Deck 15: Reactions of Aromatic Compounds

Question 1

Which one of these molecules can be a reactant in a Friedel-Crafts reaction?

A)Aniline
B)Nitrobenzene
C)Chloroethene
D)Bromobenzene
E)p-Bromonitrobenzene

Answer 1

Bromobenzene

Question 2

This molecule does not normally participate as a reactant in a Friedel-Crafts reaction.

A)Benzene
B)Chlorobenzene
C)Nitrobenzene
D)Toluene
E)tert-Butylbenzene

Answer 2

Nitrobenzene

Question 3

Which of these is the rate-determining step in the nitration of benzene?

A)Protonation of nitric acid by sulfuric acid
B)Protonation of sulfuric acid by nitric acid
C)Loss of a water molecule by the protonated species to produce the nitronium ion
D)Addition of the nitronium to benzene to produce the arenium ion
E)Loss of a proton by the arenium ion to form nitrobenzene

Answer 3

Addition of the nitronium to benzene to produce the arenium ion

Question 4

This substituent deactivates the benzene ring towards electrophilic substitution but directs the incoming group chiefly to the ortho and para positions.

A)-OCH₂CH₃
B)-NO₂
C)-F
D)-CF₃
E)-NHCOCH₃

Question 5

Which of the following structures does not contribute to the resonance hybrid of the intermediate formed when nitrobenzene undergoes meta-chlorination?

A)I
B)II
C)III
D)None of these contribute.
E)All of these contribute.

Question 6

Consider the resonance forms shown for the arenium ionformed from the bromination of acetanilide.Which resonance form contributes most to the overall resonance hybrid?

A)I
B)II
C)III
D)IV
E)All contribute equally.

Question 7

Which of these liquids would be unsuitable as an inert solvent for a Friedel-Crafts reaction?

A)Chlorobenzene
B)Nitrobenzene
C)Acetophenone
D)(Trifluoromethyl)benzene
E)All of these choices could be used.

Question 8

Undesired polysubstitution of an aromatic nucleus is most likely to be encountered in the case of:

A)Friedel-Crafts alkylation
B)Friedel-Crafts acylation
C)Nitration
D)Sulfonation
E)Chlorination

Question 9

Which one of these molecules can be a reactant in a Friedel-Crafts reaction?

A)Aniline
B)Benzenesulfonic acid
C)Chloroethene
D)Bromobenzene
E)p-Bromonitrobenzene

Question 10

Consider the resonance forms shown for the arenium ionformed from the bromination of acetanilide.Which resonance form contributes most to the overall resonance hybrid?

A)I
B)II
C)III
D)IV
E)All contribute equally.

Question 11

Which reagent would you use as the basis for a simple chemical test that would distinguish between toluene and vinylbenzene (C₆H₅CH=CH₂)?

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

Question 12

In electrophilic aromatic substitution,the attacking species (the electrophile)necessarily is a:

A)neutral species.
B)positively charged species.
C)lewis acid.
D)proton.
E)carbocation.

Question 13

Which of these is the rate-determining step in the sulfonation of benzene?

A)Formation of SO₃ from sulfuric acid
B)Protonation of SO₃ sulfuric acid
C)Addition of SO₃H⁺ to benzene to form the arenium ion
D)Loss of a proton from the arenium ion to form benzenesulfonic acid
E)None of these choices.

Question 14

Which of the following structures contribute(s)to the resonance hybrid of the intermediate formed when bromobenzene undergoes para-chlorination?

A)I
B)II
C)III
D)IV
E)All of these choices.

Question 15

Which of these is the rate-determining step in the bromination of benzene?

A)Complexation of bromine with the iron(III)bromide catalyst
B)Formation of Br⁺ ion
C)Addition of Br⁺ to benzene to form the arenium ion
D)Loss of a proton from the arenium ion to form bromobenzene
E)None of these choices.

Question 16

Which of the following structures contribute(s)to the resonance hybrid of the intermediate formed when acetanilide undergoes para-bromination?

A)I
B)II
C)III
D)IV
E)All of these choices.

Question 17

The electrophilic bromination or chlorination of benzene requires,in addition to the halogen:

A)a hydroxide ion.
B)a Lewis base.
C)a Lewis acid.
D)peroxide.
E)ultraviolet light.

Question 18

Consider the structures given below.Which of them would be a relatively stable contributor to the hybrid formed when toluene undergoes para bromination?

