www.padhle.in @padhle.

in

Organic
Chemistry
CH 12 Chemistry | Class 11
Notes + 10 Years Integrated PYQ's
www.padhle.in @padhle.in

adhle.in
Thank you for using www.padhle.in.

We here at Padhle, make sure that

every piece of material reaches you

without diving deep into the tabs of

your browser. These notes have

been downloaded without

compulsorily signing up, or

submitting your personal details.

Enjoy yourselves!

To help us in maintainig this, you can contribute to

Padhle. Even a small amount can do wonders.

Contribute to UPI ID - padhle@paytm

www.padhle.in @padhle.in

adhle.in

You can contribute a little to our

efforts. Even a small amount can do

wonders.

Scan the Code in any UPI App

OR
Contribute to UPI ID -
padhle@paytm

Now... Padhle!
 # General Organic chemistry : -

Those compounds which obtained

→ are
from
living source .

Organic Compounds mainly hydrocarbons and

→ are

its derivative
ele containing oxygen Nitrogen sulphur
, , ,

phosphorus
Eg : Cally Calla , Catto CHSOH
-

, ,

of
# Nomenclature
Organic compounds
Prefix t word Root t Suffix
J
L L T

secondary Primary Primary Secondary

Tycho
te te te

substituent ane l I
-

functional
te ( when ene L group
OR sing
is
yneC ex : on
-
-

-
R
p
present CoD
-
Br
-

I
He WORD ROOT : -

Number carbon atoms

of Name

2 meth
2 eth
3
poop
4 But
5
pent
6 Hex
7 Kept
8 Oct
g non
10 Dec
11 Undeca
12 Dodeca
13 Toi deca
ly Tetradeca
 # HYDROCARBON
× .

Saturated unsaturated
Cc -
c ) ← is
Alkane CED CED
Alkene Alkyne
General Cn Hantz
Formula Cn Han Corman -

( cuz Chs) ( Cns ) ( cus D

Tg :
gene
⇐e
- -
-
-
-

minus
>

# Alkane ten) Alkyl

CHS H H
ctbcmethyl)
I
- -

CHS -
Clb
-

H CHACHI ethyl)

OR ( Alkoxy) -
04115 ( Etuoxy)
Cep
more examples : .

Ochs (
methoxy)
-

Chacha CHS ( propyl)

 It IUPAC NAMING
.

RULES : .

⑦ chain Rule :
Longest -

Numbering
should
longest
be done on the
chain
!y
on

, pi

Eg Hsc
: -
-
c -

c -

c -

cus
'
C) n ch h ,
(5)
② ④
g,
such that branched
Numbering
atoms
in a
way
carbon
numbers .
get the lowest
possible

( Rules)
Naming
(9) 1St letter capital
Ex -

5- Bromo -

Decane

(b) There should be G) dash each member

after

:b
,Br

I:c:
Y ,H it

÷
③ equivalent
If the
then
substituents are

is
found in
to
position lower no -

given
the
first order
one
coming in
alphabetical .

! . . - -
Z - -
E . -
Y
.
. -
E . -
E - -
I - -
I .

Eye
.

E:
¥1 EI
'

'

:
-

4 3-
Ethyl G
methyl octane
-
-

( Priority order) : .

Functional
Group > =
> more side chain

ooo ,
functional
1
OH acquires lowest
position group
3 31 4

Eye 9
C
f
.
-
-
-

c -

C C 5
a-
Ethyl -
u -

methyl Hexane
l l
-
3- of
C CG
Functional
-

Group
structure
suffix prefix
Alcohol of
Hydroxy
-
OH -

0
11

Aldehyde -

C -

OH -

al formyl or oxo
O
11
Ketone -
e -

O -

one -

oxo

Nitrile cent nitrile

cyano
-
-

Ether R o
R alkoxy
-
-
-

O
11

oil acid
Carboxylic -
c -

OH -

carboxy
acid
O
11
Ester R OR oat
e
alkoxy
- -
-

o
11 carbonyl
Halide
Acyl C K
Oyl chloride halo carbonyl
- -
-
-

( f. d. Brit ) Cx - U )
Amines -

Hua , - WH ,
-

Ni , amine - amino
ol -
N)
"

