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Substituent Effects in Electrophilic Aromatic Substitution

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26 views

Substituent Effects in Electrophilic Aromatic Substitution

Uploaded by

apgajula
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Substituent Effects

in Electrophilic
Aromatic
Substitution
This presentation delves into the impact of substituents on the reactivity
and orientation of monosubstituted benzene compounds in electrophilic
aromatic substitution reactions. We'll explore key concepts, mechanisms,
and practical applications.
Introduction to Aromatic
Substitution Reactions
Aromatic substitution reactions involve the replacement of a hydrogen atom on an
aromatic ring with an electrophile. Benzene, a highly stable aromatic system,
undergoes these reactions, leading to the formation of new functionalized aromatic
compounds.

1 Electrophile Attack 2 Intermediate Formation


The reaction begins with the A carbocation intermediate is
attack of an electrophile on the formed, which is stabilized by
electron-rich pi system of the resonance.
benzene ring.

3 Proton Loss
The final step involves the loss of a proton, regenerating the aromatic ring.
Factors Affecting Reactivity and Orientation
The reactivity and orientation of electrophilic aromatic substitution are influenced by the nature of the substituent already present
on the benzene ring.

Inductive Effect Resonance Effect

Electron-withdrawing substituents decrease electron density in Electron-donating substituents increase electron density in the
the ring, making it less reactive. ring, making it more reactive.
Activating and
Deactivating Substituents
Substituents can be categorized as activating or deactivating, based on their
effect on the reactivity of the aromatic ring.

Activating Increase electron Make the ring more


Substituents density in the ring reactive towards
electrophilic attack

Deactivating Decrease electron Make the ring less


Substituents density in the ring reactive towards
electrophilic attack
Ortho, Meta, and Para-Directing
Substituents
Substituents also direct the position of electrophilic attack on the benzene ring.

Ortho-Directing
Substituents that donate electrons to the ring direct the electrophile to the ortho and para positions.

Meta-Directing
Electron-withdrawing substituents direct the electrophile to the meta position.

Para-Directing
Substituents that donate electrons to the ring direct the electrophile to the para position.
Electrophilic Aromatic
Substitution: Mechanism and
Examples
Electrophilic aromatic substitution proceeds through a series of steps involving an
electrophile, the aromatic ring, and intermediates.

1 Attack
The electrophile attacks the electron-rich pi system of the benzene ring.

2 Carbocation Formation
A carbocation intermediate is formed, which is stabilized by resonance.

3 Proton Loss
The final step involves the loss of a proton, regenerating the aromatic ring.
The Role of Substituents in
Directing the Position of
Electrophilic Attack
The nature of the substituent directly influences the position of electrophilic
attack.

Electron-Donating Electron-Withdrawing
Substituents Substituents
Electron-donating substituents Electron-withdrawing
increase electron density at the substituents decrease electron
ortho and para positions, making density at the ortho and para
them more susceptible to positions, making them less
electrophilic attack. susceptible to electrophilic
attack.
Predicting the Product of Electrophilic Aromatic
Substitution Reactions
By understanding the effects of substituents, we can predict the major product of electrophilic aromatic substitution reactions.

Identify the Substituent Predict the Position of Attack Draw the Product
Determine whether the substituent is activating The electrophile will attack at the position The product will be formed by the replacement
or deactivating and ortho/para- or meta- favored by the substituent. of a hydrogen atom at the preferred position
directing. with the electrophile.
Real-World Applications of Substituent Effects in Organic
Synthesis
The principles of substituent effects are fundamental to organic synthesis, enabling the controlled synthesis of a wide range of aromatic compounds with specific
properties.

Pharmaceuticals Polymers
Substituent effects are essential in designing and synthesizing new drugs. Substituents on aromatic monomers influence the properties of polymers, such as
strength and flexibility.
Conclusion and Key
Takeaways
Substituent effects are essential for understanding and predicting the
outcomes of electrophilic aromatic substitution reactions.

1 Reactivity 2 Orientation
Substituents can activate or Substituents direct the
deactivate the benzene ring. position of electrophilic
attack.

3 Applications
These concepts are crucial for the synthesis of a vast array of
aromatic compounds.

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