Question 1

Which sequence ranks the indicated protons in order of increasing acidity?

Accepted Answer

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

Question 2

Which of the following structures is aromatic?

Accepted Answer

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

Question 3

Classify the compound below as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.

Accepted Answer

The answer of Classify the compound below as aromatic, antiaromatic,...

Question 4

Which of the following compounds has the most signals in the proton-decoupled 13C NMR spectrum?

Accepted Answer

A)  o-dibromobenzene 
B)  m-dibromobenzene 
C)  p-dibromobenzene 
D)  1,3,5-tribromobenzene 
E)  1,2,3,4-tetrabromobenzene 
A)  o-dibromobenzene 
B)  m-dibromobenzene 
C)  p-dibromobenzene 
D)  1,3,5-tribromobenzene 
E)  1,2,3,4-tetrabromobenzene

Question 5

Provide the name of the compound shown below.

Accepted Answer

o-chlorobe

Question 6

Provide the structure of the major organic product which results when phenanthrene is treated with Br2 in carbon tetrachloride.

Accepted Answer

Question 7

Classify pyrrole as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.

Accepted Answer

The answer of Classify pyrrole as aromatic, antiaromatic, or nonaromatic....

Question 8

Which of the following is also an acceptable name for 1,3,5-trimethylbenzene?

Accepted Answer

A)  styrene 
B)  mesitylene 
C)  cumene 
D)  cymene 
E)  1,3,5-xylene 
A)  styrene 
B)  mesitylene 
C)  cumene 
D)  cymene 
E)  1,3,5-xylene

Question 9

Provide the structure of 2-bromo-4-chlorobenzoic acid.

Accepted Answer

The answer of Provide the structure of 2-bromo-4-chlorobenzoic acid....

Question 10

Provide the structure of m-nitrophenol.

Accepted Answer

The answer of Provide the structure of m-nitrophenol....

Question 11

Classify pyridine as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.

Accepted Answer

The answer of Classify pyridine as aromatic, antiaromatic, or nonaromatic....

Question 12

Rank the following in order of increasing pKa (from lowest to highest pKa).

Accepted Answer

A)  1 < 2 < 3 
B)  3 < 2 < 1 
C)  2 < 1 < 3 
D)  3 < 1 < 2 
E)  2 < 3 < 1 
A)  1 < 2 < 3 
B)  3 < 2 < 1 
C)  2 < 1 < 3 
D)  3 < 1 < 2 
E)  2 < 3 < 1

Question 13

Which of the following is another name for cyclobutadiene?

Accepted Answer

A)  [2]annulene 
B)  [4]annulene 
C)  [6]annulene 
D)  Dewar benzene 
E)  antibenzene 
A)  [2]annulene 
B)  [4]annulene 
C)  [6]annulene 
D)  Dewar benzene 
E)  antibenzene

Question 14

What is the bond order of the carbon-carbon bonds in benzene?

Accepted Answer

A)  0.5 
B)  1 
C)  1.5 
D)  2 
E)  3 
A)  0.5 
B)  1 
C)  1.5 
D)  2 
E)  3

Question 15

Classify the compound below as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.

Accepted Answer

The answer of Classify the compound below as aromatic, antiaromatic,...

Question 16

How many distinct nodal planes which are perpendicular to the molecular plane are present in the π4* orbital of benzene?

Accepted Answer

A)  0 
B)  1 
C)  2 
D)  4 
E)  5 
A)  0 
B)  1 
C)  2 
D)  4 
E)  5

Question 17

Provide the structure of anisole.

Accepted Answer

The answer of Provide the structure of anisole....

Question 18

Which of the following is the same as the tropylium ion?

Accepted Answer

A)  cycloheptatrienyl cation 
B)  cycloheptatrienyl anion 
C)  cyclopentadienyl cation 
D)  cyclopentadienyl anion 
E)  cyclopropenyl anion 
A)  cycloheptatrienyl cation 
B)  cycloheptatrienyl anion 
C)  cyclopentadienyl cation 
D)  cyclopentadienyl anion 
E)  cyclopropenyl anion

Question 19

Which is more stable, cyclobutadiene or 1,3-butadiene? Explain.

Accepted Answer

1,3-Butadiene is more stable.

Question 20

Provide an acceptable name for the compound below.

Accepted Answer

para-dichl

Exam 16: Aromatic Compounds

Which sequence ranks the indicated protons in order of increasing acidity?

Which of the following structures is aromatic?

Classify the compound below as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.

Which of the following compounds has the most signals in the proton-decoupled 13C NMR spectrum?

Provide the name of the compound shown below.

Provide the structure of the major organic product which results when phenanthrene is treated with Br2 in carbon tetrachloride.

Classify pyrrole as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.

Which of the following is also an acceptable name for 1,3,5-trimethylbenzene?

Provide the structure of 2-bromo-4-chlorobenzoic acid.

Provide the structure of m-nitrophenol.

Classify pyridine as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.

Rank the following in order of increasing pKa (from lowest to highest pKa).

Which of the following is another name for cyclobutadiene?

What is the bond order of the carbon-carbon bonds in benzene?

Classify the compound below as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.

How many distinct nodal planes which are perpendicular to the molecular plane are present in the π4* orbital of benzene?

Provide the structure of anisole.

Which of the following is the same as the tropylium ion?

Which is more stable, cyclobutadiene or 1,3-butadiene? Explain.

Provide an acceptable name for the compound below.

Structure and Bonding

Acids and Bases; Functional Groups

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Alkyl Halides; Nucleophilic Substitution

Structure and Synthesis of Alkenes; Elimination

Reactions of Alkenes

Structure and Synthesis of Alcohols

Reactions of Alcohols

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Ethers, Epoxides, and Thioethers

Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy

Reactions of Aromatic Compounds

Ketones and Aldehydes

Amines

Carboxylic Acids

Carboxylic Acid Derivatives

Condensations and Alpha Substitutions of Carboxyl Compounds

Carbohydrates and Nucleic Acids

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

Which of the following compounds has the most signals in the proton-decoupled ¹³C NMR spectrum?

Provide the structure of the major organic product which results when phenanthrene is treated with Br₂ in carbon tetrachloride.

How many distinct nodal planes which are perpendicular to the molecular plane are present in the π₄^* orbital of benzene?