Question 1

Which of the following reagents is required to convert benzene to bromobenzene via electrophilic aromatic substitution?

Accepted Answer

$$\mathrm{Br_2$}$$, $$\mathrm{$$FeBr_3$$}$$

Question 2

What is the major product when benzene is treated with $$\mathrm{SO_3$}$$ and $$\mathrm{H_2SO_4}$$?

Accepted Answer

Benzenesulfonic acid

Question 3

Which of the following statements about Friedel–Crafts alkylation is TRUE?

Accepted Answer

Vinyl halides and aryl halides do not react in Friedel–Crafts alkylation.

Question 4

Which group will deactivate a benzene ring toward electrophilic aromatic substitution and direct new substituents to the meta position?

Accepted Answer

$$\mathrm{NO_2$}$$

Question 5

A benzene ring with a methyl group is treated with $$\mathrm{Br_2$}$$ and $$\mathrm{$$FeBr_3$$}. $$What is the major product?

Accepted Answer

Ortho- and para-bromotoluene

Question 6

Which of the following is a necessary condition for the oxidation of an alkyl benzene to benzoic acid using $$\mathrm{$$KMnO_4$$}$$?

Accepted Answer

The alkyl group must have at least one benzylic hydrogen.

Question 7

Which of the following best explains why aniline ($$\mathrm{C_6H_5NH_2}) is a $$strong activator for electrophilic aromatic substitution?

Accepted Answer

The lone pair on nitrogen can delocalize into the ring, increasing electron density.

Question 8

Which of the following is the correct order of reactivity toward electrophilic aromatic substitution (from most to least reactive)?

Accepted Answer

Aniline $$\u003e$$ Toluene $$\u003e$$ Benzene $$\u003e$$ Nitrobenzene

Question 9

What is the product of the following reaction: $$p-$$chlorotoluene + $$\mathrm{$$NaNH_2$$} ($$two steps)?

Accepted Answer

$$p-$$toluidine

Question 10

Which of the following statements about Friedel–Crafts acylation is FALSE?

Accepted Answer

It can occur with a benzene ring deactivated by a nitro group.

Question 11

Which of the following is the major product when $$m-$$nitrotoluene is treated with $$\mathrm{Br_2$}$$ and $$\mathrm{$$FeBr_3$$}$$?

Accepted Answer

Bromine adds ortho to the methyl group.

Question 12

Which of the following is a correct statement about nucleophilic aromatic substitution?

Accepted Answer

It is favored by electron-withdrawing groups on the ring.

Question 13

Which of the following best describes the effect of a methyl group on a benzene ring?

Accepted Answer

It is an electron-donating group and activates the ring toward electrophilic substitution.

Question 14

Which of the following is the correct product for the oxidation of ethylbenzene with $$\mathrm{$$KMnO_4$$}$$?

Accepted Answer

Benzoic acid

Question 15

Which of the following is a reason why polyalkylation can occur in Friedel–Crafts alkylation?

Accepted Answer

The alkyl group activates the ring toward further substitution.

Question 16

Which of the following is the major product when $$p-$$nitrotoluene is oxidized with $$\mathrm{$$KMnO_4$$}$$?

Accepted Answer

$$p-$$nitrobenzoic acid

Question 17

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

Accepted Answer

Electrophilic aromatic substitution

Question 18

Which of the following is a correct statement about the reduction of nitrobenzene?

Accepted Answer

It produces aniline ($$\mathrm{C_6H_5NH_2}) as $$the major product.

Electrophilic and Nucleophilic Aromatic Substitution: Reactions and Mechanisms

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