Question 1

Which of the following is the major organic product obtained from the nitration of toluene with $$\mathrm{$$HNO_3$$}$$ and $$\mathrm{H_2SO_4}$$?

Accepted Answer

4-nitrotoluene

Question 2

In the Friedel-Crafts alkylation of toluene with tert-butyl chloride and $$\mathrm{$$AlCl_3$$}$$, what is the major product?

Accepted Answer

p-tert-butyl toluene

Question 3

Which of the following is the major product when toluene reacts with propyl chloride and $$\mathrm{$$AlCl_3$$}$$?

Accepted Answer

p-n-propyl toluene

Question 4

What is the major organic product obtained from the following sequence: Friedel-Crafts acylation of toluene with propionyl chloride and $$\mathrm{$$AlCl_3$$}$$, followed by Clemmensen reduction ($$\mathrm{Zn(Hg), HCl}$$)?

Accepted Answer

p-n-propyl toluene

Question 5

Which of the following compounds undergoes the most rapid nucleophilic aromatic substitution with hydroxide ion?

Accepted Answer

p-bromo-nitrobenzene

Question 6

Which of the following is the reactive intermediate in the nucleophilic substitution of 4-bromo-1-nitrobenzene with sodium hydroxide?

Accepted Answer

Meisenheimer complex (anionic intermediate)

Question 7

Which of the following sets of substituents are all ortho/para directing in electrophilic aromatic substitution reactions?

Accepted Answer

Br, OCH$$_3$$, C$$_2H$_5$$

Question 8

Which of the following sets of substituents are all activating groups in electrophilic aromatic substitution reactions?

Accepted Answer

C$$_6H$_5$$, OCH$$_3$$, NHCOCH$$_3$$

Question 9

Which of the following substituents is ortho/para directing and deactivating in electrophilic aromatic substitution reactions?

Accepted Answer

F

Question 10

Which of the following is NOT one of Hückel's criteria for aromaticity?

Accepted Answer

The compound must have $$(4n) pi $$electrons in the aromatic system, where $$n is a $$positive integer

Question 11

Which of the following ions is aromatic?

Accepted Answer

Cyclopentadienyl anion

Question 12

Which of the following compounds is aromatic?

Accepted Answer

Phenol

Question 13

Which of the following is the major organic product obtained from the bromination of m-nitrotoluene with Br$$_2$$ and FeBr$$_3$$?

Accepted Answer

3-bromo-4-nitrotoluene

Question 14

Which of the following fused arenes is naphthalene?

Accepted Answer

Structure 1

Question 15

Which of the following compounds is nonaromatic?

Accepted Answer

Cyclopropenyl anion

Question 16

What is the electrophile in the reaction of benzene with concentrated sulfuric acid containing dissolved sulfur trioxide?

Accepted Answer

HSO$$_3^+$$

Question 17

What is the role of $$\mathrm{$$AlCl_3$$} in $$Friedel-Crafts acylations using acid chlorides?

Accepted Answer

Lewis acid

Question 18

Which of the following undergoes the most rapid nitration upon treatment with $$\mathrm{$$HNO_3$$/H_2SO_4}$$?

Accepted Answer

Toluene

Question 19

Which of the following sets of substituents are all deactivating groups in electrophilic aromatic substitution reactions?

Accepted Answer

Br, NO$$_2$$, CCl$$_3$$

Question 20

Which of the following is the correct IUPAC name for the compound shown (bromine at position 3, nitro at position 4, hydroxy at position 1)?

Accepted Answer

3-bromo-4-nitrophenol

Step-by-Step Guidance for Organic Chemistry Aromatic Compounds and Reactions

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