Question 1

Provide the structure of o-toluic acid.

Accepted Answer

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Question 2

Provide the structure of indole.

Accepted Answer

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Question 3

How many peaks are in the proton spin decoupled 13C NMR spectrum of the compound shown?

Accepted Answer

Question 4

Describe the benzenoid band which appears in the UV-visible spectrum of most aromatic hydrocarbons.

Accepted Answer

Band centered at 254

Question 5

Which would have a smaller heat of hydrogenation? Circle your answer.

Accepted Answer

The answer of Which would have a smaller heat of...

Question 6

Which of the following compound has the highest melting point?

Accepted Answer

A)  benzene 
B)  toluene 
C)  o-dichlorobenzene 
D)  m-dichlorobenzene 
E)  p-dichlorobenzene 
A)  benzene 
B)  toluene 
C)  o-dichlorobenzene 
D)  m-dichlorobenzene 
E)  p-dichlorobenzene

Question 7

Provide the structure of o-chlorotoluene.

Accepted Answer

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Question 8

List the criteria which compounds must meet in order to be considered aromatic.

Accepted Answer

1) The structure must be cyclic.
2) Each

Question 9

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 10

In the proton NMR, in what region of the spectrum does one typically observe hydrogens bound to the aromatic ring?

Accepted Answer

A)  1.0-1.5 ppm 
B)  2.0-3.0 ppm 
C)  4.5-5.5 ppm 
D)  7.0-8.0 ppm 
E)  9.0-10.0 ppm 
A)  1.0-1.5 ppm 
B)  2.0-3.0 ppm 
C)  4.5-5.5 ppm 
D)  7.0-8.0 ppm 
E)  9.0-10.0 ppm

Question 11

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

Accepted Answer

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Question 12

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

Accepted Answer

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Question 13

What is the major difference between an antiaromatic and aromatic compound?

Accepted Answer

A)  The structure must be cyclic for aromatic but not antiaromatic compounds. 
B)  Antiaromatic compounds have at least one sp3 hybridized atom in the ring. 
C)  Antiaromatic compounds can assume a chair-like structure while aromatic compounds are nearly flat. 
D)  Aromatic compounds cannot have a charged atom in the structure. 
E)  Only aromatic compounds follow Huckle's rule. 
A)  The structure must be cyclic for aromatic but not antiaromatic compounds. 
B)  Antiaromatic compounds have at least one sp3 hybridized atom in the ring. 
C)  Antiaromatic compounds can assume a chair-like structure while aromatic compounds are nearly flat. 
D)  Aromatic compounds cannot have a charged atom in the structure. 
E)  Only aromatic compounds follow Huckle's rule.

Question 14

Provide the structure of 2,5-dichlorophenol.

Accepted Answer

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Question 15

Which of the following is an incorrect description of benzene?

Accepted Answer

A)  The CCC bond angles are all equal to 120°. 
B)  The molecule is planar. 
C)  The molecule is a 6-membered ring which contains alternating single and double carbon-carbon bonds. 
D)  The molecule is aromatic. 
E)  The molecule can be drawn as a resonance hybrid of two Kekule structures. 
A)  The CCC bond angles are all equal to 120°. 
B)  The molecule is planar. 
C)  The molecule is a 6-membered ring which contains alternating single and double carbon-carbon bonds. 
D)  The molecule is aromatic. 
E)  The molecule can be drawn as a resonance hybrid of two Kekule structures.

Question 16

3-Chlorocyclopropene is solvolyzed in methanol at a much higher rate than is chlorocyclopropane. Offer an explanation.

Accepted Answer

Cyclopropenyl cation, the carb

Question 17

Which of the following is another accepted name for methyl phenyl ketone?

Accepted Answer

A)  anisole 
B)  cresol 
C)  acetophenone 
D)  benzophenone 
E)  cresone 
A)  anisole 
B)  cresol 
C)  acetophenone 
D)  benzophenone 
E)  cresone

Question 18

Is the [10]annulene shown below aromatic? Explain.

Accepted Answer

No. The ring cannot achieve a

Question 19

Classify 1,3,5-heptatriene as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.

Accepted Answer

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Question 20

Which is more basic, pyridine or pyrrole? Explain.

Accepted Answer

Pyrrole is a much weaker base

Exam 16: Aromatic Compounds

Provide the structure of o-toluic acid.

Provide the structure of indole.

How many peaks are in the proton spin decoupled 13C NMR spectrum of the compound shown?

Describe the benzenoid band which appears in the UV-visible spectrum of most aromatic hydrocarbons.

Which would have a smaller heat of hydrogenation? Circle your answer.

Which of the following compound has the highest melting point?

Provide the structure of o-chlorotoluene.

List the criteria which compounds must meet in order to be considered aromatic.

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

In the proton NMR, in what region of the spectrum does one typically observe hydrogens bound to the aromatic ring?

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

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

What is the major difference between an antiaromatic and aromatic compound?

Provide the structure of 2,5-dichlorophenol.

Which of the following is an incorrect description of benzene?

3-Chlorocyclopropene is solvolyzed in methanol at a much higher rate than is chlorocyclopropane. Offer an explanation.

Which of the following is another accepted name for methyl phenyl ketone?

Is the [10]annulene shown below aromatic? Explain.

Classify 1,3,5-heptatriene as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.

Which is more basic, pyridine or pyrrole? Explain.

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

How many peaks are in the proton spin decoupled ¹³C NMR spectrum of the compound shown?