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3.3 Organic Chemistry
3.3.10 Aromatic Chemistry (A-level only)
3.3.10.3 Reactivity of Aromatic Compounds
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Benzene consists of a six-carbon ring with each carbon atom bonded to one hydrogen
atom
The π electrons in benzene are confined to individual bonds.
False
The six carbon atoms in benzene form a flat, hexagonal structure.
True
Delocalization of π electrons in
benzene
makes it more stable and less reactive.
True
Delocalization of π electrons in benzene makes it more reactive than alkenes.
False
Order the common reactions of aromatic compounds:
1️⃣ Nitration
2️⃣ Halogenation
3️⃣ Sulfonation
4️⃣ Friedel-Crafts Alkylation
5️⃣ Friedel-Crafts Acylation
Match the reaction with its reagents:
Nitration ↔️ HNO₃, H₂SO₄
Halogenation ↔️ Cl₂, FeCl₃
Sulfonation ↔️ Concentrated H₂SO₄
Friedel-Crafts Alkylation ↔️ R-X, AlCl₃
What is the shape of benzene?
Planar
What type of electron system does benzene have?
Delocalized π electrons
Why is benzene less reactive than alkenes?
Delocalization of π electrons
Aromatic compounds undergo electrophilic
substitution
Friedel-Crafts alkylation uses
AlCl₃
as a catalyst.
True
Match the EAS reaction with its reagents:
Halogenation ↔️ Cl₂, FeCl₃
Nitration ↔️ HNO₃, H₂SO₄
What is the product of sulfonation in EAS?
Benzenesulfonic acid
Common electrophilic substitution reactions include nitration, halogenation, sulfonation, and Friedel-Crafts
reactions
What is required to introduce new functional groups in electrophilic substitution reactions?
Specific reagents and conditions
Why does electrophilic aromatic substitution preserve the aromatic ring structure?
Greater stability of aromatic system
Which type of electron system enhances the stability of aromatic compounds?
Delocalized π electrons
Steps in the electrophilic aromatic substitution (EAS) mechanism
1️⃣ Formation of an electrophilic species
2️⃣ Electrophilic attack on the aromatic ring
3️⃣ Wheland intermediate formation
4️⃣ Deprotonation to give the substituted product
What does the acronym EAS stand for in chemistry?
Electrophilic Aromatic Substitution
Steps in the mechanism of Electrophilic Aromatic Substitution
1️⃣ Electrophilic Attack
2️⃣ Wheland Intermediate Formation
3️⃣ Deprotonation
Why do aromatic compounds undergo substitution rather than addition reactions in EAS?
To preserve stability
In Friedel-Crafts alkylation, the catalyst used is
AlCl₃
In EAS, the electrophile replaces a
hydrogen
on the aromatic ring.
The key difference between EAS and alkene addition is that EAS preserves the aromatic ring structure, while alkene addition breaks the
double bond
.
True
Why are alkenes more reactive than aromatic compounds?
Strained π system
Which type of substituent increases electron density in an aromatic ring?
Activating
Activating substituents direct electrophiles to the ortho- and para- positions.
True
Aromatic compounds are generally
less
reactive than alkenes.
Unlike cyclohexane, benzene has a
planar
shape.
The π electrons in benzene are
delocalized
What type of reaction is characteristic of aromatic compounds like benzene?
Electrophilic substitution
In electrophilic aromatic substitution, a
Wheland
intermediate is formed.
The delocalized π electrons in benzene stabilize the molecule and make it less
reactive
.
Cyclohexane has a planar shape.
False
Benzene has equal bond lengths between carbon atoms.
True
Arrange the properties of aromatic rings in the correct order:
1️⃣ Planar shape
2️⃣ Delocalized π electrons
3️⃣ Lower reactivity
Match the reaction with its product:
Nitration ↔️ Nitrobenzene
Halogenation ↔️ Chlorobenzene
Arrange the steps of the EAS mechanism in the correct order:
1️⃣ Formation of an electrophilic species
2️⃣ Electrophilic attack on the aromatic ring
3️⃣ Wheland intermediate formation
4️⃣ Deprotonation
EAS preserves the stability of aromatic compounds through delocalization.
True
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