Question 1

Which of the following compounds is classified as aromatic according to Hückel's rule?

Accepted Answer

Benzene ($$C_6H_6)$$

Question 2

What is the IUPAC name for the compound shown in image 2 (benzene ring with two iodine atoms on adjacent carbons)?

Accepted Answer

1,2-diiodobenzene

Question 3

Which of the following best describes the stability of benzene compared to other cyclic compounds with alternating double bonds?

Accepted Answer

Benzene is more stable due to aromaticity and delocalized $$\pi$$ electrons.

Question 4

Which compound would react fastest in an SN1 reaction?

Accepted Answer

Chlorotoluene

Question 5

Which of the following is the correct ortho, meta, para nomenclature for the compound shown in image 13 (chlorotoluene)?

Accepted Answer

m-chlorotoluene

Question 6

Which compound is most acidic among the following: benzoic acid, phenol, and toluene?

Accepted Answer

Benzoic acid

Question 7

Which nitrogen in imidazole is more basic?

Accepted Answer

The nitrogen with a lone pair not involved in aromaticity

Question 8

Which of the following compounds is antiaromatic?

Accepted Answer

Cyclobutadiene ($$C_4H_4)$$

Question 9

What is the product of the electrocyclic closure of (2Z,4E)-hexa-2,4-diene under thermal conditions?

Accepted Answer

Trans-cyclohexene

Question 10

Which substrate would react fastest in an SN1 reaction: bromocyclobutene, bromocyclopentadiene, or bromotoluene?

Accepted Answer

Bromotoluene

Question 11

Which of the following compounds is nonaromatic?

Accepted Answer

Cyclooctatetraene ($$C_8H_8)$$

Question 12

Which compound is most nucleophilic: pyrrole or pyrrolidine?

Accepted Answer

Pyrrolidine

Question 13

Which of the following is the correct IUPAC name for the compound shown in image 3 (benzoic acid derivative with chlorine at the meta position)?

Accepted Answer

3-chlorobenzoic acid

Question 14

Which of the following fused ring systems contains 14 $$\pi$$ electrons and is aromatic?

Accepted Answer

Phenanthrene

Question 15

Which compound is antiaromatic according to the Frost circle diagram for a seven-membered ring?

Accepted Answer

Cycloheptatriene cation ($$C_7H_7^+)$$

Question 16

Which of the following is the correct common name for the compound shown in image 4 (isopropylbenzene with a hydroxyl group at the para position)?

Accepted Answer

p-isopropylphenol

Question 17

Which compound is aromatic according to the criteria for aromaticity: planarity, cyclic conjugation, and $$4n+2$$ $$\pi$$ electrons?

Accepted Answer

Cyclopropenyl cation ($$C_3H_3^+)$$

Question 18

Which compound would be expected to have the highest rate of SN1 reaction due to aromatic stabilization of the carbocation intermediate?

Accepted Answer

Bromotoluene

Question 19

Which of the following is the correct IUPAC name for the compound shown in image 5 (tert-butyl group and hydroxyl group on benzene, chlorine at the meta position)?

Accepted Answer

3-chloro-4-tert-butylphenol

Pericyclic Reactions and Aromaticity: Study Guide for CHEM 2425 Module 08

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