Resonance

Resonance: resonance is a important concept of organic chemistry when a compound said to be in

resonance potential energy decrease. Whenever potential energy is decrease stability increase
when a compound said to be resonance compound show more than one structure but transmission
of - electron when a compound show more than one structure these all structure having same
atomic Skelton, same number electron, same type of charge when a compound show resonance
resonating structure of a compound separated by two sided arrow. When a compound said to be
resonance these resonating structure are hypothetical structure theses structure are due for
explanation of bond explanation of real structure explanation of intermediates for understanding
the concept of resonance first we see these concept related with bonding electron first of all we see
localized electron . localized electron we see when the electron are equally or unequally shared
between two atoms they are called localized electron incase of localized electron no resonance
concept apply in case of localized electron compound not show any other structure in case of
localized electron no other structure we can form by this localized electron system resonance is only
possible whenever electrons are in delocalization let us see what is mean by localization.
Delocalization of electron: basically delocalization of electron is a transmission of electron when a
compound are in intermediates is in certain condition we see one condition of delocalization when
-bond conjugate with -bond this type of structure we see in benzene we know Benzene is a
aromatic compound in Benzene -bond when -bond conjugate with -bond localized electron now
we see localized electron system the best example for localized electron system is Benzene in
benzene we see -bond conjugate with -bond in Benzene when -bond get delocalized more than
one structure we can form these structure are known as resonating structure canonical structure or
contributing structure later on we see resonating structure of Benzene and some more concepts of
resonance of Benzene some other type of link concept here we see one more example for
delocalization Butadiene. In Butadiene we see -bond conjugate with -bond when -bond get
delocalized the -bond change the position and we get one more structure we see in this animation
-bond get delocalized with -bond when -bond move Carbon number 2, 3 than carbon number 3 ,

4 between -bond shift on carbon one positive charge appear on carbon four negative charge one
more delocalization we can form by butadiene structure. In this structure on C 1 carbon negative
charge and C3 carbon negative in place negative positive appear. What is difference between in
other resonating structure C1 carbon having negative charge and C4 Carbon having positive charge?
What is difference between these two structures here these difference C1 carbon positive in
another structure C1 Carbon negative. In fourth structure, C4 carbon negative and next structure C4
carbon positive. But in similarity both structure having C2C2 carbon double bond in actually this
Butadiene having same type of bond length between C1C2, C2C3 and C3C4. By the use of resonance
we can explain the bond length between butadiene is resonance hybrid we see in resonance hybrids
are bond length are equal. But in real structure we see C1C2 between -bond C2C3 single bond C3C4
again -bond. But in resonating structure C1C2 single bond C2C3 -bond and again C3C4 single bond
and next resonating structure also we can seen C1C2 single bond C2c3 in next resonating structure
we seen C1C2 single bond C2C3 -bond and C3C4 single bond in resonance hybrid which is real
structure of this Butadiene we see all bond length are equal partial double bond and charge overall
positive negative and this real structure we see all C1C2, C2C3, C3C4 bond length are equal we can
explain by use concept of resonance this is delocalization of electron here resonance take place and
by resonance we get two resonating structure and resonance hybrid is real structure which show
resonance.
If the electrons are shared by more than two atoms, such electrons are called delocalized electrons.
These delocalized electrons are responsible for resonance. Whenever these delocalized electrons
participate in delocalization, resonance take place.
When resonance takes place, compounds shows more than one structure known as resonating
structure or canonical structure or contributing structure.
Whenever compounds shows these type of structure, potential energy is decrease and we say
compound is in resonance. When compound is in resonance compound show more than one
structure, these structure are having same atomic skeleton, same type of charge. If electrons are
under the delocalization, they are said to be in resonance and all resonating structure we can form
by the delocalization of delocalized electrons.

