Question 1

Which of these species is aromatic?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) V 
A) I 
B) II 
C) III 
D) IV 
E) V

Question 2

We now know that the two Kekulé structures for benzene are related in the following way:

Accepted Answer

A) They are each equally correct as a structure for benzene. 
B) Benzene is sometimes one structure and sometimes the other. 
C) The two structures are in a state of rapid equilibrium. 
D) Neither of the two structures adequately describes benzene; benzene is a resonance hybrid of the two. 
E) None of these choices. 
A) They are each equally correct as a structure for benzene. 
B) Benzene is sometimes one structure and sometimes the other. 
C) The two structures are in a state of rapid equilibrium. 
D) Neither of the two structures adequately describes benzene; benzene is a resonance hybrid of the two. 
E) None of these choices.

Question 3

How many monochloronaphthalenes are possible?

Accepted Answer

A) 2 
B) 3 
C) 4 
D) 5 
E) 6 
A) 2 
B) 3 
C) 4 
D) 5 
E) 6

Question 4

Draw the structure corresponding to the following name:
3-bromo-5-phenylaniline

Accepted Answer

The answer of Draw the structure corresponding to the following...

Question 5

In the molecular orbital model of the cyclopentadienyl cation,how many non-bonding molecular orbitals are there?

Accepted Answer

A) 1 
B) 2 
C) 3 
D) 4 
E) 0 
A) 1 
B) 2 
C) 3 
D) 4 
E) 0

Question 6

The compound illustrated below is found to have the following signals in its broadband decoupled 13C spectrum:
190.77,140.91,134.82,130.89 and 129.45 $\delta$
Using resonance theory,assign the C-13 peaks to the appropriate carbons.

Accepted Answer

The answer of The compound illustrated below is found to...

Question 7

Which dichlorobenzene might theoretically yield three mononitro products?

Accepted Answer

A) o-Dichlorobenzene 
B) m-Dichlorobenzene 
C) p-Dichlorobenzene 
D) None of these choices. 
E) All of these choices. 
A) o-Dichlorobenzene 
B) m-Dichlorobenzene 
C) p-Dichlorobenzene 
D) None of these choices. 
E) All of these choices.

Question 8

Which dihydroxybenzene can yield only one mononitro derivative?

Accepted Answer

A) o-Dihydroxybenzene 
B) m-Dihydroxybenzene 
C) p-Dihydroxybenzene 
D) More than one of these choices. 
E) None of these choices. 
A) o-Dihydroxybenzene 
B) m-Dihydroxybenzene 
C) p-Dihydroxybenzene 
D) More than one of these choices. 
E) None of these choices.

Question 9

In the molecular orbital model of cyclobutadiene,how many pairs of degenerate $\pi$-antibonding molecular orbitals are there?

Accepted Answer

A) 1 
B) 2 
C) 3 
D) 4 
E) 0 
A) 1 
B) 2 
C) 3 
D) 4 
E) 0

Question 10

Benzene,while unusually unreactive with electrophiles,will react under certain conditions.However,when it does react,it does so by ___ rather than by addition.

Accepted Answer

The answer of Benzene,while unusually unreactive with electrophiles,will react under...

Question 11

Which of the following would you expect to be antiaromatic?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) V 
A) I 
B) II 
C) III 
D) IV 
E) V

Question 12

Explain briefly why cyclopentadiene readily reacts with strong bases.

Accepted Answer

The acidity of a substance can be often

Question 13

The heats of hydrogenation for cyclohexene and benzene are given below.Calculate the resonance stabilization energy of benzene.
C6H10 + H2 $\to$ C6H12 $\Delta$Ho = -120 kJ/mol
C6H6 + 3H2 $\to$ C6H12 $\Delta$Ho = -208 kJ/mol

Accepted Answer

The resonance stabilization energy of be

Question 14

Which of these would you expect to have significant resonance stabilization energy?

Accepted Answer

A) I 
B) II 
C) III 
D) All of these choices. 
E) None of these choices. 
A) I 
B) II 
C) III 
D) All of these choices. 
E) None of these choices.

Question 15

In the molecular orbital model of cyclobutadiene,how many non-bonding molecular orbitals are there?

