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


A) six atomic 2p-orbitals overlap to form six p-molecular orbitals
B) there are three bonding p-molecular orbitals and three p-antibonding molecular orbitals
C) the ground state electronic configuration of benzene has six electrons in three p-bonding molecular orbitals
D) the bonds alternate in length around the ring

E) None of the above
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?

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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) H<sub>2</sub>SO<sub>4</sub> B) NaOH, H<sub>2</sub>O C) K<sub>2</sub>Cr<sub>2</sub>O<sub>7</sub>, H<sub>2</sub>SO<sub>4</sub> D) LiAlH<sub>4</sub>


A) H2SO4
B) NaOH, H2O
C) K2Cr2O7, H2SO4
D) LiAlH4

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

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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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Which orbital contains the lone pair on the nitrogen atom of pyrrole?


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

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

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Which of the following compounds is antiaromatic?


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

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

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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 > 1 > 3 C) 3 > 2 > 1 D) 1 > 3 > 2


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

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

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

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The oxygen is sp2 hybridized. One lone p...

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What is the hybridization of the oxygen atom of furan?


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

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

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Which is the correct assignment of the names of the following substituted benzenes? Which is the correct assignment of the names of the following substituted benzenes? A) 1 = phenol; 2 = m-cresol; 3 = toluene B) 1 = m-cresol; 2 = resorcinol; 3 = m-xylene C) 1 = anisole; 2 = catechol; 3 = m-xylene D) 1 = m-cresol; 2 = anisole; 3 = cumene


A) 1 = phenol; 2 = m-cresol; 3 = toluene
B) 1 = m-cresol; 2 = resorcinol; 3 = m-xylene
C) 1 = anisole; 2 = catechol; 3 = m-xylene
D) 1 = m-cresol; 2 = anisole; 3 = cumene

E) All of the above
F) None of the above

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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 > 1 > 3 C) 3 > 2 > 1 D) 1 > 3 > 2


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

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

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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) H<sub>2</sub>SO<sub>4</sub> B) NaOH, H<sub>2</sub>O C) K<sub>2</sub>Cr<sub>2</sub>O<sub>7</sub>, H<sub>2</sub>SO<sub>4</sub> D) H<sub>2</sub>/Pd


A) H2SO4
B) NaOH, H2O
C) K2Cr2O7, H2SO4
D) H2/Pd

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

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Which orbitals contain the lone pairs on the nitrogen atoms labeled i and ii in the imidazole ring? Which orbitals contain the lone pairs on the nitrogen atoms labeled i and ii in the imidazole ring? A) i = sp<sup>2;</sup>; ii = sp<sup>3</sup> B) i = p<sup>;</sup>; ii = sp<sup>3</sup> C) i = p<sup>;</sup>; ii = sp<sup>3</sup>. D) i = p<sup>;</sup>; ii = sp<sup>2</sup>


A) i = sp2;; ii = sp3
B) i = p;; ii = sp3
C) i = p;; ii = sp3.
D) i = p;; ii = sp2

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

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How many p orbital electrons are present in cyclopentadienyl anion?


A) 4
B) 6
C) 7
D) 8

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

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What is the correct assignment of the names of the following heterocycles? What is the correct assignment of the names of the following heterocycles? A) 1 = pyrrole; 2 = thiophene; 3 = pyridine B) 1 = thiophene; 2 = furan; 3 = pyrrole C) 1 = pyridine; 2 = thiophene; 3 = furan D) 1 = pyridine; 2 = thiophene; 3 = pyrrole


A) 1 = pyrrole; 2 = thiophene; 3 = pyridine
B) 1 = thiophene; 2 = furan; 3 = pyrrole
C) 1 = pyridine; 2 = thiophene; 3 = furan
D) 1 = pyridine; 2 = thiophene; 3 = pyrrole

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

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Which of the following is true about [10]annulene? Which of the following is true about [10]annulene? A) [10]annulene is planar B) [10]annulene is nonaromatic C) [10]annulene undergoes addition reactions similar to simple alkenes D) [10]annulene has 10 pi electrons


A) [10]annulene is planar
B) [10]annulene is nonaromatic
C) [10]annulene undergoes addition reactions similar to simple alkenes
D) [10]annulene has 10 pi electrons

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

Correct Answer

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