GENERAL

ORGANIC
CHEMISTRY
(GOC)
 JEE Main Exam 2025 Syllabus

GENERAL ORGANIC CHEMISTRY

Covalent bond fission - Homolytic and heterolytic: free radicals,
carbocations, and carbanions; stability of carbocations and free
radicals, electrophiles, and nucleophiles.

Inductive effect, electromeric effect, resonance, and hyperconjugation.

Substrate + Reagent ⎯→ Reaction intermediate ⎯→ Product

Different electronic Attacking Intermediates

displacement effects reagents
(EDE) 
Carbocation CH3
Inductive effect Electrophiles

•
Carbon free radical CH3
Resonance e– deficient species

Mesomeric effect Nucleophiles Carbanion CH3

Hyperconjugation e– rich species Carbene ••CH2

Nitrene ••NH

•
•
Benzyne
 Bond cleavage

Homolytic bond Heterolytic bond

cleavage cleavage
Electronic Displacement Effects (EDE)

This effect will decide the electron density variation in the substrate and
these effects are:

Inductive Effect Resonance

Hyperconjugation Mesomeric effect

Inductive Effect

It is a permanent effect.

It operates only on sigma electron.

It is a distance-dependent effect and decreases with an increase in

distance and can be ignored after 5 carbon atoms.

Example

𝜹−
𝟑 𝜹−
𝟐 𝜹−
𝟏
+

C C C Z
Inductive Effect

✓ Permanent partial displacement of sigma electron in any covalent bond

due to difference in electronegativity (a reference to C-H) is known as
the inductive effect of attached atom/group on the entire carbon chain.

C C C C H
Z

E.N. Z > C E.N. Z < C

–I -effect +I -effect
Strength of +I order

Anionic > Alkyl > Isotopic

O C C
⊖ ⊖
⊖ ⊖
–CH2 > –NH > –O > –C – O > –C –C > –C – C – C > –C – C – C – C
C
> –T > –D
Factors Affecting +I Effect

1
+I ∝
E.N.

Isotopic effect

Order of bond length Order of bond Strength

C−H > C−D > C−T C−T > C−D > C−H
Factors Affecting –I Effect Group

-I ∝ E.N. ∝ % s character

Order of –I

F > O(sp2)> N(sp)

> O(sp
> 3) N(sp
> 2) >C(sp) > N(sp3) > C(sp2)
C(sp3)
Overall Strength of –I Group

+ ve charge > partial +ve charge >

neutral
⊕ ⊕ ⊕
−NR3 > −SR2 > −NH3 > −NO2 > −CN > −COOH > −F >−Cl > −Br >−I

>−COOR > −OR > −COR > −SH > −SR > −OH > −C≡CR > −Ar > −HC=CR2
 NOTE

For comparison of + I and –I groups of alkyl chain,

D N P

Distance No. of Power of that

groups group

F NO2
–C –C –C < –C –C –C
F NO2

–C –C –C > –C –C –C
Cl Cl F
–C –C –C > –C –C –C
Types of Intermediate

Carbocation Carbon-free radical Carbanion

 • ⊖
CH3 CH3 CH3

Bond pair 3 3 3

Lone pair 0 0 1
Vacant orbital 1 0 0
Unpaired e- 0 1 0
Magnetic Property Dia Para Dia

Valence e- 6 7 8

Octet status Incomplete Incomplete Complete

Types of Intermediate

Carbocation Carbon free-radical Carbanion

 • ⊖
CH3 CH3 CH3

e- status e¯ deficient e¯ deficient e¯ rich

Stabilized by +I +I -I

Hybridization sp2 sp2 sp3

Bond angle 1200 1200 1070

Geometry Trigonal planar Trigonal planar Pyramidal

Nature Neither Lewis acid

Lewis acid Lewis base
nor Lewis base
Application of Inductive Effect

∝
Stability of carbocation ∝ +I– Effect 𝟏
−𝐈 –𝐄𝐟𝐟𝐞𝐜𝐭

1
Stability of free radical ∝ +I– Effect ∝
−I –Effect

1
Stability of carbanion ∝ -I– Effect ∝
+I –Effect
Example

  
1. MeCH2 < Me2CH < Me3C

2.  <  < 

F Cl

 

3. < <

  
4. CH3 < CD3< CT3
Example

1. MeCH2 < Me2CH < Me3C

2. < <
F Cl

3. < <
Example

⊖ ⊖ ⊖
1. MeCH2 Me2CH Me3C
< <

⊖ ⊖ ⊖
2. CH3-CH2 < CH2= CH < CH≡C

3. CH3CH2CH–O¯ < CH3CHCH2–O¯

CH3 CH3
Bredt’s Rule

Double bonds and carbocation can almost never be formed(unless one of

the ring is 8-membered) at bridgehead carbons in bicyclic systems, this
principle is known as Bredt’s rule.

Bridgehead carbon Can’t get planar because of

(where ‘bridge’ joins ring) bicyclic structure
RESONANCE
Resonance

If a single structure cannot explain all of the properties of a molecule,

then multiple structures are required, and then it is said that molecules
are showing resonance. It is due to the delocalization of electrons within
the molecule.

Conditions of Resonance
1. System must be planar.
2. System must be in conjugation (i.e., parallel p orbital are required).
Types of Resonance

(a) lone pair to π−bond conjugation

(b) π bond to π bond conjugation

(c) Negative charge to π bond conjugation

(d) π bond to free radical conjugation

(e) π bond to vacant p/d orbital conjugation

(f) Lone pair to vacant p/d orbital conjugation(Back bonding)

Resonance Structure

⊖ 
CH2=CH−NH2 CH2−CH=NH2

p-orbital and
⊖ delocalised ⊖
CH2 = CH − CH2 CH2 − CH = CH2

sp2
Resonance Structure

CH2 = CH − CH2 CH2 CH=CH2

sp2

⊕ ⊕
CH2 = CH − CH2 CH2 − CH = CH2
Stability of Resonating Structure

Different resonating structures contribute differently to the

resonance hybrid.

A more stable resonating structure will have a greater contribution

to resonance hybrid.
Rule-1

The complete octet containing R.S. is the most stable than the incomplete
octet R.S. More the number of covalent bonds higher is the stability.

⊕
:
R—C=O R—C≡O Stability (II) > (I)
:

:
(I) (II)

Rule-2

In a complete octet containing R.S., the minimum charge or neutral R.S. is

the most stable.

O O⊖

⊕
: :
H3C — C — O — H H3C — C = O — H Stability (I) > (II)

:
(I) (II)
Rule-3

The negative charge is more stable on a more electronegative atom.

A positive charge is more stable on less electronegative atoms.

⊖ ⊖
CH2 CH O CH2 CH O Stability (a) < (b)
(a) (b)
Rule-4

Resonating structures having unlike charges closer to each other and

like charges farther to each other are more stable.

Me ⊕ Me Me ⊕ Me
N N
⊖

(a) (b)

Stability Order (b) > (a)

Example
Which of the following is not a valid resonance structure of the others?

(1) (2) ⊝



(3) ⊝ (4) ⊝


Solution

Ans. (4)
Application of Resonance

Comparison of bond order/bond length/bond strength

(1) Bond Order (for identical canonical forms)

No. of bonds involved in resonance

Bond Order =
No. of R.S.