Conditions required for Delocalization:

Some conditions are required for delocalization, when a compound follow these conditions and
when compound having this type of conditions, then only we said compound is in resonance.
Resonance Hybrid:
When a compound shows resonance, the true structure of compound is known as resonance hybrid.
Resonance hybrid is a real structure when a compound show resonance the total explanation of this
resonance hybrid is given by resonating structures or canonical forms.
Later on we see that what type of conditions are required to delocalized of electron, delocalized of
- electron, formation of resonating structure.
Resonance is a important concept for explanation of bond length, explanation of intermediate
stability, explanation of acidic nature, explanation of basic nature, explanation of aromatic character
etc.
Resonance is a phenomenon of explanation of energy regarding resonating structure, resonance is a
phenomenon which we use to explain the intermediates explain the stability of intermediate,
explain the aromatic character, explain the acidic nature or basic nature generally in aromatic
chemistry.
The true form of molecules is known as resonance hybrid which cannot be drawn on the paper,
therefore this structure is represent hypothetical form is called resonating structure or canonical
form. This resonance is a completely is hypothetical phenomenon.
The canonical form which is most stable will contribute more in resonance hybrid. In all resonating
structures, resonance hybrid is a most stable resonating structure. This is due to is a real structure of
compound which shows resonance. The energy of resonance hybrid is lower than energy of any
canonical form i.e. it is most stable than all resonating structures. Resonance hybrid is lower than
the energy of any canonical form that means resonance hybrid is more stable than all resonating
structure thats why if energy is less stability is more.

The canonical form which is most stable has more probability of existence. More stable canonical
form is more in existence, the more contribution in real structure.
To explain the stability of many compounds, we used the concept of resonance effect. Scientist
called these phenomenon as mesomeric effect and Heisenberg termed this as resonance affect.
Basically both phenomenon were to explain by carbon dioxide, Benzene etc are stabler than
expected. But truly speaking there are differences between resonance and mesomeric effect will.
In resonance, we see no use of mesomeric effect, but when we see in mesomeric effect we applied
the concept of resonance. Thermodynamically, the extra energy by which molecule is stable is
called as resonance energy.
Resonance energy = to energy which related with observation - energy which related to theoretical.
Observation heat of formation and theoretical heat of formation by use of these heats of formation
observe and theoretical we find out value of resonance energy. The difference between observe
heat of formation and theoretical heat of formation we find out what is the value of resonance
energy.
Graph between energy and heat of formation theoretical and observed:
We know observe heat of formation is large and theoretical heat of formation is small now we
calculate the difference between them is basically resonance energy. If we burn Benzene, we
obtained heat of combustion observe
C6H6 + 15/2 O 6CO2 + 3H2O + heat
Here the energy is heat of combustion and is observed to find out the value of this heat.
Theoretically,
Heat of formation = 3 (Bond Dissociation Energy of C C) + (BDE of C = C) + 6 (BDE of C H)
+

(BDE O2 = O2) - 6 (2 BDE C = O) + 3 ( 2 BDE O H).

There is a difference of energy between observed heat and theoretical heat. This difference is
known as resonance energy.
Here we easily calculate the resonance energy = heat of combustion observed and heat of
theoretical
To explain, we can draw two meaningful resonating structure of Benzene.
When bond get delocalized, we get another resonating structure which having same atomic
Skelton but difference in delocalization of - electrons. The actual structure of this Benzene is
represented by three parallel lines which are known as resonance hybrid. In resonance hybrid we
see all Carbon-Carbon bonds having partial double bond character. Therefore, here a partially ring is
form is a real structure of Benzene known as resonance hybrid of Benzene is a basically real
structure.
In resonating structure we see in first structure between 1 and 2 double bond but in second
structure 1 and 2 there is single bond. But in real 1 and 2 are partial double bond character and all
Carbon-carbon bond have equal bond length and equal bond strength. But in resonating structure 1,
2 is different type of bond it is known Ortho para.
Resonance energy of Benzene
Here 36 kilo calorie per mole resonance energy for benzene, calculation of energy by heat of
hydrogenation and cyclo-hexane react with hydrogen converts cyclo-hexane here 28.6 kilo calorie
per mole we get.
When 2

bond, two hydrogen molecules involve and convert in cyclo-hexane here 57.2 kilo calorie

per mole we get.

For 3 - bond, three hydrogen molecules convert in cyclo-hexane here 85.8 kilo calorie per mole we
get.
In only one - bond, energy to 28.6 kilo calorie per mole.
For 2 - bond, 2 hydrogen involve energy just twice 57.2 kilo calorie per mole.

