Resort

when 2 or more Lewis structures

are possible for a molecule no single structure
is sufficient to describe its true é distribution
The true structure is called resonancetiybridm
and various Lewis structure are called

canonicalstructures.mn

2
252 z p
6C
FI FI around
Excited
HE Fiji
I EEE p's
pure
sp2 p orbital
Hybrid CIT
orbitals

Ego 1
I

pure p

Trigonalplanar
sp2 1200
 n e
Mn
B'i
Mohegan
nom
H

FEMME
or

_i EiIé
2
Ei

canonical
3 i suit i zuni
structure

I II

4 Butexperimentally in Benzene all

bond length are equal ie 1 39 A
 ton D
D
6 P A O 6MO

Ii
Released
ta

Thicalisation
in system 1
3g
é
H
of
conjugated

gyyqq
HYBRID

Finally
EI EI
Face
Ianonical
structures
Hybrid
Real

Imaginary
 Conditionsforresonance

Conjugated system
A i e

min 3p orbitals
Adjacent
We up in some me

so that there is Effective overlap btw

unhybridised orbitals

B No atom can contribute more than one

orbital towards conjugation

typesofconjugationmo LI
Tbondtbondconjugationmm

e.no tee

2
Ibond cation
cha Eez Eez creates
3
Tbond Anionne

CHI CH a o Eez atcha

4
Tbonddlpies
CHI CH Ha a Ea Ch Ites

5
Tbondesingleen
CHIEH Cha so Cha CH C Hz

6 more EN atom
tbondband
chic 8
craft on E

7 n

hey É R É CHz
 vacgggositltanionj n dz
CHI
empty

Ee I
le do

Cios conjugation
In a cross conjugated
compound three IT bonds are present two of
which are not conjugated with each other

although each is conjugated with third

Reef resonance
1 The in all
connectivity must be the same

contributing structures i.e

only the electron
 position may vary in contributing structures

d
contributing
structures
and Ej
2 All atoms covered
by delocalisation should
lie in same plane ie conjugated
system

Ex Cyclo octatetraene does Not exhibit

resonance booz it exist in Ib shape

I Tub shape

EXIT NOT a

system
conjugated
3 Each contributing structure must have the
same number of electrons and the same
net
charge
Ex
At
If At
4 Each contributing structure must have the same
number electrons
of unpaired
Ex
At A
two unpaired
no unpaired
electrons electrons

2
A A true resonance

5 contributing structures in which the octet rule

is exceeded for second row elements make no
contribution
octet rule be exceeded for elements beyond
may
2nd row
nitrogen can
not have
mfg
CH
MI ay 5 bonds
 100 cannot
Hz 1443 possible in
É
ID of
to
y Nitrogen

6 Resonance Hybrid is
stable than any
more

of the contributing structures i e every

contributing structure contributes its bit to
the overall stability of the system

7
contributing structures should be of almost
the energy
same If a contributing structure
has very high compared to the
energy
other it makes no contribution

EE EI E II
take
NO contribution

Resonance is stabilizing phenomenon

8 Species with equivalent contributing structure
is morestable than one with non equivalent

contributing structures

É É
Ex cuz É cHz o
L 8

E F

É CHEEKED ED
Acetate ion is highly stable compared to phenol

9 when all structures

contributing are equal
then the species having more number of
contributing structures is more stable

D CHACH É É Cho

D 5200 EE
Phenoxide ion is more stable than enolate
ion
 Resonance in carbocation

D CHEE Ea e Hea ch cha Esten cts

Hybrid

2 Cha CH Hz Hz ch NH3 Nitrogen

can Not have
IOE
5 Bond

does not exist

3

I
Ph NH3 anilium ion two canonical
so
finally for
structures possible
NH3 173
Imonical
I FI structures

II
4
why Phenyl cation is LETABLE
One atom can max contribute one

orbital in resonance

one
 É

Hybrid

EI
Tropylium cation
FEI EI ED
EI EI EI
ac tires

f
same

I Hybrid
 EFF
Ex

III is more stable than

Explain it

And

Draw
tyg
Ex the canonical structures of

EI Draw the canonical structures of Nhs

MHz MHz
 Reaceathanion
1 of CHIT Ea ch cha I Éz cm di

If
Phenoxide
Ee Ly Ey
É_IÉ

OR

É
É
opto El Je'anonical

Charge always rotate at ortho and para

position in phenyl ring wart ipso group
Ex

Eyes E t

E
oh

Instructions

phenyl anion this eve charge is

NOT in conjugation

Ed This bridgehead anion can not

Bredt'ssule
go in resonance

Ed
H m Total number of
canonical structures

of M

Ans 5