A Brief Introduction About

Carbanion
 Negetively charged Organic species in which carbon
carries three bond pair and one lone pair, is known as
Carbanion. It s represented as-
 Characstics of Carbanions
 Hybridysation and geometry: Alkyl carbanion has
three bond pairs and one lone pair.Thus its
hybridysation is sp3.Thus its geometry is Pyramidal.

 It is formed by heterolytic cleavage of C-C bond.

 It behaves as charged nucleophiles and so on.
 Stability of Carbanions
Some factors on which Stability Of Carbanions
depnds:
I. Inductive Effect( +I & -I).
II. Extent of congugation 0f of negetively charged
carbon of Carbanion.
III. Hybridyzation of charge pairing carbon atom is
another effect which decides the stability of
Carbanions.
IV. Aromi.ticity also leads to the stsbility of
Carbanions and etc....
(A)Inductive Effect:
 If the groups attached to the carbon atom are electron
donating in nature (i.e +I effect),it will increase the
electron density on carbon atom and makes the
carbanion unstable.
 e.g methyl group(R) has +I effect ,so the order of the
stability of methyl carbanion is such as-
 If the groups attached to the carbon atom are
electronegetive or electron withdrawing (i.e – I effect)
in nature,then it will decrease the electron density on
carbon atom and makes the carbanion stable.
 e.g. Cl is an electronegetive atom. So the order of the
stability of carbanion
(b) Extent of congugation of Carbanion:
 If negetively charged carbon atom is in congugation
with a double bond, the resonance effect will stablieses
the carbanion by spreading out the charge by
rearranging the electron pair.
 e.g. Allyl and benzyl carbanions are stablised by
delocalisation of negetive charge.
 (1)

 (2)
(c) Hybridyzation:
 More the “s” character in hybrid orbital higher will be
the stability.
In sp3 hybrid orbital S character is 25%
In sp2 hybrid orbital S character is 33% and
In sp hybrid orbital S character is 50%.
 So the Carbanion generated from alkyne is more stable
than the Carbanion generated from alkene rather than
that of Carbanion generated from alkane.
(d)Aromiticity:
 In some Cabranion the lone pair of carbon is involved in
delocalization to add the aromatic charactern on the molecule
which keeps them extra stability. e.g

 Aromatic carbanions are most stable.

 Anions obeying Huckel rules are stable because they are
aromatic and there is complete delocalization of negetive charge.
Stability of different type of carbanions in
decreasing order:
> Benzyl Carbanion > Allyl-
Aromatic Carbanions

Carbanion > CH= > CH2 > Alkyl Carbanion

 Thank
You.
From: Sabir Sk