ELECTROMERIC EFFECT

Introduction
• The electromeric effect is a reversible reaction where
there is a complete transfer of a pi-electron pair due to
the influence of an electrophile or a nucleophile. It is a
transient effect that occurs when a reagent assaults a
multiple-bonded molecule, producing a full shift of pi
electrons to one of the bonds of two atoms. The effect
disappears upon withdrawal of the attacking reagent.
• OR
• Electromeric effect refers to a shift of pi-electron
density towards one of the bonded atoms in a
molecule due to presence of an approaching or
attacking reagent.
• This effect is shown by those organic
compounds containing multiple bonds. When a
double bond or triple bond is attacked by an
attacking reagent, a pair of bonding electrons
involved in the pi-bond is transferred
completely from one atom to another.

• This is a temporary effect and will remain as

long as the attacking reagent is present. As soon
as the reagent is removed, the polarized
molecule will come back to the original state.
• Electromeric effect is represented by “E”.
This effect can be visualized by drawing
curved arrows to show the direction of transfer
of π-electrons to an atom across a multiple
bond.
 Features of Electromeric Effect:

• It occurs only in the presence of attacking reagent

which may be an electrophile or a nucleophile.
• It occurs in a compound having a multiple bond
(double or triple bond).
• It results in shifting of the pi-electrons to an atom
across a multiple bond.
• It is a temporary effect.
• It helps us in deciding possible outcomes of a reaction
on multiple bond.
 Electromeric Effect and
Symmetry/Polarity of Multiple Bond
• In the presence of an attacking reagent, pi
electrons of a symmetrical or non-polar
multiple bond may be displaced or shifted in
either direction. For example in case of
ethylene and acetylene.
 Electromeric Effect in unsymmetrical/ Polar Multiple Bonds

• In the presence of an attacking reagent, pi

electrons of an unsymmetrical or polar
multiple bond will be displaced or shifted in
one direction only i.e., towards more
electronegative atom. For example in case of
ketones and nitriles.
• Similarly, in propylene (an unsymmetrical
alkene) electron shift can occur only in one
direction because of electron donating nature
of methyl group.
 Types of Electromeric Effect:
• There are two types of electromeric effect:
• 1. Positive Electromeric Effect (+E)
• When the pi-electron density of a multiple
bond shifts or transfers to that atom which is
approached by the attacking reagent, it is
termed as the +E effect. After the transfer takes
place, the reagent gets attached to the atom
where the electrons have been transferred to
and the other atom acquires positive charge.
• The addition of acids to alkenes is an example
of the +E effect.
 2. Negative Electromeric Effect (-E)

• When the pi-electron density of a multiple

bond shifts or transfers away from that atom
which is approached by the attacking reagent,
it is termed as the -E effect. After the transfer
takes place, the reagent gets attached to the
electron deficient atom and the pi-electrons are
transferred completely to the other atom.
Importance/Uses of Electromeric Effect:
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