When three - bond, three hydrogen molecule involve energy three times 28.6 kilo calorie per mole
3.
When three - bonds involve in Benzene, three Hydrogen molecule reacts and convert cyclo-hexane
three times 28.6 kilo calorie per mole and here we calculate the value related with Benzene
hydrogenation 85.8 kilo calorie per mole.
Since benzene has three double bonds, the heat involved should have been 3 28.6 kilo calorie per
mole here we get 85.8 kilo calorie per mole, but experimentally it is found to be 49.8 kilo calorie per
mole.
Therefore benzene involves
85.8 - 49.8 = 36 kilo calorie per mole less energy than hypothetical cyclo-hexa tryene.
This 36 kilo calorie per mole extra energy is known as resonance energy related with Benzene.
Therefore the resonance energy of Benzene is 36 kilo calorie per mole which is due to delocalization
of - electron in Benzene. Due to this 36 kilo calorie per mole extra energy we say this Benzene is
extraordinary stable than any cyclo-hexatryene.
Electronic Conditions for Resonance:
These are the conditions where resonance takes place and compound show more than one
structure:
First Condition for Resonance : (When - bond conjugate with - bond):
This condition we see in Benzene and in Butadiene.
First we take the example of Butadiene. In Butadiene when -bond conjugate with - bond
CH2 = CH CH = CH2
Here we see -bond conjugate with -bond, Here two possibilities for resonance:

First we mark as C1, C2, C3, C4 first double bond C1, C2 shift on C2, C3 single bond and double bond
C3,C4 shift on C4. Here on number one Carbon after resonance on C1, positive charge appear
between C2, C3 double bond on C4 negative charge.
One more condition we can form here when C1 carbon negative charge C4 carbon positive charges it
is just apposite of resonating structure second if we assume first is over starting structure. By first
we form second resonating structure and by first again third resonating structure. In third
resonating structure we can see number one carbon having negative charge C 2, C3 partial double
bond C2, C3 and on C4 Carbon Positive charge. By resonating structure first, second third we can seen
C1, C2 double bond C3, C4 single bond and again C3, C4 double bond but in resonating structure
second and third here common thing is C2, C3 carbon having double bond. In first starting structure
we see C2, C3 having single bond, but in resonating structure second and third having double bond
C2,C3 is a common part on seconds and thirds .But in second and third resonating structure we also
see a difference. In second number one Carbon positive charge in third number one carbon negative
charge. In second number four Carbon negative charge in third number four Carbon positive
charges. Theoretically, difference when we leveled number one carbon in first structure is no charge
and second positive charge on number one carbon in third number one carbon having negative
charge
One common point we see 1, 2, 3 resonating structure, first is neutral (no charge), Second positive
negative again neutral, Third negative positive neutral. But here first, second, third we can see the
real structure which has resonance hybrid here C1C2, C2C3 all bond are equal bond strength equal
bond length and equal type of bond. But in resonating structure we see C 1C2 first double bond,
second C1C2 single bond, and third C1C2 single bond. But in real structure, we see C1C2 partial double
bond, C2C3 partial single bond second double bond and third again double bond. And resonance
hybrid equal type of bond partial double bond. In first resonating structure C3C4 double bond
second single bond, third single bond but in real resonance hybrid again partial double bond. Since
resonance hybrid having type of bond equal strength of bond is a real structure of Butadiene.
Experimentally we see this structure of Butadiene. By resonance we only explain these bond are all
neutral all are having same type of change.

