Inductive, Mesomeric, Electomeric Effect-1
Inductive, Mesomeric, Electomeric Effect-1
Key Features:
- 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.
- 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:
- They make the attached atoms or groups less reactive towards electrophiles.
- 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:
- 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.
Key Features:
- The effect is most significant in conjugated systems (alternating single and double bonds).
- 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:
- 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:
- 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).
- 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.
Key Features:
- 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.
- 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.
- 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.