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


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

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

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Why is sulfuric acid used in aromatic nitration?


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

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

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What is a major problem with Friedel-Crafts alkylation?


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 D)
F) None of the above

Correct Answer

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How can polyalkylation be minimized in Friedel-Crafts alkylation?


A) Use a large excess of alkyl halide relative to the aromatic compound.
B) Use a large excess of benzene relative to the alkyl halide.
C) Use an alkyl halide without a Lewis acid catalyst.
D) Use a large excess of the Lewis acid catalyst.

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

Correct Answer

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B

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) A) and C)

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) A) and D)
F) A) and C)

Correct Answer

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

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

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


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

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

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

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

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Why is the nitro group a meta director?


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

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

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Rank the following activating groups in order of decreasing strength of activation,listing the most activating first. Rank the following activating groups in order of decreasing strength of activation,listing the most activating first. A) IV > II > III > I B) II > III > IV > I C) III > IV > II > I D) II > IV > III > I


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

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

Correct Answer

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B

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

Correct Answer

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Which aryl fluoride reacts the fastest with NaOH? Which aryl fluoride reacts the fastest with NaOH? 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 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 B)
F) All 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) A) and D)
F) A) and C)

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

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

Correct Answer

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B

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