The stability order: first is more stable than second and third equal and this resonance hybrids is no
doubt a must stable which is due to real structure.
We take one more example is also diene type structure, but here we see different stability of
resonating structure.
CH3CH = CH CH =CH2
two possibility again here -bond conjugate with -bonds.
First possibility -bond shift on C2 Carbon two between C3C4 and C4C5 between C4 and C5 -bond
shift negative charge appear 6 number carbon positive appear second number Carbon and double
bond C3 and C4.
One more structure C2 Carbon negative, C5 carbon positive, here we see resonating first , second
third both are having different type of stability. First is stable is a neutral among second and third in
second Carbo-cation is most stable and one degree carboanion is more stable thats why second is
more stable than third. In third carboanion secondary less stable, carbocation primary less stable
thats why the stability order is
1st > 2nd > 3rd
of this -bond conjugate -bond containing this compound.
We take one more example for -bond conjugate with -bond
CH2 = CH CHO
Here oxygen is more electronegative, thats why oxygen takes electron and this -bond shift on C2C3
Carbon. Here potential energy is increases, is basically second resonating structure one more
possibility here we having C1 Carbon negative charge and Oxygen is positive charge but here the
potential energy very high. The reason is more electronegative atom always tendency to take
negative charge not positive charge. Whenever positive charge is present on highly negative atom
this type of resonating structure is less countable, thats why among second and third second is
more stable then third and wattage average of third resonating structure is approximately zero. The

canonical form in which highly electro negative like Oxygen consist six electron and positive charge
is highly electro negative charge on high energy. Such structure no contribution in resonance hybrid
thats why third is not is in existence thats why the stability order is
1st > 2nd > 3rd
Third is approximately negligible and no contribution in real structure.
One more thing we can say in case of
CH2 = CH CHO
only two resonating structure we can form first, second the highly electro negative atom can hold
the negative charge properly whereas it can hold positive charge due to increase in potential
energy. Whenever highly electro negative atom third positive charge potential energy increase
highly.
Second condition for resonance: (when -bond conjugate with positive charge)
This is condition we see in Alyl Cation
CH2 = CH CH2+
is Alyl Carbo Cation.
In Alyl carbo Cation when -bond move positive charge shift on number one Carbon. Here two
resonating structure we can form.
In first double bond between C1C2 Carbon
In second resonating structure double bond between C2C3 carbon
But in resonance hybrid we see -bond just split and C1C2C3 having equal type of bond C1C2 having
partial double C2C3 partial double bond and positive charge just move on complete move on Alyl
Cation. And positive charge appear on complete Alyl cation.
Here common thing is all are positively charged.

-bond conjugate with positive charge we take one more example.

CH3CH = CH CH2+
is a first resonating structure where again -bond is conjugate with positive charge when -bond
shift on C2C3 carbon C3C4. When -bond shift positive charge shift from four number Carbon to two
number carbon among first and second in first primary Carbo Cation and second secondary Carbo
Cation in resonance hybrid C2C3 and C3C4 having same type of bond. But in first resonating structure
C2C3 -bond double bond C3C4 single bond in second resonating structure C3C4 double bond C2C3
primary but in resonance hybrid C2C3 partial double and C3C4 partial double and positive charge split
on C2C3 Carbon here first is less stable than second.
We see one more -bond is conjugate with -bond and -bond is conjugate with positive charge.
Here three resonating structure we can found. When -bond move on positive charge containing
Carbon positive just shift on 5th number carbon to three number Carbon again -bond can
delocalized positive appear number one carbon. Here second is a secondary Carbo Cation thats why
it is a more stable and first third is equal type of Carbo Cation equal type of primary conjugate with v
thats why first and third is equally stable second is constant.
Third condition for resonance:
In this condition we take example Alyl anion here negative charge conjugate with -bond in this
case first negative charge convert in -bond after converting negative charge on -bond. -bond
convert negative charge here on first resonating structure double bond in between C 1C2 Carbon in
second resonating structure double bond appear between C2C3 Carbon but in resonance hybrid bond equally split C1C2 and C2C3 having same type of partial double bond and this negative charge
appear on whole alyl Carbo Anion.
We take on more examples.
CH3CH = CH CH2
anion here again -bond is conjugate negative charge. First negative charge convert in -bond. Bond convert in negative charge by negative charge is convert -bond here potential energy is high

in first potential energy is low this is due to in first resonating structure Carbo anion is primary in
second resonating structure Carbo Anion secondary thats why potential energy is high satiability
order is first is stable is more stable than second.
One more example we take(CH2 = CH O-) negative charge first convert in -bond. -bond convert in negative charge. in
second resonating structure we get in first double bond between Carbon-Caron in second double
bond between Carbon-Oxygen here negative charge on first appear on Oxygen but in second
resonating structure negative charge on carbon. The stability order the first is more stable than
second this is due to negative charge always stable on more electro negative atom.
Fourth condition for resonance:

