Isomerism

Isomers : - lil Different compounds which have

same Molecular formula .

til
They have different physical properties .

Classification Isomerism
of

structural ( constitutional stereoisomerism

| |
Isomerism )
Conformational
Chain Isomers
① Iso .

② position ±, , , , configuration ae
Isomers
③ function , , .

④ Metamerism Geometrical Iso .

⑤ Ring chain Iso . optical Iso .

⑥ Tautomerism Enantiomers

Diastercomers
 Structural Isomerism

have Sanne M F but different

Compounds which . .

structural formula are known as structural

Isomers .

① chain Isomers ! -
Isomers which have

different size of main chain

side chain
Er .

( same F. G.
,
same position of F. G.
Er
M - B -

substituent )

4
h ( C- I. I
EE : -
① CyHlo 3
,
3

2 4 4

(c- I )
2
② (
g- 11,2=7 23 , 3
-

3 5 1

2
4 2 4
3 3
5 ,
3 ⇐ - I -
)
, g-

side chain

is different
④ f- I I -

⑤
( C- I .
)

⑥ ( C- I .
)

3 I
⑦ 2
' 2
⇐ I
-
.
)
y ,
3

Butene 2- Mathey -1 -
Propene

② Position Isomers ! -

structural Isomers

which have same size

of
main chain ¥ side chain but different
F- G.
position of ,
Mr B .

Er substituent -

y 2 Cl 4 2

① 3
EE - 3 5 1 ( P . I -
)
,

5
ice
② ( P.I. )

OH
"
2 ↳
③ 3 I
4
23
5
g- 2
,

5 3 1

OH
OH

£004 3
4
⑨ 3
2 y
2
( c. I .
)
5

Cot FI ) .

/ Coon

Br
'
21
I y

⑤ 3 ( C-I. I
'
5 4 3 2
z
,
,
,
(not P - I )
t '
2
l Br

⑥ Dimethyl Benzene

me me me

me

me

4,27 ( 1,31 me 11,4 )

ortho meta Para

(P -
I. I
⑦ Trimcthye Benzene : -

Me me
me
me
me me

Me
me
(1) 2,31

(1) 3 's )
me
c. I. 1
(1) 2,41

⑧ Tetra chloro Benzene : -

ce ce
ce
a ce
ce ce ce

ce
ce

ce ce
(1) 213,41
( 1,213,5 ) ( 1,214,5)

(P -
I .
)
E- Draw all Possible P.I.
of given Mof . : -

⑨ Di bromo chloro Benzene

⑥ Bromo chloro Methyl Benzene

② Trichloro cyclohexane
⑨ Tetra chloro
cyclo Butane

⑨ chloro nap thalene

⑦ Dibromonapthalene
⑨ chloro biphenyl

④ Dichloro
biphenyl
Bv
Br

ME ⑨ Br Br ③ Br
⑥
① ⑥
① ④ ⑥ ⑥
② ④
② ⑤
Br

2 + 3 + I

total P.I. = 6
 Br
Br
Br 5 a
② ,
ce lo lo

6 9
7 q
2
y 8
3
ce

4 + 4 + 2

total P - I -
= lo

ce
ce ce ce ce
ce
(2+1)
② ce

(1+1+1)

ce

ce ce
ce
ce
ce
ce ce

ce
ce

ce

total P.I. = 6

ce ce ce
ce 2+2
⑨ ce ce 2+1+1
ce
ce 11-1+1+1
ce
ce
ce
ce ce
ce
a
ce
( total P
- I - = 5)
ce
ce a
ce
 ✗ d

⑨ p p total P.I. = 2

P P
✗ ✗

ce

⑦ 7
•
••
Cl
6 1 10

5
2 8
q • ••
3
4
7- 1- 3

total PI = to

2 3 3 2

⑨
I 1 total P.I. =3

2 3 3 2

11 I 2 3 4 6 7 9 10

•• a•
Cl g-

I 2 3 4 8 9 10
ce
(5) (5)
11 12
• •

• • (2) ( Total P.I. = 121

ooo ooo

12

ce
③ Functional Isomers ! -
Compounds which

have but have

same M-F .

different
Functional groups .

Note ÷ Do not consider P.I. and size of chain .

E ⑨ Alkene , Alkynes and

cyclo alkanes : -

② cuz -
CEC -

cuz ( F- I .
)
,

④
'

1° 2- and 3 Amine '

.
-

CH3

EE: -

① non
in
, ,
1
CHS
Ntlz ( F- I ) -

② NHZ
NH ( F I I
-
-

1. Amine 2- Amine
 1°
.

&
② 3 Amides
'

2 '
-

, .

0
i
c- NH2 C NH ( cH3
Hz N
-
-

, ,

•
If CHZ
/ Auricle
Auricle
'

2 3
'

Auricle

( F- I. )

⑨ Alcohol ,
Ether and phenols ! -

T T
when -0h group When OH bonded
group
-

is bonded with sp3 carbon with Aromatic ring .

EE: -
①
,
0 ( F. I .
)

OH

OH O
CHZ OH CH }
-
-

②
- Chs

(O -
Cresol )
(Alcohol ) f- I
( .
)
③
( FI .
)
>

Alcoholic Phenolic

④
( F. I ) .

(Alcoholic) ( Phenolic)

Alkenol
(E) Aldehyde
Ketone
, , , Aloxyalkeneet .
;

EI: ↳ Hbo :
§
-
① - OH
]
-
µ ,
,

( F- I .
)
OCHZ , O '

② É -
n

( F- I .
)
 CHS

(F) carboxylic Acid Ester etc

'

.EE
.

%
É
-
.

① Cztlu 02 : -

C
H O
CH } OH Ch ,
-

ctlz -
É -
4 etc .