Amides -
c -

Hua amide -

carbomoyl
Sulphuric acid -

som sulphuric acid sulphur

% no
Acid Oic
anhydride
- -
c -

O -
c - -

anhydride
# Rule : -

Tf functional group
has carbon . Then

during numbering position given to

is
-
2

And
functional group .

if functional group
does have not carbon then lowest
to that
possible number is
given
functional group
.

3 2

I or
Eye Chs
fu CHS 2-
methylpnpanacid
- -
- - -

Coon
2

functional
#
Priority order
of Group : -

f- )
1 . Coon %
§
o
2- soot - -

3 C CO

)
.
o

cook
%-)
y .

5- cod o -

E
6 comma →
f- NH
)
-
.

7 . -
CEN
8 -

CHO
B
g -
e -

10 -

OH
11 -

NHA
# Bond line Notation : .

Clc , Cyd →
can be

represented as

It cyclic compounds
:3 y 3 2 I

CH z -
Cha -
CH -

CH z

y
2 I

2-
Cyclo propyl -
Butane

get
Eg
: -

21
cuz -
cu -

CHS
21 ( gmportant Note :-)
Is →
Naming is substituents

\ / are done
by
3
"
-

y
using ( x
)
( methyl ethyl) cyclopentane
'
2- s -
# Benzene Naming
-

Prefix t word root t

suffix
Lls dis
sub .
Cyclo ane function
ene

yne
group
Sub t
Benzene +
functional Group

§§
"
G ' -

acid
Benzene i
carboxylic
-
-

Note : -

→ can be
represented as

Gpnpehny?
sing
can
Eg :
"

• -

3 -

hydroxy Benzene -
I -

Carboxylic
acid
Roy
5

y
# Bicycle compounds : -

1- Naming
Bicycle Ex ,y ,
word root
v f
carbon
Bridgehead
us no .

of c in
bigger ring ( except bridge
Head carbon )
tabanid :D
smaller
g in
ring
e
y
- no .

2 → no .

of carbon in
bridge
Eg : .

Bicycle ( 4. 2. 2) no name

Rule : Identify the bridge Head carbon and

-

head carbon
begin numbering at
bridge one

to and
and then
follow
head
the
longer
Then
path
bridge
2nd
carbon continue
.

numbering
longest path
numbered .
until all atoms are
# Spin compounds
: -

↳ ( Bicycle )
compound having
2 Carbon common

G II fogodewqognjgmben.gg
: -

↳ common
carbon
Spinola ,y ] word soot

→
Numbering of ring starts in the small

ring next to ring Junction ,

passed around
this
ring
and
through the
ring junction
into the
longer sing .

2
Spin [ 3. 4) octane

(common)
 enteral Organic Chemistry
BOND CLEAVAGE : -

formation
Organic reaction
intermediate .
takes
place through of
reactive

These intermediates formed due to covalent

'

bonds .
are
cleavage of
These intermediates are : -

I .
Carbocation ( CHP ) ( Spr)
2 . Carbo anion ( CH -0 ) ( Sps)
,

3 .
Free radical ( CHS)

# HOMO LYTIC BOND CLEAVAGE : -

X
H -
H → 2H°
Free Radical
# HETERO LYTIC BOND CLEAVAGE : -

A -43 → Att BO

cation Atnion

# Electronic Displacement Effect : -

1 .
Inductive Effect
2.
Pyesonance or Mesmeric Effect
3.

