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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) A) and D)

Correct Answer

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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 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) B) and D)

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

Correct Answer

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

Correct Answer

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


A) Increasing the electronegativity of the halogen increases the reactivity of the aryl halide.
B) Increasing the number of electron-withdrawing groups increases the reactivity of the aryl halide.
C) Electron-withdrawing groups stabilize the intermediate carbanion, and lower the energy of the transition state.
D) When a nitro group is located meta to the halogen, the negative charge of the intermediate carbanion can be delocalized onto the NO2 group, thus stabilizing it.

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

Correct Answer

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


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

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

Correct Answer

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


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

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

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? <sup> </sup>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) B) and C)
F) A) and B)

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

Correct Answer

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Which of the following halides will not work as an electrophile in a Friedel-Crafts alkylation reaction? Which of the following halides will not work as an electrophile in a Friedel-Crafts alkylation 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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Which of the following statements about the mechanism of electrophilic aromatic substitution is not true?


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.

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

Correct Answer

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Which set of reagents would most likely bring about the following transformation? Which set of reagents would most likely bring about the following transformation? A) Br<sub>2</sub> and FeBr<sub>3</sub> B) NBS and light C) Br<sub>2</sub> in CCl<sub>4</sub> D) NaBr and H<sub>2</sub>O


A) Br2 and FeBr3
B) NBS and light
C) Br2 in CCl4
D) NaBr and H2O

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

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

Correct Answer

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