Accepted Answer

A) 1 
B) 2 
C) 3 
D) 4 
E) 0 
A) 1 
B) 2 
C) 3 
D) 4 
E) 0

Question 16

How many different dichloronitrobenzenes are possible?

Accepted Answer

A) 8 
B) 7 
C) 6 
D) 5 
E) 4 
A) 8 
B) 7 
C) 6 
D) 5 
E) 4

Question 17

Which of the following is true of benzene?

Accepted Answer

A) Benzene tends to undergo addition rather than substitution reactions. 
B) All of the hydrogen atoms of benzene are equivalent. 
C) The carbon-carbon bonds of benzene are alternately short and long around the ring. 
D) The benzene ring is a distorted hexagon. 
E) Benzene has the stability expected for cyclohexatriene. 
A) Benzene tends to undergo addition rather than substitution reactions. 
B) All of the hydrogen atoms of benzene are equivalent. 
C) The carbon-carbon bonds of benzene are alternately short and long around the ring. 
D) The benzene ring is a distorted hexagon. 
E) Benzene has the stability expected for cyclohexatriene.

Question 18

Xylene is the name commonly assigned to:

Accepted Answer

A) Hydroxybenzene 
B) Aminobenzene 
C) Dimethylbenzene 
D) Ethylbenzene 
E) Methoxybenzene 
A) Hydroxybenzene 
B) Aminobenzene 
C) Dimethylbenzene 
D) Ethylbenzene 
E) Methoxybenzene

Question 19

How many resonances would be expected in the broadband proton-decoupled 13C spectrum of:

Accepted Answer

A) 5 
B) 6 
C) 7 
D) 8 
E) 9 
A) 5 
B) 6 
C) 7 
D) 8 
E) 9

Question 20

3-Chloro-4-nitrobenzoic acid is:

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) V 
A) I 
B) II 
C) III 
D) IV 
E) V

Exam 14: Aromatic Compounds

Which of these species is aromatic?

We now know that the two Kekulé structures for benzene are related in the following way:

How many monochloronaphthalenes are possible?

Draw the structure corresponding to the following name: 3-bromo-5-phenylaniline

In the molecular orbital model of the cyclopentadienyl cation,how many non-bonding molecular orbitals are there?

The compound illustrated below is found to have the following signals in its broadband decoupled 13C spectrum: 190.77,140.91,134.82,130.89 and 129.45 δ\deltaδ Using resonance theory,assign the C-13 peaks to the appropriate carbons.

Which dichlorobenzene might theoretically yield three mononitro products?

Which dihydroxybenzene can yield only one mononitro derivative?

In the molecular orbital model of cyclobutadiene,how many pairs of degenerate π\piπ -antibonding molecular orbitals are there?

Benzene,while unusually unreactive with electrophiles,will react under certain conditions.However,when it does react,it does so by ___ rather than by addition.

Which of the following would you expect to be antiaromatic?

Explain briefly why cyclopentadiene readily reacts with strong bases.

The heats of hydrogenation for cyclohexene and benzene are given below.Calculate the resonance stabilization energy of benzene. C6H10 + H2 →\to→ C6H12 Δ\DeltaΔ Ho = -120 kJ/mol C6H6 + 3H2 →\to→ C6H12 Δ\DeltaΔ Ho = -208 kJ/mol

Which of these would you expect to have significant resonance stabilization energy?

In the molecular orbital model of cyclobutadiene,how many non-bonding molecular orbitals are there?

How many different dichloronitrobenzenes are possible?

Which of the following is true of benzene?

Xylene is the name commonly assigned to:

How many resonances would be expected in the broadband proton-decoupled 13C spectrum of:

3-Chloro-4-nitrobenzoic acid is:

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In the molecular orbital model of cyclobutadiene,how many pairs of degenerate $\pi$ -antibonding molecular orbitals are there?

The heats of hydrogenation for cyclohexene and benzene are given below.Calculate the resonance stabilization energy of benzene. C₆H₁₀ + H₂ $\to$ C₆H₁₂ $\Delta$ H^o = -120 kJ/mol C₆H₆ + 3H₂ $\to$ C₆H₁₂ $\Delta$ H^o = -208 kJ/mol

How many resonances would be expected in the broadband proton-decoupled ¹³C spectrum of: