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Module 6: Organic Chemistry and Analysis
6.1 Aromatic Compounds
6.1.2 Electrophilic substitution reactions
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Electrophilic substitution reactions involve the replacement of a hydrogen atom on an aromatic ring by an
electrophile
Steps in the general mechanism for electrophilic substitution on benzene rings
1️⃣ Formation of the electrophile
2️⃣ Electrophilic attack on the benzene ring
3️⃣ Loss of a proton
The electrophilic attack forms a positively charged intermediate.
True
The electrophile substitutes a hydrogen atom on the benzene ring.
True
Benzene's negative charge attracts
electrophiles
.
True
The second step in electrophilic substitution is electrophilic
attack
on the benzene ring.
In the first step of electrophilic substitution, an electron-seeking species called an
electrophile
is formed.
During electrophilic attack, the electrophile forms a positively charged intermediate by attacking the
benzene
ring.
True
What happens to Br₂ when it reacts with FeBr₃ in electrophilic substitution reactions?
Forms Br⁺
Electrophilic substitution reactions maintain the
aromatic
structure of the ring.
True
In the formation of the electrophile, Br₂ reacts with FeBr₃ to form
Br⁺
Electrophilic substitution reactions are a type of
organic
reaction.
Benzene's pi electrons form a delocalized electron
cloud
above and below the ring.
Benzene's delocalized pi electrons create high electron
density
in the ring.
Regeneration of the aromatic ring involves the loss of a
proton
.
True
Give an example of how an electrophile is formed in electrophilic substitution reactions.
Br₂ reacts with FeBr₃ to form Br⁺
In the third step of electrophilic substitution, a
proton
is lost to regenerate the aromatic ring.
Order the steps in the general mechanism for electrophilic substitution on benzene rings.
1️⃣ Formation of the electrophile
2️⃣ Electrophilic attack on the benzene ring
3️⃣ Loss of a proton
What is unique about the pi electrons in benzene?
They form a delocalized cloud
Benzene is highly attractive to electrophiles due to its partial negative charge from the
pi electron cloud
.
True
What is the sigma complex in electrophilic substitution reactions?
A positively charged intermediate
The sigma complex is crucial because it allows the aromatic structure of
benzene
to be maintained during the substitution reaction.
True
In the regeneration of the benzene ring, a
proton
is lost from the sigma complex.
Name four examples of electrophiles used in aromatic substitution reactions.
Nitronium ions, Sulfonium ions, Halogens, Acyl ions
Electrophilic substitution reactions maintain the aromatic structure while introducing the
electrophile
.
Electrophilic substitution reactions are a type of
organic
reaction.
True
An electrophile is an electron-seeking
species
.
Steps in the general mechanism for electrophilic substitution on benzene rings:
1️⃣ Formation of the electrophile
2️⃣ Electrophilic attack on the benzene ring
3️⃣ Loss of a proton
What happens during the electrophilic attack step in the mechanism?
Br⁺ attacks benzene
Benzene features a planar aromatic ring with six carbon atoms and delocalized
pi
electrons.
Benzene's negative charge attracts electrophiles, leading to electrophilic substitution reactions.
True
What type of ring does benzene feature in its structure?
Aromatic ring
The pi electrons in benzene are confined to individual bonds.
False
Benzene is highly attractive to electrophiles due to its
negative
charge.
What type of intermediate is formed in the formation of a sigma complex?
Positively charged
The loss of a proton from the sigma complex regenerates the aromatic structure of benzene.
True
Which electrophile is used in nitration reactions?
Nitronium ion
Nitration of benzene produces
nitrobenzene
.
Aromatic substitution reactions increase the diversity of aromatic compounds in
organic synthesis
.
True
The electrophile in electrophilic substitution reactions attacks the electron-rich
benzene
ring.
True
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