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Inductive, Mesomeric, Electomeric Effect-1

The document explains three key effects in organic chemistry: the inductive effect, mesomeric effect, and electromeric effect. The inductive effect involves the shifting of electron density along sigma bonds due to electronegativity differences, while the mesomeric effect refers to the delocalization of π-electrons in conjugated systems. The electromeric effect is a temporary shift of electron density during interactions with reagents, crucial for understanding reaction mechanisms.

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0% found this document useful (0 votes)
24 views4 pages

Inductive, Mesomeric, Electomeric Effect-1

The document explains three key effects in organic chemistry: the inductive effect, mesomeric effect, and electromeric effect. The inductive effect involves the shifting of electron density along sigma bonds due to electronegativity differences, while the mesomeric effect refers to the delocalization of π-electrons in conjugated systems. The electromeric effect is a temporary shift of electron density during interactions with reagents, crucial for understanding reaction mechanisms.

Uploaded by

Hamza Saleem
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© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
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1.

Inductive Effect (I-Effect)


The inductive effect is the shifting of electron density along a sigma bond due to the difference in
electronegativity between atoms. When an electronegative atom is attached to a carbon chain, it pulls
electron density toward itself, creating a polarization of the bond.

Key Features:

- It occurs along sigma bonds (single bonds).

- The effect weakens as the distance from the electronegative atom increases.

- It is a permanent effect, meaning it exists as long as the electronegative atom or group is present.

Types of Inductive Effect:

1. +I Effect (Electron Donating):

- Groups that push or donate electron density toward the rest of the molecule.

- Examples: Alkyl groups like –CH₃ (methyl), –C₂H₅ (ethyl), –CH₂CH₃. These groups are less electronegative
than hydrogen and tend to push electrons toward more electronegative parts of the molecule.

Effects of +I:

- Alkyl groups stabilize positive charges by donating electron density.

- They make the attached atoms or groups less reactive towards electrophiles.

2. –I Effect (Electron Withdrawing):

- Groups that pull or withdraw electron density from the rest of the molecule.

- Examples: Halogens (–Cl, –Br, –I), nitro group (–NO₂), cyano group (–CN), carboxyl group (–COOH),
hydroxyl group (–OH). These groups are more electronegative and pull electron density toward
themselves.

Effects of –I:

- Electron-withdrawing groups stabilize negative charges and increase acidity.

- These groups increase the reactivity of molecules toward nucleophiles.


Example:

- In chloroethane (CH₃CH₂Cl), chlorine (Cl) is highly electronegative and pulls electron density away from
the ethyl group. This causes a partial positive charge on the carbon atom next to chlorine, which in turn
polarizes the molecule.

Importance of Inductive Effect:

- It influences the acidity and basicity of organic compounds.

- Acids: Electron-withdrawing groups increase acidity by stabilizing the conjugate base.

- Bases: Electron-donating groups increase basicity by increasing the electron density.

- It affects reactivity in organic reactions, particularly in electrophilic and nucleophilic reactions.

2. Mesomeric Effect (M-Effect)


The mesomeric effect refers to the delocalization of π-electrons across a conjugated system, leading to a
shift in electron density through resonance. The delocalization helps stabilize the molecule by spreading
out charge over several atoms.

Key Features:

- It involves π-electrons (found in double bonds or lone pairs).

- The effect is most significant in conjugated systems (alternating single and double bonds).

- It is a permanent effect that occurs in molecules with resonance structures.

Types of Mesomeric Effect:

1. +M Effect (Electron Donating Groups):

- Groups that donate electrons into the conjugated system through resonance.

- Examples: Hydroxyl group (–OH), amino group (–NH₂), alkoxy group (–OCH₃), and halogens (–Cl, –Br).

Effects of +M:

- Increases electron density in the conjugated system.

- Makes the molecule more reactive to electrophiles (species that accept electrons).
2. –M Effect (Electron Withdrawing Groups):

- Groups that withdraw electrons from the conjugated system through resonance.

- Examples: Nitro group (–NO₂), carbonyl group (–C=O), cyanide (–CN), and sulfonyl (–SO₃H).

Effects of –M:

- Decreases electron density in the conjugated system.

- Stabilizes the negative charge, making the molecule more reactive to nucleophiles (species that donate
electrons).

Example:

- In phenol (C₆H₅OH), the hydroxyl group (–OH) donates electron density into the benzene ring through
resonance. This increases the electron density in the ring, making it more reactive toward electrophilic
substitution reactions (like nitration and halogenation).

Importance of Mesomeric Effect:

- Reactivity in Reactions: The mesomeric effect influences how a molecule behaves in reactions. Electron-
donating groups (+M) make a molecule more reactive toward electrophiles, while electron-withdrawing
groups (–M) make it more reactive toward nucleophiles.

- Stability: The mesomeric effect can stabilize a molecule by delocalizing charge. For instance, in
carboxylates (R–COO⁻), the negative charge is spread across both oxygen atoms, stabilizing the ion.

3. Electromeric Effect (E-Effect)


The electromeric effect is a temporary shift of electron density in a molecule when it interacts with a
reagent. This effect only occurs during the approach of an attacking species (like an electrophile or
nucleophile) and disappears once the reaction is over.

Key Features:

- It involves the complete transfer of π-electrons in a double or triple bond.

- It is a temporary effect, only happening in the presence of an attacking reagent.

- It usually occurs in unsaturated compounds (those with double or triple bonds).


Types of Electromeric Effect:

1. +E Effect (Electron Donating):

- Electrons from a double or triple bond move toward the attacking species, donating electron density.

- Example: When a nucleophile (electron-rich species) attacks a carbonyl compound, the electrons from
the double bond shift toward the nucleophile, allowing the reaction to occur.

2. –E Effect (Electron Withdrawing):

- Electrons from a double or triple bond move toward the electronegative attacking species (like an
electrophile).

- Example: When HCl reacts with an alkene, the pi-electrons from the double bond shift toward the
electrophilic hydrogen, leading to the formation of a carbocation.

Example:

- In the reaction of ethylene (CH₂=CH₂) with HCl, the electrons from the double bond shift toward the
hydrogen atom of HCl, making the carbon atoms more susceptible to bonding with the chloride ion.

Importance of Electromeric Effect:

- It plays a crucial role in reaction mechanisms, particularly in electrophilic addition reactions (such as the
addition of acids to alkenes or alkynes).

- It helps explain how certain reagents interact with double or triple bonds during chemical reactions.

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