Inductive effect and Resonance effect

By

Nehal K. Patel
Roll No. I13CY031
Applied Chemistry Department
Int. M.Sc. 4th year
S.V.N.I.T. Surat.
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Content

Introduction
Inductive effect
Resonance effect
Electrometric effect
Hyperconjugation
3 Introduction
4 Homolyatic fission
5 Heterolytic fission
6 Inductive effect

The polarization of a bond due to electron withdrawing or electron

donating effect of adjacent groups or atoms is calledinductive effect.

OR
The inductive effect is related to the ability of substituent(s) to either
withdraw or donate electron density to the attached carbon atom

Positive Inductive effect (+I effect, Electron releasing effect) :

When an electro positive atom or group (more electro positive than
hydrogen) is attached to the terminal of the carbon chain in a
compound, the electrons are displaced away from the attached atom or
group.

(CH3)3C- > (CH3)2CH- > -C2H5 > - CH3

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Negative Inductive Effect (-I effect, Electron withdrawing

effect) : when an electronegative atom or group (more electro
negative than hydrogen) is attached to the terminal of the carbon
chain in a compound, the electrons are displaced in the direction of
the attached atom or group.

-NO2 > -CN > -COOH > F > Cl > Br > I > OH > C6H5
>H
8 Example

Inductive effect is useful in explaining the strength of some organic acids

and bases.

(a) Effect of substituent on the acid strength of aliphatic acids.

HCOOH > CH3COOH > (CH3)2CHCOOH
Reason : Acidic strength decreases as +I effect of the alkyl group
increases.

(b) O2NCH2COOH > FCH2COOH >CICH2COOH >BrCH2COOH> ICH2COOH

> CH3COOH
Reason : Acidic strength decreases as -I effect of the group or halogen
decreases in column(top to down).
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(c) Cl3CCOOH > Cl2CHCOOH> ClCH2COOH > CH3COOH

Reason : Acidic strength decreases as the number of halogen atoms
decreases.

(d) CH3CHClCOOH > CH2ClCH2COOH

Reason : Acidic strength decreases as the distance of the halogen
from carboxylic group increases.

(e) Benzoic > acetic acid

Reason : due to I effect of phenyl group.
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11 Resonance effect

The flow of electrons from one part of a conjugated system to the other
caused by phenomenon of resonance is called resonance effect or
mesomeric effect.

The resonance structures (canonical structures or contributing structures)

are hypothetical and individually do not represent any realmolecule.

Positive Resonance Effect (+R or +M effect) : In this effect, the

transfer of electrons is away from an atom or substituent group attached
to the conjugated system. This electron displacement makes certain
positions in the molecule of high electron densities.

+R effect: halogen, OH, OR, OCOR, NH2, NHR, NR2, NHCOR,

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OMe OMe
OMe OMe

Negative Resonance Effect (- R or - M effect) : This effect is

observed when the transfer of electrons is towards the atom or
substituent group attached to the conjugated system.
R effect: COOH, CHO, >C=O, CN, NO2

O O O O O O O O
N N N N
13 Example

O O
N O O
N
Repels
E

E
Attracts

OMe

OMe OMe
Attracts
E E

Repels
E
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15 Electromeric effect
Electromeric effect is defined as the complete transfer of electrons
of a multiple bond towards one of the bonded atoms at the demand
of an attacking reagent.
It is shown by those compounds containing multiple bond
It is a purely temporary effect & is brought into play only at the
requirement of attacking agent.

+E effect : electrons of the multiple bond are transferred to that

atom to which the reagent gets attached
e.g : addition of H+ to alkene.
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-E effect : - electrons of the multiple bond are transferred to that

atom to which the attacking reagent does not get attached
e.g : addition of cyanide ion(CN-) to the carbonyl group.
17 Hypercojugation
It involves delocalisation of electrons of CH bond of an alkyl group
directly attached to an atom of unsaturated system or to an atom with an
unshared p orbital.
Hyperconjugation is a general stabilising interaction.
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19 Reference

NCERT class 11 Chemistry textbook

Organic Chemistry, 11th Edition by Solomon
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