104
② C3HG0z ! -

É
11 -
€0
Ctlz CHZ OH cuz
-

CH ,
- -

,
-

104
OH
ñ i
?
e
C -

H
O '
, ,
, OH
on
CHZ

( all are F. I. )
 COOH 0

"
③
( F I -
- )

cH3

O o

④ 11 o
0 1 ( F. I )
.

(Eston ) ketone
& Ether

(G) Cyanide , Isocyanide : -

N C
CEN ,

( F. I ) .

NHZ
CH=NH ,

Imine amine

④ Nitro ,
nitrite : -

=° =°
R - N
,
R - O - N
( F.I ) .

30
nitrite
Nitro
 Amide oxime !
(I ) ,
-

EE -

① Chz -
É -

NHZ ② CHZ -
cH=N
-04

③ cuz -

cuz
- N=0 e

① & ② F- I .

① & ③ =) F- I .

④ Metamerism ! -

Compounds which contain

polyvalent F- G. can show metamerism .

F- G. which can divide

carbon chain in more

than one part .

Examples of Polyvalent F- G. ! -

① Ether : -
R -
O -
R
② Ester ! -

R -
É -
O -
R

2. Amine :
③ -
R -
Nn -
R

⑨ R
R
RY
-

3. Amine :
-

⑤ 2. Amide : -

R -
É
-
WH -
R

⑥ 3- Amide : -
R -
É -
N
-

-
R

⑦ Thioethcr : -
R - S -
R

⑧ Anhydride : -

R -
É -
o -
É -
R

⑨ Sulphuric Esten : -
0

R -
I -
or etE
¥
 Somers which have some
Metamer s ! -

polyvalent

F- G. but have different types of alkyl ( R)

group .

Note : -

Do not consider P-
I. and size
of chain ..

Ex : -
① CHS

( metamer)
=

② i
1,
C. Hz -0 -
cats ,
Czts - C - o -
CH }

( metamer ) )

③ o
0

" "
•
S - O -
S - O

to ,
to
( metamer )

( metamer )
⑤ °c -0-013
11
11
- o
-
ch
}

(metamer )

( metamer )

⑦
ñ
C -
Wh - Me c -
Nn - Me
,
11
0

( metamer )

Priority order : -

( Tautomerism F. I. metamerism c. I. P.I. )

⑤ chain Isomers :-( Commonly
Ring win be F- I ) -

will be
one compound cyclic and other one

Acyclic .

IF I - I

E¥ - &
( R.CI ) .

②
( F. I .

& R - C I -
-
)

( F- I. )
③
&(RCI )

⑨ (R -
C I
-
.
)

Br
⑤
( F.I .

And R -
C- I .
)
E- Identify all Possible structural Isomers ?

① ↳ Hoo : -

② Cy Hio : - ②

③ G- 412 :
③
-

④ ↳ Hiy : -

⑤ G- His '
-

7
 9

⑥ Cookie : -
① ③ ①

② ②
one -
Et I
① 3

7 I 3
①

② ② ②

I
2 I
2

( total =/
8)
E-
 § Identify all Possible Structural Isomers : -

① Cz Hz :
C- c- c- c- d- c ②
-

③
②
② ④ ⑨
cytlq ! -

③ ③
②

inI -

Beaty ! - C-c- C- c- ,
gso : -
C
/
c

se C f
f
! - C -
c - -

, += : -

c-

C C
④
③ G- Hi , : -
② ② ⑦

⑤
① ④ ⑥
③ ①
① ①

③ ④

2 3 7 10 10

④ CGH / 3 '

.
-
'
''
9
9
56
.

" 4 8
}
2
, ,
13 13 ,
"°
15 17
. A total 17
'
13 16
14 16 ME
 a

⑤ ↳ 47 -
ce : -

ce
②

⑥ Gua -
ce : -
⑨

⑦ G- Hi , -6 : -
⑧

⑧ ↳ His -6 : -
⑦

⇐ cfdentify all possible structural Somers ?

① ↳ HG ? -

(000--1) Acyclic !-

cyclic ! -

② Cy Hg : - (1300--1) ! -

cyclic ! -
⑤
,
③ G- Hw :-( Dou 1) Acyclic

's
-_

cyclic ! -

total __ ④ ☒
=

4
④ ↳ Hk !
-

Acyclic ! -

l 3 2 4 7
I 5 6
z

12

9 9 13
8 8 11 12
12 =) 13
12
10

Cyclic ! -

12

total = 25

A
 Identify all Possible Structural Isomers ?