-bond conjugate with lone pair alyl alcohol in alyl alcohol lone

pair of Oxygen conjugate with -bond in this case first lone pair shift on Carbon-Oxygen convert in v
and simultaneously -bond between C1C2 convert on C1 Carbon here C1 Carbon having negative
charge and Oxygen appear on positive charge .one more possibility here when we see the
resonating structure first and second first is neutral or second charge thats why first is more stable
than second when we meet resonance hybrid here partial double bond character between C 1C2 and
partial double bond character between Carbon Oxygen when we take one mo more example
CH2 = CHOCH3 here again lone pair of Oxygen delocalized with - bond convert in -bond
simultaneously -bond convert in negative charge and we get resonating structure here again first
is more stable than second.
We take one more example when OH attach with -bond containing Cyclohexane here -bond lone
pair in conjugation first lone pair convert in -bond and -bond convert in negative charge here
after permission of second resonating one more possibility arise here negative charge convert bond. Here negative charge convert in-bond simultaneously -bond convert in negative charge
here in negative charge convert in -bond simultaneously -bond convert in negative charge here
three resonating structure we can form the stability order here we explain it is most stable than
second than third, -bond conjugate with free radical in free radical odd number of electron.

Fifth condition for resonance: When free radical containing carbon conjugate with -bond in
presence of free radical electron this -bond get hemolytic bond cleavage and after hemolytic bond
cleavage one electron again form a -bond between C2C3 and we get free radical containing Carbon
on First Carbon but is difference between in first Free radical Carbon is Carbon number three but in
resonating structure first Carbon on first Carbon is appear free radical in first resonating structure
double bond between C1C2 carbon in second double bond between C2C3 carbon the resonance
hybrid is CH2 partial double bond CH than partial double bond CH2 here free radical electron split in
all three Carbon we take one more example
CH3CH = CHCH2 free radical after hemolytic bond cleavage we get second resonating structure in
first and second is most stable this is due to in second resonating structure free radical is secondary.
Secondary free radical is more stable than primary free radical thats why their stability order is
second is more stable than first.
Sixth condition for resonance:
These are known as self resonance condition. In this condition positive charge existence in lone pair
containing atom is a extra ordinary stable in this condition no requirement for charge dispersion no
requirement for electron transmission is already stable here positive charge stabilize by lone pair
this condition we use in lot of places and direct to nature of group when attach on benzene ring by
self resonance condition we explain when Halogen attach on benzene ring the incoming electro file
attach on Ortho Para position when ever lone pair containing compound directly attach on benzene
at this time due to self resonance concept we explain by ortho Para position for better position for
incoming electro file by self resonance concept this is more contributing in comparison to -bond
containing and is a more stable than -bond containing Carbo Cations.
Necessary Condition for Resonance:
When we see in Butadiene, all Carbons are in sp2 hybridization stage.
In CH2 CH CH CH2, all carbons are in sp2 hybridization stage. Therefore, it is planner. When we
see in benzene, all carbons are in sp2 hybridization stage. Therefore, in Benzene all Carbons are in a

plane, thats why in Benzene resonance is possible and resonance -bond gets delocalized and we
get more than one resonating structure of Benzene or Butadiene.
Example of non-planar compound:
(i) (CCH3)3 C CH2 C CH2
C attached with three methyls and (CCH3)2
This is basically non-planar structure.
Here we see - bond conjugate with - bond and all carbons in sp2 but non-planar. Therefore,
resonance is not possible here.
(ii) In Benzoic acid, one CH3 attached. In presence of CH3 like bulky group whole molecules appear
out of plane. This structure is non-planar. Due to non-planarity of the structure, here COOH does
not show (-M) effect.
This effect is known as ortho effect and here, ortho effect is known as Steric Inhibition of Resonance
or SIR effect, which is restriction OR obstacle for resonance.
Due to SIR effect, here COOH does not show (-M) effect. COOH is not in resonance. Here, whole
benzene system works as electron withdrawing group. Resonance takes place when electrons are
released. But due to non-planarity it works as (-I) representing group. All carbons are in sp2
hybridization stage. Due to more percentage as character, here, (-I) effect is more. Due to SIR effect,
this ortho substituted Benzoic acid works as more acidic than benzoic acid.
Sometimes, due to steric hindrance, p-orbital twist out of the plane and no longer remain in the
planar. Therefore, here resonance is absent and its not possible to make a resonating structure.
Example:

CH3CH = CHCH3

Here, C = C, bond length is A.

