Question 1

What is the product of the following sequence of reactions?

Accepted Answer

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

Question 2

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 3

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

Question 4

What is the major product of the following reaction?

Accepted Answer

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

Question 5

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

Question 6

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 7

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 8

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

Accepted Answer

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

Question 9

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

Question 10

What is the electrophile in aromatic nitration?

Accepted Answer

A) NO+ 
B) NO2+ 
C) NO3+ 
D) NO2H 
A) NO+ 
B) NO2+ 
C) NO3+ 
D) NO2H

Question 11

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 12

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 13

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 ring 
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 ring

Question 14

Which of the following substituents is a meta director?

Accepted Answer

A) ¾ N(CH3)2 
B) ¾ OCH3 
C) ¾ NHCOCH3 
D) ¾ SO3H 
A) ¾ N(CH3)2 
B) ¾ OCH3 
C) ¾ NHCOCH3 
D) ¾ SO3H

Question 15

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 16

In addition to the product shown,what other product is formed in the following reaction?

Accepted Answer

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

Question 17

What reagents would be necessary to produce the following product from benzene?

Accepted Answer

A) CH3CH2C(O)Cl,AlCl3 2.HNO3,H2SO4 3.Zn(Hg),HCl 
B) HNO3,H2SO4 2.CH3CH2C(O)Cl,AlCl3 3.Zn(Hg),HCl 
C) CH3CH2C(O)Cl,AlCl3 2.Zn(Hg),HCl 3.HNO3,H2SO4 
D) Zn(Hg),HCl 2.CH3CH2C(O)Cl,AlCl3 3.HNO3,H2SO4 
A) CH3CH2C(O)Cl,AlCl3 2.HNO3,H2SO4 3.Zn(Hg),HCl 
B) HNO3,H2SO4 2.CH3CH2C(O)Cl,AlCl3 3.Zn(Hg),HCl 
C) CH3CH2C(O)Cl,AlCl3 2.Zn(Hg),HCl 3.HNO3,H2SO4 
D) Zn(Hg),HCl 2.CH3CH2C(O)Cl,AlCl3 3.HNO3,H2SO4

Question 18

What is the product of the following reaction?

Accepted Answer

A) I 
B) II 
C) III 
D) None of these 
A) I 
B) II 
C) III 
D) None of these

Question 19

Which of the following statements about nucleophilic aromatic substitution is true?

Accepted Answer

A) For the addition-elimination pathway,the nucleophile may become attached either at the site bearing the leaving group or at the site bearing the ortho hydrogen atom. 
B) For the elimination-addition pathway,the nucleophile becomes attached only at the site bearing the leaving group. 
C) The elimination-addition mechanism is not as common as the addition-elimination mechanism. 
D) In the addition-elimination mechanism,the aromatic ring first accepts a pair of electrons from a nucleophile to form a cationic intermediate. 
A) For the addition-elimination pathway,the nucleophile may become attached either at the site bearing the leaving group or at the site bearing the ortho hydrogen atom. 
B) For the elimination-addition pathway,the nucleophile becomes attached only at the site bearing the leaving group. 
C) The elimination-addition mechanism is not as common as the addition-elimination mechanism. 
D) In the addition-elimination mechanism,the aromatic ring first accepts a pair of electrons from a nucleophile to form a cationic intermediate.

Question 20

What is the major product of the following reaction?

Accepted Answer

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

Exam 16: Reactions of Aromatic Compounds

What is the product of the following sequence of reactions?

What is the product of the following reaction?

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?

What is the major product of the following reaction?

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

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

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

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

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

What is the electrophile in aromatic nitration?

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

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

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

Which of the following substituents is a meta director?

What is the electrophile in aromatic sulfonation?

In addition to the product shown,what other product is formed in the following reaction?

What reagents would be necessary to produce the following product from benzene?

What is the product of the following reaction?

Which of the following statements about nucleophilic aromatic substitution is true?

What is the major product of the following reaction?

Structure and Bonding

Acids and Bases

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 Related Compounds

Alkenes and Addition Reactions

Alkynes and Synthesis

Oxidation and Reduction

Radical Reactions

Conjugation,resonance,and Dienes

Benzene and Aromatic Compounds

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones - Nucleophilic Addition

Carboxylic Acids and the Acidity of the O-H Bond

Carboxylic Acids and Their Derivatives Nucleophilic Acyl Substitution

Substitution Reactions of Carbonyl Compounds at the a Carbon

Carbonyl Condensation Reactions

Amines

Carbon-Carbon Bond-Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Synthetic Polymers

Lipids

Spectroscopy A: Mass Spectrometry

Spectroscopy B: Infrared Spectroscopy

Spectroscopy C: Nuclear Magnetic Resonance Spectroscopy

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