Hyper conjugation
H .
Electro mesic Effect

INDUCTIVE EFFECT : -

Permanent of chain
polarisation caused
by displacement 6 electron
along carbon is

known as Inductive Effect

.
→ CHARACTERISTICS OF INDUCTIVE
i' EFFECT: -

I It effect
. is a
permanent .

It difference of
2 .
arises due to
electronegativity .

It bond depended effect , with distance

3 .

operates through 6 . It is a distance decreases .

→ TYPES OF INDUCTIVE EFFECT : -

(a) TI Effect (b) -

I Effect

( INDUCTIVE EFFECT )
(a) TI EFFECT : -

These due to of
are
presence electron
releasing groups .

B
c- -
c-
k

→
Following group shows TI Effect

-702
1. .
Anionic species

alkyl groups
.
All

3 .

Isotopes of
Hydrogen f -
H, -
D, -
T
)
Groups
'
4 .
or atom having Electronegative less than Sp carbon .

→ Metals not considered

:
-8 f c
are

Nato
ionic bond

→ Como arison of +I 1 Effect : -

1. TI effect of anionic
groups
is
greater than neutral
groups .

CHIT -

CHS

2. TIX no . of branded alkyl chains .

Cuz CH3
d
CHF dl CH , cuz > ( Hz CHIH's
- -
- -
- -

l
( Hz H

3 .
If branches are same then TIX no . of c- atoms .

C. Hz
Clb
l l
-

l
C -

CHzf -

C -

CH, -
( Hz
l
H H
 TI effect ?
cuz
¥13 I
-
C
l
-

CHS ) -
C
l
-

GH
-

CHS
(
Hz H 413

+I
effects 1-

Electronegativity
of
key element
1 CHI > -0
NH > o_0 > di o_0
examples →
-
- -
- -
.

( Hz
CHS H
I l l

2 I cuz > CHS

-

C
> C
Gt3
-
- -

l l
l
CHS H H

B .
70137 -
T > -

D> -

# -

I Effect : -

Tinese due to electron

are
withdrawing group .

IEEE
S > Sz > Ss >
,
Sy

Groups showing - I
⑦
effect : -

f) Caloric
group e.g
.
-

HRs
(2) of
IL
Electronegativity key element
-

I Effect : -

1 . F > U > Br > I

2 .
-

M¥37 -

Hoz > -

MHz
3 .
-

OH > -

OR ( in basic medium
)
# CARBOCATION
4113
stability
Ctb
: -

cuz
d d
Hsc C CH
) H kHz
>H H
-
- - - - -

⑦ ⑤ ⑤
O O

5 2 I
"
÷% > :*> ion .
n . "

5 I I
O O
"
c'
'
1 . C -

C → → O_O 2 . C -

C -

C -
O_O
In l

F U

⑤ 72

Because Ftounne is
,
more
Electronegative than

U .

6 ②
£
exit c c →
'
c' o_0
f.
→ -

K
U

② < ②

)
# t I Effect → Stabilise cation
-

I Effect → Stabilise Anton

# APPLICATION OF INDUCTIVE EFFECT : -

ACIDITY ) BASICITY
-0
HD # H⑤t A

the acid
More stable the anion ,
stronger
-

I Effect in
acidity 9 ( Anion Stabilised )
)
,

I Effect T
acidity t ( Anion Destabilise
+
, ,

Eon E' on> Eon

c-
§ > g- c-
g
c
-
-
-

L 2 3

I > ②> 3

Anion Stability
OH
PH
& TI
PH
Effect

'
no
> > in:::÷e* is not
.

applicable at

,
Rz 1h10, Meta
position

(a) (b) d)

#
Stability : -

I
cuz "

> d ,
Hsc C Ctb H CH
)
- -

H
f CHS
-
-

- -

l l
C C Cto
⑤ ⑤
#
f -
in -

cur
! -

o_0 2

CH
,
-

CH
,
-
I
'
-
O_O 2

U -

cur ! -
o_0 3

17372

#
Electronegativity : -

EN sp3LSp2LSp(%ST)
Ph >
CICHY CH=CHa > Cha Ctb
f- )
-
- -
- -

Effect
¥4.2
E'
¥ ¥ ¥ .

