Deck 15: Reactions of Aromatic Compounds

Question 1

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

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

Answer 1

C₆H₅CH₂CH₂OH + PCl₅ -- $\rightarrow$

Question 2

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

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

Answer 2

C₆H₅CH₂CH₂OH + SOCl₂ -- $\rightarrow$

Question 3

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

Answer 3

Friedel-Crafts alkylation

Question 4

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 5

Consider the following reaction: what is the expected product?

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

Question 6

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 7

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 8

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 9

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

Question 10

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 11

Which of the following reactions would produce isopropylbenzene?

A)

B)

C)

D)

E) All of these

Question 12

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

A)

B)

C)

D) All of the above
E) None of the above

Question 13

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

Question 14

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

A)

B)

C)

D)

E) All of these

Question 15

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 16

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

Question 17

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 18

Which of the following reactions would produce cumene?

A)

B)

C)

D)

E) All of these

Question 19

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 could be used.

Question 20

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

A)

B)

C)

D)

E) All of these

Question 21

Which of the following compounds would yield the greatest amount of meta product when subjected to ring nitration?

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

Question 22

Which of the following is not an ortho-para director in electrophilic aromatic substitution?

A) -CF₃
B) -OCH₃
C) -CH₃
D) -F
E) -NH₂

Question 23

Which would be the product of the following reaction sequence?

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

Question 24

What would be the product of the following reaction sequence?

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

Question 25

Which of these compounds gives essentially a single product on electrophilic substitution of a third group?

A) p-chlorotoluene
B) m-ethylanisole
C) 1-bromo-2-chlorobenzene
D) m-xylene
E) 3-hydroxybenzoic acid

Question 26

The reaction of benzene with (CH₃)₃CCH₂Cl in the presence of anhydrous aluminum chloride produces principally which of these?

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

Question 27

Arrange the following compounds in order of decreasing reactivity in electrophilic 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 28

Which of the following is not a meta-directing substituent when present on the benzene ring?

A) -NHCOCH₃
B) -NO₂
C) -N(CH₃)₃⁺
D) -C $\equiv$ N
E) -CO₂H

Question 29

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 the above.No reaction will occur.

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

The reaction of benzene with in the presence of anhydrous aluminum chloride produces principally which of these?

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

Question 32

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
E) None of these

Question 33

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 34

Which would be the product of the following reaction sequence?

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

Question 35

What would be the product of the following reaction sequence?

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

Question 36

(Trifluoromethyl)benzene,C₆H₅CF₃,will

A) nitrate rapidly in the ortho-para positions.
B) nitrate slowly in the ortho-para positions.
C) nitrate rapidly in the meta position.
D) nitrate slowly in the meta position.
E) fail to nitrate under any conditions.

Question 37

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

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

Question 38

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

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

Question 39

Which is the best prediction of the site(s)of substitution when 3-methylphenol is nitrated?

A) C-2
B) C-4
C) C-5
D) C-6
E) C-4 and C-6

Question 40

The reaction of benzene with in the presence of anhydrous aluminum chloride produces principally which of these?

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

Question 41

Which reagent(s)would you use to carry out the following transformation? cumene -- $\rightarrow$ 2- and 4-chlorocumene

A) Cl₂,light,and heat
B) Cl₂,FeCl₃
C) SOCl₂
D) C₂H₅Cl,AlCl₃
E) HCl,peroxides

Question 42

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 43

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 44

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 45

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 46

Which reagent(s)would you use to carry out the following transformation? isopropylbenzene -- $\rightarrow$ 2- and 4-chloro-1-isopropylbenzene

A) Cl₂,light,and heat
B) Cl₂,FeCl₃
C) SOCl₂
D) C₂H₅Cl,AlCl₃
E) HCl,peroxides

Question 47

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 48

Which reagent(s)would you use to synthesize 2- and 4-bromo-1-cyclopentylbenzene from cyclopentylbenzene?

A) N-Bromosuccinimide (NBS),CCl₄,light
B) PBr₃
C) Br₂,FeBr₃
D) CH₃CH₂Br,AlBr₃
E) HBr,ROOR

Question 49

Which reagent(s)would you use to carry out the following transformation? ethylbenzene -- $\rightarrow$ 2- and 4-chloro-1-ethylbenzene

A) Cl₂,light,and heat
B) Cl₂,FeCl₃
C) SOCl₂
D) C₂H₅Cl,AlCl₃
E) None of these

Question 50

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 51

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 52

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 53

Which reagent(s)would you use to carry out the following transformation? t-butylbenzene -- $\rightarrow$ p-chloro substitution product

A) Cl₂,light,and heat
B) Cl₂,FeCl₃
C) SOCl₂
D) C₂H₅Cl,AlCl₃
E) HCl,peroxide

Question 54

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 55

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 56

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 57

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 58

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 59

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 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

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

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

Question 62

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 63

Which reagent would you use to carry out the following transformation? tert-butylbenzene
-- $\rightarrow$
P-tert-butylbenzenesulfonic acid
+
O-tert-butylbenzenesulfonic acid

A) HNO₃/H₂SO₄
B) tert-C₄H₉Cl/AlCl₃
C) H₂SO₃/peroxides
D) SO₃/H₂SO₄
E) SO₂/H₂SO₃

Question 64

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

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

Question 65

Which of the following compounds would be most reactive to ring bromination?

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

Question 66

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 67

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 68

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 the above

Question 69

Which of the following compounds would be most reactive toward ring nitration?

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

Question 70

Which of the following compounds would be most reactive toward ring bromination?

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

Question 71

Which of the compounds listed below would you expect to give the greatest amount of meta-product when subjected to ring nitration?

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

Question 72

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 73

Which of the compounds listed below would you expect to give the greatest amount of meta-product when subjected to ring bromination?

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

Question 74

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 75

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

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

Question 78

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 79

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 80

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

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