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

Question 19

Which of the following structures contribute(s)to the resonance hybrid of the intermediate formed when chlorobenzene undergoes para-chlorination?

A)I
B)II
C)III
D)IV
E)All of these choices.

Question 20

Which of the following contributors to the resonance stabilized hybrid formed when aniline undergoes para-chlorination would be exceptionally stable?

A)I
B)II
C)III
D)IV
E)None of these choices.

Question 21

Which of the following reactions would produce isopropylbenzene?

A)
B)
C)
D)
E)All of these choices.

Question 22

Which of these is a satisfactory synthesis of 1-chloro-2-phenylethane?

A)C₆H₅CH₂CH₃ + Cl₂,Fe $\to$
B)C₆H₅CH₂CH₃ + Cl₂,400 ^$\circ$ C $\to$
C)C₆H₅CH₂CH₂OH + PCl₅ $\to$
D)C₆H₅CH=CH₂ + HCl,peroxide $\to$
E)C₆H₆ + CH₃CH₂Cl,AlCl₃ $\to$

Question 23

Which of the following reactions would yield cumene as the major product?

A)
B)
C)
D)
E)All of these choices.

Question 24

Which of the following reactions could be used to synthesize tert-butylbenzene?

A)
B)
C)
D)All of these choices.
E)None of these choices.

Question 25

Which reagent or test could you use to distinguish between phenylacetylene and vinylbenzene?

A)NaOH/H₂O
B)Br₂/CCl₄
C)IR Spectroscopy
D)CrO₃/H₂SO₄
E)Concd.H₂SO₄

Question 26

Which of the following reactions could be used to synthesize tert-butylbenzene?

A)
B)
C)
D)All of these choices.
E)None of these choices.

Question 27

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

A)
B)
C)
D)
E)All of these choices.

Question 28

What would you expect to be the major product obtained from the following reaction?

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

Question 29

Which of the following reactions would produce cumene?

A)
B)
C)
D)
E)All of these choices.

Question 30

What would you expect to be the major product obtained from the following reaction?

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

Question 31

What is the chief product of the Friedel-Crafts alkylation of benzene with 1-butene and AlCl₃?

A)butylbenzene
B)2-phenylbutane
C)2-methyl-1-phenylpropane
D)t-butylbenzene
E)2,2-diphenylbutane

Question 32

Which of these is a satisfactory synthesis of 1-chloro-2-phenylethane?

A)C₆H₅CH₂CH₃ + Cl₂,Fe $\to$
B)C₆H₅CH₂CH₃ + Cl₂,400 ^$\circ$ C $\to$
C)C₆H₅CH₂CH₂OH + SOCl₂ $\to$
D)C₆H₅CH=CH₂ + HCl,peroxide $\to$
E)C₆H₆ + CH₃CH₂Cl,AlCl₃ $\to$

Question 33

What is the chief product of the Friedel-Crafts alkylation of benzene with 1-butene and HF?

A)butylbenzene
B)2-phenylbutane
C)2-methyl-1-phenylpropane
D)t-butylbenzene
E)2,2-diphenylbutane

Question 34

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

A)
B)
C)
D)
E)All of these choices.

Question 35

Which of the following reactions would give the product(s)indicated in substantial amounts (i.e.,in greater than 50% yield)?

A)I
B)II
C)III
D)All of these choices.
E)None of these choices.

Question 36

Consider the following reaction: what is the expected product?

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

Question 37

A mixture of chlorobenzene (1 mol)and anisole (1mol)is allowed to react with Br₂ (0.5 mol)in the presence of trace amounts of FeBr₃.What is the principal product of the competing reactions?

A)1-bromo-4-chlorobenzene
B)1-bromo-2-chlorobenzene
C)1-bromo-3-chlorobenzene
D)4-bromoanisole
E)3-bromoanisole

Question 38

Which of the following reactions could be used to synthesize tert-butylbenzene?

A)
B)
C)
D)All of these choices.
E)None of these choices.

Question 39

A mixture of chlorobenzene (1 mol)and acetanilide (1mol)is allowed to react with Br₂ (0.5 mol)in the presence of trace amounts of FeBr₃.What is the principal product of the competing reactions?

A)1-bromo-4-chlorobenzene
B)1-bromo-2-chlorobenzene
C)1-bromo-3-chlorobenzene
D)4-bromoacetanilide
E)3-bromoacetanilide

Question 40

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

A)
B)
C)
D)All of these choices.

