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INDUCTIVE EFFECT
Definition:
Process of electron shift along the chain of atoms due to the presence of polar
covalent bond in a molecule is known as inductive effect.
SIGMA ELECTRONS MOVE IN THIS PROCESS
The inductive effect is an experimentally observable effect of the transmission
of charge through a chain of atoms in a molecule, resulting in a permanent dipole in
a bond.
Inductive effect is an effect in which permanent polarization arises due to the partial
displacement of sigma electrons along carbon chain / carbon electrons towards most
electronegative atom along carbon chain.
e.g.
Bond Polarization:
Covalent bonds can be polarized depending on the relative electronegativity of the
atoms forming the bond. The electron cloud in a σ-bond between two unlike atoms is not
uniform and is slightly displaced towards the more electronegative of the two atoms. This
causes a permanent state of bond polarization, where the more electronegative atom has a
fractional negative charge (δ–) and the less electronegative atom has a fractional positive
charge (δ+).
For example, the water molecule H2O has an electronegative oxygen atom that
attracts a negative charge. This is indicated by δ- in the water molecule in the vicinity of the
O atom, as well as by a δ+ next to each of the two H atoms. The vector addition of the
individual bond dipole moments results in a net dipole moment for the molecule.
Types of inductive Effect:
+ I effect – electron donating groups
e.g., CH3, C2H5
C(CH3)3 > CH(CH3)2 > CH2CH3 > CH3- > H
-I effect – electron withdrawing groups
e.g., - NO2, –CN
COCl > CONH2 > F > Cl > Br > I > -OH
Muhammad Muneeb
D16M137
University College of Pharmacy,
University of the Punjab, Lahore
It is transmitted through sigma bond.
Magnitude decreases while moving away from the electronegative atom.
It is a permanent effect.
It influences physical and chemical properties of the molecule.
Chloroacetic acid is a stronger acid than acetic acid because
O O
Cl - CH2 C Cl-CH2 - C +
+ H
OH -I O
Since this effect is transmitted through a chain it becomes less effective with
distance.
–NH3+ > –NO2 > –SO2R > –CN > –SO3H > –CHO > –CO > –COOH > –COCl> –CONH2 >
–F > –Cl > –Br > –I > –OR > -OH > –NH2 > –C6H5 > –CH=CH2 > –H
The strength of inductive effect is also dependent on the distance between the
substituent group and the main group that react; the greater the distance, the weaker the
effect.
Muhammad Muneeb
D16M137
University College of Pharmacy,
University of the Punjab, Lahore
Inductive effects can be measured through the Hammett equation, which describes
the relationship between reaction rates and equilibrium constants with respect to
substituents.
Applications:
It produces stability of Carbocations and Carbanions.
Muhammad Muneeb
D16M137
University College of Pharmacy,
University of the Punjab, Lahore
Examples:
Example 1:
Muhammad Muneeb
D16M137
University College of Pharmacy,
University of the Punjab, Lahore
Example 3:
O O
O O
O
H3C CH one aldehyde group.
Example 4:
Example 5:
(A) I > IV > II > I (B) II > I > IV > III (C) III > I > IV > II (D) IV > I > III > II
Muhammad Muneeb
D16M137
University College of Pharmacy,
University of the Punjab, Lahore
N N N
H N H H
(I) (II) (III) (IV)
Example 6:
O
O
H3C C CH2 COOH > CH3 CH2 COOH
CH3CCH2COOH CH3CH2COOH (a)
(A) (b)
Example 7:
CCl3CH2CH2CH2NH2 or CCl3CH2CH2NH2
Muhammad Muneeb
D16M137