ft effect
Electronegative ⑤
-

Cha > F
- Cst > p
St

st
-

NO, > f
-

riots > -

I÷oHC -

Coo 'D
 → electronegativity
ENI
NLC
Csp)

# EN of N is less than Sp hybridise d carbon .

# ISOTOPIC EFFECT : -

I.
Effect
depend on distance ( Bond length)
> CDs)
+ I
effect CB (
Hg
- -
-

Bond
Strength : .

C -

T > c- D
> C- H

Bond
length : -

C TLC
-
-

DLC H -

#
Compare the
Stability : -

CTS CB
> Dsc -

CDs
> Hsc -

Hs
# Compare Acidic
Strength on
.

MHz
- - -

H CEC
-

Hac -_
CH
q
H T T
MHz H -

CEC -

H Hao Hac #
CHA
I 2 3
4
( Hz -

CHI
it
( Hz -

CHS
5

Anton
→ Determined
by stability of : -

3 7 27 I 7 4 75

#
Resonance : -

when all a
properties of compound
cannot
structure
be
then
explain
it is single
by represented
two or more structures and this by ,

phenomena is
""
known as
Resonance
and these structures are known as
Resonating
structure canonical structure ( )
These structures not real
they
are ,

are
hypothetical .
 Real Structure
of a
Compound B
called
.
Resonating hybrid .

* :

-
Resonating structure tfsoifyanbnd
88 f) 888¥ :÷:i:{ d.e.ion.sa.io
bond
.

of A

O
.

# Condition for Resonance : -

Planarity
1 .

compound should be planes .

 ' '
' '

Sp Sp sp sp
( planes )
Eg Cha CH CHIH
: -
-_ -

,
'

¥7 Sp2
' '

sp sp Sp
( non planes)
.

CHE CH -

CHA -
CH =
Cha -

Is Resonance not exist

2-
Conjugation
should be
present
-

should
conjugated system be
present
.

→
conjugated system
d) C -
C -
C =
C
ca ) = -

(3) = -

t
Cy ) = -

vacant orbital
(5) = -
E

&) = -
.
o
→
f- see radical
⑦ = -
# → lone
pair
G) t -
. -

1. T it
conjugation G-0
- -

Mac
A
=C
A
-

C -1112 G Hae -

CHEH -

Chato
4 In
2. → a- -
t
conjugation G- -

to )
→ to ⑦
112C CH C Ha →
= -

CHA -

CH =
Cha

3 .
a- -

free Radical
Hain Hai -

cH=eHa

4 . A -

lone pair conjugation

Hic en Fini Ha I Hai -

CH =
a

A ⑦ ve
charge conjugation
5 .
-

A CA -0 -0
Hac = CH -
C Ha → Hac -
CH = CH z

6 .
A -

Vacant orbital
⑦
Hac ECHT CBH a ←s Hac -

CH a BHP
tone
charge conjugation
7 lone
pair -

CH -

O cuz I CH 2=0+0 CHS -

⑦ ve
charge conjugation
① ve
charge
8. -

CHI -

PHI → CHE PHS

 for
# Rules Drawing Resonating structure : -

from lower
1- Electron moves
higher electron
density to

electron
density
A f⑦ -0
( Ha = HC -

Cha → Cha -

CH =
Cuz

If electron from
electron
density to is same than moves
2 .

elements
less
electronegative more
electronegative .

CHETNIK CHI
-

cH=HC -
O

structures
3. No .
of
unpaired electrons in all
resonating
must be same

as
CHE CH - C. Hat> c.Ha -

CH =
Cha

converted
4. lone
pair can be into bond
pair and
vice versa

Cutch -fiina←> CHE -

CH =
Ha

t
I i
eg
-

: -
 # Mesmeric Effect :( it effect)
Permanent polarisation caused donation
by
or

electron
withdrawn
of A
from a
conjugated system
-

is known Mesmeric
by an
group
as
effect
.