Question 41

What would you expect to be the major product obtained from the following reaction?

A)I
B)II
C)III
D)IV
E)Equal amounts of II and IV.

Question 42

What would be the product of the following reaction sequence?

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

Question 43

What would be the product of the following reaction sequence?

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

Question 44

What might be predicted to happen when the following substance undergoes Friedel-Crafts acylation?

A)Substitution occurs in ring B, p- to the methylene group.
B)Substitution occurs in ring A,o- to the nitro group.
C)Substitution occurs in ring A,o- to the methylene group.
D)Substitution occurs in ring B,m- to the methylene group.
E)None of these choices.No reaction will occur.

Question 45

Which would be the product,X,of the following reaction sequence?

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

Question 46

Which would be the product of the following reaction sequence?

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

Question 47

Which would be the product,X,of the following reaction sequence?

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

Question 48

Which would be the product of the following reaction sequence?

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

Question 49

What would be the product of the following reaction sequence?

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

Question 50

Which would be the product of the following reaction sequence?

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

Question 51

The major product(s),D,of the following reaction, would be:

A)I
B)II
C)III
D)IV
E)Approximately equal amounts of I and II.

Question 52

What would be the product of the following reaction sequence?

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

Question 53

The major product(s)of the following reaction, would be:

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

Question 54

Which would be the product of the following reaction sequence?

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

Question 55

What would be the product of the following reaction sequence?

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

Question 56

What would be the product of the following reaction sequence?

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

Question 57

The major product,D,of the following reaction, would be:

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

Question 58

What would you expect to be the major product obtained from the following reaction?

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

Question 59

What would you expect to be the major product obtained from the following reaction?

A)I
B)II
C)III
D)IV
E)Equal amounts of II and IV.

Question 60

What would you expect to be the major product obtained from the following reaction?

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

Question 61

What would you expect to be the major product obtained from the following reaction?

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

Question 62

The major product(s),C,of the following reaction, would be:

A)I
B)II
C)III
D)Approximately equal amounts of I and II.
E)Approximately equal amounts of I and III.

Question 63

What would you expect to be the major product obtained from the following reaction?

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

Question 64

What would you expect to be the major product obtained from the following reaction?

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

Question 65

What would be the major product(s)of the following reaction?

A)I
B)II
C)III
D)IV
E)Approximately equal amounts of II and IV.

Question 66

What would you expect to be the major product(s)obtained from the following reaction?

A)I
B)II
C)III
D)IV
E)Equal amounts of I and II.

Question 67

The major product(s),A,of the following reaction, would be:

A)I
B)II
C)A mixture of I and II.
D)III
E)IV

Question 68

The major product(s)of the following reaction,

A)I
B)II
C)A mixture of I and II.
D)III
E)IV

Question 69

The major product(s),D,of the following reaction would be:

A)I
B)II
C)III
D)IV
E)Equal amounts of I and II.

Question 70

What would you expect to be the major product obtained from the following reaction?

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

Question 71

What would be the major product(s)of the following reaction?

A)I
B)II
C)III
D)Equal amounts of I and IV.
E)Equal amounts of II and IV.

Question 72

What would be the major product(s)of the following reaction?

A)I
B)II
C)III
D)Equal amounts of I and IV.
E)Equal amounts of II and IV.

Question 73

What would you expect to be the major product obtained from the following reaction?

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

Question 74

What would you expect to be the major product obtained from the following reaction?

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

Question 75

What would you expect to be the major product(s)obtained from the mononitration of m-dichlorobenzene?

A)I
B)II
C)III
D)Equal amounts of I and II.
E)Equal amounts of I,II and III.

Question 76

Which would be the major product(s)of the following reaction?

A)I
B)II
C)III
D)I and II in roughly equal amounts.
E)I and III in roughly equal amounts.

Question 77

Which would be the major product(s)of the following reaction?

A)I
B)II
C)III
D)I and II in roughly equal amounts.
E)I and III in roughly equal amounts.

Question 78

What would you expect to be the major product obtained from the following reaction?

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

Question 79

What would you expect to be the major product obtained from the monobromination of m-dichlorobenzene?

A)I
B)II
C)III
D)Equal amounts of I and II.
E)Equal amounts of I,II and III.

Question 80

Which would be the major product(s)of the following reaction?

A)I
B)II
C)III
D)I and II in roughly equal amounts.
E)I and III in roughly equal amounts.