Question 1

Which of the following is NOT true of benzene?

Accepted Answer

A) Benzene tends to undergo substitution rather than addition reactions,even though it has a high index of hydrogen deficiency. 
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) Only one o-dichlorobenzene has ever been found. 
E) Benzene is more stable than the hypothetical compound 1,3,5-cyclohexatriene. 
A) Benzene tends to undergo substitution rather than addition reactions,even though it has a high index of hydrogen deficiency. 
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) Only one o-dichlorobenzene has ever been found. 
E) Benzene is more stable than the hypothetical compound 1,3,5-cyclohexatriene. C

Question 2

Which reagent(s)/technique would serve to distinguish between azulene and bicyclo[5.3.0]decane?

Accepted Answer

A) Br2,CCl4 
B) KMnO4,OH-,H2O 
C) NMR Spectroscopy 
D) NaBH4,H2O 
E) Two of these choices. 
A) Br2,CCl4 
B) KMnO4,OH-,H2O 
C) NMR Spectroscopy 
D) NaBH4,H2O 
E) Two of these choices. C

Question 3

Draw all significant resonance structures for azulene,C10H8

Accepted Answer

Question 4

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

Accepted Answer

A) 1 
B) 2 
C) 3 
D) 4 
E) 5 
A) 1 
B) 2 
C) 3 
D) 4 
E) 5

Question 5

4-Bromo-2-nitroaniline is:

Accepted Answer

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

Question 6

Which of the following would you expect to be aromatic?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) All of these choices. 
A) I 
B) II 
C) III 
D) IV 
E) All of these choices.

Question 7

How many equivalent resonance structures can be written for the cyclobutadienyl dication?

Accepted Answer

A) 1 
B) 2 
C) 3 
D) 4 
E) No equivalent resonance forms can be drawn. 
A) 1 
B) 2 
C) 3 
D) 4 
E) No equivalent resonance forms can be drawn.

Question 8

Which of the following would you expect to be aromatic?

Accepted Answer

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

Question 9

Anisole is the name commonly assigned to:

Accepted Answer

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

Question 10

Draw all significant resonance structures for pyridine,C6H5N

Accepted Answer

Question 11

Which of the following statements regarding the cycloheptatrienyl radical is correct?

Accepted Answer

A) It is aromatic. 
B) It is not aromatic. 
C) It obeys Hückel's rule. 
D) It undergoes reactions characteristic of benzene. 
E) It has a closed shell of 6 pi electrons. 
A) It is aromatic. 
B) It is not aromatic. 
C) It obeys Hückel's rule. 
D) It undergoes reactions characteristic of benzene. 
E) It has a closed shell of 6 pi electrons.

Question 12

How many different dihydroxybromobenzenes 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 13

Which of the following statements regarding the cyclopentadienyl cation is correct?

Accepted Answer

A) It is aromatic. 
B) It is not aromatic. 
C) It obeys Hückel's rule. 
D) It undergoes reactions characteristic of benzene. 
E) It has a closed shell of 6 pi electrons. 
A) It is aromatic. 
B) It is not aromatic. 
C) It obeys Hückel's rule. 
D) It undergoes reactions characteristic of benzene. 
E) It has a closed shell of 6 pi electrons.

Question 14

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

Accepted Answer

A) 1 
B) 2 
C) 3 
D) 4 
E) 5 
A) 1 
B) 2 
C) 3 
D) 4 
E) 5

Question 15

Hückel's Rule requires ___ $\pi$ electrons for an aromatic compound.

Accepted Answer

The answer of Hückel's Rule requires ___ $\pi$ electrons for...

Question 16

Why would 1,3-cyclohexadiene undergo dehydrogenation readily?

Accepted Answer

A) It is easily reduced. 
B) Hydrogen is a small molecule. 
C) 1,3-Cyclohexadiene has no resonance energy. 
D) It would gain considerable stability by becoming benzene. 
E) It would not undergo dehydrogenation. 
A) It is easily reduced. 
B) Hydrogen is a small molecule. 
C) 1,3-Cyclohexadiene has no resonance energy. 
D) It would gain considerable stability by becoming benzene. 
E) It would not undergo dehydrogenation.

Question 17

Which reagent(s)would serve as the basis for a simple chemical test that would distinguish between benzene and 1-hexene?

Accepted Answer

A) NaOH in H2O 
B) Br2 in CCl4 
C) AgNO3 in C2H5OH 
D) NaHSO3 in H2O 
E) None of these choices. 
A) NaOH in H2O 
B) Br2 in CCl4 
C) AgNO3 in C2H5OH 
D) NaHSO3 in H2O 
E) None of these choices.

Question 18

Although all bond lengths in benzene are identical,that is not always true for all aromatic compounds.In naphthalene,for instance,the C1-C2 bond is shorter than the C2-C3 bond.Explain,using resonance theory.

Accepted Answer

The major resonance structures for napht

Question 19

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

Accepted Answer

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

Question 20

Molecular orbitals of equal energy are referred to as ___ orbitals.

Accepted Answer

The answer of Molecular orbitals of equal energy are referred...

Exam 14: Aromatic Compounds

Which of the following is NOT true of benzene?

Which reagent(s)/technique would serve to distinguish between azulene and bicyclo[5.3.0]decane?

Draw all significant resonance structures for azulene,C10H8

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

4-Bromo-2-nitroaniline is:

Which of the following would you expect to be aromatic?

How many equivalent resonance structures can be written for the cyclobutadienyl dication?

Which of the following would you expect to be aromatic?

Anisole is the name commonly assigned to:

Draw all significant resonance structures for pyridine,C6H5N

Which of the following statements regarding the cycloheptatrienyl radical is correct?

How many different dihydroxybromobenzenes are possible?

Which of the following statements regarding the cyclopentadienyl cation is correct?

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

Hückel's Rule requires ___ π\piπ electrons for an aromatic compound.

Why would 1,3-cyclohexadiene undergo dehydrogenation readily?

Which reagent(s)would serve as the basis for a simple chemical test that would distinguish between benzene and 1-hexene?

Although all bond lengths in benzene are identical,that is not always true for all aromatic compounds.In naphthalene,for instance,the C1-C2 bond is shorter than the C2-C3 bond.Explain,using resonance theory.

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

Molecular orbitals of equal energy are referred to as ___ orbitals.

The Basics

Families of Carbon

Acids and Bases

Nomenclature and Conformations of Alkanes and Cycloalkanes

Stereochemistry

Nucleophilic Reactions

Alkenes and Alkynes I

Alkenes and Alkynes II

Nuclear Magnetic Resonance and Mass Spectrometry

Radical Reactions

Alcohols and Ethers

Alcohols From Carbonyl Compounds

Conjugated Unsaturated Systems

Reactions of Aromatic Compounds

Aldehydes and Ketones

Carboxylic Acids and Their Derivatives

Reactions at the Α Carbon of Carbonyl Compounds

Condensation and Conjugate Addition Reactions of Carbonyl Compounds

Amines

Transition Metal Complexes

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

Filters

Draw all significant resonance structures for azulene,C₁₀H₈

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

Draw all significant resonance structures for pyridine,C₆H₅N

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

Hückel's Rule requires ___ $\pi$ electrons for an aromatic compound.

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