Example

⊕ ⊕
CH2 = CH − CH2 CH2 − CH = CH2

3
(B.O.) C C
=
2
(2) Bond Length

1
Bond Length ∝
Bond Strength, B.O.

Example

Compare Bond Length

•
•
(1) CH2 CH F •
• CH3—CH2—F

•
•
B.L. Order (b > a)
a b
Example
Among the following compounds, which one has the shortest C—Cl bond?
H3C
[JEE Main 2020]
(1) H3C–Cl (2) H3C Cl

Cl CH3
CH

(3) CH2 (4) HC Cl

CH2

Solution

Ans. (3)
 Types of M–Effect

+M / +R Effect –M / –R
Effect

Any atom or group which gives Any atom or group which accepts
electrons to a conjugated system. electron from the conjugated
system.
Group or atom having positive
Group or atom having lone pair charge or polar  bond shows –M
or (–)ve shows +M effect. effect.
O O O O
⊖ ⊖ ⊖
-O, -NH, -CH2-, -F, -Cl, -Br, -I, –C–H , –C–R , –C–OR , –C–NR2 ,
-OH, -OR, -SH, -SR, -PR3, -NH2 etc.
–NO2, –C  N etc.
 Order of +M Effect

O O
–O– > –NH2 > –NHR > OH > –OR > –NH—C—R > –O—C—
R
> –Ph > –F > –Cl > –Br > –I
 Order of –M Effect

O O O
–NO2 > –CN > –SO3H > –CHO > –C– > –C—O—C—R

O O
> –CO2H > –C—OR > –C—NH2
Groups Which Don’t Show Mesomeric Effect

Groups which do not have vacant p or d-orbital, or lone

pair on the connecting atom have no M-effect’.

R (Alkyl); –CH3 ; –Et ; –CMe3

⊕ ⊕
–NH3 ; –NR3 ; – NC

–CX3 ; –CCl3 ; –CBr3 ; –CF3

Groups Which Show Both +M and -M Effect

–CH = CH2 ; –N = O ; –N = NH

–S = O ; –SH ; –SCH3
OH

; –PH2
Strength of +M Group

Effect of Overlapping

CH2=CH–F > CH2=CH–Cl

2p-2p overlapping 2p-3p overlapping

(More effective) (Comparatively less effective)
Effect of Electronegativity

1
+M ∝
E.N.
In the case of halogens, the inductive effect dominates, and they are EWG.
Order of -I –F > –Cl > –Br > –I
Order of +M –F > –Cl > –Br > –I

The overall Electron withdrawing order of halogens when

combining the effect of +M and –I effect of halogen are
compared.
–I > –Br >–Cl > –F

Electron density in the ring in fluorobenzene is higher than in the

chlorobenzene.
Cl F

Electron density in the ring, (A) < (B)

Mesomeric Effect in Benzene Ring

  
NH2 NH2 NH2 NH2 NH2
⊖
⊖

(Aniline)
e– density: o = p > m

Higher e– density (–ve charge) is present at o & p-position so the –NH2

group act as the o/p directing group.
Example
When –CHO is attached to benzene ring (Benzaldehyde)
⊖ ⊖ ⊖
O=C–H O–C–H O–C–H O–C–H O=C–H
⊕
⨁

e– density: o = p < m

e– density decreases at the o & p-position, hence acting as a

deactivating group and hence act as a meta-directing group.
Example
Which is the most stable structure of arenium ion?

CH3 CH3 CH3 CH3

NO2 
(1) H (2) (3) (4) H
 
H NO2 H NO2  NO2

Solution

Ans. (3)
 Example
The order of relative stability of the contributing structure is:
:O: :O: ⊝

:
[JEE Main - 2024]
||  |
CH2 = CH – C – H CH2 – CH = C – H
I II

: O :
_ |
: CH2 – CH = C – H
III
Choose the correct answer from the options given below:
(1) I > II > III (2) II > I > III (3) I = II = III (4) III > II > I

Solution

Ans. (1)
Dancing Resonance (Sigma Bond Resonance)

In cyclopropyl methyl cation, carbocation is highly stabilized by 2,3 and

2,4 C-H 𝜎 bond, this phenomenon is called dancing resonance.

3
2  H  

H
1
4
Summary

✓ +M group stabilizes carbocation.

Stability of Carbocation ∝ +M

✓ -M group stabilizes carbanion.

Stability of Carbanion ∝ -M
Example
In the following molecules,
a
H3 C
b c
C== C—O
H H

The hybridisation of carbon a, b and c, respectively are: [JEE Main 2021]

(1) sp3, sp, sp (2) sp3, sp2, sp (3) sp3, sp2, sp2 (4) sp3, sp, sp2

Solution

Ans. (3)
Example
The correct order of stability for the following alkoxides is: [JEE Main 2020]
O– O– O
–
O2 N
NO2 NO2
(A) (B) (C)

(1) (C) > (B) > (A) (2) (C) > (A) > (B)
(3) (B) > (C) > (A) (4) (B) > (A) > (C)

Solution

Ans. (1)
Example
 [JEE Main 2021]
CH2
  
CH2=CH CH3–CH2 HC≡C

A B C D
The correct order of stability of a given carbocation is:
(1) A > C > B > D (2) D >B > C > A (3) D > B > A > C (4) C > A > D > B

Solution

Ans. (1)
Example
The decreasing order of hydride affinity for following carbocations
is: +
CH2 = CH—C—CH3 [JEE Main 2023]
A. |
CH3
+
C6H5—C—C6H5
B. |
C6H5
+
H3C—C—CH3
C. |
CH3
+
C
D.

Choose the correct answer from the options given below:

(1) A, C, B, D (2) C, A, B, D
(3) C, A, D, B (4) A, C, D, B
Solution

Ans. (2)
Example
 
CH2 CH2  
CH2 CH
H
H O [JEE Main 2021]
(A) (B) (C) (D)
Among the given species the resonance stabilized carbocations are:
(1) (C) and (D) only (2) (A), (B) and (D) only
(3) (A) and (B) only (4) (A), (B) and (C) only

Solution

Ans. (3)
Example
Resonance in carbonate ion CO2−
3 is
O O– O–
C C C
–O –O
O– O O O–
[JEE Main 2023]
Which of the following is true?
(1) It is possible to identify each structure individually by some physical or
chemical method.
(2) All these structures are in dynamic equilibrium with each other.
(3) Each structure exists for an equal amount of time.
3 has a single structure i.e., resonance hybrid of the above three
(4) CO2−
structures.
Solution

Ans. (4)
Aromaticity
Aromaticity

Aromatic Anti-aromatic Non-aromatic

Compounds Compounds Compounds

(a) Cyclic (a) Cyclic (a) If an atom is sp3

(b) Planar (b) Planar hybridized in the ring.

(c) Conjugated 𝜋 e (b) Acyclic

(c) Follow 4n 𝜋 e–
follow Huckel’s rule: - i.e. (Where n= 1,2,3…)
(4n + 2) 𝜋 e where
unstable at room
n  {(Whole number)} temperature.

Stability: Aromatic > Non-aromatic > Anti aromatic

Anti – Aromatic Compound

Room temperature

Dimerization
QUASI-aromatic Compounds

Some compounds which become aromatic due to charge

delocalization in the ring are known as QUASI-aromatic compounds.


O O
Example

( 6 – Annulene) ( 8 – Annulene)
Aromatic Non - Aromatic

Me
Me

( 10 – Annulene) ( 10 – Annulene)
Non - Aromatic Non - Aromatic
Example

In Azulene and Naphthalene, which one is more soluble in polar solvent?

