Question 1

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

Accepted Answer

A)  Benzene is planar. 
B)  Benzene has three short double bonds alternating with three longer single bonds. 
C)  The electrons in the pi bonds are delocalized around the ring. 
D)  Benzene has six pi electrons. 
A)  Benzene is planar. 
B)  Benzene has three short double bonds alternating with three longer single bonds. 
C)  The electrons in the pi bonds are delocalized around the ring. 
D)  Benzene has six pi electrons. B

Question 2

Which of the following is not a criterion for antiaromaticity?

Accepted Answer

A)  The molecule must be cyclic. 
B)  The molecule must have (4n + 2) pi electrons. 
C)  The molecule must be planar. 
D)  The molecule must be completely conjugated. 
A)  The molecule must be cyclic. 
B)  The molecule must have (4n + 2) pi electrons. 
C)  The molecule must be planar. 
D)  The molecule must be completely conjugated. B

Question 3

Which of the following compounds is not aromatic?

Accepted Answer

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

Question 4

Which of the following compounds is not aromatic?

Accepted Answer

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

Question 5

What is the correct structure for anisole?

Accepted Answer

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

Question 6

What is the name of the following compound?

Accepted Answer

A)  2,6-dimethylbenzene 
B)  5-methyltoluene 
C)  anisole 
D)  1,3-dimethylbenzene 
A)  2,6-dimethylbenzene 
B)  5-methyltoluene 
C)  anisole 
D)  1,3-dimethylbenzene

Question 7

Which of the following ions is aromatic?

Accepted Answer

A)  Only I and II 
B)  Only II and III 
C)  Only III and IV 
D)  Only II and IV 
A)  Only I and II 
B)  Only II and III 
C)  Only III and IV 
D)  Only II and IV

Question 8

Which of the following molecules has the most acidic hydrogen atoms?

Accepted Answer

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

Question 9

What is the IUPAC name of the following compound?

Accepted Answer

A)  3,6-Dichloroaniline 
B)  2,5-Dichloroaniline 
C)  2,5-Dichloroaminobenzene 
D)  2,5-Dichloroanisole 
A)  3,6-Dichloroaniline 
B)  2,5-Dichloroaniline 
C)  2,5-Dichloroaminobenzene 
D)  2,5-Dichloroanisole

Question 10

Which of the following statements about the molecular orbital (MO) theory is true?

Accepted Answer

A)  When two p orbitals of similar phase overlap side-by-side, a F1F1F1S1F1F1F10* antibonding molecular orbital is formed. 
B)  When two p orbitals of opposite phase overlap side-by-side, a F1F1F1S1F1F1F10 bonding molecular orbital is formed. 
C)  A F1F1F1S1F1F1F10 bonding molecular orbital is higher in energy than the two atomic p orbitals from which it is formed. 
D)  A F1F1F1S1F1F1F10* antibonding molecular orbital is higher in energy than the two atomic p orbitals from which it is formed. 
A)  When two p orbitals of similar phase overlap side-by-side, a F1F1F1S1F1F1F10* antibonding molecular orbital is formed. 
B)  When two p orbitals of opposite phase overlap side-by-side, a F1F1F1S1F1F1F10 bonding molecular orbital is formed. 
C)  A F1F1F1S1F1F1F10 bonding molecular orbital is higher in energy than the two atomic p orbitals from which it is formed. 
D)  A F1F1F1S1F1F1F10* antibonding molecular orbital is higher in energy than the two atomic p orbitals from which it is formed.

Question 11

What orbitals are used to form the indicated bond?

Accepted Answer

A)  sp3 
B)  sp2 
C)  p 
D)  sp3 and sp2 
A)  sp3 
B)  sp2 
C)  p 
D)  sp3 and sp2

Question 12

What is the correct assignment of the names of the following substituted benzenes?

Accepted Answer

A)  I = Phenol; II = anisole; III = toluene. 
B)  I = Benzaldehyde; II = phenol; III = anisole. 
C)  I = Benzaldehyde; II = phenol; III = toluene. 
D)  I = Phenol; II = anisole; III = styrene. 
A)  I = Phenol; II = anisole; III = toluene. 
B)  I = Benzaldehyde; II = phenol; III = anisole. 
C)  I = Benzaldehyde; II = phenol; III = toluene. 
D)  I = Phenol; II = anisole; III = styrene.

Question 13

What is the correct assignment of the names of the following fused aromatic compounds?

Accepted Answer

A)  I = naphthalene; II = anthracene; III = phenanthrene. 
B)  I = naphthalene; II = phenanthrene; III = anthracene. 
C)  I = naphthalene; II = phenanthrene; III = benzo[a]pyrene. 
D)  I = anthracene; II = naphthalene; III = phenanthrene. 
A)  I = naphthalene; II = anthracene; III = phenanthrene. 
B)  I = naphthalene; II = phenanthrene; III = anthracene. 
C)  I = naphthalene; II = phenanthrene; III = benzo[a]pyrene. 
D)  I = anthracene; II = naphthalene; III = phenanthrene.