⑨ ↳ 480
⑤ cytlioo ( DOU -_ 0 )
② CJHIZO

⑨ CG HMO
OH

¥ ⑨ 3¥ !
-
Alcohol : -

OH

Ether ! -
Czts
-
O -
CH } ③ ME

④ Cytlioo : -
Alcohol : -

Cy Hq -
OH ④

Ether ! -
Czhs -
O -

Czts : -
①

O CH ] : ②
↳ Hz
- -
-

7-
AE

CSH ,zO Alcohol ! ↳ Hi , 8

② ! OH
-
-
-

ch }
Ether : Cyhq o 4
-
- -

2
↳ Hz -0 -

Cats
14

ME
④ ↳ Higo ? - Alcohol ! -
Cgtliz -
OH 17

Ether : -

G- Hi , -
O -

CH } 8

Czts 4
Cy Hq O
- -

h n O ↳ 47 3
o
Czyz
-
- -
-

n -
o - i
32
i -
o -
i

Gdentify all Possible structure Somers : -

⑨ CUNEO
E
carbonyl
Ketone )
G- 4100 Compound
( Aldehyde &
⑨
② CGH 120

⑥ Cy 4802
(1300--1)
only
⑨ G- 141202 Ester

ME ⑨ Cyhooo : -

Aldehyde : -

Czhz
-
É
11
-
n ②
i
ketone !
①
CH3
-

czHs=C
-

③
AE
⑥ G- 4100 : -

Aldehyde : -

Cytlq -
É - H ④

Ketone ! -

czH7 -
É -

cuz ②

Czhs -
É -

cats ①

7-
ME

② CGHIZO : -

Aldehyde ! -
Costly -
É -
H ⑧

Ketone : -

Cytlq -
É -

Chs ⑨

↳ 47 -
É -

cats ②

14
ME

⑥ CyH802 : -

czh , -
-0 -

CHS ①

cuz -
É -0 -

cats ①

H -
É -
o -

↳ Hf 2

4 B-
② ( 541002 ! -

Czyz -
% -0 -
CH
}
②

Czhs -
É -0 -
cis ①

GHz ②
Ctlz
-0 -

H -
E -
o -

cyhq ④
⑨ ME

⇐ Identify all structural Isomers ? -

⑨ CyHyN
] ( Dou )
__ 0

⑥ C. 5413N

AE ⑨ Cy Hun : -

Amine Ntlz ④
•

/ Cy Hq -

2 Acuine
'

↳ Hz - NH -
CH } ②

Czhs NH (245
①
-
-

3.Amine ↳
Chzyw / ①

£4s 8
⑤ CSHISN : -

|
C-
5h11 MHz
-

1. Amine

2. amine ang - un -
en
, ④

( 347 - NH -
cats ②

3. Amine CH3
CH3
- w/ ②

47

①
CH3\µ,CzH5
I 17
Czts ME
 frtereo - Isomerism

tftereo isomers ! -
Isomers which have same

structural formula but have different

arrangement of atoms
groups
in space ( 3D ) .

Stereoisomerism

KP " " "

configurational ( Non guter
) conformational

( )
convertible # Fenter convertible
>
Geometrical
Isomers
# Non Separable

s optical
Isomers

ÉM' .
-

Stereoisomers which

are not Ginter convertible into each other

at boom
temp .
( they are convertible
by
breaking and reformation of
Bonds) .
ÉwIs : -

Stereoisomers which

are not Ginter convertible into each other

at eeoom temp .
due to presence of

Restricted Rotation .

They have different distance btw two

particular groups .

Ex : ① 2- Butene ! CH }
Choo CHIH
- - -
-

(structural
formula )

L
,
H
H
I =c
-
H ,
c=c
-573
/ 1
#H
CH} kHz CHz4
K +
d ,
(Trans )
( Cis ) d , -1-42

# Stereoisomers

# Configurational Isomers

# Geometrical Isomers ( G.I. )

 3D structure of C=c : -

ZP
H

EEE
"
2s

C ( G. s . ) : -
l
'
Chz
Chz
- -

2s 7
-
-
-
-
-

c( E. s ) :
-

. - -

Pz
SPZ sp2 Spl
77
c( 4. s .
) : -
7

H
"

""
"" ,,
,nnuH C -
c
c c

Bfq• Sooo
CHZ
CH} CH3
CHS
 Conditions for Geometrical Isomerism ! -

① Geometry of compound should be contain min .

2 relative distance b/w two

types of

positions of same atom / group .

② Compound should be
containing double Bond

( c=c , c=N ,
N=N 10¥ Substituted seeing .

( Restricted rotation )

③ Both corners
of geometrical centres should

be 2-2
containing different groups .

Ex : -
① K -
c -=c -

y CGI -7 ✗

②
)c=cf , xyc=cxy
K -1-91

( G. I. ) -

ce ce
③ ( G. I. I ✗
B
I
B-
⑨
(di=dz ) G. I. (X )
c

⑤ ↳ ↳
Planar
Iq
spy ,
.

>
<
↳
÷
.

↳ ( G.I ) 4) .

⑥ G. I. (w )

P
(T -
B P
- .
)

⑦ sit
N y
t ( GI /
.
✓

a
y se
T
No free

notation
 Geometrical centres :
Types of
-

④ G. I. in C=c containing group .

C=N Il Il
⑤ -11
- -

-11
-
-

Il Il
② N=N
- -

Il Il
-
-
-
-

⑤ -11 - it -
substituted beings .

⑤ ein clue to C=c of

Il il
cyclo alkene
- - -

being .

⑦ -11 -11 -
in ceemueenes (Alienee )

⑨ -11 -11 -
in Spiro compounds .

④ -
11 -11 -
in Bicycle compounds .

et

(A) Geometrical Isomerism in c=c containing

:
groups
-

Structural formula Stereo formula

H H Ph
H
Ex : Ph ,
-
①
-
CH -_ CH -
Ph
C c
c=d
l '
ti
Stilbene Ph Ph
Ph
(Trans )
Cis )
 oh
② H°°cz=gC°°H Hy
go ,=g
'
Hc=CH

ftp.ooc/iHBut-endioic
C-
-
OH /
no -

µ
acid fist Trans )
( Maleic Acid /
Ecumenic Acid )

Cook
" "
③ Ph Coote H
\c=d
Chan
=D
- -

-
c.
1
' in
Cinnamic Acid Ph Coon Ph

( Cis ) (Trans )

⑨ H

CH -
CH C
}

CH3
Me me
&

CHz
C

H
Me
 ④ Geometrical Isomerism in c=N Containing

:
groups
-

•
ooo

Structure : d, -1-12
-

c = N

SPZ gp2

conditions for G. I .

Ñ
Nyc = -
G

se # y

formation c=N : -

of

§=§?=T!¥Ñ
" ⑦
-

a
'
> c=ñi
-

1120 G
Aldehyde

Ketone

Note : -

se
se
, c=N
+ NHL -
G )

,c=0 -1720
y
G

y key
1-

( Unsymmetrical Carbonyl Compound )

 y
c=N
G
N

(2 geo
- Iso -

D= Identify no oxime products for following

of
.
-
,

Reaction .

OH
HZN -

,
① 2 oxime
chz - Cho s

② % É NHZ -
OH
,
1+2=3
>
+ ph
cH3 ( Excess)
oximes

Acetone Acctophenone

ME

③
-4=0 c=o
-1 -

c=o +
1
I 1 µ "
H Me
me

mix .

