Question 1

Is cyclooctatetraene a planar molecule? Explain.

Accepted Answer

No. In addition to increasing other forms of strain, a planar conformation would make this molecule antiaromatic.

Question 2

Provide the name of the compound shown below.

Accepted Answer

m-iodobenzaldehyde or 3-iodobenzaldehyde

Question 3

Show how the participating p orbitals interact to form the highest energy π molecular orbital of benzene.

Accepted Answer

All adjacent interactions are antibonding.

Question 4

Which of the following structures, if flat, would be classified as antiaromatic?

Accepted Answer

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

Question 5

Provide the structure of 4-isopropylbenzaldehyde.

Accepted Answer

The answer of Provide the structure of 4-isopropylbenzaldehyde....

Question 6

Is the all-cis form of [10]annulene aromatic? Explain.

Accepted Answer

No. Planarity, which

Question 7

Provide an acceptable name for the compound below.

Accepted Answer

aniline or

Question 8

Provide the structure of o-bromostyrene.

Accepted Answer

The answer of Provide the structure of o-bromostyrene....

Question 9

Which of the following compounds may correctly be classified as being aromatic?
(More than one answer is possible.)

Accepted Answer

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

Question 10

Is the molecule below aromatic, antiaromatic, or nonaromatic?

Accepted Answer

The answer of Is the molecule below aromatic, antiaromatic, or...

Question 11

Provide the structure of sodium cyclopentadienide.

Accepted Answer

The answer of Provide the structure of sodium cyclopentadienide....

Question 12

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 13

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

Accepted Answer

The answer of Classify cyclopropenyl cation as aromatic, antiaromatic, or...

Question 14

When toluene is treated with bromine (shown below), the bromine doesn't react with the double bond to form a viscinal dihalide, but instead a substitution of one of the benzylic hydrogens takes place. Why?

Accepted Answer

Addition of Br₂ to the double bonds of be

Question 15

Is the molecule below aromatic, antiaromatic, or nonaromatic?

Accepted Answer

The answer of Is the molecule below aromatic, antiaromatic, or...

Question 16

Provide an acceptable name for the compound below.

Accepted Answer

ortho-xyle

Question 17

When cyclohexene is treated with KMnO4, H2O, the syn-1,2-diol is produced. What reaction occurs when benzene is similarly treated?

Accepted Answer

No reactio

Question 18

Circle and name the aromatic heterocycles in the following structure, which has been found to be effective against inflammatory diseases including Alzheimer's disease and rheumatoid arthritis (J. Med. Chem. 2007, 4728).

Accepted Answer

The answer of Circle and name the aromatic heterocycles in...

Question 19

Describe the occupied π molecular orbitals in the ground state of cyclobutadiene.

Accepted Answer

Two electrons are paired in a

Question 20

An unknown compound gives the following spectral data. Propose a structure that is consistent with this information. In addition, show the fragmentations that give the 91 and 122 peaks in the MS.
MS (m/z): 91, 108 and 122 (M+)
1H NMR (δ): 7.05(2H, d), 6.78 (2H, d), 3.7 (3H, s), 2.26 (3H, s)

Accepted Answer

Exam 16: Aromatic Compounds

Is cyclooctatetraene a planar molecule? Explain.

Provide the name of the compound shown below.

Show how the participating p orbitals interact to form the highest energy π molecular orbital of benzene.

Which of the following structures, if flat, would be classified as antiaromatic?

Provide the structure of 4-isopropylbenzaldehyde.

Is the all-cis form of [10]annulene aromatic? Explain.

Provide an acceptable name for the compound below.

Provide the structure of o-bromostyrene.

Which of the following compounds may correctly be classified as being aromatic? (More than one answer is possible.)

Is the molecule below aromatic, antiaromatic, or nonaromatic?

Provide the structure of sodium cyclopentadienide.

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

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

When toluene is treated with bromine (shown below), the bromine doesn't react with the double bond to form a viscinal dihalide, but instead a substitution of one of the benzylic hydrogens takes place. Why?

Is the molecule below aromatic, antiaromatic, or nonaromatic?

Provide an acceptable name for the compound below.

When cyclohexene is treated with KMnO4, H2O, the syn-1,2-diol is produced. What reaction occurs when benzene is similarly treated?

Circle and name the aromatic heterocycles in the following structure, which has been found to be effective against inflammatory diseases including Alzheimer's disease and rheumatoid arthritis (J. Med. Chem. 2007, 4728).

Describe the occupied π molecular orbitals in the ground state of cyclobutadiene.

An unknown compound gives the following spectral data. Propose a structure that is consistent with this information. In addition, show the fragmentations that give the 91 and 122 peaks in the MS. MS (m/z): 91, 108 and 122 (M+) 1H NMR (δ): 7.05(2H, d), 6.78 (2H, d), 3.7 (3H, s), 2.26 (3H, s)

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

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When cyclohexene is treated with KMnO₄, H₂O, the syn-1,2-diol is produced. What reaction occurs when benzene is similarly treated?

An unknown compound gives the following spectral data. Propose a structure that is consistent with this information. In addition, show the fragmentations that give the 91 and 122 peaks in the MS. MS (m/z): 91, 108 and 122 (M⁺) ¹H NMR (δ): 7.05(2H, d), 6.78 (2H, d), 3.7 (3H, s), 2.26 (3H, s)