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

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 3

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

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  All of the above 
E)  None of the above 
A)  I 
B)  II 
C)  III 
D)  All of the above 
E)  None of the above

Question 4

How many resonances would be expected in the broad-band decoupled C-13 spectra 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

Cyclopentadiene is unusually acidic for a hydrocarbon.An explanation for this is the following statement.

Accepted Answer

A)  The carbon atoms of cyclopentadiene are all sp2-hybridized. 
B)  Cyclopentadiene is aromatic. 
C)  Removal of a proton from cyclopentadiene yields an aromatic anion. 
D)  Removal of a hydrogen atom from cyclopentadiene yields a highly stable free radical. 
E)  Removal of a hydride ion from cyclopentadiene produces an aromatic cation. 
A)  The carbon atoms of cyclopentadiene are all sp2-hybridized. 
B)  Cyclopentadiene is aromatic. 
C)  Removal of a proton from cyclopentadiene yields an aromatic anion. 
D)  Removal of a hydrogen atom from cyclopentadiene yields a highly stable free radical. 
E)  Removal of a hydride ion from cyclopentadiene produces an aromatic cation.

Question 6

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 7

Which of the following would you expect to be aromatic?

Accepted Answer

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

Question 8

In the molecular orbital model of benzene,the six p-orbitals combine to form how many molecular orbitals?

Accepted Answer

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

Question 9

Draw all significant resonance structures for the cyclopentadienyl anion.

Accepted Answer

The answer of Draw all significant resonance structures for the...

Question 10

Predict the product of the reaction of one equivalent of hydrochloric acid with the organic
compound shown:

Accepted Answer

The answer of Predict the product of the reaction of...

Question 11

Which of the following would you expect to be aromatic?

Accepted Answer

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

Question 12

Briefly explain why the aromatic hydrocarbon azulene,C10H8,possesses a significant dipole moment.Use diagrams as needed to illustrate/clarify your answer.

Accepted Answer

Azulene has the bicyclic structure shown

Question 13

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

Question 14

Explain briefly why cyclopentadiene readily reacts with strong bases.

Accepted Answer

The acidity of a substance can be often

Question 15

Which is the only one of these reagents which will react with benzene under the specified conditions?

Accepted Answer

A)  Cl2,FeCl3,heat 
B)  H2,25°C 
C)  Br2/CCl4,25°C,dark 
D)  KMnO4/H2O,25°C 
E)  H3O+,heat 
A)  Cl2,FeCl3,heat 
B)  H2,25°C 
C)  Br2/CCl4,25°C,dark 
D)  KMnO4/H2O,25°C 
E)  H3O+,heat

Question 16

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 17

Which of the following statements about cyclooctatetraene is NOT true?

Accepted Answer

A)  The compound rapidly decolorizes Br2/CCl4 solutions. 
B)  The compound rapidly decolorizes aqueous solutions of KMnO4. 
C)  The compound readily adds hydrogen. 
D)  The compound is nonplanar. 
E)  The compound is comparable to benzene in stability. 
A)  The compound rapidly decolorizes Br2/CCl4 solutions. 
B)  The compound rapidly decolorizes aqueous solutions of KMnO4. 
C)  The compound readily adds hydrogen. 
D)  The compound is nonplanar. 
E)  The compound is comparable to benzene in stability.

Question 18

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 19

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 20

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

Exam 14: Aromatic Compounds

Which of these species is aromatic?

Which of these species is aromatic?

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

How many resonances would be expected in the broad-band decoupled C-13 spectra of:

Cyclopentadiene is unusually acidic for a hydrocarbon.An explanation for this is the following statement.

Which of these species is aromatic?

Which of the following would you expect to be aromatic?

In the molecular orbital model of benzene,the six p-orbitals combine to form how many molecular orbitals?

Draw all significant resonance structures for the cyclopentadienyl anion.

Predict the product of the reaction of one equivalent of hydrochloric acid with the organic compound shown:

Which of the following would you expect to be aromatic?

Briefly explain why the aromatic hydrocarbon azulene,C10H8,possesses a significant dipole moment.Use diagrams as needed to illustrate/clarify your answer.

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

Explain briefly why cyclopentadiene readily reacts with strong bases.

Which is the only one of these reagents which will react with benzene under the specified conditions?

Which of the following would you expect to be antiaromatic?

Which of the following statements about cyclooctatetraene is NOT true?

How many different dihydroxybromobenzenes are possible?

Which of these species is aromatic?

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.

Carbon Compounds and Chemical Bonds

Representative Carbon Compounds: Functional Groups, Intermolecular Forces, and Infrared Ir Spectroscopy

An Introduction to Organic Reactions: Acids and Bases

Alkanes: Nomenclature, Conformational Analysis, and an Introduction to Synthesis

Stereochemistry: Chiral Molecules

Ionic Reactions - Nucleophilic Substitution and Elimination Reactions of Alkyl Halides

Alkenes and Alkynes I: Properties and Synthesis, Elimination Reactions of Alkyl Halides

Alkenes and Alkynes Ii: Addition Reactions

Nuclear Magnetic Resonance and Mass Spectrometry: Tools for Structure Determination

Radical Reactions

Alcohols and Ethers

Alcohols From Carbonyl Compounds Oxidation-Reduction and Organometallic Compounds

Conjugated Unsaturated Systems

Reactions of Aromatic Compounds

Aldehydes and Ketones I Nucleophilic Addition to the Carbonyl Group

Aldehydes and Ketones Ii Aldol Reactions

Carboxylic Acids and Their Derivatives Nucleophilic Addition - Elimination at the Acyl Carbon

Synthesis and Reactions of Beta-Dicarbonyl Compounds: More Chemistry of Enolate Ions

Amines

Phenols and Aryl Halides: Nucleophilic Aromatic Substitution

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

Filters

Briefly explain why the aromatic hydrocarbon azulene,C₁₀H₈,possesses a significant dipole moment.Use diagrams as needed to illustrate/clarify your answer.