Solution

⊖

Azulene Zwitter ion (polar) → More soluble
 Example
Compare the Rotational Energy and Dipole Moment barrier between a and b.

a b

Solution

Ans. Rotational Energy → a > b

Dipole moment → b > a
Example

(A) (C)
(B)

Compare the carbon-carbon bond rotation energy across A, B and C:

(1) A > B > C (2) A > C > B (3) B > A > C (4) C > A > B

Solution

Ans. (4)
 Example
Which one of the following compounds is non-aromatic?

(1) (2) (3) (4)
O 
[JEE Main 2021]
Solution

Ans. (1)
Example

Which of the following structures are aromatic in nature? [JEE Main 2022]

⊖ ⊖
⊕
A B C D
(1) A,B,C and D (2) Only A and B
(3) Only A and C (4) Only B, C and D

Solution

Ans. (2)
Example
Assertion A: [6] Annulene. [8] Annulene and cis –[10] Annulene, are
respectively aromatic, not-aromatic and aromatic.

Cis-[10] Annulene H
[6] Annulene [8] Annulene H

Reason R: Planarity is one of the requirements of aromatic systems.

In the light of the above statements, choose the most appropriate answer
from the options given below.
(1) Both A and R are correct, and R is the correct explanation of A.
(2) Both A and R are correct, but R is NOT the correct explanation of A.
(3) A is correct but R is not correct.
[JEE Main 2022]
(4) A is not correct but R is correct.

Solution
Ans. (4)
Example
Given below are two statements: [JEE Main 2023]
Statement I: Tropolone is an aromatic compound and has 8 electrons.
Statement II:  electrons of >C = O group in tropolone is involved in
aromaticity.
In the light of the above statements, choose the correct answer from the
options given below:
(1) Both Statement I and Statement II are true
(2) Statement I is true, but Statement II is false
(3) Statement I is false, but Statement II is true
(4) Both Statement I and Statement II are false

Solution O

Ans. (2)
Example
On reaction with acid, 4-pyrone gives a very stable cationic product. Which
of the following structures show the protonation site in that product?
O

4-Pyrone
O
O
H
O O O
H
H 
(1) (2) (3) (4)
 
O O H O O
H
H

Solution

Ans. (3)
 Example
[JEE Main - 2024]
Among the given organic compounds, the total number of aromatic
compounds is

(1) (2)

(3) : (4)

⊝
Solution

Ans. (3)
 Example
Among the following, the total number of meta-directing functional groups
is: (Integer based)
– OCH3, –NO2, –CN, –CH3 –NHCOCH3,
– COR, –OH, – COOH, –Cl

Solution [JEE Main 2024]

Ans. 4
 Example
Which of the following molecule/species is most stable? [JEE Main - 2024]
 

(1) (2)

:
(3) (4)

Solution

Ans. (1)
 Example
The functional group that shows a negative resonance effect is:
(1) –NH2 (2) –OH (3) –COOH (4) –OR

Solution

[JEE Main 2024]

Ans. 3
 Example
The interaction between  bond and a lone pair of electrons present on an
adjacent atom is responsible for:
(1) hyperconjugation (2) inductive effect
(3) electromeric effect (4) resonance effect

[JEE Main 2024]

Solution

Ans. 4
 GENERAL
ORGANIC
CHEMISTRY
(GOC)
Resonance Energy
Resonance Energy

The amount of energy by which a hybrid resonating structure is more

stable over its most stable contributing resonating structure.

R.E. = Energy of most stable R.S. — Energy of Resonance Hybrid

Or

The difference between expected and actual HOH is called resonance

energy.

R.E = Expected/Theoretical H.O.H – Actual/Experimental H.O.H

Resonance Energy

RE
+ Theoretical
36.0

Energy (kcal/mol)
3H2 value

+ 85.8 +
2H2 3H2
57.2 49.8

+ 28.6
H2
Rule

1. Resonance energy for all resonating structures of the same compound

is always the same.

 

R.E. Order

(a) (b) (a)=(b)

2. Resonance energy for analogous compounds having equivalent R.S. is

higher.

O O
⊖
R –C –O R –C –OH R.E. Order (a) > (b)
(a) (b)
3. Extended conjugation has more R.E. than the cross conjugation.

O O a>b
(a) (b)

4. More extended is the resonance, more is the resonance energy.

O O O

(a) (b) (c)

R.E. Order (c) < (b) < (a)

5. Better resonance implies, more resonance energy.

R.E Stability
⊖ ⊖
CH2—CH == CH2 CH2 a<b a<b
(a) (b)

6.

(a) (b) (c)

R.E. Order (a) < (b) < (c) R.E./ring Order (a) > (b) > (c)
 Example
The difference in energy between the actual structure and the lowest energy
resonance structure for the given compound is:
(1) electromeric energy (2) resonance energy
(3) ionisation energy (4) hyperconjugation energy

[JEE Main 2024]

Solution

Ans. 2
Hyperconjugation
Hyperconjugation

It is a permanent and distance-independent effect.

Hyperconjugation phenomenon is predominatly observed in:

Carbocation

Free Radical

Alkene

Benzene
 No. of 𝛼-H No. of hyperconjugative
structures


1. CH3 CH2 3 3


2. Me CH CH3 6 6


3. Me C Me
9 9
Me

CH3

4. CH3 C CH2 0 0
CH3
Alkene

It is a permanent polarisation caused by the delocalisation of 𝜎 –

electron pair of the C – H bond through overlapping of its (sp3–s) 𝜎–
orbital with 𝜋* orbital of adjacent C=C bond.
H H
⊖
H C CH CH2 H C CH CH2 (H.S.-1)
H H
H

H ⊖
⊖
H C CH CH2 (H.S.-3)
H C CH CH2 H
H
(H.S.-2)
Total number of hyperconjugative structure = 3
Order of +H -CH3 > -CD3 > -CT3
Example

Compare the Stability of Alkene:

(a) (b) (c)

(Isolated) (conjugated) (cumulated)

Solution

Ans. b > a > c

Stability of Alkene

CH2
(a) (b)
(c)

(d) (e) (f)

Stability Order (a > b > c > d > e > f)

Example

Which one of the following dienes would you expect to be the most stable?

(1) (2) (3) (4)

Solution

Ans. (3)
Reverse Hyperconjugation/ -ve Hyperconjugation

If the electron density flows in the opposite direction (from π-orbital to

empty σ∗-orbital), than it does in the more common hyperconjugation
(from σ-orbital to empty p-orbital or 𝜋* C=C bond).

⊖ ⊖ ⊖
CCl2 Cl CCl2 Cl CCl2 Cl CCl2 Cl
⊕ ⊕

CCl3
✓ It is also known as -H effect.

✓ If both +H & -H operates simultaneously +H dominates.

✓ It is observed in -CCl3 , -CF3 Group.

 Example
Hyperconjugation is best described as:
(1) delocalisation of pi electrons into a nearby empty orbital
(2) delocalisation of sigma electrons into a nearby empty orbital
(3) the effect of alkyl groups donating a small amount of electron density
inductively into a carbocation
(4) the migration of a carbon or hydrogen from one carbocation to another

Solution

Ans. (2)
Example

Compare the stability of free radical:

•
•
CH2

•
CH2

•
CH2

•
CH2 CH2

CH3 CH2CH3
(a) (b) (c) (d) (e)

Solution

Ans. a > b > c > e> d

Heat of Hydrogenation : (H.O.H)

The amount of energy released when one mole of double bond

undergoes hydrogenation.

