ADHYAY Batch ISOMERISM LECTURE -3

Geometrical Isomerism (steronomeri)

-n e e men

Geometrical
* arises
isomerism when there is

a restricted rotation around two atom bonded

(In X-Bond).
covalently. general around

rotationsBoard
Restricted e

-6
a Y
a
↳ X -9 -
C I
= C
- C C
=

6/ 76 they are 6/ -a
-
-

The rotation aboutthe

T-Bond not
is
possible.
structural
having
so then
two molecules same

arrangement of different
atoms
formula
the
but is

in 3-D ssall.

9 a -not
identical
%
G.I.
W I =C

A
-
- -
c C a
=

/ -a
6
- identical
#-

-
cc -
L
=

-a
a
 isomers notthe
mirror
There two
images
are

each other there

of
& isomers are called
Diastereomers.

② rotation due to
-u
Ch
Ring
a
a

they
I
X
-

l
6
e
6
-

E O

9 6

I E I
a a
6 X
9

I 6
I
6
③ due stelic hinderne!-
Reention to

-(3)(B,By)y3 towding.
EX 4--

Et))de) It
inderence (refrulsion)
↓

hinderence
Bu -nosteric

Al CH3

E
I
-
3
L
-

I /
C
I
C
-

-1,11111111"
C=C
-

-t It

(
i -,
a R

B5
Bu rotation
Et restricted
-
,43 A X I
-- ⑤
3
L
-

-
Let
1/7
I /
C A I C -

-1,11111111"
C=C /
-

i -, CH3
a R
 ⑳ G. IX.

C3 F
3 u - /
/ C

us
-

-
un
- C

F
---

CH3
7 -
F
-
--
rical
--
↳den
I

C = c
-
un s U

for
a
compound show
to G1. 976.

-
H 13
- -
Mi , 7
C

un
C I

u
-
H C
--
hi 1z
12

a.
=

trans But-zene is- But-zene

I

li= 12 no
then be obeseved.
If
* G.I will

& lifts G.I will be observed.

if then
 CIS-Trans Isomerism

a= -CHS c =C
-413
-H
trans is
- -

-
-

trans-But-zene g
↳-But-zene

is-form -thesameatomsde group of the

at

atoms
transform The same as
group of atoms
-

als on
opposite
the side.

E-Uz(up) * u-up(above)
[3E *
CH3(up)
[↳" 43- down

is-form transfer
 wheather these
1:write given compound
down an trans or is.

H
⑧
H
②
-

[] oin
- -

①[Y
-
is
I
-
-n H

trans
1 i
③
⑭
[3
is
is I I
n
-
H

in trans A
⑥
⑤
[it - -- in
- H

④
F
0
F is
⑱
0 ⑧
L
0 ↑
-
-
trans
-
N -

⑲
↳13
113 u
⑨ ⑩ ↳
W
-

i
0 u
-

↑ is -
0 Hans
-
⑭
F CH3

- -
I - 13
⑪ ⑫
[3

OO
⑬ ⑭
- -

⑮ ⑯
E
-
-

0
17 ⑩
- -

Et
⑳
IXXE
⑲
is
For
④
I
 -
nomenclature: ↑

F
F Bu 12
u
-
c c
=S
/
-
atte -,I
L
W
c C
=

--
1
u -
Br
R -
Geometrical isomers

clarify
as
them trane
we can not or
his
form.
groups (ie.
because no two as same all as

different)
E-
opposite I trans
Enteganan
-

Z. zusamann- same side. I s

Rull! Rulet
Cahn-Ingold-Prlog
Rale
Rules should
① All the be
followed in
sequence
the
below:
&

gwen
higpriority.
her
have
Higher
(a) atomic no.

