Question 1

Why is sulfuric acid used in aromatic nitration?

Accepted Answer

A)  To keep the reaction from getting too basic 
B)  To form the active electrophile NO2+ 
C)  To protonate the aromatic ring 
D)  To keep the reaction from getting too acidic 
A)  To keep the reaction from getting too basic 
B)  To form the active electrophile NO2+ 
C)  To protonate the aromatic ring 
D)  To keep the reaction from getting too acidic

Question 2

What is the electrophile in aromatic sulfonation?

Accepted Answer

A)  H2SO3 
B)  H2SO4 
C)  SO3+ 
D)  HSO3+ 
A)  H2SO3 
B)  H2SO4 
C)  SO3+ 
D)  HSO3+

Question 3

Which aryl fluoride reacts the fastest with NaOH?

Accepted Answer

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

Question 4

What is the best choice of reagent to bring about the following transformation?

Accepted Answer

A)  [1] LiAlH4; [2] H2O 
B)  Zn (Hg), HCl 
C)  NH3, NaOH 
D)  H2, Pd-C 
A)  [1] LiAlH4; [2] H2O 
B)  Zn (Hg), HCl 
C)  NH3, NaOH 
D)  H2, Pd-C

Question 5

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 chloride 
A)  the tert-butyl cation 
B)  a complex of tert-butylchloride and aluminum chloride 
C)  a proton 
D)  aluminum chloride

Question 6

What is the product of the following reaction?

Accepted Answer

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

Question 7

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

Question 8

Which of the following substituents is a meta director?

Accepted Answer

A)  "F1F1F1S1F1F1F10 N(CH3)2" 
B)  "F1F1F1S1F1F1F10 OCH3" 
C)  "F1F1F1S1F1F1F10 NHCOCH3" 
D)  "F1F1F1S1F1F1F10 SO3H" 
A)  "F1F1F1S1F1F1F10 N(CH3)2" 
B)  "F1F1F1S1F1F1F10 OCH3" 
C)  "F1F1F1S1F1F1F10 NHCOCH3" 
D)  "F1F1F1S1F1F1F10 SO3H"

Question 9

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

Accepted Answer

A)  I < II < III < IV 
B)  II < I < IV < III 
C)  III < IV < I < II 
D)  II < I < III < IV 
A)  I < II < III < IV 
B)  II < I < IV < III 
C)  III < IV < I < II 
D)  II < I < III < IV

Question 10

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. 
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.

Question 11

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

Question 12

Which of the following substituents are deactivators in electrophilic aromatic substitution?

Accepted Answer

A)  HO F1F1F1S1F1F1F10 
B)  CH3NH F1F1F1S1F1F1F10 
C)  CH3O F1F1F1S1F1F1F10 
D)  (CH3)3N+ F1F1F1S1F1F1F10 
A)  HO F1F1F1S1F1F1F10 
B)  CH3NH F1F1F1S1F1F1F10 
C)  CH3O F1F1F1S1F1F1F10 
D)  (CH3)3N+ F1F1F1S1F1F1F10

Question 13

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. 
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.

Question 14

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

Accepted Answer

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

Question 15

What is the driving force for losing a proton as the last step in electrophilic aromatic substitution?

Accepted Answer

A)  To neutralize the base that is present 
B)  To make room for the electrophile 
C)  To make the ring more reactive 
D)  To rearomatize the ring system 
A)  To neutralize the base that is present 
B)  To make room for the electrophile 
C)  To make the ring more reactive 
D)  To rearomatize the ring system

Question 16

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

Accepted Answer

A)  Only I and II 
B)  Only I and III 
C)  Only II and III 
D)  Only IV 
A)  Only I and II 
B)  Only I and III 
C)  Only II and III 
D)  Only IV

Question 17

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

Accepted Answer

A)  III < II < I 
B)  I < II < III 
C)  III < I < II 
D)  I < III < II 
A)  III < II < I 
B)  I < II < III 
C)  III < I < II 
D)  I < III < II

Question 18

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

Accepted Answer

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

Question 19

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

Accepted Answer

A)  Carbocation 
B)  Radical 
C)  Benzyne 
D)  Carbanion 
A)  Carbocation 
B)  Radical 
C)  Benzyne 
D)  Carbanion

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)  Carbanion 
A)  Carbocation 
B)  Radical 
C)  Benzyne 
D)  Carbanion

Exam 18: Electrophilic Aromatic Substitution

Why is sulfuric acid used in aromatic nitration?

What is the electrophile in aromatic sulfonation?

Which aryl fluoride reacts the fastest with NaOH?

What is the best choice of reagent to bring about the following transformation?

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

What is the product of the following reaction?

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

Which of the following substituents is a meta director?

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

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

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

Which of the following substituents are deactivators in electrophilic aromatic substitution?

What is a major problem with Friedel-Crafts alkylation?

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

What is the driving force for losing a proton as the last step in electrophilic aromatic substitution?

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

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

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

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

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

Structure and Bonding

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Introduction to Organic Molecules and Functional Groups

Alkanes

Stereochemistry

Understanding Organic Reactions

Alkyl Halides and Nucleophilic Substitution

Alkyl Halides and Elimination Reactions

Alcohols, Ethers and Epoxides

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Mass Spectrometry and Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

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Conjugation, Resonance, and Dienes

Benzene and Aromatic Compounds

Carboxylic Acids and the Acidity of the O-H Bond

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones Nucleophilic Addition

Carboxylic Acids and Derivatives

Substitution Reactions of Carbonyl Compounds at the Alpha-Carbon

Carbonyl Condensation Reactions

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Carbon-Carbon Bond Forming Reactions in Organic Synthesis

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