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


A) CH3O ¾
B) Cl ¾
C) NO2 ¾
D) HSO3¾

E) None of the above
F) All of the above

Correct Answer

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


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

E) A) and B)
F) All of the above

Correct Answer

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


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

E) C) and D)
F) None of the above

Correct Answer

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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 least reactive in electrophilic aromatic substitution? Consider the tetracyclic aromatic compound drawn below,with rings labelled as I,II,III,and IV.Which of the four rings is least reactive in electrophilic aromatic substitution? A) I B) II C) III D) IV


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

E) A) and B)
F) All of the above

Correct Answer

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What is the major product of electrophilic addition of HBr to the following alkene? What is the major product of electrophilic addition of HBr to the following alkene? A) I B) II C) III D) IV


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

E) A) and D)
F) All of the above

Correct Answer

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In addition to the product shown,what other product is formed in the following reaction? In addition to the product shown,what other product is formed in the following reaction? A) I B) II C) III D) IV


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

E) A) and D)
F) None of the above

Correct Answer

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Which of the following substituents is a meta director?


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

E) None of the above
F) C) and D)

Correct Answer

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What is the electrophile in aromatic nitration?


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

E) B) and D)
F) C) and D)

Correct Answer

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What is the best choice of reagent to bring about the following transformation? What is the best choice of reagent to bring about the following transformation? A) [1] LiAlH<sub>4</sub>; [2] H<sub>2</sub>O B) Zn (Hg) ,HCl C) NH<sub>3</sub>,NaOH D) H<sub>2</sub>,Pd-C


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

E) None of the above
F) B) and C)

Correct Answer

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

E) B) and C)
F) None of the above

Correct Answer

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What is the best choice of reagent to bring about the following transformation? What is the best choice of reagent to bring about the following transformation? A) [1] LiAlH<sub>4</sub>; [2]H<sub>2</sub>O B) Zn (Hg) ,HCl C) NH<sub>3</sub>,NaOH D) H<sub>2</sub>,Pd-C


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

E) B) and D)
F) B) and C)

Correct Answer

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What are the two distinct pathways for nucleophilic aromatic substitution?


A) Addition-substitution and substitution-addition
B) Addition-elimination and elimination-addition
C) Addition-addition and elimination-elimination
D) Elimination-substitution and substitution-elimination

E) A) and C)
F) A) and B)

Correct Answer

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What is the major organic product obtained from the following reaction? What is the major organic product obtained from the following reaction? A) I B) II C) III D) IV


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

E) A) and C)
F) B) and C)

Correct Answer

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What is the structure of compound A? What is the structure of compound A? A) I B) II C) III D) IV


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

E) C) and D)
F) B) and D)

Correct Answer

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

E) All of the above
F) A) and C)

Correct Answer

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What reagents would be necessary to produce the following product from benzene? What reagents would be necessary to produce the following product from benzene? A) CH<sub>3</sub>Cl,AlCl<sub>3</sub> 2.HNO<sub>3</sub>,H<sub>2</sub>SO<sub>4</sub> 3.KMnO<sub>4</sub> B) HNO<sub>3</sub>,H<sub>2</sub>SO<sub>4</sub> 2.CH<sub>3</sub>Cl,AlCl<sub>3</sub> 3.KMnO<sub>4</sub> C) KMnO<sub>4</sub> 2.CH<sub>3</sub>Cl,AlCl<sub>3</sub> 3.HNO<sub>3</sub>,H<sub>2</sub>SO<sub>4</sub> D) KMnO<sub>4</sub> 2.HNO<sub>3</sub>,H<sub>2</sub>SO<sub>4</sub> 3.CH<sub>3</sub>Cl,AlCl<sub>3</sub>


A) CH3Cl,AlCl3 2.HNO3,H2SO4 3.KMnO4
B) HNO3,H2SO4 2.CH3Cl,AlCl3 3.KMnO4
C) KMnO4 2.CH3Cl,AlCl3 3.HNO3,H2SO4
D) KMnO4 2.HNO3,H2SO4 3.CH3Cl,AlCl3

E) A) and B)
F) C) and D)

Correct Answer

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


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

E) None of the above
F) B) and C)

Correct Answer

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


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.

E) A) and B)
F) B) and C)

Correct Answer

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What reagents would be necessary to produce the following product from benzene? What reagents would be necessary to produce the following product from benzene? A) CH<sub>3</sub>CH<sub>2</sub>C(O) Cl,AlCl<sub>3</sub> 2.HNO<sub>3</sub>,H<sub>2</sub>SO<sub>4</sub> 3.Zn(Hg) ,HCl B) HNO<sub>3</sub>,H<sub>2</sub>SO<sub>4</sub> 2.CH<sub>3</sub>CH<sub>2</sub>C(O) Cl,AlCl<sub>3</sub> 3.Zn(Hg) ,HCl C) CH<sub>3</sub>CH<sub>2</sub>C(O) Cl,AlCl<sub>3</sub> 2.Zn(Hg) ,HCl 3.HNO<sub>3</sub>,H<sub>2</sub>SO<sub>4</sub> D) Zn(Hg) ,HCl 2.CH<sub>3</sub>CH<sub>2</sub>C(O) Cl,AlCl<sub>3</sub> 3.HNO<sub>3</sub>,H<sub>2</sub>SO<sub>4</sub>


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

E) B) and D)
F) None of the above

Correct Answer

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What is the major organic product of the following reaction? What is the major organic product of the following reaction? A) I B) II C) III D) IV


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

E) A) and B)
F) A) and C)

Correct Answer

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