H.O.H ∝ No. of 𝝅 bonds

H.O.H ∝ 1/Stability of Alkene

Example

H.O.H order:

(a) (b) (c)

Alkene stability order : c>b>a

H.O.H order : c<b<a

Heat of Combustion (H.O.C)

H.O.C ∝ No. of Carbon atom

H.O.C ∝ 1/Stability of the species

For the different numbers of C-atoms, we can compare HOC per CH2
to relate it with stability.
Effect of Resonance and Hyperconjugation on C–C / C=C Bond Length,
Bond Strength and Bond Rotational Energy

CH3 CH CH2 H3C

C CH2
H3C
a
b

Bond Length = (b) > (a)

Bond Strength = (b) < (a)
 Example
[JEE Main 2021]
Given below are two statements:
Statement I: Hyperconjugation is a permanent effect.
+
Statement II: Hyperconjugation in ethyl cation (CH3–CH2) involves the
overlapping of Csp2 – H1s bond with empty 2p orbital of other carbon.
Choose the correct option:
(1) Both Statement I and Statement II are false
(2) Statement I is incorrect, but Statement II is true
(3) Statement I is correct, but Statement II is false
(4) Both Statement I and Statement II are true

Solution

Ans. (3)
 Example
The correct stability order of carbocations is:
+ + +
(1) CH3 3 C > CH3 − CH2 > CH3 2 CH > CH3
+

+ + + +
(2) CH3 > (CH3 )2 CH > CH3 − CH2 > (CH3 )3 C
+ + + +
(3) (CH3 )3 C > (CH3 )2 CH > CH3 − CH2 > CH3
+ + + +
(4) CH3 > CH3 − CH2 > CH3 − CH > CH3 C
CH3 [JEE Main 2024]
Solution

Ans. 3
 Example
A species having carbon with a sextet of electrons and can act as an
electrophile is called:
(1) carbon-free radical (2) carbanion
(3) carbocation (4) pentavalent carbon

Solution [JEE Main 2024]

Ans. 3
Example
The correct order of heat of combustion for the following alkadienes is:

(a) (b) (c)

(1) (a) < (b) < (c) (2) (b) < (c) < (a)
(3) (c) < (b) < (a) (4) (a) < (c) < (b) [JEE Main 2020]

Solution

Ans. (1)
Comparison of C-H Bond Energy with Examples

-H
a. CH3 H CH3

-H
b. Me3C H Me3C

Stability order of carbon free radical

Me3C > CH3

𝟏
C-H Bond energy ∝
𝐒𝐭𝐚𝐛𝐢𝐥𝐢𝐭𝐲 𝐨𝐟 𝐜𝐚𝐫𝐛𝐨𝐧 𝐟𝐫𝐞𝐞 𝐫𝐚𝐝𝐢𝐜𝐚𝐥
Example
Match List -I with List II: [JEE Main 2024]

List - I List - II
Mechanism steps Effect
+
NH2 NH2
(I) – E effect
(A)

H
(B) + H+ (II) – R effect
+
− –
(C) + CN (III) + E effect
CN
ON=O –O N →
(D) + O (IV) + R effect
Choose the correct answer from the options given below:
(1) (A) – (IV), (B) – (III), (C) – (I), (D) – (II)
(2) (A) – (III), (B) – (I), (C) – (II), (D) – (IV)
(3) (A) – (II), (B) – (IV), (C) – (III), (D) – (I)
(4) (A) – (I), (B) – (II), (C) – (IV), (D) – (III)

Solution
Ans. 1
 Example
Which among the following is an incorrect statement?
(1) Electromeric effect dominates over inductive effect
(2) The electromeric effect is, a temporary effect
(3) The organic compound shows an electromeric effect in the presence of
the reagent only
(4) Hydrogen ion (H+) shows a negative electromeric effect
[JEE Main 2024]
Solution

Ans. 4
 Example
The correct order of stability of carbanion is:

a b c d
(1) c > b > d > a (2) a > b > c > d
(3) d > a > c > b (4) d > c > b > a
[JEE Main 2024]
Solution

Ans. 4
Acidic Character
Acidic Character

An acid is a substance which donates an H+ ion.

HA H+ + A-

Acid Conjugate Base

More stable the conjugate base, more acidic is the compound.

1
pH ∝ pKa ∝
Ka
 Important Acidic Strength Order:

(1)
O O
> CH3 -OH > H2O R-OH > R-C ≡CH
> > H2 > NH3
R=alkyl
except H and Me
 Important Acidic Strength Order:
OH
NO2 NO2 HO
(2) HCl > Ph−SO3H > > >
HO O
NO2
OH OH OH
NO2 NO2
RCOOH ≈ > H2CO3 ≈ > >
NO2 NO2
OH OH OH

> > CH3 -OH > H2O >

NO2
Factor Affecting Stability of Conjugate Base/Anion

1. Size

Stability of C.B. ∝ Size of the central atom

⊖ ⊖ ⊖ ⊖
I < Br < Cl < F

2. Electronegativity

Stability of C.B. ∝ Electronegativity of central atom

⊖ ⊖
Cl > SH
3. Resonance

More number of resonating structures, more will be the stability of

the conjugate base, and the higher will the acidic character of its
acid.
O
⊖ ⊖
R C O > RO
(a) (b)

4. Inductive Effect

If all the above rules fail then, the stability of anion/C.B. is decided
by the inductive effect.
1
Stability of C.B. ∝ -I– Effect ∝ +I
⊖ ⊖ ⊖
MeCH2-O > Me2CH-O > Me3C-O
Comparison of Acidic Strength of Alcohol, Phenol and its
Derivatives:

Generalized acidity order of phenol, alcohol and thiol are:

ArS−H > ArO−H > RO−H

Example

OH OH OH OH OH

NO2 CN Me OMe
(a) (b) (c) (d) (e)

Solution

Ans. a > b > c > d > e

Example

OH OH OH
NO2 O2N NO2

NO2 NO2 NO2

(a) (b) (c)

Solution

Ans. c > b > a

Example

OH OH OH OH
NO2

NO2
NO2
(a) (b) (c) (d)

Solution

Ans. b > a > c > d

Example
Circle represent the most acidic hydrogens in these molecules. Which of
the following is the correct representation?
OH O
MeO2C
(1) (2)
OH
CF3 HO CO2H

S
(3) (4) All of these

Solution

Ans. (4)
Comparison of Acidic Strength of Carboxylic Acid

Steric Inhibition of Resonance (SIR)

Inhibition of resonance due to steric factor is known as SIR effect.

SIR effect is not observed in atoms, linear groups and non-planar groups.

Atoms Linear Groups Non planar groups

−F −C≡N O

−Cl −C≡C−H −S−OH

−Br −NH2 O

−I −OH
Example

Groups which are affected by SIR:

Me O
−N
−N→O
Me
H O
−N
⊖
Me −C−O

O
−C−OH

Groups which exert SIR:

−I, −C(Me)3, −Br etc.

