The Unusual Reactivity and Stability of Benzene

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60 Questions

Which of the following is a characteristic of aromatic compounds?

They have a low heat of hydrogenation

According to Hückel's rule, how many π electrons are required for a compound to be aromatic?

6

Which of the following compounds is antiaromatic?

Cyclobutadiene

Which of the following compounds satisfies all the criteria for aromaticity?

Benzene

Which of the following compounds is not aromatic?

Cyclooctatetraene

How many π electrons are required for a completely conjugated, planar, 8-membered ring to be aromatic?

14

Which of the following compounds is NOT considered aromatic?

Cyclopentadiene

How many pi electrons are present in the pyrimidine-derived DNA base cytosine?

6

Which of the following statements about molecular orbital (MO) theory is correct?

MO theory explains bonding in aromatic compounds.

What is the basis of Hückel's rule?

The number of electrons in the compound.

Which of the following compounds is considered fully conjugated and aromatic?

Pyrrole

In pyridine, where is the nonbonded electron pair localized?

On the nitrogen atom

Which of the following statements about benzene is true?

Benzene has four degrees of unsaturation.

What is the result of benzene reacting with bromine in the presence of a Lewis acid?

Substitution reaction

What did August Kekulé propose about the structure of benzene?

Benzene contains a six-membered ring with alternating single and double bonds.

What is the basis for current descriptions of benzene?

Resonance and electron delocalization

What must any structure for benzene account for?

It contains a six-membered ring and three additional degrees of unsaturation.

True or False: Benzene is a highly reactive hydrocarbon.

False

Which of the following best describes the bond lengths in benzene?

Benzene has three short double bonds alternating with three longer single bonds

Which of the following statements about the resonance description of benzene is true?

The true structure of benzene is a hybrid of two Lewis structures

Which of the following correctly describes the number of π electrons in benzene?

Benzene has six π electrons

Which of the following statements about the actual bond length in benzene is true?

The actual bond length in benzene is shorter than the carbon–carbon single bond

Which of the following statements about the electron density in benzene is true?

The electron density in benzene is evenly distributed throughout the molecule

Which of the following statements about naming substituted benzenes is true?

To name a benzene ring with one substituent, you need to name the substituent and add the word benzene

Which statement best describes the molecular orbitals of benzene?

There are 6 pi molecular orbitals formed by the combination of 6 atomic p orbitals.

Which of the following is NOT a characteristic of the molecular orbitals of benzene?

The larger the number of nodes, the higher in energy the MO.

What is the inscribed polygon method used for?

Determining the aromaticity of monocyclic completely conjugated systems.

What is the relationship between the number of MOs and the number of vertices in the inscribed polygon method?

The number of MOs is always equal to the number of vertices of the polygon.

Which statement best describes pi stacking?

All of the above

What is the purpose of the inscribed polygon method in predicting aromaticity?

To determine the aromaticity of a monocyclic completely conjugated system.

According to the text, what is the basis for the current description of benzene?

Resonance and electron delocalization

What did August Kekulé propose about the structure of benzene?

It is a rapidly equilibrating mixture of two compounds with alternating bonds

Which of the following compounds is considered fully conjugated and aromatic?

Benzene

According to Hückel's rule, how many π electrons are required for a compound to be aromatic?

4n+2

Which of the following compounds satisfies all the criteria for aromaticity?

Benzene

What is the result of benzene reacting with bromine in the presence of a Lewis acid?

Substitution

Which of the following is true about the bond lengths in benzene?

All bond lengths are equal

What is the true structure of benzene?

A resonance hybrid of two equivalent Lewis structures

How many π electrons does benzene have?

6

What is the actual bond length in benzene?

Intermediate between a carbon-carbon single bond and a carbon-carbon double bond

How many atoms surround each carbon atom in a benzene ring?

3

What is a benzene substituent called?

Phenyl group

Which of the following is true about the molecular orbitals of benzene?

There are six pi molecular orbitals

What is the lowest energy bonding molecular orbital in benzene?

Ψ1

Which of the following statements about the inscribed polygon method is true?

It works for all monocyclic completely conjugated systems

What is the highest occupied molecular orbital in benzene called?

HOMO

What is the lowest unoccupied molecular orbital in benzene called?

LUMO

Which of the following is a characteristic of aromatic compounds?

They have a lower energy compared to non-aromatic compounds

Which of the following compounds satisfies all the criteria for aromaticity?

Benzene

What is the result of benzene reacting with bromine in the presence of a Lewis acid?

Substitution product

How many π electrons are required for a completely conjugated, planar, 8-membered ring to be aromatic?

10

Which of the following compounds is antiaromatic?

Cyclobutadiene

Which of the following compounds is NOT considered aromatic?

Cyclobutadiene

What must any structure for benzene account for?

All of the above

Which of the following compounds is NOT considered aromatic?

Cyclopentadiene

In pyridine, where is the nonbonded electron pair localized?

On the nitrogen atom

Which of the following compounds satisfies all the criteria for aromaticity?

Tropylium cation

What is the relationship between the number of MOs and the number of vertices in the inscribed polygon method?

The number of MOs is equal to the number of vertices minus one

Which of the following compounds is not aromatic?

Thiophene

What must any structure for benzene account for?

The presence of six pi electrons

Test your knowledge on the unusual reactivity and stability of benzene in this quiz. Explore the factors that contribute to its low heat of hydrogenation and its unique aromatic properties.

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