Question 1

Which of the following compounds is considered aromatic according to Hückel’s rule?

Accepted Answer

Benzene ($$C_6H_6)$$

Question 2

Which of the following is the correct systematic name for the compound shown below? (A benzene ring with OH at position 1, Br at positions 3 and 5)

Accepted Answer

3,5-dibromophenol

Question 3

Which of the following statements best explains why benzene does not react with $$Br_2$$ under normal conditions, while cyclohexene does?

Accepted Answer

Benzene is less reactive because it is aromatic and stabilized by delocalized $$\pi$$ electrons.

Question 4

A compound is found to be a planar, fully conjugated ring with 10 $$\pi$$ electrons. According to Hückel’s rule, this compound is:

Accepted Answer

Aromatic

Question 5

Which of the following best describes the molecular orbital (MO) diagram for benzene?

Accepted Answer

Three bonding MOs, three antibonding MOs, and six $$\pi$$ electrons filling the bonding MOs

Question 6

Which of the following compounds is most likely to undergo oxidation at the benzylic position with $$Na_2Cr_2O_7$$/$$H_2SO_4$$/$$H_2O$$?

Accepted Answer

Ethylbenzene

Question 7

Which of the following is the correct product when toluene is treated with $$Cl_2$$ and light?

Accepted Answer

Chloromethylbenzene (benzyl chloride)

Question 8

Which of the following best explains the high acidity of cyclopentadiene’s conjugate base?

Accepted Answer

The cyclopentadienyl anion is aromatic and stabilized by delocalization of 6 $$\pi$$ electrons.

Question 9

Which of the following is the correct IUPAC name for a benzene ring with a methyl group at position 1 and a bromo group at position 3?

Accepted Answer

3-bromotoluene

Question 10

Which of the following is NOT a requirement for aromaticity?

Accepted Answer

The molecule must be non-planar.

Question 11

Which of the following best describes the difference in basicity between pyridine and pyrrole?

Accepted Answer

Pyridine is more basic because its lone pair is not involved in aromaticity.

Question 12

Which of the following best explains why cyclooctatetraene is nonaromatic?

Accepted Answer

It adopts a non-planar, tub-shaped conformation, preventing overlap of p orbitals.

Question 13

Which of the following is the correct product of the Birch reduction of toluene?

Accepted Answer

A 1,4-cyclohexadiene with a methyl group at position 1

Question 14

Which of the following best describes the effect of an electron-withdrawing group on the regioselectivity of the Birch reduction?

Accepted Answer

The electron-withdrawing group is reduced to a position not adjacent to a double bond.

Question 15

Which of the following is a polycyclic aromatic hydrocarbon?

Accepted Answer

Naphthalene

Question 16

Which of the following best explains why benzylic bromides are highly reactive in $$S_N1$$ reactions?

Accepted Answer

The benzylic carbocation is resonance stabilized by the aromatic ring.

Question 17

Which of the following is the correct name for a benzene ring with methyl groups at positions 1 and 4?

Accepted Answer

para-xylene

Question 18

Which of the following best describes the stabilization energy of benzene compared to three isolated double bonds?

Accepted Answer

Benzene is more stable by about 152 kJ/mol due to aromatic stabilization.

Question 19

Which of the following is the correct order of average stabilization energy per ring for the following polycyclic aromatic hydrocarbons: benzene, naphthalene, anthracene, phenanthrene?

Accepted Answer

Benzene \u003e Naphthalene \u003e Anthracene ≈ Phenanthrene

Aromatic Compounds: Structure, Nomenclature, Stability, and Reactions

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