Question 1

Which of the following is the correct IUPAC name for the compound with the structure $\mathrm{C_6H_5CH_2CH_2CH_2CH_2CH_3}$?

Accepted Answer

n-Hexylbenzene

Question 2

Consider the following two compounds: benzene and the cyclobutadiene dianion ($\mathrm{C_4H_4^{2-}}$). All atoms in the rings are found to be $sp^2$ hybridized. What do you expect about their aromaticity?

Accepted Answer

Benzene is aromatic, cyclobutadiene dianion is aromatic

Question 3

How many isomeric dibromoanilines can be formed from aniline ($\mathrm{C_6H_5NH_2}$) by bromination?

Accepted Answer

5

Question 4

In the bromination of $p$-nitroaniline, which positions on the aromatic ring are most likely to be brominated?

Accepted Answer

Positions b and c

Question 5

During Friedel-Crafts alkylation of benzene with $n$-propyl chloride in the presence of $\mathrm{AlCl_3}$, which major product is expected?

Accepted Answer

Isopropylbenzene

Question 6

The sulfonation of naphthalene with $\mathrm{H_2SO_4}$ at low temperature gives 1-naphthalenesulfonic acid, while at high temperature it gives 2-naphthalenesulfonic acid. What does this indicate about the reaction?

Accepted Answer

The activation energy is lower for the formation of the 1-isomer, but the 2-isomer is more stable

Question 7

In the molecular orbital model of the cyclobutadiene cation ($\mathrm{C_4H_4^+}$), how many $\pi$ electrons are in nonbonding molecular orbitals?

Accepted Answer

2

Question 8

What are the products of the Friedel-Crafts acylation of benzene with acetic anhydride ($\mathrm{(CH_3CO)_2O}$) in the presence of $\mathrm{AlCl_3}$?

Accepted Answer

Acetophenone and acetic acid

Question 9

Chloroform reacts with three moles of benzene to generate triphenylmethane and HCl in the presence of aluminum chloride. What type of reaction is this?

Accepted Answer

A Friedel-Crafts alkylation

Question 10

Which of the following is the major product of the reaction between styrene ($\mathrm{C_6H_5CH=CH_2}$) and benzoyl chloride ($\mathrm{C_6H_5COCl}$) in the presence of $\mathrm{AlCl_3}$?

Accepted Answer

III

Question 11

Which of the following is NOT a characteristic of aromatic compounds?

Accepted Answer

There must be 4n $\pi$ electrons

Question 12

Which compound will NOT react with a Grignard reagent?

Accepted Answer

Compound 5 ($\mathrm{R-CN}$)

Question 13

Which of the following is the main reason that the diene below is unreactive towards dienophiles?

Accepted Answer

Because it has difficulty adopting the s-cis conformation needed to react

Question 14

Which of the following pairs of structures represent resonance forms?

Accepted Answer

IV

Question 15

In the bromination of benzene to generate bromobenzene and HBr, what is the rate-determining step?

Accepted Answer

The formation of a non-aromatic intermediate arenium cation

Question 16

Which of the following is the electrophile in the preparation of deuterated benzene by treatment of benzene with deuterated sulfuric acid?

Accepted Answer

$\mathrm{D^+}$

Question 17

Which of the following is a valid intermediate for the bromination of benzene in the presence of iron bromide?

Accepted Answer

A benzene ring with a Br attached and a positive charge on the ring

Question 18

Why does cyclobutadiene show unusually high reactivity compared to other cyclic dienes?

Accepted Answer

Because the compound is antiaromatic before it reacts

Question 19

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

Accepted Answer

The system must be free of ring strain

Aromatic Compounds and Electrophilic Aromatic Substitution: Study Guide

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