Question 1

What is (are) the product(s) of the following reaction?

Accepted Answer

A)  Only I
B)  Only II
C)  Only III
D)  Only I and IIE) B) and C)
F) A) and D)

Question 2

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

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) C) and D)
F) All of the above

Question 3

Rank the following compounds in order of increasing reactivity in electrophilic aromatic substitution.

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  II < I < III < IVE) All of the above
F) C) and D)

Question 4

Which of the following statements about the mechanism of electrophilic aromatic substitution is not true?

Accepted Answer

A)  All electrophilic aromatic substitution reactions occur via a two-step mechanism.
B)  The transition state of the first step is lower in energy.
C)  The first step is the rate-determining step.
D)  The second step is the fast step.E) All of the above
F) A) and B)

Question 5

What is the first step in the general mechanism for electrophilic aromatic substitution?

Accepted Answer

A)  Protonation of the aromatic ring
B)  Deprotonation of the aromatic ring
C)  Addition of the electrophile to the aromatic ring
D)  Loss of the electrophile from the aromatic ringE) None of the above
F) All of the above

Question 6

Consider the tetracyclic aromatic compound drawn below,with rings labelled as I,II,III,and IV.Which of the four rings is most reactive in electrophilic aromatic substitution?

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) B) and D)
F) B) and C)

Question 7

Which of the following substituents is an ortho,para director?

Accepted Answer

A)  ¾ CHO
B)  ¾ COOH
C)  ¾ NHCOR
D)  ¾ CNE) A) and C)
F) B) and D)

Question 8

What is the product of the following reaction?

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) A) and D)
F) None of the above

Question 9

What is the major organic product of the following reaction?

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) B) and C)
F) A) and C)

Question 10

What is the major product of the following reaction?

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) A) and D)
F) All of the above

Question 11

What is the electrophile in aromatic sulfonation?

Accepted Answer

A)  H2SO3
B)  H2SO4
C)  SO3+
D)  HSO3+E) A) and B)
F) A) and C)

Question 12

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

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) C) and D)
F) None of the above

Question 13

Rank the following deactivating groups in order of increasing deactivating strength,listing the least deactivating first.

Accepted Answer

A)  I 
B)  II 
C)  II 
D)  IV < III < I < IIE) B) and D)
F) A) and B)

Question 14

What is a major problem with Friedel-Crafts alkylation?

Accepted Answer

A)  It requires high temperatures.
B)  The conditions are too acidic.
C)  The starting material is frequently over-alkylated.
D)  The products coordinate with the aluminum chloride.E) A) and B)
F) A) and C)

Question 15

What is the electrophile in the Friedel-Crafts alkylation reaction with tert-butylchloride?

Accepted Answer

A)  The tert-butyl cation
B)  A complex of tert-butylchloride and aluminum chloride
C)  A proton
D)  Aluminum chlorideE) A) and D)
F) None of the above

Question 16

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

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) All of the above
F) B) and C)

Question 17

Which of the following statements about nucleophilic aromatic substitution is not true?

Accepted Answer

A)  Increasing the electronegativity of the halogen increases the reactivity of the aryl halide.
B)  Increasing the number of electron-withdrawing groups increases the reactivity of the aryl halide.
C)  Electron-withdrawing groups stabilize the intermediate carbanion,and lower the energy of the transition state.
D)  When a nitro group is located meta to the halogen,the negative charge of the intermediate carbanion can be delocalized onto the NO2 group,thus stabilizing it.E) C) and D)
F) B) and C)

Question 18

What will be the site that leads to the major mono substitution product for an electrophilic aromatic substitution reaction of the following compound?

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) B) and C)
F) C) and D)

Question 19

Rank the following compounds in order of increasing reactivity in nucleophilic aromatic substitution.

Accepted Answer

A)  III 
B)  I 
C)  III 
D)  I < III < IIE) A) and B)
F) A) and C)

Question 20

What is the reactive intermediate formed in the addition-elimination mechanism of nucleophilic aromatic substitution?

Accepted Answer

A)  Carbocation
B)  Radical
C)  Benzyne
D)  CarbanionE) None of the above
F) A) and B)

Exam 16: Reactions of Aromatic Compounds

What is the electrophile in aromatic sulfonation?

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Which of the following statements about nucleophilic aromatic substitution is not true?

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What is a major problem with Friedel-Crafts alkylation?

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Rank the following compounds in order of increasing reactivity in nucleophilic aromatic substitution.

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What is (are) the product(s) of the following reaction?

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What is the major product of the following reaction?

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What is the major organic product of the following reaction?

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Consider the tetracyclic aromatic compound drawn below,with rings labelled as I,II,III,and IV.Which of the four rings is most reactive in electrophilic aromatic substitution?

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

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

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What is the reactive intermediate formed in the addition-elimination mechanism of nucleophilic aromatic substitution?

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What will be the site that leads to the major mono substitution product for an electrophilic aromatic substitution reaction of the following compound?

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Rank the following compounds in order of increasing reactivity in electrophilic aromatic substitution.

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What is the electrophile in the Friedel-Crafts alkylation reaction with tert-butylchloride?

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What is the first step in the general mechanism for electrophilic aromatic substitution?

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Which of the following statements about the mechanism of electrophilic aromatic substitution is not true?

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Rank the following deactivating groups in order of increasing deactivating strength,listing the least deactivating first.

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

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What is the product of the following reaction?

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Which of the following substituents is an ortho,para director?

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