Exam 22: Reactions of Benzene and Its Derivatives

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Consider the reaction below to answer the following question(s). Consider the reaction below to answer the following question(s).   Fill in the blank with the appropriate letter or response. -The name of product D is ________________________. Fill in the blank with the appropriate letter or response. -The name of product D is ________________________.

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What is the major organic product obtained from the following sequence of reactions (if a reaction is likely to give you a mixture of ortho and para disubstituted compounds you should assume that they can be separated; continue the synthesis with either one)? What is the major organic product obtained from the following sequence of reactions (if a reaction is likely to give you a mixture of ortho and para disubstituted compounds you should assume that they can be separated; continue the synthesis with either one)?

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Which of the following are valid resonance structures of the electophile involved in Friedel-Crafts acylation of benzene upon treatment with CH3COCl and AlCl3? Which of the following are valid resonance structures of the electophile involved in Friedel-Crafts acylation of benzene upon treatment with CH<sub>3</sub>COCl and AlCl<sub>3</sub>?

(Multiple Choice)
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Which of the following sets of substituents are all ortho/para directing in electrophilic aromatic substitution reactions?

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Which of the following undergoes the most rapid sulfonation upon treatment with fuming sulfuric acid?

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Which mechanism accounts for the reaction of 4-bromotoluene with sodium amide to form a mixture of 3- and 4-aminotoluene?

(Multiple Choice)
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Consider the following compounds. Consider the following compounds.         Use the number of the compound to answer the following question. Place the number in the blank provided. -The compound that is the most reactive to nitration is ______. Consider the following compounds.         Use the number of the compound to answer the following question. Place the number in the blank provided. -The compound that is the most reactive to nitration is ______. Consider the following compounds.         Use the number of the compound to answer the following question. Place the number in the blank provided. -The compound that is the most reactive to nitration is ______. Consider the following compounds.         Use the number of the compound to answer the following question. Place the number in the blank provided. -The compound that is the most reactive to nitration is ______. Use the number of the compound to answer the following question. Place the number in the blank provided. -The compound that is the most reactive to nitration is ______.

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Which of the following is the reactive intermediate in the nucleophilic substitution of 4-bromo-1-toluene with sodium amide? Which of the following is the reactive intermediate in the nucleophilic substitution of 4-bromo-1-toluene with sodium amide?

(Multiple Choice)
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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?

(Multiple Choice)
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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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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?

(Multiple Choice)
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The predominant product from sequential nitration and bromination of benzenesulfonic acid is shown below. The predominant product from sequential nitration and bromination of benzenesulfonic acid is shown below.

(True/False)
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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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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?

(Multiple Choice)
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Why does anisole undergo bromination with Br2 in the absence of FeBr3 whereas bromination of benzene requires the presence of FeBr3?

(Multiple Choice)
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Consider the reaction below to answer the following question(s). Consider the reaction below to answer the following question(s).   Fill in the blank with the appropriate letter or response. -The Lewis acid catalyst in the reaction is _____. Fill in the blank with the appropriate letter or response. -The Lewis acid catalyst in the reaction is _____.

(Multiple Choice)
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Tetracyclone (shown below) is often used to trap benzynes as Diels-Alder adducts. Tetracyclone (shown below) is often used to trap benzynes as Diels-Alder adducts.   The structure of the Diels-Alder adduct that results when benzyne is trapped by tetracyclone would be  The structure of the Diels-Alder adduct that results when benzyne is trapped by tetracyclone would be Tetracyclone (shown below) is often used to trap benzynes as Diels-Alder adducts.   The structure of the Diels-Alder adduct that results when benzyne is trapped by tetracyclone would be

(True/False)
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Which of the following chlorobenzenes produces a single isomer upon treatment with NaNH2? Which of the following chlorobenzenes produces a single isomer upon treatment with NaNH<sub>2</sub>?

(Multiple Choice)
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Which of the following reactions or reaction sequences will not give isopropylbenzene as the major product?

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What is the major organic product obtained from the following reaction (assume that mixtures of ortho and para disubstituted compounds can be separated; continue the synthesis with either one)? What is the major organic product obtained from the following reaction (assume that mixtures of ortho and para disubstituted compounds can be separated; continue the synthesis with either one)?

(Essay)
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