Question 1

Is the cis-CH₂=CH-CH=CH-CH=CH₂ molecule aromatic? Explain why or why not.

Accepted Answer

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Question 2

Compounds W, X, Y and Z are all alkylbenzenes. W reacts with OsO₄ and with NBS. X reacts with NBS , but not OsO₄. Y reacts with neither NBS nor OsO₄ , and Z reacts with OsO₄ but not with NBS . Which of these structures is compound X ?

Accepted Answer

Compound X is the only one that reacts with NBS but not OsO4. The structure of X is consistent with a benzylic C-H bond being replaced with a bromine atom by NBS.

Question 3

Which of the following compounds has at least one lone pair in an sp² orbital?

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Question 4

Which of the following structures is the product of the reaction shown here?

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Question 5

Which of the following will not react with KMnO₄?

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Question 6

There are five resonance structures of 1,2-dimethoxycyclopropenyl cation.Draw all of them.

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Question 7

How many isomeric trisubstituted benzenes C₃H₃XYZ are possible?

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Question 8

Which of these structures is the major product of the reaction shown?

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Question 9

Which is the correct sequence of reactions required to transform the starting material into the product shown?

Accepted Answer

The product shown is a diol with two OH groups on adjacent carbons, which suggests that it was formed via syn dihydroxylation of an alkene. The reagent for syn dihydroxylation is KMnO4 in basic solution. Therefore, KMnO4 is required in the reaction sequence. The starting material is an alkene with a benzene ring, which suggests that it is an aromatic compound. It is known that aromatic compounds do not react with KMnO4. Therefore, a protecting group such as NHSO2C6H4 is needed to mask the aromatic ring during the reaction. The protecting group must be removed after the dihydroxylation to obtain the final product. NaBH4 is commonly used to reduce the intermediate manganese oxide to form the diol. Therefore, the correct sequence of reactions is KMnO4, then NaBH4/NHSO2C6H4. Among the given choices, only choice B has the correct order of reagents.

Question 10

Which of the following structures is the product of the reaction shown here?

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Question 11

How many nonbonding π molecular orbitals are there in furan?

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Question 12

Draw a Frost circle for cyclopentadienyl cation.Include and label all bonding, nonbonding, and antibonding molecular orbitals.Indicate the nonbonding energy level.Put the correct number of electrons in the appropriate orbitals in your drawing.

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Question 13

How many resonances could be observed in the ₁H spectrum of Dewar benzene?

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Question 14

Which of the following structures is the product of the reaction shown here?

Accepted Answer

The reactant has a double bond and a bromine atom attached to a carbon. The product has a bromine atom attached to each of the two carbons originally involved in the double bond, indicating that a bromine molecule was added across the double bond during the reaction. Among the choices given, only structure C matches this description.

Question 15

Why is cyclopentadiene a stronger acid than cycloheptatriene?

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Question 16

Is the compound shown here aromatic? Explain your answer.

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Question 17

Place the three molecules shown here in order of increasing acidity.

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Question 18

Fill in the blanks:    species is the least acidic and   species is the most acidic.

Accepted Answer

The given information indicates that there are three species with different levels of acidity, which can be represented by x, y, and z. The missing values in the statement can be filled as follows:
- The least acidic species is represented by x.
- The most acidic species is represented by z.
- The remaining species should be represented by y.
Therefore, the correct choice is B, which shows that x is the least acidic, and y is intermediate, while z is the most acidic.

Question 19

Draw a Frost circle for benzene.Include and label all bonding molecular orbitals and antibonding molecular orbitals.Indicate the nonbonding energy level. Put the correct number of electrons in the appropriate orbitals in your drawing.

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Question 20

Place the three molecules shown here in order of increasing basicity.

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Quiz 14: Aromaticity

Is the cis-CH2=CH-CH=CH-CH=CH2 molecule aromatic? Explain why or why not.

Compounds W, X, Y and Z are all alkylbenzenes. W reacts with OsO4 and with NBS. X reacts with NBS , but not OsO4. Y reacts with neither NBS nor OsO4 , and Z reacts with OsO4 but not with NBS . Which of these structures is compound X ?

Which of the following compounds has at least one lone pair in an sp2 orbital?

Which of the following structures is the product of the reaction shown here?

Which of the following will not react with KMnO4?

There are five resonance structures of 1,2-dimethoxycyclopropenyl cation.Draw all of them.

How many isomeric trisubstituted benzenes C3H3XYZ are possible?

Which of these structures is the major product of the reaction shown?

Which is the correct sequence of reactions required to transform the starting material into the product shown?

Which of the following structures is the product of the reaction shown here?

How many nonbonding π molecular orbitals are there in furan?

Draw a Frost circle for cyclopentadienyl cation.Include and label all bonding, nonbonding, and antibonding molecular orbitals.Indicate the nonbonding energy level.Put the correct number of electrons in the appropriate orbitals in your drawing.

How many resonances could be observed in the 1H spectrum of Dewar benzene?

Which of the following structures is the product of the reaction shown here?

Why is cyclopentadiene a stronger acid than cycloheptatriene?

Is the compound shown here aromatic? Explain your answer.

Place the three molecules shown here in order of increasing acidity.

Fill in the blanks: species is the least acidic and species is the most acidic.

Draw a Frost circle for benzene.Include and label all bonding molecular orbitals and antibonding molecular orbitals.Indicate the nonbonding energy level. Put the correct number of electrons in the appropriate orbitals in your drawing.

Place the three molecules shown here in order of increasing basicity.

Is the cis-CH₂=CH-CH=CH-CH=CH₂ molecule aromatic? Explain why or why not.

Compounds W, X, Y and Z are all alkylbenzenes. W reacts with OsO₄ and with NBS. X reacts with NBS , but not OsO₄. Y reacts with neither NBS nor OsO₄ , and Z reacts with OsO₄ but not with NBS . Which of these structures is compound X ?

Which of the following compounds has at least one lone pair in an sp² orbital?

Which of the following will not react with KMnO₄?

How many isomeric trisubstituted benzenes C₃H₃XYZ are possible?

How many resonances could be observed in the ₁H spectrum of Dewar benzene?