In n-Butane (CH3CH2CH2CH3)

Here, C C, bond length is B.

CH2 = CH CH = CH2
Here, C C, bond length is C.
When we compare the bond length of A, B, C, here B is purely single bond, thats why this is a
maximum bond length, then in C partial double bond character appears thats why after B in C. A is
purely double bond thats why bond length order is
B>C>A
This is a decreasing order of bond length.
Due to resonance, C has partial double bond character.
In case of radical resonance, all the canonical form has to contain is an equal number of unpaired
electrons.
In Allyl free radical, here -bond conjugates with free radicals. Due to free radical tendency of
carbon, this -bond gets homolytic bond cleavage, and after this happens, we get one-one electron
in every carbon. So, we have one-one electron on CH2CHCH2. But this is not a resonating structure.
When we see in Allyl free radicals, here number of unpaired electron is one, but after homolytic
bond cleavage, number of unpaired electrons is three, which is not possible. But when one-one
electron on C1, C2 makes a bond this is a resonating structure, we can know that the number of
unpaired electron is one. Structures one and three are both resonating structures, this is due to all
the canonical form, which has same type of charge, same type of atomic Skeleton and same number
of electrons, thats why only one and three are resonating structures for Allyl free radicals, second is
not resonating.
All the canonical form has to follow Lewis structure if possible. If any structure follows Lewis rule, it
is comparatively stable.
Example: In CH3CH2OCH2+, here carbon has six electrons.

In second structure CH3CH2OCH2 here Carbon has eight electrons and oxygen also has eight
electrons.
So, between first and second, second is more stable.
Example In CH3C = O, here one carbon, six electrons, but when oxygen loses the electrons, again
one carbon six electrons. Second structure is more stable than first.
Some set of compounds
1. CH3OCH2+
2. CH3OCH2
3. CH3NHCH2+
4. CH3NH+ = CH2
In nitrogen and oxygen, volume charge density increases, thats why NH2 is more stable then OR.
Thats why when we compare the stability order, we have
4th > 2nd > 3rd > 1st (Least Stable)

Rule 7:
If any group is attached on a conjugated system, and at least one resonating structure can be
formed, then such type of resonance is known as mesomeric effect. In mesomeric effect we use the
concept of resonance. It can be classified in two types:
When vinyl attached CH2 = CH NH2, lone pair conjugates with -bond. First the lone pair is
converted in -bond, and -bond is converted into negative charge. When -bond conjugates with
lone pair, nitrogen loses the electron, and -bond conjugates with lone pair, nitrogens lone pair
converts in -bond and -bond converts negative charge and we get CH2-CH=NH2+. Here NH2 is
electron releasing in nature when lone pair containing groups attach on conjugate system,
remember always electron releasing in nature. Here these groups are electrons releasing in nature
thats why this is known as (+M) effect.