→ characteristics
of
Mesmeric effect
It It due
1 is a
permanent effect anise
.
.

orbitals
to overlapping .

electron
Operates only
2. on IT -

3 .

Does not
depend on distance .

→
Types of Mesmeric Effect : .

② tm
effect Ith ② -

M
effect 1- R
electron electron
when
releasing group
when
withdrawing
present or electron
donating groups
are
present
group present .
Condition : -

Condition Presence
of lone (a) Presence vacant orbital
of
: .

pair or C- ve) charge at (b) Presence

of multiple bond

key element
of group/ with more
electronegative
first element second atom
of group
.
.

A fin
Ctm ) AN C -
M)
.
 Mesmeric effect In Benzene :
g
exo
Qc H
G pH
: -

ft
µ tf effect
TM effect -
M

x
x
# tm
effect
-

m
effect
anionic

q .g ?knege . uega.c.ny.pg .yp,q

→ t m
effect of
→ m
effect of
cation species
-

species is
greater
than is
greater
than neutral
neutral L
electronegativity m
effect
.
→ -

→ It depends on
types → Jima
zyaada electronegative
of overlapping
element electron
ulna
zyaada

µq÷, ←

go
,

OH > -

# Note : ② -

All anionic
species do not
shows tm
effect .

Bfg
-

-
b -

F
4- - f Not
×
possible
2 All cationic species do not shows -

effect
fun
.
t

t.FR
-
× ×
,
 # AROMATICITY
Aromatic Compounds : -

Those compounds which Hackel 's rule

follows .

# Hackel 's Rule : .

All cyclic planes completely conjugated

( Unt 2) IT electrons shows
compounds
extra having is known
stability
some which as

Aromaticity
Conditions
for Aromaticity : -

⑨ Compound should be
cycle .

(b) Compound should be

planes Gp2 hybridise)
E) Complete
(d) Presence conjugation
( ant 2) electron
where
of it

Lot , GA 10T
,
n =
O , 2,2 ,
- .

,
→ , ,

# Total
( 4nt2)
no .

and
of a electrons
should
must be
equal
n be
integer
-

A- e 6

{they )
=

'
diamagnetic
Intf
are

n
 stability order

Aromatic > Non -

Aromatic > Anti -

Aromatic

Aromatic compounds are stable and

in nature
dimagnetic
# Anti -

Aromatic compounds : -

All planes completely conjugated

cyclic which (4) IT
compounds are
having known
stability
electrons extrashows are un

as Anti -
Aromatic Compounds
# Conditions
for Anti
Aromaticity :
-

1-
Cyclic
2. Planner
3
Conjugated system Egg
-
.

Can )e ⑦
4 n
integer
-

,
.

s .

Paramagnetic →
cyclic
→

→
Conjugated I
Une
-

,
n
-
-
.

( Anti Aromatic
)
-

compound
 #
than
tmwhy Aromatic compound is more
Anti Aromatic compound ?
-
stable

Anse .
-
when we take a look at molecular
Aromatic compound
orbital
diagram of all
electrons are present in
Bonding molecular
molecular orbitals
orbital
bonding
or non -
.

And all electrons are

paired .
But, in case
Anti Aromatic
compounds
electrons
of
-

are
present
Anti
non -

bonding
molecular
molecular orbitals
orbitals
Bonding unpaired
or -

are
( )
electrons
That's
are
aromatic
.

paramagnetic
compounds
.

why more
are

stable .

Non -
Aromatic Compounds E-

Compounds which are neither Aromatic

nor Anti -

Aromatic .