Explanation

HO O HO O
C C
G

Steric Inhibition of Resonance

Example
Which among the following is the strongest acid? [JEE Main 2021]

(1) CH3CH2CH2CH3 (2)

(3) (4)

Solution

Ans. 4
Example
Arrange the following in decreasing acidic strength.
OH OH OH OH

NO2 OCH3
NO2 OCH3
(A) (B) (C) (D)

(1) A > B > C > D (2) B > A > C > D

(3) D > C > A > B (4) D > C > B > A [JEE Main 2022]

Solution

Ans. 1
Example
What is the correct order of acidity of the protons marked A–D in the given
compounds?
HD CO2HC

HA

HB

(1) HC > HD > HB > HA (2) HC > HD > HA > HB

(3) HD > HC > HB > HA (4) HC > HA > HD > HB [JEE Main 2023]

Solution

Ans. 2
Example
The descending order of acidity for the following carboxylic acid is:
A. CH3COOH B. F3C–COOH C. ClCH2–COOH D. FCH2–COOH
E. BrCH2–COOH
Choose the correct answer from the options given below:
(1) D > B > A > E > C (2) E > D > B > A > C
(3) B > C > D > E > A (4) B > D > C > E > A [JEE Main 2023]

Solution

Ans. 4
Example
The correct order for acidity of the following hydroxyl compound is:

A. CH3OH
B. (CH3)3COH
C OH

D. MeO OH

E. O2N OH

Choose the correct answer from the options given below:

(1) E > C > D > A > B (2) D > E > C > A > B
(3) C > E > D > B > A (4) E > D > C > B > A [JEE Main 2023]
Solution
Ans. 1
Example

*
KH
–H2 A ; Major products of the reaction is (are):
H2O
*
(C= C14)
Major
product
*
(1) (2) * (3) (4) Both (1) & (2)

Solution

Ans. 4
Example
Arrange the following in increasing order of their acidic strength.
O O O O O

O OCH3
(I) (II) (III) (IV)
O O O

(1) III < I < IV < II (2) II < I < IV < III
(3) I < III < IV < II (4) II < III < I < IV

Solution

Ans. 4
 Example
The ascending acidity order of the following H atoms is [JEE Main - 2024]

HC  C — H H2C  CH H3C
|
H H3C—C—H H3C—CH2—H
H3C
A B C D
(1) C < D < B < A (2) A < B < C < D
(3) A < B < D < C (4) D < C < B < A

Solution

Ans. (1)
 Example
The ascending order of acidity of –OH group in the following compounds is:

(A) Bu – OH (B) O2N— —OH (C) MeO— —OH

[JEE Main - 2024]

(D) —OH (E) O2N— —OH

NO2
Choose the correct answer from the options given below:
(1) (A) < (D) < (C) < (B) < (E) (2) (C) < (A) < (D) < (B) < (E)
(3) (C) < (D) < (B) < (A) < (E) (4) (A) < (C) < (D) < (B) < (E)

Solution

Ans. (4)
 Example
Which of the following has most highly acidic hydrogen ? [JEE Main - 2024]
O O
|| ||
C CH3 H3C CH2 C
(1) H3C C (2) C CH2 CH3
|| ||
O O

(3) H3C CH3 (4) H3C CH2 CH2

C C CH3
|| ||
O O O
Solution

Ans. (4)
 Example
Match List I with List-II [JEE Main - 2024]
List I List II
(Compound) (pKa value)
A. Ethanol I. 10.0
B. Phenol II. 15.9
C. m-Nitrophenol III. 7.1
D. p-Nitrophenol IV. 8.3
Choose the correct answer from the options given below:
(1) A-I, B-II, C-III, D-IV (2) A-IV, B-I, C-II, D-III
(3) A-III, B-IV, C-I, D-II (4) A-II, B-I, C-IV, D-III
Solution

Ans. (4)
Basic Character
Basic Character

Base is a substance which readily accepts H+ ion.

−
B + H+ B-H
Base Conjugate acid

If Kb is the dissociation constant of the base, then the higher the basic
character of the compound, the lower its pKb value.

1
pKb ∝ Basic character ∝ Kb
Kb
Basic Strength of Neutral Base

More stable is the conjugate acid of the base, more will be its
basic character.

The basic strength of the base depends upon the availability of

a lone pair.

The basic strength of the base depends upon the tendency to

donate its lone pair.
1. Effect of Electronegativity

Atoms having high electronegativity have a higher tendency to hold lone

pairs, so they have a lower tendency to donate it; hence, basic character
decreases.

H2O NH3
>

2. Effect of Conjugation

When a lone pair comes in conjugation, the tendency to its donation

decreases. Hence, basic character decreases.

>

••

••
CH3 CH2 NH2 CH2 CH NH2
3. Effect of Aromaticity

Example

NH2 ••
N N
••

H
(a) (b) (c)

Basicity: (c > a > b)

4. Inductive Effect

N
Basicity order a>b
N N

(a) (b)
5. Steric Inhibition in Protonation (SIP)

It is observed that o-derivative of aniline is less basic than aniline itself.

It is also known as ortho effect.

NH2 NH2
G
> (basicity)

Due to SIP(the ortho effect), the basicity of o-substituted aniline

decreases, than meta- and para-substituted.
NOTE

Anionic compounds are more basic than their neutral counterparts.

⊖
H2O OH
>
Example

NH2 NH2 NH2 NH2

CH3

CH3
CH3
(a) (b) (c) (d)

a>b>c>d
Guanidine Base

⊕
1 NH NH2 NH2
+H+
⊕
H2N 2 NH2 H2N NH2 H2N NH2

Guanidine base

Positive charge delocalization

Basicity order of N 1>2

Superbase

Example

NEt2 Et2N NEt2

Basicity order b>a

(a) (b)
Superbase

Example
(a)
Et2N NEt2

Basicity order b<a

NEt2
(b)
Amine Flipping

⇌
H H
N
N
H H

⇌
H

The phenomenon of flipping of nitrogen lone pair and its pyramidal

structure is called amine flipping.

Due to amine flipping, which is possible in acyclic compounds, its

basicity decreases as the availability of lone pair decreases.
Cyclic nitrogen molecules have a higher basicity than acyclic nitrogen
molecules.

:
N

:
N
<

Due to this amine flipping, acyclic nitrogen compounds where N atom is

attached to 3 different atoms or groups will become optically inactive.
Basic Nature of Amine in an Aqueous Medium

The more stable the conjugate acid of the base, higher is it’s basicity.

To compare the basicity of amine, first make their conjugate acid and
then compare stability.

