Question 1

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 C

Question 2

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 D

Question 3

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 D

Question 4

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 5

Which of the following compound is nonaromatic?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
A) 
  
B) 
  
C) 
  
D)

Question 6

Provide a brief explanation of why furan (below) is aromatic. Your answer should identify the hybridization of the oxygen atom and account for which electrons are in the pi system.

Accepted Answer

The oxygen is sp² hybridized. One lone pa

Question 7

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

Question 8

What is the hybridization of the nitrogen atom of pyridine?

Accepted Answer

A)  s 
B)  sp 
C)  sp2 
D)  sp3 
A)  s 
B)  sp 
C)  sp2 
D)  sp3

Question 9

The following compound is named (Z)-2,3-diphenyl-2-hexene.

Accepted Answer

A) True 
 B)False

Question 10

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

Accepted Answer

A)  six atomic 2p-orbitals overlap to form six π-molecular orbitals 
B)  there are three bonding π-molecular orbitals and three π-antibonding molecular orbitals 
C)  the ground state electronic configuration of benzene has six electrons in three π-bonding molecular orbitals 
D)  the bonds alternate in length around the ring 
A)  six atomic 2p-orbitals overlap to form six π-molecular orbitals 
B)  there are three bonding π-molecular orbitals and three π-antibonding molecular orbitals 
C)  the ground state electronic configuration of benzene has six electrons in three π-bonding molecular orbitals 
D)  the bonds alternate in length around the ring

Question 11

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 12

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 13

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 14

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

Accepted Answer

A)  1 = phenol; 2 = m-cresol; 3 = toluene 
B)  1 = m-cresol; 2 = resorcinol; 3 = m-xylene 
C)  1 = anisole; 2 = catechol; 3 = m-xylene 
D)  1 = m-cresol; 2 = anisole; 3 = cumene 
A)  1 = phenol; 2 = m-cresol; 3 = toluene 
B)  1 = m-cresol; 2 = resorcinol; 3 = m-xylene 
C)  1 = anisole; 2 = catechol; 3 = m-xylene 
D)  1 = m-cresol; 2 = anisole; 3 = cumene

Question 15

The product of the following reaction would be a dicarboxylic acid.

Accepted Answer

A) True 
 B)False

Question 16

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

Accepted Answer

A)  H2SO4 
B)  NaOH, H2O 
C)  K2Cr2O7, H2SO4 
D)  LiAlH4 
A)  H2SO4 
B)  NaOH, H2O 
C)  K2Cr2O7, H2SO4 
D)  LiAlH4

Question 17

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 18

Using the Hückel criteria, the compound would be ______________.

Accepted Answer

The answer of Using the Hückel criteria, the compound would...

Question 19

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 20

Identify the most acidic compound.

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
A) 
  
B) 
  
C) 
  
D)

Exam 21: Benzene and the Concept of Aromaticity

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 cyclooctatetraene?

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

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

Which of the following compound is nonaromatic?

Provide a brief explanation of why furan (below) is aromatic. Your answer should identify the hybridization of the oxygen atom and account for which electrons are in the pi system.

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

What is the hybridization of the nitrogen atom of pyridine?

The following compound is named (Z)-2,3-diphenyl-2-hexene.

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

How many p orbital electrons are present in furan?

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

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

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

The product of the following reaction would be a dicarboxylic acid.

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

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

Using the Hückel criteria, the compound would be ______________.

What is the IUPAC name of the following compound?

Identify the most acidic compound.

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

Amines

Catalytic Carbon-Carbon Bond Formation

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids

Organic Polymer Chemistry

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