When CH2 = CH CHO here oxygen is more electronegative thats why oxygen takes electrons and
-bond delocalized on C2, C3 carbon. Here on C1 carbon having positive charge C2, C3 double bond
and oxygen negative charges. Here, CHO tendency is electron withdrawing, and due to electron
withdrawing nature this is known as (-M) effect.
When OH attaches to benzene, here benzene works as a conjugate system which is basically a
phenol, here oxygen loses the electron and oxygen. When OH attaches to benzene ring, here lone
pair conjugates with -bond. Lone pair first changes in -bond, and here the benzene ring works as
an electron withdrawing system. In the presence of OH group on benzene, a negative charge
appears. Like this, when CHO attaches to benzene ring CHO is electron withdrawing in nature. In
presence of CHO on benzene, a positive charge appears. In presence of OH, benzene ring works as
an electron withdrawing system, in presence of CHO, benzene works as electron releasing system.
Depending on attaching group, benzene works as an electron releasing system or electron
withdrawing system. Whenever (+M) representing group attaches to benzene ring in case of (+M)
representing group, benzene work as electron withdrawing system.
In case of (-M) representing group, benzene works as an electron releasing system.
Mesomeric effect works at ortho position and para position with equal strength. But, mesomeric
effect is absolutely absent at meta position. It works on ortho position and para position equally,
not depending on the distance. But, in meta position mesomeric effect cannot work. On meta
position, mesomeric effect is absolutely absent while inductive effect works at all three positions i.e.
ortho position (maximum), meta position (less), on para position distance is more thats why
inductive effect is minimum on para position.
This theme we also see in following animation:
When a reference attaches to conjugate system, mesomeric effect works equally on ortho position
and para position, but in meta position it cannot work. When reference attaches to benzene on
ortho position and para position, mesomeric effect works equally.

Here basically -electron transmission works, but on meta position no -bond transmission works.
Thats why on Meta position no mesomeric effect can be applied. But in inductive effect, ortho
position, meta position and para position work equally. On ortho position, less distance maximum (I)
effect all (+M) and (-M) representing groups show (-I) effect. Maximum ortho position, then Meta,
and minimum in Para position. The order is
Ortho > Meta > Para

Rules for stability in Canonical form:

1- As the number of covalent bond increases, stability increases. If number of covalent bond
increases in resonating structure, the stability of resonating structure increases.
2- The canonical form which satisfies Lewis dot structures is most stable.
3- If charge separation increases, probability to bond formation decreases and stability of
resonating structure decreases.
A highly electro-negative atom can hold a negative charge properly. A resonating structure which
has negative charge on highly electro-negative atom is extraordinarily stable. If positive charge on
highly electro-negative atom is unstable and if, at the same time this atom consists of six electrons,
then the weightage average of this resonating structure is zero and this type of resonating structure
is not possible.
Therefore, resonating structure if positive charge on less electro-negative atom is more stable and
negative charge on high electro-negative atom is more stable. When CHO attaches to benzene ring,
here CHO is electron withdrawing in nature and CO group is also electron withdrawing. When CHO
attaches to benzene ring, then benzene ring works as electron releasing system. At this time when
CHO attaches to benzene ring, positive charge appears on benzene ring. We get second structure
where positive charge conjugates with -bond. When -bond delocalized, we get third structure
and positive shift again. When again -bond gets delocalized, we get four resonating structures.

Here, we see negative charge of oxygen again delocalized by a positive charge, we get neutral
structures between one and five, we get two, three, or four resonating structures.
The stability order we compare, one equal to five neutral is most stable, two and four equally stable,
the reason is that, here, negative charge and positive charge distance is same thats why two equal
to four, and three is least stable, this is due to opposite charge and maximum distance. If positive
charge is at minimum distance then only resonating structure is most stable thats why the stability
order is
1=5>2=4>3
One more example: CH2 = CHNH2
Lone pair conjugates with -bond is neutral.
When resonance takes place, we get second structure, first is neutral second is ion. Here the
negative and positive charge appears. But neutral structure is always stable thats why first is more
stable than second.
In benzyl carbo-cation, -bond conjugates with positive charge. When, -bond gets delocalized, we
get second resonating structure, again -bond gets delocalized and we get third resonating
structure. -bond conjugates with positive charge we get four. At last again -bond delocalized
with positive charge. Here we get five resonating structure. Stability order is (1=5) both are having
neutral benzene ring. (2=4) same distance with CH2 thats why equal stable, their stability order is
1=5>2=4>3
Example: CH2 = CH COOCH3
Here two type of conjugation we see, lone pair conjugates with -bond of oxygen, lone pair
conjugates with -bond with carbon. When we use -bond of carbon we get second resonating
structure; when we use -bond of oxygen we get third resonating structure.