  
R2NH +H
R-NH2 +H 
R-NH3 R2NH2
1° - Amine 2° - Amine


+H 
R3N R3NH
3° - Amine
Stability of Conjugate Acid Depends on the Following Factors

(i) Presence of +I-Effect 3° > 2° > 1°

(II) H–bonding in aqueous solution 1° > 2° > 3°

Lower hinderance to H-bonding 1° > 2° > 3°

On combining the above factors, the general order of basic strength becomes:

2° > 1° > 3° > -NH2 (R = -Me)

2° > 3 > 1° > -NH2 (R = -Et)

Example
The increasing order of basicity for the following intermediates is (from
weak to strong): [JEE Main 2020]
CH3
⊝ ⊝ ⊝ ⊝
(i) H3C—C
⊝
(ii) H2C=CH–CH2 (iii) HC≡ C (iv) CH3 (v) CN
CH3
(1) (v) < (i) < (iv) < (ii) < (iii) (2) (iii) < (i) < (ii) < (iv) < (v)
(3) (v) < (iii) < (ii) < (iv) < (i) (4) (iii) < (iv) < (ii) < (i) < (v)

Solution

Ans. 3
 Example
Which of the following is the strongest bronsted base?
NH2 H H
N N
(1) (2) NH (3) (4)

[JEE Main 2024]

Solution

Ans. 4
Example
The correct order in aqueous medium of basic strength in case of methyl
substituted amines is:
(1) Me2NH > MeNH2 > Me3N > NH3
(2) Me2NH > Me3N > MeNH2 > NH3
(3) NH3 > Me3N > MeNH2 > Me2NH
(4) Me3N > Me2NH > MeNH2 > NH3 [JEE Main 2023]

Solution

Ans. 1
 Example
What will be the decreasing order of basic strength of the following
conjugate bases?
ሜ Cሜl
ሜ CH3 COO,
−OH, RO,
(1) Cሜl > OH > ROሜ > CH3COOሜ (2) ROሜ > –OH > CH3COOሜ > Cሜl
(3) –OH > ROሜ > CH3 COOሜ > Cሜl (4) Cሜl > ROሜ > –OH > CH3COOሜ
[JEE Main 2024]
Solution

Ans. 2
Example
Match List I with List II
List I (Amines) List II(pKb )
A. Aniline I. 3.25
B. Ethanamine II. 3.00
C. N-Ethylethanamine III. 9.38
D. N, N-Diethylethanamine IV. 3.29

Choose the correct answer from the options given below: [JEE Main 2023]
(1) A-I, B-IV, C-II, D-III (2) A-III, B-II, C-I, D-IV
(3) A-III, B-II, C-IV, D-I (4) A-III, B-IV, C-II, D-I

Solution

Ans. 4
Acid-Base Equilibrium

In each acid-base reaction, the reaction always proceeds from strong

acid to weak acid or strong base to weak base.

Important acidic strength order

O O
(1)
> CH3 -OH > H2O >R-OH > R-C ≡CH > H2 > NH3
R=alkyl
except H and Me
 OH
NO2 NO2 HO
HCl > Ph−SO3H > > >
HO O
NO2
OH OH OH
NO2 NO2

RCOOH ≈ > H2CO3 ≈ > >

NO2 NO2
OH OH OH

> > CH3 -OH > H2O >

NO2
Example

Identify feasible reaction:

⊝ ⨁
(a) R−C≡C−H + NaOH R−C≡C Na + H2 O
⊝ ⨁
(b) R−C≡C−H + NaH R−C≡C Na + H2
⊝ ⨁
(c) R−C≡C−H + NaNH2 R−C≡C Na + NH3

Solution

H2O is more acidic than R−C≡C−H.

Ans. b, c
 Reaction with NaHCO3

(a) Stronger acid + NaHCO3 Na salt + H2CO3

than H2CO3
Example
Identify feasible reaction:
⊝ ⨁
(a) RSO3H + NaHCO3 RSO3 Na + H2CO3

⊝ ⨁
OH O Na
NO2 NO2 NO2 NO2
(b) + NaHCO3 + H2CO3

NO2 NO2

Solution

Ans. a, b
Reaction with Na
⊖
(a) R COOH + Na RCOONa + 1Τ2H2

⊖
(b) Ph OH + Na PhONa + 1Τ2H2

⊖
(c) C2H5OH + Na CH3CH2ONa + 1Τ2H2

⊖

(d) CH3 C CH + Na Me C CNa + 1Τ2H2

⊖
(e) NH3 + Na H2NNa + 1Τ2H2
Example
Decide whether Keq > 1 or Keq < 1.
 ⊖
(1) RCOOH + NaCl HCl + RCOONa Keq < 1

⊖  
⊖
Keq > 1
(2) EtLi + NH3 EtH + NH2Li

 ⊖ 
NaNH2 + CH4
⊖
NH3 + CH3Na Keq < 1
(3)

⊖ ⊖ 
(4) Ph ONa + EtOH PhOH + EtONa Keq < 1

Solution

(1) HCl is more acidic than RCOOH.

⊖ ⊖
(3) CH3 is more basic than NH2.
Example
Complete the following reaction and decide Keq.
Reaction with NaOH

RCOOH + NaOH RCOO– Na+ + H2O Keq > 1

Ph OH + NaOH PhO– + Na+ + H2O Keq > 1

Et OH + NaOH EtO– + Na+ + H2O Keq < 1

Me —OH + NaOH MeO– + Na+ + H2O Keq > 1

Solution

H2O is more acidic than EtOH.

Example
Compound(s) which will liberate carbon dioxide with sodium bicarbonate
solution is/are:
NH2 COOH OH
NO2 NO2
A= B= C=
NH2 NH2
OH NO2 [JEE Main 2021]
(1) B only (2) C only (3) B and C only (4) A and B only

Solution

Ans. 3
Example
Which one of the following compounds will readily react with dilute NaOH?
(1) C6H5CH2OH (2) C2H5OH (3) (CH3)3COH (4) C6H5OH

Solution [JEE Main 2024]

Ans. 4
Solubility
Solubility

Higher is the interaction of solvent with solute, higher is the solubility of

solute.

Organic compounds containing 6 or more than 6 carbon atoms are

sparingly soluble in H2O and mainly soluble in organic solvents like
ether.

Generally, polar molecules are soluble in polar solvents, and non-polar

molecules are soluble in non-polar solvents.
Example
Which one of the following compounds will liberate CO2, when treated
with NaHCO3?
⊕ ⊝ ⊕⊝
(1) (CH3)3NHCl (2) (CH3)4NOH
O
(3) CH3 – C – NH2 (4) CH3NH2 [JEE Main 2021]

Solution

Ans. 1
 Electrophiles,
Nucleophiles
Leaving Groups and
Solvent
Electrophiles

Electron deficient species which have a tendency to accept electrons are

called electrophile (E+).

(i) Positively charged electrophile

⊕ ⊕ ⊕ ⊕ ⊕
R H X NO NO2
⊕ ⊕
Ph N=N R–C = O
Electrophiles

(ii) Neutral electrophile having vacant p or d orbital:

BF3, BH3 etc. (vacant p orbital)

AlCl3, SO3, PCl5, PCl3, SnCl4,
(vacant d orbital)
SOCl2, POCl3, FeCl3, ZnCl2 etc.

(iii) Neutral electrophile having complete octet

CO2, RCOCl, RCHO, RCOR, Br2, Cl2 etc.

Oxygen in H3O and nitrogen in NH4 are not electrophiles due to

complete octet.
Nucleophiles

Electron rich species which tend to share electrons are called

nucleophiles.

(i) Negatively charged nucleophile (ii) Neutral nucleophile

⊖ ⊖ ⊖ ⊖ •• •• •• ••
H OH OR CN H2 O R − OH R − O − R NH3
•• •• ••
•• •• ••
⊖ ⊖ ⊖ ⊖ ⊖
X R RCOO NH2 S H R − NH2 R3N Ph − OH
Nucleophiles

(iii) -electron donor: Alkene, alkyne, benzene etc.

(iv) R – MgX, LiAlH4 and NaBH4 behave as nucleophiles.

Ambident Nucleophile

Species having two nucleophilic sites, but only one site can donate lone
pair of electron at a time, are known as ambident nucleophile.

Example
− −
CN, ONO act as ambident nucleophile.