NHZ-0h .

( Excess)
u

(21-2+2) = 6 oximes
② Geo . Isomerism in - N=N -

Containing

Compounds i -

°
Do
• o °

Structure
•

: -

N=N & N=N

sp2 Spl
•
•

Anti form
Syn form

E ① Me - N=N -
me

A zone ethane

: ☐ G
→
,

Syn
•
•

Anti

H
③ H N=N -

② Ph N=N Ph
-
-
-

Diazeue
Azobenzene
 D Geo . Isomerism in substituted being : -

Sp3 Sp3
Structure : -

d, # d2

conditions for Geo . Iso - ? -

y
gpz•
(2-+2)
minimum two Sp3 atoms
sp3•
2 G.I. = -

contain
of being should y

2- 2 different groups .

Draw possible G. I
¥ all -

of given compound ?

AE ① Me Me
Me
Me Me
Me

i. -

±H H
H

fist
me me H
H

@ G. I. I
=
Me
Me H

Trans )
 Me me
me me me me

②
& 1
Me 1
i. → I '
µ ,
µ Y ti

1
Me H
Me

126.1=-1

Br Br
③ Br Br
Br Br

'
i ' '
ie ! H
-

n
µ n
1
ce
H ce

Br
µ

I 1
(3 G. I .
)
µ
H Br

B- me me H me
☐r

⑨ I "
1 F
.
U
-
H
•
H Br
µ

ce H H

Br te
Br me

'
ce
me

✗ G.I .
)
H F H H

H
ce
 me Me
me me Me me

⑤ ^
ME
-

µ Me ME H
.
µ µ µ

Me Me H H
H Me

Me me
H
me

( 4 G. I .

) H
H
ME H
µ µ me H

me H Me
me

(E) Geometrical Isomerism in

cyclo Alkenes ÷

( due to c=c of being ) : -

%: Small cyclo alkene ( upto 7- membered )

odsomerism is possible because

geometrical not

in small cyclo alkenes only cis form exist

in nature but its trans form are unstable

due to High strain .

Ex : -
①
Cyclohexane : -

(Cis ) (Trans )
H

H H
( unstable)

( due to High ring strain )

② cyclo octane : -

(Trans )
(Cis )

H H
( Not unstable )

111 H
(lesser stable than cis )

H
11 I
 Note! -

form Transform
Ring Size cis

Exist in nature Not Exist

① Cz -

Cz

② Coo -

G, More stable lesser stable

③ More stable
clz Higher
- lesser stable

(Atlases )
F Geo .
Isomerism due to c=c in cumueene : -

Continuous c=c
containing

Polyenes .

Structure : -

Py Py Pz
Pz
E ① N k
SPZ sp SPZ "
""
:
c=c=c•q• C C C
-

Be
y y
 Structure Terminal Geo Isomerism

!
.

se y
,

&
① SPZ sp sp2 Not possible
c=c=c
Roe "" "" "
• •
di=I<

② se

.am . ns..ie
C C C C

y plane

d , # d2

③
N
SPZ sp sp2 Not possible
c=c=c=c=C•g•
y y

d , =dz

Conditions for Geo .

Iso .
in Ceemueenes : -

① Terminal ( k # y)

② odd no .

of cumulative c=C .
?⃝
?⃝
⑨ Geo . Isomerism in Spiro compound : -

Two Adjacent Spiro wings are 1- to each other .

Terminal G. I
Ex :
.

XY )
n se

① % (X)
Mr
y y
d , =d2

( )
② Gn same
"
""
÷ v1 plane

y
By
Romy
d , -1-92

Conditions for Geo .

Iso .
in Spiro compounds ! -

① Terminal ( k # y)

② odd no .

of Spiro rings .
EI ! -

③ % K
CG.I.li
a
Hi
y y

⑨
CH CH CGI ) ✓
CHZ CH
- - .

⑤
CGI ) . -
CH3 C=cµ -
CH,

⑥
Chz CGI ) . -
CH } '
'
'
' µ
µ

⑦ cuz -
\ CH -
CH
}
( GI / . ✗
 H Geo -
Isomerism In Bicycle Compounds ! -

9h bicyclic compounds Isomerism possible when

geo .

both have min 5- 5 atoms

rings .
.

③
②
Ex : -
①
=

@ )
Ir ✓
(G. I .
) ✓
(G. I. I -

④ ⑤

( G.Il
(G. I )✗ .
-

te te

Decaein : - MM MM

• E
H H

Cis ) ( Trans)
"I
111
H

1
H
'
H

H
 Configurational Nomenclature
of geometrical

centres : -

④ Relative configuration ⑤ Absolute configuration .

lil cis - Trans

configuration lil E. 2- Nomenclature

ii , Fyn -
Anti
configuration

④ it cis-Trans Nomenclature : -

Cis : Same same side

-
groups

Trans : -
Same groups opposite side

" "
H
,
,H
②
E ① '
=D
£
<
'
ce
pÉ=%
( Cis )
ce's )

③ "

cH3\c=g (Trans )
/ '

µ
czts
 I

④ 2 3% 6 7

# 4 5
11
runs )
' '
H @ is ) n

(& -
Trans -
y -
cis / Hepta -2,4 -
diene

⑤ 5 414 1 cis > Trans

3
H
Trans )
↳
I
Eis , If

diene
⑨ -
Cis -
U Trains
-
) taxa -2,4 -

CIII Syn - Anti Nomenclature : -

oximes (w r-
t.e.p-e.p.in/N--N
-

- n
,

° •
•
• . •

N=N N=N
•
•
✓

Kctoximes
Fm ) Anti 1
Aldo oximes
I. P on Sanne
OH
.

Me
R " ,
side : sum
'c=N Gyu ) ,C=N
-

.
.

