Chemistry

GOC
In One Shot Om Pandey, IIT Delhi
Topics
1 Hybridisation , pi bond , Electronegativity , Inductive Effect

2 Resonance & Mesomeric Effect

3 Hyperconjugation , Aromaticity , Heat of

Hydrogenation

4 Stability of Reaction Intermediates

4 Acidic Nature & Basic Nature

6 Tautomerism

FOR NOTES & DPP CHECK DESCRIPTION

Hybridisation of Carbon

 bond
 Electronegativity

+ Charge on EN atom

% S Character

E.N. spC sp3N

Stability Charge Density

– CH – NH – OH –F
3 2

– OH – SH
 Cleavage Of Bond
Homolytic Cleavage Heterolytic Cleavage

Complete Octet

Incomplete Octet
Electronic Displacement Effect
Permanent Effect Temporary Effect

Inductive Effect Electromeric Effect

Resonance / Mesomeric Effect

Hyperconjugation Effect
 The effect which includes push or pull of
Inductive Effect
electrons in covalent  bonds.

Properties
It generates partial (+) and (–) charge in organic compound.

It is a permanent effect.

It is a distance dependent effect.

It operates only through  bonds.

 + I Effect Types of Inductive Effect – I Effect

More electropositive than hydrogen. More electronegative than hydrogen.

It pushes electron pair towards carbon chain. It withdraw sigma electron pair from
carbon chain.

Anion Cation

Metals Halogens

Alkyl groups Groups of E.N. atoms

+ I order Anions

Alkyl Groups

- I order (i) — F — Cl — Br —I

F Cl
—C Cl
—
(ii) —C F
—

F Cl

+ +
(iii) — NH3 — OH2
– I order Different Hybridisation : — C  C — H — CH CH2 — CH3

—CN — C NH — CH2 — NH2

Different F.G. : — OH — NH2

O O
O O || ||
|| || —C — H —C — R
—C — H —C —Cl

More substituted heteroatom is more E.N. than less substituted heteroatom

+ +
(i) — O —
H —O
—
R (iii) — NH3 — NR3

(ii) — NH2 — NHR — NR2

 – I order

+ + +
— NR3 — SR2 — NH3 — NO2 —CN

—F — Cl — Br —I —O—R —O—H

—CC—R — CH = CH2
 Resonance Delocalisation of pi electrons in conjugated system

Resonating structures are hypothetical but contribute to the real structure, which is called resonance hybrid.
The resonance hybrid is more stable than any other resonating structures.
 Conjugation Necessary condition for resonance

(i)  -  Conjugation

+
(ii) Z CH2

NH2
 -
CH2

.
CH2

Rules for writing Resonating structure

(i) Follow octet rule for 2nd period element.

(ii) Sigma skeleton should not be changed.

(iii) The no. of paired / unpaired electrons should be same.

Orbital Representation of Resonance
H3C — CH3 : 154 pm — CH2 : 134 pm
H2C — Benzene C — C : 139 pm
Aromatic Compounds Antiaromatic Compounds
(i) Cyclic (i) Cyclic

(ii) Planar (ii) Planar

(iii) Conjugation (iii) Conjugation

(iv) Huckle Rule (iv) 4 n  electrons

Non-aromatic Compounds
 Benzenoid System

–
Anions –
(iii)
(i)

–
(ii) (iv)
– –
2022/26 July/Shift-II

Which of the following is not an example of benzenoid compound?

A B

NH2
C D
Cations

+ + +
(i) (v) (viii)
O

+
+
(ii)
+ (vi) (ix)
+N N

H H
+

(iii) +
(vii) (x)
+N
+
H H
(iv)
Heterocyclic Compounds

(i) (iv)
N N

(ii)
O

(iii)

S
JEE (Main) 2019

Which of the following compounds is not aromatic?

A B

C D
 Relative Aromatic Character

Benzene Thiophene Pyrrole Furan

S N O

Order of E.N. :

Electron donating tendency :

in resonance
 Aromaticity

COT

[COT]2+

[COT]2–
 O
(iv)
(i)

(ii )
(v)

(iii)
JEE Ad - 2012
Which of the following molecules, in pure form, is(are) unstable at room
temperature ?

D
2023 / 13 April / Shift-I

Among the following compounds, the one which shows highest dipole
moment is

A B

C D
Annulenes Monocyclic ring with alternate double — Single bond.

X  – CH2 / – NH / – O / – S
JEE (Advanced) - 2017
Among the following, the number of aromatic compound(s) is

⊝  

 ⊝
H2
Pd
JEE - 2005

Explain the following observations

3H2 / Pd / C
but not
JEE Main 2019

Which of the following compounds will produce a precipitate with AgNO3 ?

