Question 1

Gradable: automatic
Rank the following compounds in order of decreasing reactivity in electrophilic aromatic substitution.

Accepted Answer

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

Question 2

Why is the nitro group a meta director?

Accepted Answer

A) Because it is sterically very large. 
B) Because it adds electron density to the meta position, thus activating it. 
C) Because it stabilizes the intermediate cation. 
D) Because it removes more electron density from the ortho and para positions than the meta position, thus deactivating the meta position less. 
A) Because it is sterically very large. 
B) Because it adds electron density to the meta position, thus activating it. 
C) Because it stabilizes the intermediate cation. 
D) Because it removes more electron density from the ortho and para positions than the meta position, thus deactivating the meta position less. D

Question 3

What are the two effects that have to be considered to determine the influence a substituent will have on electrophilic aromatic substitution?

Accepted Answer

A) Steric and electronic 
B) Inductive and steric 
C) Inductive and resonance 
D) Resonance and electronic 
A) Steric and electronic 
B) Inductive and steric 
C) Inductive and resonance 
D) Resonance and electronic C

Question 4

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

Accepted Answer

A) ¾ CHO 
B) ¾ COOH 
C) ¾ NHCOR 
D) ¾ CN 
A) ¾ CHO 
B) ¾ COOH 
C) ¾ NHCOR 
D) ¾ CN

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

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

Accepted Answer

A) CH3O ¾ 
B) Cl ¾ 
C) NO2 ¾ 
D) HSO3¾ 
A) CH3O ¾ 
B) Cl ¾ 
C) NO2 ¾ 
D) HSO3¾

Question 7

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 8

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 9

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 10

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 11

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 12

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 13

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 14

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 15

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 16

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 17

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 18

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 19

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

Accepted Answer

A) HO ¾ 
B) CH3NH ¾ 
C) CH3O ¾ 
D) (CH3)3N+¾ 
A) HO ¾ 
B) CH3NH ¾ 
C) CH3O ¾ 
D) (CH3)3N+¾

Question 20

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

Exam 18: Reactions of Aromatic Compounds

Gradable: automatic Rank the following compounds in order of decreasing reactivity in electrophilic aromatic substitution.

Why is the nitro group a meta director?

What are the two effects that have to be considered to determine the influence a substituent will have on electrophilic aromatic substitution?

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

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

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

What is the product of the following reaction?

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

What is the electrophile in aromatic sulfonation?

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

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

Which of the following substituents is a meta director?

What is the major 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?

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

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

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

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

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

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

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