Question 1

Which of the following C$_6$H$_6$ compounds has a single set of chemically equivalent hydrogens?

Accepted Answer

III

Question 2

Which of the following compounds would not be aromatic according to Hückel's rule?

Accepted Answer

Cyclobutadiene

Question 3

A rose (benzene) is treated with methyl chloride and AlCl$_3$. What is the major product?

Accepted Answer

Toluene

Question 4

Which of the following is an important resonance contributor for the nitrobenzene molecule?

Accepted Answer

$\mathrm{C_6H_5-NO_2}$$

Question 5

Bromobenzene is treated with Mg in ether. What is the product?

Accepted Answer

Phenyl magnesium bromide

Question 6

Which of the following compounds is phenol?

Accepted Answer

A benzene ring with a hydroxyl group

Question 7

What is the order of reactivity of the following compounds towards electrophilic aromatic substitution: benzene, toluene, nitrobenzene?

Accepted Answer

Toluene > Benzene > Nitrobenzene

Question 8

Which of the following structures most closely represents ortho-xylene?

Accepted Answer

A benzene ring with two methyl groups on adjacent carbons

Question 9

Which of the following reagents would not give a Friedel-Crafts alkylation product when reacted with benzene?

Accepted Answer

C$_6$H$_5$Cl/AlCl$_3$

Question 10

Which of the following is the major product from the nitration of toluene?

Accepted Answer

Ortho-nitrotoluene

Question 11

Which of the following is the likely outcome from the sulfonation of naphthalene at 80°C?

Accepted Answer

1-naphthalenesulfonic acid

Question 12

Which of the following Grignard reagents would be best for the synthesis of triphenylmethanol?

Accepted Answer

PhMgBr + PhCOCH$_3$

Question 13

Which of the following is the major product from the bromination of anisole?

Accepted Answer

Ortho-bromoanisole

Question 14

Which of the following statements about the reactivity of benzene in electrophilic aromatic substitution is correct?

Accepted Answer

Benzene is less reactive than toluene

Question 15

Which of the following is the correct sequence of steps in the mechanism of nitration of benzene?

Accepted Answer

Formation of nitronium ion, attack on benzene, loss of proton

Question 16

Which of the following is the major product from the sulfonation of benzene at 100°C?

Accepted Answer

Benzene sulfonic acid

Question 17

Which of the following is the best method to prepare 3,5-dinitrobenzoic acid from benzoic acid?

Accepted Answer

Nitration with HNO$_3$/H$_2$SO$_4$ at 100°C

Question 18

Which of the following aromatic compounds is most likely to undergo nucleophilic aromatic substitution?

Accepted Answer

Nitrobenzene

Question 19

Which of the following is the major product from the Friedel-Crafts acylation of benzene with acetyl chloride?

Accepted Answer

Acetophenone

Question 20

Which of the following statements about the effect of substituents on the orientation of electrophilic aromatic substitution is correct?

Accepted Answer

Electron-donating groups direct substitution to ortho and para positions

Aromatic Compounds: Structure, Reactivity, and Substitution Reactions – Study Guide

Study Guide - Practice Questions