I \oµ Et e.P on opposite

-

H side :
Iyer Methyl ketoxime Anti
-
-
 04 ¥

R\c=N ( Anti ) Anti -

Ethyeketoxime
/ •
•

H & OH Same side '

.
-

Sum

H & 0h opposite side : - Anti

(B) Absolute configuration of geometrical centres: -

E- 2 Nomenclature : -

E =
(Entagen =
opposite ) ( higher priority groups

Opp .

)
side

2 =
( Zussausene =
Together) ( higher priority groups

on Same side )

Priority order ( as 1,2) of two groups of both

corners to
of geometrical centres according
CIP Sequence evite .

.p ①
te .

②
trip ①. ① H.P.
C =c
c=c
①
② ② (E) H.p.
② ( )
 CIP ( Cahn -

Ingold -
Prolog ) Rule : -

first
① The
group in which atom has higher

atomic no .
will be considered higher priority

group .

② off first atom

of groups are same then

consider atomic no .

of
Second atom . ( soon ) .

③ when different isotopes of same Element

present on same position in different group

then heavier isotope containing group will be

Higher priority group .

4 ( Bond pair lone pair )

⑤ when multiple Bonds are in a group then

draw a
hypothetical structure according to

following way
: -

Ch C Hz
EE :
- -

① ch CH :
-

d
>
E
-
=
,
 it
② -
c=o : → -
c -
o

l l
H h

it
③ -

CEC -
H : -
-
c -
c -
H

Ed

④ -
c=n : -
-
i -
É
'
n' a

⑤ -
n=c=o : - - n -
É É -

I 1

C N

¥ Identify absolute configuration (E) 2) for

following : -

Br
①
'
f- ②
ME I ② cha cha ce
-

① ① ① ,
c=c F=c "
- F
Ch
② Br
•
① [ 1=3
if
②
(E) ②
( )
 ce
②
②
'
① Chz cH=0
③ ④ cuz
-

cH3 CHS
①
, - [ =D
,= ,
CHI
'
/ '
H CHEON
gaz
-

CH
}
-

Cha ② ①
②
① Br (E)
(E)

②
GH
c -
-
C
⑤ ① -
H
:
⑥ ①
c- c- c
①
c=N
OH I
C Ch
①
-

^
HH ② I
c- ctlz
②
② (E)
( )

① ① ②
②
⑦ CH} ⑧ cuz Chz CHz- CDs
-

CHZ -
ce
' '
c=c c=c
/ \
D
CD} D CDz- cuz
① ②
② ①

(E) (E)

⑨ ① it °
①
a- E- Nhz
cy= ,
/

/ '
CEN
NEC
②
② (z )
 6

④
5 4 1 (Z > E)
3
(E)
2
(2)

( 22 ,
YEI Hexa -
2,4 -
diene

calculations of
no .

of geometrical Isomers : -

For dissimilar Ends ① For Similar Ends

Containing Compound Containing Compounds

{
"
° " °" " " = "" "
" "

% "" " =
&

2h -1+212 l
-

n = no .
of geo . centres G. I. =

which can show

cii ?
When
geo .
Isomerism h = odd no .

G. I. =
In-1 +
2¥
!

CHz-CH-neCH-CHTeCH-CHz-CHz@is imiIarEnces1Cn-2lG.I
-

.
= In = 22 = 4 ME

② chg -
CH = CH CH __ CH -
CH
}
-

Similar Ends

① cis-Trans n=2

② Trans -
Trans G. I. = 22-1+2%-1
③ cis -
cis = 21+20 = 2+1

=3

③ CH } -
CHIH -
CHIH -
Ch __ CH -
CH
]

Similar Ends

n =3
3- i

G. I .
= 23-1+2-2

= 22+2 ' = 4 +2

= 6
⑨ Cuz -
Ch = CH -
Ch __ CH -

CHIH -
ce

dissimilar Enes

n =3

G.I. = 23=8
⑤
cuz cH=N -011
dissimilar Ends

n= 2

G. I . =
22=4

⑥
ti
n

N = CH Ch
CH3
-

cH=N }

Similar Ends

G.I. = 23++2 n =3

G.I .
= 6

⑦ CHS

CHZ CH = Ch
[
43
✗I

Dissimilar Ends

21=2

G.I .
= 22 =
y
 CH = CH -
CH
}
"
⑧ = dissimilar Ends

n = 4
'
H G.I. = 24=16
cH=NH

⑨ Similar Ends

H H
,
n =3

CH
CH CH CH -_ CH
23-1+2
-
=
cuz
-

} g.I =
.

G.I. = 22+21
= 6

me me

④ G.I -
=6

Me
ce

me
me

①
G. I. = 6×2=12

me du
11

÷
CH3
④ CHIEH cH3 G. I. =y
-
-

CH CH CH
cuz =
- -

c l
Ch
① C) C) C

11
C ② T, T, T
CH

£43 ③ C) IT

④ T) C C
,

similar Ends'

④ (
Hz -
Ch =CH -
ch -
ch -_ ch -

cuz
n=2

I
CH
" G.I. =
22-1+22=-1
CH = 21 + 2° =3

Ét
Total G. I .
= 2×3=6

④ CHz -
Ch = CH -
CH ]

G. I. = 2
Physical Properties of Geometrical Isomers : -

① Boiling Point of G. I . ✗ Dipole moment

② Melting point of G. I .
✗
Symmetrical structure

( more symmetrical molecule have strong packing

in solid state . So they have Higher meeting

point)
# Generally Trans isomer have greater meeting
point .

③ Solubility in water ✗ Dipole moment

( of G.I . )

⑨ ✗ /
Stability of
a. I .

Vanderwaal strain

( Repulsion btw bulky group )

 ]
sp
te CH }
<" CHz
EE ! - ①
34=1 [ =L
ll=o
/ \
/ SP"
all -1-0 µ H CH , H

Cisl Trans)

( it Dipole moment : -
cis > Travis

Ciii Boiling point : - cis > Trans

Ciii , melting point : - Trans > cis

dirt Solubility in water : - Cis > Trans

(E) Stability : - Trans > cis .

