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Which of the following is the reactive intermediate formed in the electrophilic nitration of nitrobenzene with HNO3 and H2SO4? Which of the following is the reactive intermediate formed in the electrophilic nitration of nitrobenzene with HNO<sub>3</sub> and H<sub>2</sub>SO<sub>4</sub>?   A) 1 B) 2 C) 3 D) 4


A) 1
B) 2
C) 3
D) 4

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

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Which of the following substituents is ortho/para directing and deactivating in electrophilic aromatic substitution reactions?


A) COCH3
B) NH3
C) Br
D) CH2CH3

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

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Which of the following is not true about benzynes?


A) They are planar
B) They are formed upon dehydrohalogenation of aryl halides
C) They are aromatic
D) They are intermediates in nucleophilic aromatic substitution reaction which take place by an addition-elimination mechanism

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

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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) 1 B) 2 C) 3 D) 4


A) 1
B) 2
C) 3
D) 4

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

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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) 1 B) 2 C) 3 D) 4


A) 1
B) 2
C) 3
D) 4

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

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In electrophilic aromatic substitution reactions, the following molecule are considered to be ______ reactive than benzene In electrophilic aromatic substitution reactions, the following molecule are considered to be ______ reactive than benzene

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What is the major organic product obtained from the following sequence of reactions? What is the major organic product obtained from the following sequence of reactions?   A) 1 B) 2 C) 3 D) 4


A) 1
B) 2
C) 3
D) 4

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

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All of the following can act as an electrophile in an electrophilic aromatic substitution reaction. SO3 (CH3)3C+ NO2+

A) True
B) False

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MATCHING MATCH a structure or term from the following list with each description below. Place the letter of the structure or term in the blank to the left of the description. -______ The reactive electrophile in Friedel-Crafts acylation reactions.


A) benzyne
B) "+NO2"
C) R3C+
D) electron-donating
E) "+NO"
F) Meisenheimer complex
G) MATCHING MATCH a structure or term from the following list with each description below. Place the letter of the structure or term in the blank to the left of the description. -______ The reactive electrophile in Friedel-Crafts acylation reactions. A) benzyne B)  <sup>+</sup>NO<sub>2</sub>  C) R<sub>3</sub>C<sup>+</sup> D) electron-donating E)  <sup>+</sup>NO  F) Meisenheimer complex G)   H) electron-withdrawing
H) electron-withdrawing

I) A) and E)
J) B) and C)

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Provide the structure (a single resonance contributor) of the key intermediate in the following reaction . Provide the structure (a single resonance contributor) of the key intermediate in the following reaction .

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Which of the following undergoes the most rapid acylation upon treatment with acetyl chloride and AlCl3?


A) benzene
B) toluene
C) chlorobenzene
D) 1,4-dichlorobenzene

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

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Which of the following is the reactive intermediate formed in the electrophilic bromination of toluene with Br2, FeBr3? Which of the following is the reactive intermediate formed in the electrophilic bromination of toluene with Br<sub>2</sub>, FeBr<sub>3</sub>?   A) 1 B) 2 C) 3 D) 4


A) 1
B) 2
C) 3
D) 4

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

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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) 1 B) 2 C) 3 D) 4


A) 1
B) 2
C) 3
D) 4

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

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What is the electrophile in the reaction of benzene with a mixture of nitric acid and sulfuric acid?


A) HONO
B) NO+
C) NO2+
D) benzene

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

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What type of intermediate is formed upon treatment of 1-chloro-2,4-dinitrobenzene with sodium hydroxide to give 2,4-dinitrophenol?


A) Meisenheimer complex
B) benzyne
C) cyclohexadienyl cation
D) benzyl radical

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

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Which of the following cannot be prepared from benzene in two synthetic steps? Which of the following cannot be prepared from benzene in two synthetic steps?   A) 1 B) 2 C) 3 D) 4


A) 1
B) 2
C) 3
D) 4

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

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What is the role of AlCl3 in Friedel Crafts acylations using acid chlorides?


A) Lewis acid
B) electrophile
C) base
D) nucleophile

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

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Which of the following sets of substituents are all deactivating groups in electrophilic aromatic substitution reactions?


A) Cl, OH, CH2CH3
B) CH3, Br, COCH3
C) CH3, NH2, OH
D) COCH3, NO2, Br

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

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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?

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The number of mononitro products that can be produced when the following reactant is treated with nitric and sulfuric acids is _______. The number of mononitro products that can be produced when the following reactant is treated with nitric and sulfuric acids is _______.

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