Resonance
Finding Number of π Electrons
π electrons are of two types, one bonded another unbonded.
+
Example : CH 2 = CH C H 2
In the given structure 2π electrons which are bonded and have
a tendency of delocalisation.
+ − +
CH 2 C H C H 2 ; CH+
2 CH = CH 2
Example : CH2 = CH—CH2– in the given structure
4π electrons 2π bonded and unbonded.
CH2–—CH+—CH2–
CH2–—CH = CH2
Example : CH3—CH2—CH2+ → sp2
CH3—CH2—CH2– → sp3
If negative charge is in resonance, then it is sp2 hybridised.
CH2 = CH—CH2– → sp2
Example : CH2 = CH—CH2—CH2– 2π electrons only
H 2
Example : CH 2 = CH N
4π electrons 2π bonded 2π unbonded.
Example : 6π electrons 4π bonded, 2π unbonded.
5.2
Some Key Points
1. Non polar structure is the most stable structure
2. In case of polar structure, stable is that which has more
number of covalent bonds with complete octet.
3. Negative charge on electronegative and positive charge on
electropositive, it is stable.
= O is stable
= O– — is stable
—O+ or = O+ are unstable
4. If opposite charges are near to each other, the stability is more.
Q.1. In HCN find out the stability order
(a) H—C ≡ N (b) H—C– = N+ (c) H—C+ = N–
Ans. a > c > b
Q.2. In HCOOH find out the stability order.
(a) (b)
(c) (b)
Ans. a > d > c > b
5.3
Q. 1. Find out the stability order of the given:
Ans. c > b > a > d
Q. 2.
Ans. d > c > b > a
Q. 3.
Ans. b > a > c
Q. 4.
Ans. b > a > c
5.4
Mesomeric Effect
Use of Mesomeric Effect
Basic Nature of Amine
Amine is Lewis base and for more basic nature electron density
on ‘N’ should be more.
••
Basic nature of (a) CH3CH2NH2 and (b) CH 2 = CH NH 2
In ‘a’ more electron density while in case of ‘b’ lone pair goes to
‘sp2’ hybridised unsaturated carbon.
Example : CH2 = CH—NH2 is more basic then
••
CH2 = CH—CH = CH—NH 2
Because in second more delocalisation of lone pair so less
basic nature.
Example : Basic nature order of the given
(a) CH3—CH = (b) CH2 = CH—CH = CH—
(c) CH3—NH—CH3
Ans. c > a >b
7.2
Example : Basic nature order of the following
(a) CH2 = CH— (b) CH2 = CH—CH = CH—
(c) CH3—CH2—NH2
Ans. c > a > b
Example: Basic nature order of the following.
Ans. c > a > b
On = bonded nitrogen if lone pair is there then it is not having
mesomeric effect.
CH2 = CH— CH3—CH =
Example : Basic nature order of the given.
Ans. a > b > c
Example : Find out which is more basic
Ans. ‘a’ because in ‘b’ lone pair is in resonance
7.3
Acidic Nature of —OH Group
For more acidic nature removal of H+ should be easy and negative
charge on ‘O’ should be less.
If negative charge on ‘O’ is in resonance then acidic nature will
be more.
Example : CH3—CH2—OH and CH2 = CH—OH more acidic
is CH2 = CH—OH because removal of H+ is easy due to
resonance.
− −
+
CH 2 = CH O H CH 3 CH 2 O H +
In this negative charge is having de localisation
Q. 1. Which is more acidic
Ans. (a) Removal of H+ is easy in since more
delo-calisation in of negative charge then so more
acidic.
Example : More acidic is
Ans. a > c > b
7.4
Example : More acidic hydrogen is in.
(c) H2O (b) Both equal
Ans. ‘b’
Example : Acidic order
(a) A > B > C > D (b) A > D > C > B
(c) D > C > B > A (d) B > C > D > A
Ans. ‘b’
Example : Most acidic is
Ans. ‘d’
Example: Acidic order
(a) A > B > C > D (b) A > C > B > D
(c) B > C > D > A (d) C > D > A > B
Ans. ‘b’
Note: All the explanation are in video’s.
Example: Acidic order of the given
(a) H2S (b) H2O (c) NH3
Ans. a > b > c
7.5
CH3—CH2—SH is more acidic then CH3—CH2—OH becau
se –ve charge on ‘S’ is easily dissolved on its large size while
size of ‘0’ is small and – ve charge is not dissolved on it so
more attraction on H+.
But in case of CH2 = CH—OH acidic nature is more then
CH2 = CH—SH because it is due to more resonance in
CH2 = CH—OH as compare to CH2 = CH—SH.
Stability of Carbocation
In case of stability of carbocation +ve charge is delocalised by
hyperconjugation, Resonance or mesomeric effect.
In case of resonanance
In case of mesomenc effect
More effective is mesomeric effect. So more stable is
Q. Which is more stable
Ans. (a) Because more mesomeric effect.
7.6
Use in Bond Breaking
In case of bond breaking first of all we see the type of group which
is bonded with alkene and it’s effect on alkene.
–
In —CH = CH2 breaking is as —CH+—CH2 because
— is positive mesomeric group and bond breaking is away
from the group.
Example : Find out product of the reaction
H O
Example : NH2—CH = CH—CH—CH = CH—OH
2 →
Solution : NH2—CH+—CH–—CH = CH—OH
7.7
Use in Aromatic Reaction
1. If a +M group is there then it is known as Ring Activating.
2. If –M group is there it is known as Ring deactivating to
words electrophilic substitution reaction.
3. +M group also known as ortho and para directing and –M
group known as meta directing.
4. If both are +M then the attack will be according to senior
+M.
5. If one is +M and other is –M then attack is according to +M.
6. Both are –M then attack is according to senior –M.
7. If a function group is at meta position then it is having
inductive effect no mesomeric.
8. Halogens are +M but weakly deactivating and having more
effective inductive effect as compare to mesomeric.
9. Alkyl group are having hyperconjugation effect and
inductive not mesomeric.
10. Benzene ring it self is +M group.
Order of mesomeric effect is having effective as.
7.8
7.9
Some Important Questions
7.10
7.11