A B

C D
 Rules for stability of resonating structures
a) More no. of  bonds, with complete octet, is more stable.

+
NH2 — CH2

b) If  bonds are same, then less ionized Resonating Structure is more stable.

NH2

c) If  bonds are same and –ve charge is present at same period elements .
Then –ve charge is more stable at more electronegative atom.

O
|| -
CH3 —C —CH2
d) If  bonds are same and –ve charge is present at different period elements.
Then –ve charge is more stable at larger size atom.
O
||
CH3 —C —S
-
e) If  bonds are same, then aromatic resonating structures is more stable.
O -

C
O H

f ) In fused benzene ring system, structure with more no. of kakule benzene will
be more stable.
OP* = Octet → Neutral → (-)ve charge on EN → Distance between + & - → Benzenoid System → - I effect

   
O=C=O O–C O O=C–O

The most stable resonating structure contribute maximum to the resonance hybrid and
less stable resonating structure contribute minimum to resonance hybrid.
OP* = Octet → Neutral → (-)ve charge on EN → Distance between + & - → Benzenoid System → - I effect


  
OCH3 OCH3 OCH3

O O O O
 
HO NH2 HO NH2 HO NH2 HO  NH2

 
O  NH O NH O NH
QUESTION (27 Jan, 2024 / Shift-II)

The order of relative stability of the contributing structure is :

••  
••
••
O O O

••
••

••
••
 
CH2 = CH – C – H CH2 – CH = C – H CH2 – CH = C – H

••
(I) (II) (III)
Choose the correct answer from the options given below :

A I > II > III

B II > I > III

C I= II = III

D III > II > I

 JEE - 2009

The correct stability order of the following resonating structures is :

+ – + – – + – +
H2C = N = N H2C – N = N H2C – N  N H2C – N = N
(I) (II) (III) (IV)

A (I) > (II) > (IV) > (III)

B (I) > (III) > (II) > (IV)

C (II) > (I) > (III) > (IV)

D (III) > (I) > (IV) > (II)

 Stability of Resonating structures of different molecules
(i) Larger conjugation is more stable than smaller conjugation.

- -
CH2 CH2

(ii) Linear conjugated system is more stable than cross conjugation.

(iii) If nature of bonding is different then (–)ve charge is more stable at more
electronegative atom and (+)ve charge is more stable at less electronegative atom.

O- O O
|| ||
O- CH3 —C —O - CH3 —S —O-
||
O

+ +
NH2 HO
(iv) – ve charge is more stable at larger size element.

O O O
C C C
-S S- -O S- -O O-

(v) Benzenoid system having more no. of Kakule benzene is more stable.
Bredt’s Rule Bridgehead atom can not be planar

H +

- -
Mesomeric Effect

Flow of electron

-NH

+
CH2
 Types of Mesomeric Effect
+ M Groups – M Groups
If first atom of the group has –ve charge If first atom of the group has vacant orbital
or lone pair

If group has x, y relation .

+ M Order
(v)
-
— CH
-
— NH
-
—O
(i) 2
— NH2

(ii) — OH — NH2
H
O O —N
|| || CH3
(iii) —O—C —CH3 —NH —C —CH3

CH3
—N
(iv) — OH — O — CH3 CH3
 + M Order

- - -
— CH2 — NH —O — NH2 — NHR — NR2

O O
|| ||
— OH — OR —NH —C — R —O—C — R

—F — Cl — Br —I
 – M Order

O O O O O
|| || || || ||
(i) —C — NH2 —C —OH (ii) —C —OH —C —O—C — R

O O
|| ||
(iii) —C —OH —C —OR (v) — NO2 —C N

O O
|| ||
(iv) —C — H —C —CH3
– M Order
O O
|| ||
— NO2 —C N —C — H —C —CH3

O O O O O
|| || || || ||
—C —O—C — R —C —OR —C —OH —C — NH2

- - -
—C —O —C — NH —C —CH2
|| || ||
O O O
QUESTION (01 Feb, 2024 / Shift-II)

The functional group that shows negative resonance effect is :

A –NH2

B –OH

C –COOH

D –OR
 + M and – M Effect on Benzene
+ M Groups O-

– M Groups
H
C

There is no effect, at meta position.

Select the position for maximum electron density.
O—H Cl

(i) (iv)

O
||
NH —C —CH3

G
(ii) (v)

(iii)

O N O
QUESTION (27 Jan, 2024 / Shift-I)

Among the following, total number of meta directing functional groups is

(Integer based)

–OCH3. , –NO2. , –CN , –CH3 , – NHCOCH3 ,

–COR , –OH , –COOH , –Cl

QUESTION (01 Feb, 2024 / Shift-I)

Which of the following compound will most easily be attacked by an electrophile?