Among first, second and third, first is more stable and is neutral thats why, then third we see Lewis
structure all having eight electrons thats why, second carbon has six electron thats why second is
least stable.
Stability order is
1st > 3rd > 2nd
Mesomeric effect: Mesomeric effect is the effect where we use the concept of resonance. In
mesomeric effect, we classify as below,
1. Inductive effect
2. Hyper conjugation effect
3. Electromeric effect
Mesomeric effect is also classified in two types : (+M) and (-M).

+Mesomeric effect: Whenever electron releasing group attaches with conjugate system, if
conjugate system is benzene, then in presence of (+M) representing group, benzene ring becomes
activated, and ortho para position of benzene ring becomes electron rich. In presence of (+M)
representing group, incoming electrophiles attach on ortho para position.
Aromatic compound shows electrophilic substitution reaction. In presence of (+M) representing
group, electrophiles attach more easily. When (+M) representing group attaches to benzene ring,
we see one example C6H5OH, when benzene attaches OH, a lone pair of oxygen conjugates with bond. First lone pair changes in -bond and -bond change in negative charge then negative
conjugates with -bond. Again negative change in -bond. -Bond changes in negative, and again
negative change in -bond. - Bond change in negative at last negative change in bond and positive
charge again neutralized by -bond.
Basically, here, 1 and 5 are neutral and 2, 3, 4 are charged. Between 1 and 5 we get three canonical
structures, these are less stable.

Groups which show (+M) OH, OR, NHCOCH3, halogen, SH, NH2, NHCH3 these are groups whenever
attached to conjugate system due to lone pair these all show (+M) effect.
(-M) Effect: Whenever electron withdrawing group attaches on benzene ring, benzene ring becomes
deactivated and ortho para position of benzene ring becomes electron deficient. When we compare
with benzene, (-M) representing group attaches to benzene, this time electrophilic substitution
tendency decreases. This is because, in presence of (-M) representing group, electron losing
tendency decreases in comparison to benzene. In presence of (-M) representing group, benzene ring
becomes deactivated, this time incoming electrophiles attach only at meta position.
When CHO attaches to benzene, CHO has a tendency to attract electrons, oxygen takes electrons
becomes negatively charged, and here benzene works as an electron releasing system. Here -bond
gets delocalized with -bond on oxygen negative charge, on benzene ring positive charge, now bond conjugates with positive charge we get third structure. Again -bond conjugates with positive
charge we get fourth resonating structure. At last negative charge of oxygen again gets converted in
-bond and -bond uses the electron and the positive charge of benzene is neutralized and we get
neutral CHOC6H5.
Here again between 1 and 5, three ionic resonating structures we get. These are known as canonical
structures. These are less stable than 1 and 5. When we convert 1 into 5, we get these three
resonating structures
(-M) representing groups are:
CHO, COCl, COOH, NO2, COR, CONH2, SO3H are some (-M) representing groups.
Test following groups whenever we attach with conjugate system show (+M) or (-M).
1. CHO and CHO attached on benzene rings shows (-M)
2. CN shows (-M)
3. CONH2 shows (-M)
4. COOH shows (-M)
5. NHCOCH3 here, N has lone pairs thats why it shows (+M)

6. OCHCH3 oxygen has lone pairs thats why it shows (+M).

When CH3OCH3 attaches to benzene ring, here CO is electron withdrawing in nature, here COOCH3
when attached to conjugate system here CO is electron withdrawing, thats why it is (-M)
representing group.
When NO2 attaches to benzene ring, NO2 is again electron withdrawing in nature, thats why it
shows (-M). OCH2CH3 whenever attached with conjugate system, here oxygen has lone pair thats
why (+M) representing group. When NO attaches with benzene ring due to lone pair, this shows
(+M) due to N = O, oxygen is electron withdrawing in nature thats why it shows (-M), but here, (-M)
is always terminate.
Rules for Writing Resonating structures:
Some rules required for making resonating structure. When a compound set to be a resonance
when we follow some rules, then only to make the resonating structure of organic compound.
1- Resonating structures are called canonical forms and they exist only on paper.
2- Resonating structures are absolutely hypothetical.
3- In real level, there is no existence of resonating structure.
4- These resonating structure can only be used for explanation of intermediate explanation
of bonds explanation of real structure. The true structure is known as resonance hybrid.
True structure is only in existence.