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Which of the following represents the energy levels of the molecular orbitals of cyclobutadiene? Which of the following represents the energy levels of the molecular orbitals of cyclobutadiene? A) 1 B) 2 C) 3 D) 4


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

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

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Consider the following structure. Consider the following structure. -Using the Hückel criteria, the compound would be ______________. -Using the Hückel criteria, the compound would be ______________.

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Which of the following compounds is aromatic?


A) ethane
B) cyclobutadiene
C) benzene
D) cyclooctatetraene

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

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What is the best choice of reagent to achieve the following reaction? What is the best choice of reagent to achieve the following reaction? A) Br<sub>2</sub>, CCl<sub>4</sub> B) HBr, H<sub>2</sub>O C) Br<sub>2</sub>, light D) NaBr


A) Br2, CCl4
B) HBr, H2O
C) Br2, light
D) NaBr

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


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

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

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Consider the following structure. Consider the following structure. The <sup>1</sup>H NMR spectrum of [14]annulene at -60<sup> \circ </sup>C shows two peaks, one at 0 ppm and one at 7.6 ppm. -The NMR data would seem to indicate that this compound is ____________. The 1H NMR spectrum of [14]annulene at -60 ∘\circ C shows two peaks, one at 0 ppm and one at 7.6 ppm. -The NMR data would seem to indicate that this compound is ____________.

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Which of the following has the compounds shown in the correct order of decreasing acidity (i.e., more acidic > less acidic) ? Which of the following has the compounds shown in the correct order of decreasing acidity (i.e., more acidic > less acidic) ? A) 1 > 2 > 3 B) 2 > 3 > 1 C) 3 > 2 > 1 D) 1 > 3 > 2


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

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

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What is the IUPAC name of the following compound? What is the IUPAC name of the following compound?

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4-chloro-3...

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The product of the following reaction would be 1-bromo-1-phenylethane. The product of the following reaction would be 1-bromo-1-phenylethane.

A) True
B) False

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The following compound is named (Z)-2,3-diphenyl-2-hexene. The following compound is named (Z)-2,3-diphenyl-2-hexene.

A) True
B) False

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Which of the following has the compounds shown in the correct order of decreasing acidity (i.e., more acidic > less acidic) ? Which of the following has the compounds shown in the correct order of decreasing acidity (i.e., more acidic > less acidic) ? A) 1 > 2 > 3 B) 2 > 3 > 1 C) 3 > 2 > 1 D) 1 > 3 > 2


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

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

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What is the IUPAC name of the following compound? What is the IUPAC name of the following compound? A) 1-bromo-2-fluoro-4-toluene B) 4-bromo-2-fluorotoluene C) 2-bromo-4-fluorophenol D) 4-bromo-2-fluoroxylene


A) 1-bromo-2-fluoro-4-toluene
B) 4-bromo-2-fluorotoluene
C) 2-bromo-4-fluorophenol
D) 4-bromo-2-fluoroxylene

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

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What is the IUPAC name of the following compound? What is the IUPAC name of the following compound?

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Which of the following does not undergo oxidation in the presence of H2CrO4? Which of the following does not undergo oxidation in the presence of H<sub>2</sub>CrO<sub>4</sub>? A) 1 B) 2 C) 3 D) 4


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

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

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Which of the following statements is not true about the structure of benzene?


A) the carbon-carbon bonds are all the same length
B) the structure rapidly transforms between two resonance contributors
C) the structure is an average of two resonance contributors
D) the ring of six carbon atoms is planar

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

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What is the hybridization of the oxygen atom of furan?


A) s
B) sp
C) sp2
D) sp3

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

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Provide a brief explanation of why the cyclopentadienyl anion (below) is aromatic. Your answer should identify the hybridization of each carbon atom and account for which electrons are in the pi system. Provide a brief explanation of why the cyclopentadienyl anion (below) is aromatic. Your answer should identify the hybridization of each carbon atom and account for which electrons are in the pi system.

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The all five carbons are sp2 hybridized. ...

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What is the intermediate in the reaction of ethylbenzene with NBS in the presence of benzoyl peroxide to give 1-bromo-1-phenylethane?


A) Benzylic anion
B) Benzylic cation
C) Benzylic radical
D) Benzylic carbene

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

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What are the relative positions of the substituents in the following structure? What are the relative positions of the substituents in the following structure? A) anti B) meta C) ortho D) para


A) anti
B) meta
C) ortho
D) para

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

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