of these

Question 72

Predict the major product for the following reaction.

Question 73

Predict the major product for the following reaction.

A) I
B) II
C) III
D) IV
E) none of these

Question 74

Provide the reagent(s) that are necessary to carry out the following conversion. t-butylbenzene $\to$ 1-t-butyl-4-chlorobenzene

A) Cl₂, heat
B) Cl₂, FeCl₃
C) SOCl₂, pyridine
D) HCl
E) PCl₃

Question 75

Predict the major product for the following reaction.

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

Question 76

Predict the major product for the following reaction.

A) I
B) II
C) III
D) IV
E) no reaction

Question 77

Give the preferred products from the nitration of bromobenzene.

Question 78

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

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

Question 79

Predict the major product for the following reaction.

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

Question 80

Predict the major product for the following reaction.

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