− −
In KCN, CN acts as ambident nucleophile whereas in AgCN, CN does not
act as ambident nucleophile.
 CN⊝

KCN AgCN

ionic covalent

K+  C  N Ag—C  N

Here, C and N both Here, only N acts

act as as
e– donating site e– donating site
 NO⊝2

KNO2 AgNO2

ionic covalent

O
K+ N Ag—O—N == O
O–

Here, N and O both Here, only N acts

act as as
e– donating site e– donating site
Leaving Group

Groups which get eliminated with a pair of e– (anion) or neutral

compounds are known as leaving groups.

Types of leaving group

Excellent leaving group

Good leaving group

Poor leaving group

Excellent Leaving Group

Compounds which leave as neutral molecules are generally excellent

leaving groups.

 H
R—O ⎯→ R+ + H2O
H Leaving group

 
R—CH2—N2 ⎯→ R—CH2 + N2
Leaving group

 H R+ + H — O — R’
R—O ⎯→
R’ R’+ + H — O — R
Leaving group
Good Leaving Group

Good leaving groups are those that become quite stable ions after they
leave because the leaving group generally leave as a negative ion.

Weaker bases are stable and hence are better leaving groups. Conjugate
bases of strong acids are good leaving groups.

Example
O

— —
—
–O –O — S — R’
X– — C — R’

—
—
—
X = Cl, Br, I O O
Poor Leaving Group

The conjugate bases of weaker acids (e.g. H–, H3C– alkyl anions) are
stronger bases and therefore, are poor leaving groups.

Example

—NH2 , —OH , —F Poor leaving group

Conversion of Poor Leaving Group into Good Leaving Group

O
R—OH + TsCl R—OTs Cl—S CH3 (TsCl)
O
Bad leaving Good leaving
group group

Mechanism

O O
–HCl
R—O Cl—S CH3 R—O—S CH3

O O
H
(R—OTs)
 Solvent

Non-polar Polar

Polar Protic Polar Aprotic

Non-polar Solvent

These solvents have an overall zero dipole moment.

They have low dielectric constant.

Neither cation nor anion is solvated.

Example

CCl4, CS2, Benzene, Toluene, etc.

Example
The correct pair(s) of the ambident nucleophiles is (are): [JEE Main 2021]
(A) AgCN/KCN (B) RCOOAg/RCOOK
(C) AgNO2/KNO2 (D) AgI/KI
(1) (B) and (C) only (2) (A) only
(3) (A) and (C) only (4) (B) only

Solution

Ans. 3
 Reaction
Intermediates
Reaction Intermediates

Reaction intermediates are formed during the reaction for short time
intervals and are unstable at room temperature.

They are the species of measurable stabilities formed during the

conversion of reactant into product.

They are formed by bond cleavage/fission.

Generation of Carbocation

Dissociation of compounds containing L.G.

 ⊝
—C—L.G —C + L.G
sp3

 
R—OH2 R + H2O

 
R—N2 R + N2 

By reaction of alkene/alkyne with electrophile

C== C + E C—C

E
Carbocation Rearrangement

Observed in those reactions in which carbocation is formed as an

intermediate.

Rearrangement always take place from less stable carbocation to more

stable carbocation in each and every step.

Rearrangement of carbocation takes place by,

⊖ ⊖
▪ 1,2- Hydride (H ) or Alkyl Shift (R )
▪ Ring Expansion
▪ Ring Contraction
1,2-Hydride (H⊖) or Alkyl Shift (R⊖)

H H
⊖
1,2- H shift
(1) H3C C CH2 H3C C CH2

CH3 CH3

 1,2–H shift  1,2–CH3 shift

(2) Me3C–CH2–CH2 Me3C–CH–CH3

CH3

H3C–C–CH2–CH3

 ⊖
1,2- H shift
(3)

(4) H3C—CH=CH No rearrangement

NOTE

Cunsaturated never rearranges.

(5) ⊖
1,2-CH3 shift
Example
Calculate a number of 1,2-shift to get the most stable carbocation:
Ph Ph

Solution

Ph Ph

Ans. 4,
Example
Find the most stable rearranged carbocation:

Solution

Ans. No rearrangement
Ring Expansion

If there is C next to a 4 or 5-membered ring, then ring expansion takes

place.

A 4-membered ring converts into a 5-membered ring, and a 5-

membered ring converts into a 6-membered ring.

Example

(1)
(2)

(3) 1,2–H shift Ring

Expansion

1,2–H shift
Ring Contraction

 
 NOTE

6 to 7-membered ring expansion takes place only when carbocation

gets stabilized via mesomeric effect after rearrangement.

OH 
OH
Example
Find the most stable rearranged carbocation:

Solution

Ans.
Example
Find the most stable rearranged carbocation:

OH

Solution

Ans. No rearrangement
Carbene
Types of Carbene
1. Singlet Empty -orbital

Non-bonding electrons pair

H
𝝈 Bond C
H

1 Two electrons are present in one orbital 6 Carbon is sp2 hybridized

2 One empty p-orbital is present 7 Experience more

repulsion
3 Two sigma bonds (𝝈) are present
8 𝟏 𝟏
Spin (s)  𝟐 − 𝟐 = 𝟎
4 Singlet carbene is diamagnetic
Total spin = 2 𝒔 +1
5 Singlet carbene acts as Lewis’s acid 2×0+1=1
Types of Carbene
2. Triplet
Non-bonding electrons

H
𝝈 Bond C
H

1 One electron is present in one orbital 6 Carbon is sp hybridized

2 Two unpaired electrons are present 7 Triplet carbene contains

less repulsion
3 Two sigma bonds (𝝈) are present
8 𝟏 𝟏
Spin (s)  + = 𝟏
𝟐 𝟐
4 Triplet carbene is paramagnetic
Total spin = 2 𝒔 +1
5 Triplet carbene acts as Lewis's acid 2×1+1=3
NOTE

In general triplet carbene is more stable than singlet carbene. Because

in singlet carbene there is more repulsion between two electrons present
in a single orbital.

Singlet carbene becomes stable if any back-bonding or resonance is

present in the system.

In the presence of a polar solvent, singlet carbene is stable, and in the

presence of a non-polar solvent, triplet carbene is stable.
Nitrene

Nitrene is electron-deficient. [neutral nitrogen-containing intermediates]

Types of Nitrene

1. Singlet 2. Triplet

Empty p-orbital Pure p-orbital

sp2
sp
R N Non-bonding electron R N

Triplet nitrene is more stable than singlet because of less repulsion.

