Question 1

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

Accepted Answer

Benzene ($$C_6H_6)$$

Question 2

Which of the following is NOT a requirement for a compound to be aromatic?

Accepted Answer

The molecule must have exactly 6 pi electrons.

Question 3

A student is asked to rank the acidity of the following benzoic acids: $$p-$$bromobenzoic acid, benzoic acid, and $$p-$$nitrobenzoic acid. Which is the correct order from most acidic to least acidic?

Accepted Answer

$$p-$$nitrobenzoic acid \u003e $$p-$$bromobenzoic acid \u003e benzoic acid

Question 4

Which of the following reactions is an example of electrophilic aromatic substitution?

Accepted Answer

Bromination of benzene with $$Br_2$$ and $$FeBr_3$$

Question 5

Which of the following compounds is antiaromatic?

Accepted Answer

Cyclobutadiene ($$C_4H_4)$$

Question 6

A chemist wants to synthesize $$p-$$nitrobenzaldehyde from benzaldehyde. Which sequence of reactions would be most appropriate?

Accepted Answer

Nitration with $$HNO_3$$/$$H_2SO_4$$ only

Question 7

Which of the following substituents on a benzene ring is meta-directing in electrophilic aromatic substitution?

Accepted Answer

Nitro group ($$-NO_2$)

Question 8

Which of the following is the correct IUPAC name for the compound shown below?

A benzene ring with a methyl group at position 1 and a bromine at position 4.

Accepted Answer

4-bromotoluene (or $$p-$$bromotoluene)

Question 9

Which of the following statements about aromaticity is TRUE?

Accepted Answer

Aromatic compounds are stabilized by resonance and follow Hückel's rule ($$4n+2 pi $$electrons).

Question 10

Which of the following is the major product when toluene is treated with $$Br_2$$ and $$FeBr_3$$?

Accepted Answer

Ortho-bromotoluene

Question 11

A student is asked to rank the basicity of the following anilines: $$p-$$nitroaniline, aniline, and $$p-$$methoxyaniline. Which is the correct order from most basic to least basic?

Accepted Answer

$$p-$$methoxyaniline \u003e aniline \u003e $$p-$$nitroaniline

Question 12

Which of the following reagents would you use to convert benzene to $$p-$$tert-butylbenzenesulfonic acid?

Accepted Answer

$$SO_3$$, $$H_2SO_4$$, then $$t-$$BuCl, $$AlCl_3$$

Question 13

Which of the following compounds is NOT aromatic?

Accepted Answer

Cyclobutadiene ($$C_4H_4)$$

Question 14

Which of the following is the correct product for the reaction of benzene with $$CH_3CH_2COCl$$ and $$AlCl_3$$?

Accepted Answer

Benzene with a propionyl group ($$C_6H_5COCH_2CH_3)$$

Question 15

Which of the following is the correct order of acidity for the following benzoic acids: $$p-$$cyanobenzoic acid, $$p-$$methylbenzoic acid, benzoic acid?

Accepted Answer

$$p-$$cyanobenzoic acid \u003e benzoic acid \u003e $$p-$$methylbenzoic acid

Question 16

Which of the following is the correct synthetic route to convert benzene to $$p-$$bromoethylbenzene?

Accepted Answer

Step 1: Friedel-Crafts alkylation with $$CH_2CH_3$$, $$AlCl_3$$; Step 2: Bromination with $$Br_2$$, $$FeBr_3 ($$para product)

Question 17

Which of the following is the major product when $$p-$$xylene is oxidized with $$H_2CrO_4$$?

Accepted Answer

Terephthalic acid ($$p-$$phthalic acid)

Question 18

Which of the following is the correct order of basicity for the following anilines: $$p-$$cyanoaniline, aniline, $$p-$$methyl aniline?

Accepted Answer

$$p-$$methyl aniline \u003e aniline \u003e $$p-$$cyanoaniline

Question 19

Which of the following is the correct product when $$p-$$nitrobenzaldehyde is reduced with $$H_2$$, $$Pd/C$$?

Accepted Answer

$$p-$$aminobenzaldehyde

Aromaticity, Nomenclature, and Reactions of Benzene and Substituted Benzenes

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