ADHYAY Batch GOC & ISOMERISM LECTURE -4

structures the

of
ainenstabi l i t o
y f Resonating
⑪ will the in stated
follow
we rules
sequence
as

below
② That structure will
be which
donating change. I neutral more etable
has
thrged)
is more stable

③ That
whichreconating
the octetucture be more stable
will
autom is
compl e te
in than
of every
that
Octet
which
in

any if
atom has
i n compl e te
⑰ of
CH3 C -
-
-

↳- C5-c=
dr se-
↓
er [ be Yer et
↳incom slete octet
nee

④ That structure will be

resonating
more stable

is
in which
positive
the
change
on
electropolit
we element and
negative charge
on
is

electronegative
element than the
way
other
 carbon and oxygen
between
electronegativity in the
therefore
- of oxygen is more.

* stability o
I
8e

CH2 H -S CH2 c H
-
=
-c -

↓ S be err
Ye ger 2-

+
De 6e-
o -
08
⑰ I I
↳ H
CH2 H c
c CH2=
-
-
-

↓ ↓ ↓ 7 jee- e
get
-

se
6e
-

⑤
that onthe
ting
structure will be more stable

opposite changes are clos

than the
charges far apart
& like all

other.
ge
8e ↓
JEEADVANCED 0
-
3 ↓ ⑰ ⑦yer 1733274
IIT-2009
- ⑪ CH2 = M N =

re
+ 8e-
⑪-
~CH2 -N =

(ii)--N a. -
-
N -> ge
se
I
482-
⑰
(IV) CH2-M N
=

↓ ↓

wer
der se
 antiatomatic
Aromatic non-alomatic,
stability
-

structures
resonating
the
compare stability
~Otse of
I Il V

⑪
[ :
[↳
8e
17
[
17
- -

I
- I -
8e-
⑰ ⑦ I
i0
=
⑰ Y -
o
o
-

=
N -
8 -

o ↓ -
ger
Benzenoid Q
⑭
② &
CH2= CH-CH=CH-0-413

②CH2-CH = CH-CH=8-CH3

i-em=cH-E-o-cy
③

④ ⑰
CHI-CH=CH-CH-0-C3
⑦ .

⑤ ⑦
CH2-4-cH= CH-0-113

↑
CH5-CH2NH2
x

Effect on bond
length! CH2=CH-NH2
-

-j
I
⑦ ⑰
CH2-4 NH2=

In X-resonance. There x<Y

meomeric
effect!
-
(Resonance)

If
-
I /

↓having pai
lone

is
pushing electrons towards carton
y
x the

chain then we
say
that it is
showing + R(+M)
effect.

eg.-nitz-int(-xike
- -

(-tR
E
(oderof+in effect)
FI

E Bi- Corbital
-

cp-2PO
>- i 7
3p 2p
-
/
-

4p 24
-

5p -

2p
overlapping)
1 I A -
4t3
C
-

13 3
-

-
NH-C -
-
N-

- 13
-

10r
Il
>
-

-
o- R - - c- R.

wat
Ex-
 A Ar
x=

I
a

group pulls
thithere
a
chain then
we
say
itis
applying effect
O

·
O 7 - NY-cEN, in
eg
-c-H,
-
-

-0
->
- 0 Is
4-o-,
0
-4 -
R) Il
-c- o-4-R) -

l
Il
-
- - ECH) -

(+ M/-M)
only
operates at
* in
effect
I
&
Si
~
- meta
otho &
pala positions butnot on

substituted
position in benzene
G

compounds/ins.
ho
I ~artho-

I Imita
-

O
m 4 metal
[
P I.
-
-

I
pala

m
 Resonance)
mescomyon: (No band

*Uz
My-ks"
&

-ca
C
⑭ "...
3 I
3 ⑰

- Us- C3-CH-42
> #
-

⑰
S
CH5-CH2 (TV)
>

[I 7 (I)