 Example
[JEE Main -
Among the given organic compounds, the total number of aromatic 2024]
compounds is

(1) (2)

(3) : (4)

⊝
Solution

Ans. (3)
 Example
The correct sequence of acidic strength of the following aliphatic acids in
their decreasing order is:
CH3CH2COOH, CH3COOH, CH3CH2CH2COOH, HCOOH
(1) HCOOH > CH3COOH > CH3CH2COOH > CH3CH2CH2COOH
(2) HCOOH > CH3CH2CH2COOH > CH3CH2COOH > CH3COOH
(3) CH3CH2CH2COOH > CH3CH2COOH > CH3COOH > HCOOH
(4) CH3COOH > CH3CH2COOH > CH3CH2CH2COOH > HCOOH
[JEE Main 2024]
Solution

Ans. 1
 Example
The total number of aromatic compounds among the following compounds is
___. 
[JEE Main 2024]
, , , , ,
N

Solution

Ans. 1
 Example
Correct order of basic strength of Pyrrole , Pyridine and
N
H N
Piperidine is:
N
H
(1) Piperidine > Pyridine > Pyrrole (2) Pyrrole > Pyridine > Piperidine
(3) Pyridine > Piperidine > Pyrrole (4) Pyrrole > Piperidine >Pyridine

Solution [JEE Main 2024]

Ans. 1
 Example
The relative stability of the contributing structures is:
O O– O+
+ –
CH2=CH–C–H CH2–CH=C–H CH2–CH=C–H
(I) (II) (III)
(1) (I) > (III) > (II) (2) (I) > (II) > (III)
(3) (II) > (I) > (III) (4) (III) > (II) > (I) [JEE Main 2024]

Solution

Ans. 2
Example
How many compounds among the following compounds show inductive,
mesomeric as well as hyperconjugation effects? [JEE Main 2024]
OCH3

, O ,
NO2
,
, ,
Cl
NO2
CH3 COCH3
, ,
CH3
CH3
Solution
Ans. 4
 Example
Ionic reactions with organic compounds proceed through:
(A) Homolytic bond cleavage [JEE Main 2024]
(B) Heterolytic bond cleavage
(C) Free radical formation
(D) Primary free radical
(E) Secondary free radical
Choose the correct answer from the options given below:
(1) (A) only (2) (C) only
(3) (B) only (4) (D) and (E) only

Solution

Ans. 3
 Example
The correct stability order of the following resonance structures of
CH3 –CH = CH–CHO is: [JEE Main 2024]
–
O O
– 
CH3–CH–CH=C–H  CH3–CH–CH=C–H
I II
O
 CH3–CH=CH–C–H
III
(1) II > III > I (2) III > II > I (3) I > II > III (4) II > I > III

Solution

Ans. 2
 Example
With respect to the compounds I-V, choose the correct statement(s).
H [JEE (Advanced) 2020]
H

H
H–CH3 H H

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

(A) The acidity of compound I is due to delocalization in the conjugate base.
(B) The conjugate base of compound IV is aromatic.
(C) Compound II becomes more acidic, when it has a -NO2 substituent.
(D) The acidity of compounds follows the order I > IV > V > II > III.

Solution

Ans. (A,B,C)
 Example
Consider the following four compounds I, II, III, and IV.
H3C CH3
NH2 N
H3C CH3 O2N NO2 O2N NO2
NH2 N

NO2 NO2
(I) (II) (III) (IV)
Choose the correct statement(s). [JEE (Advanced) 2020]
(A) The order of basicity is II > I > III > IV.
(B) The magnitude of pKb difference between I and II is more than that
between III and IV.
(C) Resonance effect is more in III than in IV.
(D) Steric effect makes compound IV more basic than III.
Solution
Ans. (C,D)
 Example

The correct stability order for the following species is:

[JEE (Advanced) 2008]
  
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

Solution

Ans. (D)
 Example

The correct acidity order of the following is:

[JEE (Advanced) 2009]
OH OH COOH COOH

Cl CH3
(I) (II) (III) (IV)

(A) (III) > (IV) > (II) > (I) (B) (IV) > (III) > (I) > (II)
(C) (III) > (II) > (I) > (IV) (D) (II) > (III) > (IV) > (I)

Solution

Ans. (A)
 Example

The correct stability order of the following resonance structures is

⊕ Θ ⊕ Θ
(1) H2 C = N = N (II) H2 C – N = N
Θ ⊕ Θ ⊕
(III) H2 C– N = N (IV) H2 C– N = N
(A) (I) > (II) > (IV) > (III) (B) (I) > (III) > (II) > (IV)
(C) (II) > (I) > (III) > (IV) (D) (III) > (I) > (IV) > (II)

[JEE (Advanced) 2009]

Solution

Ans. (B)
 Example

Amongst the following, the total number of compounds soluble in aqueous

NaOH is: [JEE (Advanced) 2010]
H3C N CH3 COOH OCH2CH3 OH NO2
CH2OH

OH
CH2CH3 COOH
CH2CH3

H3C N CH3

Solution

Ans. (4)
 Example

Among the following compounds, the most acidic is [JEE (Advanced) 2011]
(A) p-nitrophenol (B) p-hydroxybenzoic acid
(C) o-hydroxybenzoic acid (D) p-toluic acid

Solution

Ans. (C)
 Example

The total number of contributing structures showing hyperconjugation

(involving C–H bonds) for the following carbocation is:
H3C  CH2CH3 [JEE (Advanced) 2011]

Solution

Ans. (6)
 Example

The carboxyl functional group (–COOH) is present in –

(1) picric acid (B) barbituric acid
(C) ascorbic acid (D) aspirin [JEE (Advanced) 2012]

Solution

Ans. (D)
 Example

Identify the binary mixtures (s) that can be separated into individual
compounds by differential extraction, as shown in the given scheme:
NaOH(aq)
Compound 1 + Compound 2
Binary mixture containing
Compound 1 and Compound 2
NaHCO3(aq)
Compound 1 + Compound 2

(A) C6H5OH and C6H5 COOH (B) C6H5COOH and C6H5CH2OH

(C) C6H5CH2OH and C6H5OH (D) C6H5CH2OH and C6H5CH2COOH
[JEE (Advanced) 2012]
Solution

Ans. (B,D)
 Example

Which of the following molecules, in pure form, is (are) unstable at room

temperature?
O O

(1) (2) (3) (4)

Solution [JEE (Advanced) 2012]

Ans. (B,C)
 Example

The compound that does NOT liberate CO2, on treatment with aqueous
sodium bicarbonate solution, is
(A) Benzoic acid (B) Benzenesulphonic acid
(C) Salicylic acid (D) Carbolic acid (phenol)
[JEE (Advanced) 2013]
Solution

Ans. (D)
 Example
The hyperconjugative stabilities of tert-butyl cation and 2-butene,
respectively, are due to
(A) s → p (empty) and s→p electron delocalisations
(B) s → s and s → p electron delocalisations
(C) s → p (filled) and s→p electron delocalisations
(D) p (filled)→ s and s→p electron delocalisations [JEE (Advanced) 2013]

Solution

Ans. (A)
 Example

Hydrogen bonding plays a central role in the following phenomena

(A) Ice floats in water
(B) Higher Lewis basicity of primary amines than tertiary amines in aqueous
solutions
(C) Formic acid is more acidic than acetic acid
(D) Dimerisation of acetic acid in benzene [JEE (Advanced) 2014]

Solution

Ans. (A,B,D)
 Example
The number of resonance structures for N is: [JEE (Advanced) 2015]
OH
NaOH Na

Solution

Ans. (9)
 Example

The order of basicity among the following compounds is:

NH NH2
N NH HN N
H3C NH2 H2N NH
I IV
II III
(A) II > I > IV > III (B) IV > II > III > I
(C) I > IV > III > II (D) IV > I > II > III
[JEE (Advanced) 2017]
Solution

Ans. (D)
 Example
Among the following, the number of aromatic compound (s) is:
⊝  

 ⊝

[JEE (Advanced) 2017]

Solution

Ans. (5)
 Example
The correct order of acid strength of the following carboxylic acids is:
O O O OH
H H OH MeO H3C
OH OH O
H
I II III IV
(A) I > III > II > IV (B) III > II > I > IV
(C) II > I > IV > III (D) I > II > III > IV

Solution [JEE (Advanced) 2019]

Ans. (D)
Thank
You!