CH3
A B

Cl OH
C D
 Hyper Conjugation
De-localisation of  electron with (i) p orbital (ii) * orbital

H
+ H
Carbocation C—C
H
H H

H
H H
H
 H
. H
Radical C—C
H
H H

H H
Alkene C—C
H CH2
H

H
H C H
Benzene
JEE (Advanced) - 2013

The hyperconjugative stabilities of tert-butyl cation and 2-butene, respectively, are

due to

A  → p (empty) and  → * electron delocalisations.

B  → * and  →  electron delocalisations

C  → p (filled) and  →  electron delocalisations.

D p (filled) → * and  → * electron delocalisations.

NOTE : Hyper conjugation generates double bond character in single bond and
single bond character in double bond.

H R
H C H R — C— R
Find no. of  hydrogen present in following molecule for hyperconjugation ?

H H H3C CH3
(i) C C (ii) C C
H H CH3 CH3

Stability of Alkene
 F
Negative Hyper Conjugation
F — C— F
F
-
—
H2C — C — F
F
QUESTION (29 Jan, 2024 / Shift-I)

The interaction between  bond and lone pair of electrons present on an adjacent atom
is responsible for

A Hyperconjugation

B Inductive effect

C Electromeric effect

D Resonance effect
QUESTION (09 April, 2024 / Shift-I)

How many compounds among the following compound show inductive, mesomeric as
well as hyperconjuygation effects ?

OCH3 NO2

, , , , ,
Cl
O
NO2
CH3 COCH3
, ,
CH3
CH3
 Reaction Intermediates
Carbocation Carbanion Free Radical

- .
C
+ C C

Nature :

Stability :
QUESTION (08 April, 2024 / Shift-II)

The shape of carbocation is :

A Trigonal planar

B Diagonal pyramidal

C Tetrahedral

D Octahedral
 Order of Effectiveness

Resonance +
CH2

Hyperconjugation +
CH2

Inductive Effect +
CH2

But for halogens :

 + + +
Stability of Carbocation (a) CH3 CH3 — CH2 CH3 —C —CH3
|
CH3
+
CH2
+   
(b) CH3 —C —CH3 H3C – CH2 CH2 = CH HC  C
|
CH3

+ + + + +
CH2 CH2 CH2 CH2 CH2

(c)

CN Cl OCH3
QUESTION (30 Jan, 2024 / Shift-II)

The correct stability order of carbocations is

+ + +
A (CH3)3 C+ > CH3 – CH2 > (CH3)2CH > CH3
+ + + +
B CH3 > (CH3)2 CH > CH3 – CH2 > (CH3)3 C
+ + + +
C (CH3)3 C > (CH3)2 CH > CH3 – CH2 > CH3
+ + +
D CH3 > CH3 – CH2 > CH3 – CH > (CH3)3 C+
CH3
2021/27 July/Shift-I


CH2

  
CH2 = CH H3C – CH2 HC  C
A B C D

The correct order of stability of given carbocations is :

A A>C>B>D

B D>B>C>A

C C>A>D>B

D D>B>A>C
QUESTION (06 April, 2024 / Shift-II)

Number of carbocation from the following that are not stabilized by hyperconjugation
is ____________________.

+  +
, , CH3
(tert.-butyl) (tert.-Butyl)
+
+ + +
, CH2 – CH3 , N – CH2
 Hydride Ion Affinity

+ + +
CH3 CH3 — CH2 CH3 —C —CH3
|
CH3
 2022 / 20 July / Shift - I
 
CH2 CH2  
H CH2 CH

H O
(A) (B) (C) (D)

Among the given species the Resonance stabilized carbocations are :

A (A), (B) and (C) only

B (C) and (D) only

C (A), (B) and (D) only

D (A) and (B) only

JEE - 2008

The correct stability order for the following orbitals :

  
O O 

(I) (II) (III) (IV)

A (II) > (IV) > (I) > (III)

B (I) > (II) > (III) > (IV)

C (II) > (I) > (IV) > (III)

D (I) > (III) > (II) > (IV)

CPM [ Cyclopropylmethyl carbocation ]

H H
C

Bent Orbital Overlapping

2023/30 Jan/Shift-II

The most stable carbocation for the following is :

NH2 NH2 NH2 NH2

 



(a) (b) (c) (d)

A c

B d

C b

D a
 Rearrangement of Carbocation

H
| +
CH3 —CH —CH2

CH3 H
+
H3C – C – C – C – CH3

H2N H CH3
Ring Expansion +
CH2

+
Ring Contraction
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