F(u(Br)I
S)F)0> N) CYH
 ② ①
Of
① ③
I
Br
a
a
C C
=
E
-Bu
②

①
same
priority on sameside
the same
priority
on
is
opposite side
the

2
form. E-form.
-

⑧
of isotopes, higher higher
In care atomic mass

be
will
priority.
7) D> HX

(14) c12
② has
is
form more
priority
than
transform
2 has
2 male
priority
than
E-form.
(d)

Formajority of compounds, only

rubrules (a re

Elaboration Rule (9):

of
-
 to
directly
stors attached central
the atom

mustb e
sequenced firstaccording Aubule (a)
to

still
remains
I priority
the the
same then

one
pauses over the
tonext in
atom the
group
until
2 the
exploration continues a decision

made the subrule (as

of
is on bains

-
7
Ca-4-CH2-H

M-oh 7 -

CH2=NH2

He-U-Br)-CHz-U-

It be noted that the rubrule (6) must

may
*

completely
notbe and the
untill subrule (1) is

exhausted -

CH2-C-47-D2-CHE-H
-

Cr?Dg-H37-4-42-t3 -
 In
group bifurcates, proced
*
care a one must

along providing highestprecedence

blanch
the the

untill a
difference is encounted

The decision must be made at the

earliest

opportunity & be
charged
conce made, can not

consideration
of restitutes
farther along
the
the
from
chain.

Ma)-cH-
-

13 C13
7
I I
-

4-c- cC-H
-

CHz-c-42-OH
13 i
I with
of
* the atom
can atoms
multiple linkages,
which bonded be
to
they
are
multiply must

duplicated
A
or
triplicated as the
case
may
be

ends the
of
both bonds.
at
multiple
0
H
-
k- or 7 -
- I
oH
-
OH
0-C
I
- c-0H
Chypothetical structure)
↓ -
c

⑩ M
-

EN -

C-
NH2
-He
Identify Elz nomenclations
of following compound.
the

② ②
⑥
Or,
(
ulz
NCH3
① 14
I
/
-C
=C
①
Opr I
0I -
3 z

③
u
D D ④ =3

*
② a
C C
-m,
L
n
->

①
a
-

A 0
② in
Et
⑰
②
⑤
⑧n ⑤
Or =C
Ot
-

Op(- FO H
Ou
=C

①
2

⑩
X
⑧

⑦
- I CH2

· ⑧ (M
4
=

Br
=- =

-=CH
-
-

upy
⑨ ⑩ C3
o
CH2-C3
H
us
= -
M24
 anti li

3
-

=N/O
Ymes an
-
C3

- -

anti isomers (G.I.)

syn or

side
syn-
same
nee

-posite
anti

0
13
c
in
⑪ is
most
to of

⑪mon &anti
art 01: to

(oxime)
⑭
0:
-
Minimum no
of
carbon atoms
required for a

show
compound to G.I.
Note."
-

of cycle
alkanes.
-
In
care

sings donot geometric

3, 4, 5, 6, 7 membered the
*
- te A bond.
↓
they rigid
as are

8,9,10- show G.I.

for them v
~-

generalis
-

In
Form transform 3
in 7 trans
stable
-
more statele eus
nee nee

* 11, 12,13,--- show Geometrical isomerism

Etransferableis
for
-
the

[3>·it
-
8

is
↳ trans
form.
acten -
-
-

IDat tram
do
form not exist
 Geometrical isomers.
of
number
-

of
① different.
If the
end
groups
are molecule
Lie the

unsymmetrical
is

Total Geometrical a"

of
no isomers =

where stero centres or area.

↓genic
is

where G.I. is
possible.
is
4- 1
C-M-c =

-
n
1,
=

-
trans
-
TNGI 2
=
= 2
-

② end
When the identical
groups are

when the
molecule is
symmetrical)
Total 24-1+aP-1
of
no. G-1 =

when is his
p I if
even

is odd
p ifhis
g4+ +gE-
=>
0⑧
TNG =

1- 1
n2 = 22 t
=
2
3
2 1
=
+

-
-
 Physical of
isomers.
properties Geometrical

e
*
moment!
In
general inform has more
dipole moment

transform
than

EWG
EWG
> EWG

-
H Ewa ~=
H
cX ENG
↓
n /uF0 u0
=

Electron -
-

-( 1,
-

M)
withdrawing goul
-

&
electron
group donating
when one is

withdrawing
other is electron then Utram) Mcis.

Ew9 ED4
↓ -H
Ewa
↑
In
I /
·

c C
=
↳ <
↳ =
↳ EDG
n UFO MF0
-

②
point! B. P. X molecular
weight
2
emface area

a Vander waal attraction

for y
H-Bonding
<
&
dipole-moment
ing
point.
Packing efficiency
a vandes wall
forces

yspau(voide
In
general M.P. trans> M.P. is

x
x optical homerism
-
-
=
-

x
97
6
xc c
=
=

-? =