Question 1

What is the correct IUPAC name for the compound shown below?

$$\begin{array}{c}
	ext{A benzene ring with two nitro groups at positions 2 and 6.}
\end{array}$$

Accepted Answer

2,6-dinitroanisole

Question 2

Which type of reaction is illustrated by the following transformation?

$$\begin{array}{c}
	ext{Benzene + CH_3Cl} \xrightarrow{	ext{Lewis acid}} 	ext{Chlorobenzene}
\end{array}$$

Accepted Answer

An electrophilic aromatic substitution

Question 3

Which of the following compounds would you expect to be aromatic?

$$\begin{array}{c}
	ext{I: Cyclopentadienyl anion} \
	ext{II: Cycloheptatriene} \
	ext{III: Pyrrole} \
	ext{IV: Benzene} \
	ext{V: Cyclobutadiene}
\end{array}$$

Accepted Answer

IV

Question 4

Which of the following is a necessary condition for a compound to be aromatic according to Hückel's rule?

Accepted Answer

It must have (4n+2) π electrons.

Question 5

A student reacts benzene with bromine in the presence of FeBr$$_3. $$What is the major product?

Accepted Answer

Bromobenzene

Question 6

Which of the following statements best explains why benzene does not undergo addition reactions easily?

Accepted Answer

Addition reactions would disrupt the aromatic stabilization energy.

Question 7

Which reagent would you use to convert benzene to nitrobenzene?

Accepted Answer

HNO$$_3$$ and H$$_2SO$_4$$

Question 8

Which of the following is the correct mechanism for the nitration of benzene?

Accepted Answer

Electrophilic aromatic substitution

Question 9

A compound has the molecular formula C$$_6H$_6. $$Which of the following structures is most likely for this compound?

Accepted Answer

Benzene

Question 10

Which of the following is a common misconception about aromatic compounds?

Accepted Answer

Aromatic compounds must have alternating single and double bonds.

Question 11

Which of the following is the correct order of reactivity for electrophilic aromatic substitution (EAS) for the following groups attached to benzene: NO$$_2$$, CH$$_3$$, OH?

Accepted Answer

OH \u003e CH$$_3$$ \u003e NO$$_2$$

Question 12

Which of the following is NOT a feature of aromatic compounds?

Accepted Answer

Saturated carbon atoms

Question 13

Which of the following reactions is used to introduce an alkyl group onto a benzene ring?

Accepted Answer

Friedel-Crafts alkylation

Question 14

Which of the following is the correct formula for the resonance energy of benzene?

Accepted Answer

$$E_{res} = E_{expected} - E_{actual}$$

Question 15

Which of the following is a real-world application of aromatic compounds?

Accepted Answer

Benzene is used as a precursor in the synthesis of drugs like aspirin.

Question 16

Which of the following best describes the electronic structure of benzene?

Accepted Answer

Delocalized π electrons over six carbon atoms

Question 17

Which of the following is the major product when toluene is nitrated?

Accepted Answer

Ortho-nitrotoluene

Question 18

Which of the following is the correct structure for pyrrole?

Accepted Answer

A five-membered ring with one nitrogen atom and two double bonds

Question 19

Which of the following is the correct condition for Friedel-Crafts alkylation?

Accepted Answer

AlCl$$_3 as a $$catalyst

Question 20

Which of the following is a limitation of the Friedel-Crafts alkylation reaction?

Accepted Answer

Carbocation rearrangement can occur, leading to unexpected products.

Aromatic Compounds, Electrophilic Aromatic Substitution, and Aromaticity

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