② cH3 Br H
Br
- , /
c=c c=c leis greater
I " 1 "
H CH H
H }

Cis ) Frans )

( it Dipole moment : -
cis Trans

Ciii Boiling point : - cis trans

Ciii , melting point : - Trans cis

dirt Solubility in water : - ce's Trans

(E) Stability : - Trans cis .

 ( maleic Acid ) ( fumeric Acid )

② COOH COOH
HOOC µ

c=c É=c ee -1-0

/ "
Coote \H
(leis H H

greater ) Irons )
cis ,

( it Dipole moment : -
cis Trans

Ciii Boiling point : - cis trans

Ciii , melting point : - Trans cis

dirt Solubility in water : - ce's Trans

(E) Stability : - Trans cis .

 Conformational Isomerism

① Conformations : -

Different
3D
arrangement of

atoms of groups of a compound which are

Garter convertible into each other at room

temp Bonds
.

by notation of 0 are called

conformations .

Stable conformations are called conformers

= Rota mens =
Configurational Isomers

we can't separate these isomers .

② Dihedral Angle / Torsional Angle : -

Angle btw

two bonds which are

atoms
present of two adjacent .

se
< y
( Angle in ,
C- hand C-
of y
••

2- c- c- y )
③ Staggered conformation ! -

Conformations in which value

of dihedral
is 185,300
-

60
-

angle ,

÷
••

⑨ Eclipsed conformations ! -

which dihedral 0,120°

Conformations in angle is ,

240
.

A
.

••

⑤ Skew conformations ! -

Conformations other

than Staggered and Eclipsed .

Represented of Staggered and Eclipsed : -

ftaggcrea Eclipsed

Newmann : -

••
••

② Faw -
Horse : -

•
ooo

ooo •

•
.
•

③ wedge -
Dash : -

•q Hq ←É
←É •
•

so -30Gt • •
•

G. É Go
⑥ Energy Barrier = Conformational Energy ! -

Energy acquired for complete rotation of

a Bond .

Energy difference b/w most and least stable

conformation .

H
" H
② it
EI : -
①
I
y
-
d -
c -
H
C C H /
I 1
-

µ
-

te
/
J th
µ
cH3
14kt / not
12 KT / met

30 KT/ not

7-
③ ⑨ - - - -

Trunsoia
H H
l l Tt
CH -
c -
c
-
CH
}
}
1 T '
te n
l
19 KT / mole
( cissoid )

26 - ICT / neo )
I
⑦
 Energy Barrier ✗ Presence of Bulky group

-
11 -
11 -
2 Multiple Bond Character

⑦ Factors Affecting Stability of conformations :

-

④ Torsional strain = Eclipsed strain : -

d) Repulsion density
-0
b) we

of two dihcdr I angles :

.

Ii ) Eclipsed Staggered
( Torsional strain )

Iii Staggered > Eclipsed ( stability of

conformations )

④ Vander -
waae Strain ? -

Repulsion btw groups which are

present on dihedral angle .

② Sutra molecular H -
Bonding ; -

Staggered conformations which have odutraruoleculas

H Bonding is / are most stable .

Ex : -

① Ethane : -
( Catto )
=

H
H

C C H
H

H H
H
H H

te
H te
H H
360° Go
.

'

" H
H H
H
µ µ µ
⑤
H
④ H ④
⑦tagger eat
.

300
[Eclipsed ,
120
.

H
H
H
H H
H "
240 '
180 .

n
% H
"
ii
µ H H
⑤ H ②
④
 ← 100% ) C- 0%7

Stability : -
Staggered > Eclipsed

00
no .

of conformations =

no conformational isomers 3
Of
-
=

Barrier 12kt tweet

Energy =

A
② ⑤ ④
Eclipsed a

12kt /
not

T
Energy

Staggered
DO

0° "
120
'

180
'
240
'
300
'

360
'

Go

Rotation
?⃝
 Ex : -

① Butane : -
( cutin )
=

H H
,
C. Hz
ga Ys CH
-
-

}
-

te te
w.r.t.cz Cz -
Bond ! -

Chz CHS Ch3

CH
CH3 H }
360° Go
.
H CH3
'

" H
H H
H
µ µ µ

⑦ µ( Gauche ) ④ H ⑧
(fully Eclipsed / Gauche I
.

300

120
.

CH
]
CH3 cH3
µ µ
H "
240 '
180 .

H
Ii H
H CH
H
}

CH} H H
⑤ Ch> ②
④
(Partially
( Anti ) (Partially Eclipsed)
Eclipsed )
 Stability ! -

Anti Gauche Partially Eclipsed

( 100%1
fully Eclipsed

( not .
)

no -

of conformations = to

isomers =3
no -

of conformational
Gauche )
( 1 Anti ¥ 2

A
fully ④
Eclipsed

Partially ② ⑤
+ Eclipsed
19kt/ not
Energy

Gauche
④ ^
FO
4kt / not 14kt / MOI

Anti u

>
0° 300
.

360 '

Go 120 180 240

' ' ' '

Rotation →
E- Draw most stable conformation of given

compound ?
H

tr CH3

ME ①
cuz -44
-

CHZ
-
CH
}

cH3
C.
Hz CHZ
ti

St
s -

H
O
②
-

Ho -

Cha -

CH -
0h : - '
, '

:O :|,
H

③ Ho -

Cha -
Cha - F

ti
te
⑨ Ho -

Cha -
CHZ
-
CHO

Gauche ( most stable)

⑤ HO -
Ctlz
-
CHL -
COOH

- •
§
⑥ to -

CHL -

cuz -
NHL Gauche > Staggered

( stability )

Intramolecular
( due to H -
Bonding )
 H

⑦ ÑHz Chz Ctlz Ñhz

IN
-
- -

- H
'
'

in -
H
H
1
H

H
H

( Gauche )

Cooh
icon .