Question 14

Why is the following compound not aromatic?

Accepted Answer

A)  It has 4n electrons. 
B)  It is not cyclic. 
C)  It has 4n+2 electrons. 
D)  The F1F1F1S1F1F1F10 electron system is not continuous. 
A)  It has 4n electrons. 
B)  It is not cyclic. 
C)  It has 4n+2 electrons. 
D)  The F1F1F1S1F1F1F10 electron system is not continuous.

Question 15

What is the IUPAC name of the following compound?

Accepted Answer

A)  1-Chloro-4-ethyl-3-propylbenzene 
B)  1-Chloro-4-ethyl-5-propylbenzene 
C)  4-Chloro-1-ethyl-2-propylbenzene 
D)  4-Chloro-2-propyltoluene 
A)  1-Chloro-4-ethyl-3-propylbenzene 
B)  1-Chloro-4-ethyl-5-propylbenzene 
C)  4-Chloro-1-ethyl-2-propylbenzene 
D)  4-Chloro-2-propyltoluene

Question 16

Why is the following compound not aromatic?

Accepted Answer

A)  It has 4n pi electrons. 
B)  It is not cyclic. 
C)  It has 4n+2 pi electrons. 
D)  The F1F1F1S1F1F1F10 electron system is not continuous. 
A)  It has 4n pi electrons. 
B)  It is not cyclic. 
C)  It has 4n+2 pi electrons. 
D)  The F1F1F1S1F1F1F10 electron system is not continuous.

Question 17

What is the correct assignment of the names of the following aromatic heterocycles?

Accepted Answer

A)  I = pyridine; II = pyrimidine; III = furan. 
B)  I = pyrimidine; II =pyrrole; III = furan. 
C)  I = pyridine; II = pyrrole; III = furan. 
D)  I = pyrimidine; II = pyrrole; III = tetrahydrofuran. 
A)  I = pyridine; II = pyrimidine; III = furan. 
B)  I = pyrimidine; II =pyrrole; III = furan. 
C)  I = pyridine; II = pyrrole; III = furan. 
D)  I = pyrimidine; II = pyrrole; III = tetrahydrofuran.

Question 18

Rank the following compounds in order of decreasing acidity, starting with the most acidic.

Accepted Answer

A)  I > II > III 
B)  III > II > I 
C)  III > I > II 
D)  I > III > II 
A)  I > II > III 
B)  III > II > I 
C)  III > I > II 
D)  I > III > II

Question 19

Which of the following is not one of the Hückel's criteria for aromaticity?

Accepted Answer

A)  The molecule must be cyclic. 
B)  The molecule must be planar. 
C)  The molecule must be completely conjugated. 
D)  The molecule must have 4n pi electrons. 
A)  The molecule must be cyclic. 
B)  The molecule must be planar. 
C)  The molecule must be completely conjugated. 
D)  The molecule must have 4n pi electrons.

Question 20

Which of the following heterocycles is not aromatic?

Accepted Answer

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

Exam 17: Benzene and Aromatic Compounds

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

Which of the following is not a criterion for antiaromaticity?

Which of the following compounds is not aromatic?

Which of the following compounds is not aromatic?

What is the correct structure for anisole?

What is the name of the following compound?

Which of the following ions is aromatic?

Which of the following molecules has the most acidic hydrogen atoms?

What is the IUPAC name of the following compound?

Which of the following statements about the molecular orbital (MO) theory is true?

What orbitals are used to form the indicated bond?

What is the correct assignment of the names of the following substituted benzenes?

What is the correct assignment of the names of the following fused aromatic compounds?

Why is the following compound not aromatic?

What is the IUPAC name of the following compound?

Why is the following compound not aromatic?

What is the correct assignment of the names of the following aromatic heterocycles?

Rank the following compounds in order of decreasing acidity, starting with the most acidic.

Which of the following is not one of the Hückel's criteria for aromaticity?

Which of the following heterocycles is not aromatic?

Structure and Bonding

Acids and Bases

Introduction to Organic Molecules and Functional Groups

Alkanes

Stereochemistry

Understanding Organic Reactions

Alkyl Halides and Nucleophilic Substitution

Alkyl Halides and Elimination Reactions

Alcohols, Ethers and Epoxides

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Oxidation and Reduction

Mass Spectrometry and Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Radical Reactions

Conjugation, Resonance, and Dienes

Electrophilic Aromatic Substitution

Carboxylic Acids and the Acidity of the O-H Bond

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones Nucleophilic Addition

Carboxylic Acids and Derivatives

Substitution Reactions of Carbonyl Compounds at the Alpha-Carbon

Carbonyl Condensation Reactions

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Carbon-Carbon Bond Forming Reactions in Organic Synthesis

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