[stability
order!I)I>ILIV.
according
to
-I
effect
actual order:-IVLI> > I

of hyperconjugation:
cass

Onegation
of charge:
the

i ⑰ H H
. C =Uz
-
H - -
CH - >

H
n
↓
0 ↓
carbocation

↳-carbon -H
-
-
should be

we have
(there
spe hybridized
3 c-H)
has
hyperconjugative
this
callocation a structures
 andare
C3 ⑰

⑦0
I
- -
Utz CJCH
-

Mz
↓ 0 C
ACHIC
u callocation I-carbon ↓
<-canton ↓x-casors
x1 1 =

x -
H2
=
x-
n 3
=

a -
0
=

be the
ter
of greates
0
* no
the 2-4 will
-
- qua
King
state
In
*
callocation the
electron tramfestakes
come
of
place from sc-H
p-arbital.
empty
to

②
pecoryigation
radicals
of fue
in care

dis· ⑳

-
HH*
↳
C CHe
cicovalent
hypucojugation
↑- C -

CH2 n =

n' ↳
f ladical

↳X-carbon
-
-
2-H
should be
sp hybridized.
of be the
Gates the will
greater stability.
*
no cut

radical
of you stablity
order.
13 413 -

E CH3 CH [4-ite[3-He
⑳°
E

C C
C2
- - -
-

des
War En
u

0
= = 1 = 2
= 3
=
 P I
12 So
C-
4-4
- UB
a
I canof enter
peladicals,the molecular orbital
deckcal
take
on
* the

↳single occupied
③
hyperconjugation calbanions
in call
of
have vacant
since do not
cabanious
partitale
why they undergo hyperconjugation.
that's do not

us-a -> X.

④nation
of
in can alkenes -

O H I
↳"L C C
O
-H 3 <H
④In alkenes transfer of
the

A / I
place from
-

e-takes
↳
0 xc-n
-
H
n↓

P
= C
bonds ** C C.
of
=

to
/ I
C
2 -

34 sp3 3 ↑ i
I n H
C ⑦-
-

H -

-
-

-
H

-
-
-
 ④
no.
of
- creater the be the
greater
X

stability
all will

of
alkenes-
nox
↓
U12 CH2
=

E CH-CH= CH2 CH5C=CH-CH3

H
↓ i
↓
3a ↓ at
2 6xH
C =C
H
on

X - X

9
-
Cz-CH= CH-43 CHI-CHI CH2
CH=

a 62H ⑪ ② 201

13
* CH3 - 42 =

-H
-

>>
stability
Sobutene
* is more stable than trans-abutene &

is 2-butene

structures
identical
Thisis due to
hypercojugative
 combustion: (HOC) It
of
Heat is the released when
-

drocarbon is quent in
energy
imol of of oxygen.
excess

noc-1-
hoy
HO2a carson
atom
stability of
alkene

I E
/
0
-
en
-
S --
a

trans z-butene 1-butene

isobutene
62H 2x11
6xH

H H
- Resonance
*
is man dominant

[ B [ I hyperconjugation.
that
>
I
-

I H -C I

4x4
-
I -M
↑

*Resonance is
always more effective than

hyperconjugation
-

-
X with resonance alkene man
is stable

compared unconngatlove)
as to

resonance
 (HOM)
hydrogenation!
It is heat releand
energy
androgenated
when mole
Iam
one
-

hydrocason
Hon x
alkene
stability of
bonds.
9:
2D<I]
-
-

-
L
2 4 G
/
&->
[I [I [↳
↑

I I
-
L
⑳ ③
an , Yar

HOH ③ >0z

27073
statility
order=
-
 effect;
Americ
(temporary effact)
-

demand)
If di -on
E I
day 7
-
I in

Lunched sile-nucleus
loving
Polarization Bonds bonds) due
of
the
incoming
to

reagent (nucleophile
or
Electrophile) is called
<electron loving)
ne

Electromeric
effect.