⑧ 9h Acidic
H
§
Mek
'
Coo H >
on

H H

Succinic Acid
H
(Gauche )
Gm Basic
Coo
-

Medium
-

Coo
Coo
-

H H

H
H

Coo
-

( Anti )
 '
"
-

o
-
no
COOH
⑨ 11
C
H
H OH HO
-

H OH

OH
C-
Coo H
H Il
°
Tartaric
'
Meso
Qµ
-
,

acid
( Anti 1

OH
OH
H

( Gauche )

H Coo h

COO H
 Conformations of cyclo hexanes : -

Bayer 's Ring strain : -

gtis represented by

difference b/w Actual Bond angle and ideal

bond Angle in wings .

109
•
5-
109.5
' -

Gd eat Angle 109.5° 109.5

.

: -

108
'
120
Go 90
'
'

Actual Angle ! -

1.5 10.5°
.

Ring 49-5 19.5

'

strain ! -

Stability ! -
5 > 674 > 3 ( Expected )

Stability ! -

Cyclohexane > cyclopentane > cyclo butane

( Experimental) > Cyclopropane
di cyclohexane is won planar Structure .

di , gt Exists in chair conformation .

Ciii ) The chair conformations are gut - convertible

into each other .

①1 other conformations of cyclo hexanes are : -

Boat Twist Boat Half Chair

④ chair conformation of cyclohexane : - ai

I
5 6 A
e,

ul oooo
I
@6
\ As
@
3 2

5 6

ese
a = axial
a>
96 ez
=
equiton.ae
3
z

E3
Ey A2

:
 6 axial and 6 eauitorial Positions
#

# C, -
C2 11 Cy -
Cs

Cz -

Cz 11 Cs -
Cs

11 C, Co
Cz Cy
-

109.5)
# No Angle Strain ( B. A. =

: a]
e,
as ai

as
et
Ey É_oge3 ez
3
:
-

5 6
g-
2 1
es y
93 96 6
ez
3 ET '" El
Egli
z
•
E3 AG 92
Ey az qy

:
# No torsional strain ( staggered conformation]

Identification of cis-Trans ! -

① Cis position writ . 9 ,

=
ez , 93 ,
eh ,
95 , EG

② Trans position w - wt -
ai =
92 , ez ,
94 ,
@5
, 96
③ Cis position writ .
ei az , ez , ay ,
es , 96

④ Trans position writ .

el @ 2,93 ,
@
4,95 , EG

IF Chair
These conformations are Ginter convertible

which is known as flipping in cyclohexane and

other conformations are

forming in btw two

Chair conformations .

#
During flipping in
cyclohexane ( chair conformation)
axial and equatorial positions are interchanged .

se

'

y
q

'
-
P
p
B
P

✗
X se

y
# Alternate axial positions are move closer than

equitorial.la , , 93,95 ) & ( Az , ay ,

96 ) . So

these axial positions are more steric hindered

position therefore Bulky group is more stable

on eauitoriul position .

ELI: . ① Methyl Cyclohexane

H

Me

Chore stable ) ( less stable )

H

(95 ( 5-
•

1.)
)
'
.

me
④ Boat conformation : -

u
e
f. p . F. P .

4 e e
i e e
e e
t e

g-
16 = G
z g-
a z
a
e
e
3 2
a
a
•
a a
a

# F. P . : -

flag pole Position

Angle strain ( B. A. )
.

# No = 109.5

Max . torsional Strain

( Eclipsed conformation )

* Repulsion : -
( E.p. -
F. p .
> axial -
axiae )
② Twist Boat Conformation : -

# Partial Angle Strain

# Partial torsional

strain

④ Half chair conformation : -

# High angle strain

# High torsional strain

G- ability order of conformations of cyclohexane s : -

Chair Twist Boat Boat form Half chair

 Order Interconversion :
of -

④ BO ② DO ⑤ ⑦
Twist
chair Twist Boat Half
'

Half chair -

Boat Boat chair

ti
⑥
chair

⑧
Half

÷
chair

④ 43
Boat

(
.
9

Energy

Twist
Boat ⑤
25

ktlruol
Chair
④

Interconversion
 Heat of combustion : -

Catty +
@ ¥102
+
> Kcoz
-1¥ H2o
+ Heat

of
combustion

Heat of combustion ✗ no .

of carbon atoms

Heat combustion ✗ 1
of ( for Isomers )

Stability

II. -

H, Hz H} Hy

H ( Per motel 1737112

corny .
: -

Hq > > H,

H
( Per Hy
Chu
¥ If E-
comb . : -

e-
E- Draw most stable conformations 1-

① I -

Ethyl -
l -

methyl cyclohexane : -

Me

Et

② I -
Ethyl -
2-
Methyl cyclohexane : -

ti
te

Et
Et

H Me

ti
me

( Cis ) (Trans )
( More stable )
( Higher Heat of combustion )

H cis
comes :
. - > Trans

stability ; -
Trans > cis
 diol
Cyclohexane
'

③ -1,3 -
.
-

( Cis )
H -
-
-
OH
-
O
OH H

te
te

OH
(a) a)
(e) e) I

H
(more stable )

(due to 9. ntrainoleculas

H
Bonding /

Trans : -

OH OH

( a. e)
 optical Isomerism

CI ) optical Activity ! -
Compounds which can

rotate vibrational plane of

plane polarized light ( PPL ) are caned

optical Active compound .

and the phenomenon
is called
optical Activity .

Stereoisomers which have different optical

Activity are called

optical Isomers .