Eggs SPI
}
'
,

"
{ Non -
Aromatic
compound
LSP
{ Anti
-

}
ca,
-

Aromatic

{ }
+

③ Aromatic
+
 +

④
{ Aromatic
}
# Quasi Aromatic
compounds : -

Polar Aromatic
Compounds are known as

Quasi Aromatic
compounds
o
-
.

It
eye
.

← T
( Aromatic)
( ate )
①
cyclic
→

→ Planer
→
conjugated system
# Dipole moment increases in ②

( JEE MAINI TEE ADVANCE )

Anti Aromatic
concept : when
compound
-
-

healed
general ) they undergo
are in
dime negation ( not
always
eye →
÷

→
i.

(Anti -
Aromatic) (Non -
Aromatic )
 # RESONANCE ENERGY
→ more stable the
compound more

greater will be the

Resonance energy .

1.
Resonance Energy
Aromatic > Non -
Aromatic > Anti Aromatic -

ego M
.

(
stability)
N

H
2.
Compounds Equivalent
having will have
resonating
structure
greater
Resonance
A
Energy .

o
E '
R -

c ← R -

to -

Xo
( Equivalent Resonating structure
 Extended
Simple >
(
stability)
> cross

conjugation
rag
-

↳ 0

G times) ( 3 times)

# JEE HAINS /ADVANCE

#= of
Heat
Hydrogenation : -

It is heat released when mole

of
a one

compound reacts with

hydrogen gas .

HOH X bond
no .

of A

Ystability
of compound
HOH L
4

÷÷:÷)
per a- bond

.. %,
# Conjugated bonda are more stable
than isolated .
# Heat
of combustion (Hoc) : -

It is heat released when mole

a one
combusted I burned to
of
compound is
completely
give
& Hao
Co2 .

Hoc L C atom
of
no .

Hoc L Y stability of compound

Stability
' '
d
nd
p
of compound
# HYPERON JUGATE ON
Hyper conjugation is a
general stabilising
interaction It involves de localisation
of
.

r electrons
of C H bond
of an
alkyl group
-

directly attached to an atom

of
unsaturated
unshared
to atom with
system or an an

p orbital The electrons C H bond

ofr
of
-
.

the
alkyl group enter into
with the attached
partial
unsaturated
conjugation with the unshared orbital
system or
p .

Is
Hyper conjugation a
permanent effect .
# Types of Hyper
conjugation
: -

+ HE L
shown
by C H, C- D. CT
- - -

CTS CDs EH,

I l l
CB -

C t CDs -

Ct Hsc -
C t

l l l
Ctg CDs CHS

Cl ) H) CHD
Note bond
: -

th
effect me
johoke sabse weak
hota hat Wo break et ko
stabilise
Karya .

effect : shown
halogen
H A-
by
-
-

fu e
Halogen
-
-

→ I → t

CHF I CHF U
g
C
q
- -
←s C -
-

U U

⑦ 'd
→ cha -
c=c
\
I
# Electromesic Effect CE effect) : -

It is a
effect bond
temporarymultiple It .
is shown
by
compound having
in
presence
of an
attacking agent only .

It complete transfer
is
shared
defined as

electrons to
of the pair of
A -

one
of
presence
attacking
atoms In
.

of .

(2) t E Effect : -

In this effect electron multiple bond

A-
of
are
transferred to that atom to which

reagent getesahtffahufadng agent

I cf c -

② E Effect In this
type electron
of
:
- -

A-
bond
transferred
to that
of multiple are

atom to which does

not attached
attacking agent
attacking agent
.

→
K -

if
CN
 # JEE MAIN & ADV .

( Acid -
base Trends )
The Weaker The Conjugate Base, The Stronger The Acid. So Any Factor
Which Stabilizes The Conjugate Base Will Increase Acidity
An acid base reaction involves the donation of a proton (H+) from an acid to a base. The four actors in
every acid base reaction are:
The species which loses H+ is the acid
The species which gains H+ is the base
The conjugate base is what becomes of the acid after it loses H+
The conjugate acid is what becomes of the base after it gains H+
All else being equal, charged species are more unstable than neutral species. Since an acid is
becoming more negative upon loss of a proton, the stability of the new lone pair on the conjugate base
is a key factor in determining how favorable the reaction will be.

