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Which of the following is another name for cyclobutadiene?


A) [2]annulene
B) [4]annulene
C) [6]annulene
D) Dewar benzene
E) antibenzene

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

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Which of the following structures is aromatic?


A) Which of the following structures is aromatic? A)    B)    C)    D)    E)
B) Which of the following structures is aromatic? A)    B)    C)    D)    E)
C) Which of the following structures is aromatic? A)    B)    C)    D)    E)
D) Which of the following structures is aromatic? A)    B)    C)    D)    E)
E) Which of the following structures is aromatic? A)    B)    C)    D)    E)

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

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Rank the following in order of increasing pKa (from lowest to highest pKa) . Rank the following in order of increasing pKa (from lowest to highest pKa) .   A)  1 < 2 < 3 B)  3 < 2 < 1 C)  2 < 1 < 3 D)  3 < 1 < 2 E)  2 < 3 < 1


A) 1 < 2 < 3
B) 3 < 2 < 1
C) 2 < 1 < 3
D) 3 < 1 < 2
E) 2 < 3 < 1

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

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Which of the following compounds has the most signals in the proton-decoupled 13C NMR spectrum?


A) o-dibromobenzene
B) m-dibromobenzene
C) p-dibromobenzene
D) 1,3,5-tribromobenzene
E) 1,2,3,4-tetrabromobenzene

F) B) and D)
G) A) and B)

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Provide the structure of the major organic product which results when phenanthrene is treated with Br2 in carbon tetrachloride.

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Which sequence ranks the indicated protons in order of increasing acidity? Which sequence ranks the indicated protons in order of increasing acidity?   A)  1 < 2 < 3 B)  2 < 3 < 1 C)  3 < 1 < 2 D)  3 < 2 < 1


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

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

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Provide an acceptable name for the compound below. Provide an acceptable name for the compound below.

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para-dichl...

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Provide the structure of anisole.

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Which of the following is the same as the tropylium ion?


A) cycloheptatrienyl cation
B) cycloheptatrienyl anion
C) cyclopentadienyl cation
D) cyclopentadienyl anion
E) cyclopropenyl anion

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

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Provide the name of the compound shown below. Provide the name of the compound shown below.

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o-chlorobe...

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Provide the structure of 2-bromo-4-chlorobenzoic acid.

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How many distinct nodal planes which are perpendicular to the molecular plane are present in the π4* orbital of benzene?


A) 0
B) 1
C) 2
D) 4
E) 5

F) B) and D)
G) B) and E)

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What is the bond order of the carbon-carbon bonds in benzene?


A) 0.5
B) 1
C) 1.5
D) 2
E) 3

F) D) and E)
G) C) and D)

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Classify pyrrole as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.

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Classify the compound below as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network. Classify the compound below as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.

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Classify pyridine as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.

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Provide the structure of m-nitrophenol.

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Classify the compound below as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network. Classify the compound below as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.

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Which is more stable, cyclobutadiene or 1,3-butadiene? Explain.

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1,3-Butadiene is more stable. ...

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Which of the following is also an acceptable name for 1,3,5-trimethylbenzene?


A) styrene
B) mesitylene
C) cumene
D) cymene
E) 1,3,5-xylene

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

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