Question 1

Which of the following is not true about [the bridged [10]annulene shown below?

Accepted Answer

A)  all of the carbon atoms of bridged [10]annulene are all in the same plane 
B)  bridged [10]annulene is aromatic 
C)  bridged [10]annulene undergoes substitution reactions similar to benzene 
D)  bridged [10]annulene has 10 pi electrons 
A)  all of the carbon atoms of bridged [10]annulene are all in the same plane 
B)  bridged [10]annulene is aromatic 
C)  bridged [10]annulene undergoes substitution reactions similar to benzene 
D)  bridged [10]annulene has 10 pi electrons

Question 2

What is the major organic product obtained from the following reaction?

Accepted Answer

The answer of What is the major organic product obtained...

Question 3

What is the best choice of reagent to achieve the following reaction?

Accepted Answer

A)  Br2, CCl4 
B)  HBr, H2O 
C)  Br2, light 
D)  NaBr 
A)  Br2, CCl4 
B)  HBr, H2O 
C)  Br2, light 
D)  NaBr

Question 4

What is the major organic product obtained from the following reaction?

Accepted Answer

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

Question 5

Which of the following is not true about cyclooctatetraene?

Accepted Answer

A)  The planar conformation is antiaromatic 
B)  In the planar conformation there are two electrons in degenerate nonbonding pi orbitals. 
C)  In the tub conformation the pi system is not conjugated 
D)  The tub conformation is aromatic 
A)  The planar conformation is antiaromatic 
B)  In the planar conformation there are two electrons in degenerate nonbonding pi orbitals. 
C)  In the tub conformation the pi system is not conjugated 
D)  The tub conformation is aromatic

Question 6

What are the relative positions of the substituents in the following structure?

Accepted Answer

A)  anti 
B)  meta 
C)  ortho 
D)  para 
A)  anti 
B)  meta 
C)  ortho 
D)  para

Question 7

What is the IUPAC name of the following compound?

Accepted Answer

A)  2-nitro-6-carboxybromobenzene 
B)  2-bromo-1-nitro-4-benzoic acid 
C)  2-bromo-4-carboxynitrobenzene 
D)  3-bromo-4-nitrobenzoic acid 
A)  2-nitro-6-carboxybromobenzene 
B)  2-bromo-1-nitro-4-benzoic acid 
C)  2-bromo-4-carboxynitrobenzene 
D)  3-bromo-4-nitrobenzoic acid

Question 8

Which of the following represents the energy levels of the molecular orbitals of cyclobutadiene?

Accepted Answer

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

Question 9

Which of the following heterocycles is not aromatic?

Accepted Answer

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

Question 10

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

Accepted Answer

A)  1 = styrene; 2 = benzaldehyde; 3 = cumene 
B)  1 = anisole; 2 = benzaldehyde; 3 = toluene 
C)  1 = styrene; 2 = xylene; 3 = toluene 
D)  1 = aniline; 2 = phenol; 3 = cumene 
A)  1 = styrene; 2 = benzaldehyde; 3 = cumene 
B)  1 = anisole; 2 = benzaldehyde; 3 = toluene 
C)  1 = styrene; 2 = xylene; 3 = toluene 
D)  1 = aniline; 2 = phenol; 3 = cumene

Question 11

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

Accepted Answer

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

Question 12

What is the IUPAC name of the following compound?

Accepted Answer

A)  1-bromo-2-fluoro-4-toluene 
B)  4-bromo-2-fluorotoluene 
C)  2-bromo-4-fluorophenol 
D)  4-bromo-2-fluoroxylene 
A)  1-bromo-2-fluoro-4-toluene 
B)  4-bromo-2-fluorotoluene 
C)  2-bromo-4-fluorophenol 
D)  4-bromo-2-fluoroxylene

Question 13

How many p orbital electrons are present in furan?

Accepted Answer

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

Question 14

What is the intermediate in the reaction of ethylbenzene with NBS in the presence of benzoyl peroxide to give 1-bromo-1-phenylethane?

Accepted Answer

A)  Benzylic anion 
B)  Benzylic cation 
C)  Benzylic radical 
D)  Benzylic carbene 
A)  Benzylic anion 
B)  Benzylic cation 
C)  Benzylic radical 
D)  Benzylic carbene

Question 15

Which of the following is not true about [18]annulene?

Accepted Answer

A)  [18]annulene is planar 
B)  [18]annulene is aromatic 
C)  [18]annulene gives one peak in the 1H NMR spectrum 
D)  [18]annulene has 18 pi bonds 
A)  [18]annulene is planar 
B)  [18]annulene is aromatic 
C)  [18]annulene gives one peak in the 1H NMR spectrum 
D)  [18]annulene has 18 pi bonds

Question 16

What is the major organic product obtained from the following reaction?

Accepted Answer

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

Question 17

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

Accepted Answer

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

Question 18

What is the correct assignment of the names of the following fused arenes?

Accepted Answer

A)  1 = naphthalene; 2 = anthracene; 3 = pyrene 
B)  1 = naphthalene; 2 = phenanthrene; 3 = coronene 
C)  1 = naphthalene; 2 = anthracene; 3 = benzo[a]pyrene 
D)  1 = anthracene; 2 = naphthalene; 3 = coronene 
A)  1 = naphthalene; 2 = anthracene; 3 = pyrene 
B)  1 = naphthalene; 2 = phenanthrene; 3 = coronene 
C)  1 = naphthalene; 2 = anthracene; 3 = benzo[a]pyrene 
D)  1 = anthracene; 2 = naphthalene; 3 = coronene

Question 19

List all of the requirements of a molecule for it to be considered aromatic.

Accepted Answer

An aromatic molecule has an un

Question 20

Which of the following represents the energy levels of the molecular orbitals of cyclopentadienyl anion?

Accepted Answer

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

Exam 21: Benzene and the Concept of Aromaticity

Which of the following is not true about [the bridged [10]annulene shown below?

What is the major organic product obtained from the following reaction?

What is the best choice of reagent to achieve the following reaction?

What is the major organic product obtained from the following reaction?

Which of the following is not true about cyclooctatetraene?

What are the relative positions of the substituents in the following structure?

What is the IUPAC name of the following compound?

Which of the following represents the energy levels of the molecular orbitals of cyclobutadiene?

Which of the following heterocycles is not aromatic?

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

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

What is the IUPAC name of the following compound?

How many p orbital electrons are present in furan?

What is the intermediate in the reaction of ethylbenzene with NBS in the presence of benzoyl peroxide to give 1-bromo-1-phenylethane?

Which of the following is not true about [18]annulene?

What is the major organic product obtained from the following reaction?

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

What is the correct assignment of the names of the following fused arenes?

List all of the requirements of a molecule for it to be considered aromatic.

Which of the following represents the energy levels of the molecular orbitals of cyclopentadienyl anion?

Covalent Bonding and Shapes of Molecules

Alkanes and Cycloalkanes

Stereoisomerism and Chirality

Acids and Bases

Alkenes: Bonding, Nomenclature, and Properties

Reactions of Alkenes

Alkynes

Haloalkanes, Halogenation, and Radical Reactions

Nucleophilic Substitution and Beta-Elimination

Alcohols

Ethers, Epoxides, and Sulfides

Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Mass Spectrometry

An Introduction to Organometallic Compounds

Aldehydes and Ketones

Carboxylic Acids

Functional Derivatives of Carboxylic Acids

Enolate Anions and Enamines

Dienes, Conjugated Systems, and Pericyclic Reactions

Reactions of Benzene and Its Derivatives

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