Acidity Trend #1: Charge

All else being equal, the lower the charge density, the more stable a species is. So stability increases as
we go from O(2-) to HO(-) to H2O. This is demonstrated in the acidity/basicity trends of water and related
species, shown here. H3O(+) is the most acidic (most stable conjugate base); HO(-) is the least acidic
(least stable conjugate base).

? tous
-

:
:: s te in
Hessen stability )
charge)
a

H -

Etty t
H2O :
y
'
tezot tea most stable
( weakest Base)

cstrougesata.dz
 Acidity Trend #2: The More “Polarizable” The Atom, The Better It Is Able To
Stabilize Negative Charge
High charge densities tend to be less stable than low charge densities. The more “spread out” a
charge can be, the more stable it will be. So as we go down the periodic table from F(-) to I(-), notice
that the magnitude of the negative charge doesn’t change, but the volume that it occupies does.
Iodide ion, being considerably larger than fluoride ion (206 pm vs. 119 pm) is more stable, which
means that H-I is a stronger acid than H-F.

table
greater polarizability
stab uses
down the
periodic negative change
going
, .

if :3 .ee?s:i.3ic:EiocmosEaue ,
:

strongest HI > te Bo > Hcl > Hf

-

acid

Acidity Trend #3: Electron Withdrawing Groups Stabilize Negative Charge

The last post described how stability of a negative charge increases with increasing electronegativity of
the atom. Adding electron withdrawing groups to an atom can have the a similar effect to that of
increasing electronegativity. For example, in the molecule below, the stabilization of the negative charge
increases with every hydrogen that is substituted for chorine.

is
negative change by adjacent
stabbed
withdrawing groups
electron

( Inductive Effect
)

¥ -7g Ig
'

H - :O L U -

Lce ? L U - ? ( MOST STABLE)

,
Acidity Trend #4: Resonance Stabilizes Negative Charge By Spreading It Out
Over A Greater Area 
Resonance is another means by which negative charge can be dispersed in a molecule. If the
conjugate base has a charge which can interact with adjacent double bonds or p orbitals, its stability will
increase. This leads to increased acidity of the conjugate acid.

is stabbed
C-We
by
delocalize
change changes
resonance which
,

. .
o
K
RE . -

o
L
-
stabbed
by
resonance

Acidity Trend #5: The Greater The s-Character Of The Hybrid Orbital The More
Stable The Negative Charge
Increasing the “s-character” of an orbital has a similar effect as that of increasing electronegativity and
adding electron withdrawing groups; it brings the negative charge closer to the positively charged
nucleus, which , according to Coulomb’s Law, is a favorable interaction. So as we go from sp3 (alkane)
to sp2 (alkene) to sp (alkyne) hybridization, the stability of the negative charge increases. So alkynes
are remarkably acidic compared to alkanes.

is stabbed includes
change hybridization
C-We as the

S orbitals .

"

chafing
C L te ?

eye
-

x x
X

's spa sp
Sp ( MOST STABLE)
A Special Case: Aromaticity
A special case is that of aromaticity – usually dealt with in the first few weeks of second-semester
organic chemistry – which is a special type of stability exhibited by some conjugated molecules.
Without going into details, I’ll just say that if the conjugate base is aromatic, this will lead to a
tremendous increase in acidity relative to similar (but non-aromatic) molecules.

special case
,
C-We is
charge
electrons
especially if the part of
stable are an

aromatic
system .

KEI *

(Taste of PY )
✓
Because compound is
the not
planer .

%%→ SPB
carbon
H

H
 ✓

✓ r

Anti -
Aromatic compounds
has Cent electrons