Free Practice Quiz Question List

04 Aromatic Compounds in Synthesis Online Quiz Questions

Use this free practice quiz with 20 questions to review 04 Aromatic Compounds in Synthesis, test your knowledge, and prepare for your next test or exam.

20 questions

True or false

1 point

True or false: Halogens on an aromatic ring are deactivating, yet generally direct incoming electrophiles to the ortho and para positions.

A
True
B
False

Choose one

1 point

When toluene undergoes nitration, which product pattern is expected to predominate?

A
Mainly meta-nitrotoluene
B
Mainly ortho- and para-nitrotoluene
C
Equal amounts of all three positional isomers
D
Only the ipso substitution product

Written response

1 point

After reducing an aromatic nitro group with iron or tin under acidic conditions, what functional-group class does the substituent become?

Fill in the blank

1 point

In electrophilic aromatic substitution, an electrophile replaces a ring , and loss of H⁺ restores .

True or false

1 point

True or false: In the addition–elimination pathway of nucleophilic aromatic substitution, the leaving group departs before the nucleophile adds.

A
True
B
False

Written response

1 point

What is the name of the partially reduced ring product formed when an arene undergoes a Birch reduction?

Choose one

1 point

For an activated nitroaryl halide to undergo nucleophilic aromatic substitution by the addition–elimination pathway, where should the nitro group be relative to the leaving group to stabilize the key intermediate by resonance?

A
Meta to the leaving group
B
Only at a position remote from the leaving group
C
Ortho or para to the leaving group
D
Its position does not matter

Fill in the blank

1 point

Complete the usual sequence of steps in the palladium-catalyzed Suzuki–Miyaura cycle: , , then .

Choose one

1 point

What bond-forming result is expected when an aryl halide couples with an arylboronic acid in a Suzuki–Miyaura reaction?

A
A carbon–carbon bond joining the two aryl fragments
B
A carbon–oxygen bond joining the two aryl fragments
C
A bond that saturates both aromatic rings
D
A carbon–hydrogen bond replacing the halide

Choose all

1 point

When planning an electrophilic aromatic substitution on a ring that already has two substituents, select all accurate guidelines for predicting where the new group will enter.

A
Compare both substituents' directing effects and consider steric hindrance.
B
The more strongly activating group often has greater influence on the incoming electrophile's position.
C
The deactivating substituent must always control the position, regardless of the other group.
D
Substituent directing effects can be ignored whenever two groups are already present.

Choose all

1 point

A target is a biaryl bearing a nitro group. Select all synthesis-planning strategies supported for reaching it while accounting for selectivity and compatibility.

A
Couple a nitro-substituted aryl halide with an arylboronic acid if the substrate and conditions are compatible.
B
Form the biaryl first, then introduce the nitro group by EAS if the directing effects favor the target position.
C
Assume either sequence will give the target position regardless of directing effects or substrate compatibility.
D
Use EAS alone to join two separately prepared aromatic fragments through a biaryl bond.

Open ended

1 point

A molecule contains an aromatic ring and a separate, more reactive alkene. You need to reduce the alkene while retaining the aromatic ring. Which hydrogenation approach should you choose, and how does it differ from the conditions used to convert an arene fully to a cycloalkane?

Choose one

1 point

An aryl amine is present at a ring position where you need an iodine substituent, and direct ring substitution is difficult. Which route uses the diazonium strategy described for making this change?

A
Use direct electrophilic aromatic substitution to replace the amine with iodine.
B
Diazotize the aryl amine, then replace the diazonium group with iodine.
C
Reduce the aryl amine to a cyclohexane, then add iodine.
D
Use nucleophilic aromatic substitution on the aryl amine without an activating group.

True or false

1 point

True or false: Friedel–Crafts acylation followed by carbonyl reduction is a common alternative for installing an alkyl group when direct Friedel–Crafts alkylation may give rearrangements.

A
True
B
False

Written response

1 point

When an aromatic –NO₂ group is reduced using iron or tin under acidic conditions, what substituent is formed?

Written response

1 point

Which group can replace an aryl diazonium group to form an aryl nitrile?

Choose one

1 point

Nitration of toluene is carried out by electrophilic aromatic substitution. Which product distribution is expected mainly because of the methyl substituent?

A
Mainly meta-nitrotoluene
B
Mainly ortho- and para-nitrotoluene
C
Only unsubstituted benzene
D
Mainly the benzylic carbon is nitrated

Choose one

1 point

A nitroaryl halide undergoes addition–elimination SₙAr. Which placement of the nitro group best supports this reaction by resonance stabilization of the anionic intermediate?

A
A nitro group meta to the leaving group
B
A methyl group meta to the leaving group
C
A nitro group ortho or para to the leaving group
D
Any substituent, regardless of position

Choose one

1 point

A benzene ring is treated with an alkali metal in liquid ammonia and an alcohol proton source. What ring product is characteristic of this reduction?

A
A 1,4-cyclohexadiene
B
A cyclohexane
C
A phenol
D
An aryl amine

Choose one

1 point

A molecule contains both an aromatic ring and a more reactive alkene. Which outcome is possible under mild hydrogenation conditions?

A
Any hydrogenation catalyst immediately converts an arene to a cyclohexane
B
An aromatic ring is reduced more readily than an ordinary alkene
C
Mild hydrogenation always reduces both the arene and every alkene
D
Milder hydrogenation can reduce a more reactive alkene while leaving the aromatic ring intact