(TI) plane Polarized light ( PPL ) : -

light wave

whose vibration occurs in Single plane ,

perpendicular w.int .

propagation of light

n n n

-
v v

Normal Nicole Priam (ppl )

light ( Cavite )
 n n n

-
v v

Normal Nicole Priam (ppl )

light ( Cavite )

n n n

light not
-

visible
u w

normal Nicole Priam (ppl )

light ( Cavite )

sample
Normal Nicole pvizm
tube
light ( Cavite )

(TI) polarimeter : -

By using the polarimeter we can

measure the value observed

of

rotation vibrational PPL in

of plane of

presence of optical Compound .

' '
" 1
-9in ,
'
-19:
n n n
,

-
I
=
-
u w

Nicole Priam
normal
(ppl ) Analyzer 1 '

light ( Cavite ) 1=180

.

prism
⑦ Observation on Polarimeter : -

For optical 9h active compound

(0 .
I. c- )

0=0
'

D= obs .
rotation

for optical Active Compounds ( O -

A. c- 1

For clockwise rotation for Anticlockwise

hot atiou
. ° '

+0
.

-0
→
c

u
c-

Dextro rotatory compound Laeuooeototory compound

(d) A) (1) C- )
The
Magnitude of optical rotation depends upon

following factors : -

Nature substance
① of

② Length of sample tube

③ concentration of Solution

⑨ wavelength of light ( usually Na -

D lamp .

=
589hm )

⑤ Solvent

⑥ Temp .
et± .

④ Specific Rotation ✗ : -

② d l
t -25C -

0
02 C L =

☐ C. e-

02 1. c
O = obs .
rotation ( degree )

① = [d) c. e. C = Cone .

of sample ( in gon / me)

f- length of sample tube

( in dml

1dm = 10cm
¥ For a solution of an optical active compound

optical rotation is
.

the value 13.4

of .

Cone solution is 2 gun in to me and length

of
.

of sample tube is 25cm .

find out

specific rotation ?

B- ②
=
13.4° =
13.4×2

[a)
(E) HEHE
=

26.8°
=
ME

#-) chiral carbon = Assy metric carbon :

-

Four different groups containing tetrahedral

carbon ( SPB ) is called chiral carbon .

Note : -
① only one chiral atom containing compounds

are always Active

optically
.
 with dissimilar
② when more than
Always optically
Ends
chiral atoms Active
one

are present with

may be optically
Similar Ends
Active maybe

not Active

( Consider 3D Structure )

4- Identify no .

of chiral carbon : -

Cl Two
① ② o•

C 0 A. c.
•

@ A. c.) ••
•

µ
Br
Br
D

④
③ zero
• •• T④

0 -
I - C .

⑤ ⑥

Two
zero
0 A C
.
- .
 CI CI
Br

⑦
• ••
⑧ • •

•o

•o •
Two
six
e•

0 - A. c.
a
Psuedo
carbon
Chiral

⑨ cuz -
CH = Ch - th -
CH -_
ch -

Chz
For
① cis cis ( X)
Trans Trans ( X )
②

③ cis Trans ( w)

④ Trans Cis ( v)

Condition for optical Activity : ① Active

optical
-

compounds are not

superimposed on its mirror image structure .

This is Chiral
property called
chirality .

molecules are
optical Active .

Chirality is necessary and

sufficient condition
for optical Activity .
② Centre of Symmetry ( Cost ,
Plane of Symmetry

( Pcos ) I
Alternating Axis
of symmetry are

not present in optical Active compounds .

( chiral molecule ) .

Out of these elements of

symmetry if any one

element of symmetry will be present in

molecule
,
then compound will be optically
9h active .

CETI) Elements of Symmetry : -

④ Axis of symmetry (c)

Useful for
④ Plane of symmetry ( o
)
gdeuti fiction

for optical
② Centre of symmetry ( j)
Active compound

④ Alternating Axis of symmetry ( s )

④ Axis of symmetry ( c ) : -
Gt is an
imaginary

axis which passed through a molecule when

,

we rotate this molecule around this axis

by 360 obtain
.

then we identical arrangement

( more than one ) coir t - -

original arrangement .

↳ axis ( Cn )
Ex : -

① Bfz : F- ,
@ n=
'

=3
-

= "
"
B F one
Cz axis

e-
F

F
Three Czaxis

B F
① 00 c, axis .

Czaxis

n=%÷=2

H
② CHY ! -

B. A. = 109.5°

C H
Bond Angles = G
B H C
H
H
te

4 Cz axis .

3 Cz axis .
 A B C D E H I K M N 0 ST
Cz axis =

( Present) U W X T Z

Cz axis = F , G ,
J, L , P , Q ,
R

( X)

④ Plane of Symmetry : -

( Post
9T is an
imaginary plane which bisects the

/ object in two
molecule equal Half parts and

these both Half parts should be mirror

image of each other .

② Centre Symmetry = Point of Symmetry

of

= Inversion centre : -
Gt is an
imaginary

point in the centre of molecule from

which if line is drawn to the direction

of a particular group and it is Extended in

opposite direction it meets two mirror

,

image groups ,
on equal distance from centre

of molecule .
 Cl H

µf=c(
,

Pos 3+1 4
F
= =

Ex :
-
①
F
B Cos = ✗

Pos = 6+1 =
7
②
Cos = ✓

Pos = 2
③ Y
Cos = ✗
H H

⑥ 02=0 Pos = do

cos = ✓
 a

⑤ Pos = 2

Cos = ✗

⑥ ce
Pos = 2

- - - -
cos = x

ce

⑦ Pos 2
f a =
-

Cos = ✗

Pos =3
⑧
ce ce
cos = ✓

⑨ ce
&
Pos =3
,
C = C- Cos = ✓

'
a

" Pos = 2
④ ce
-
c =D cos = ✗
'
/
ti
µ
Note : -
All planar molecules have minimum one

plane of Symmetry ( always ) .

So planar

gnactive ( Achiral)
molecules are optically

H "
① c- Bond Angles = 6
In
B. A -
=
109.5°
c
"
Rog Pos 6
o.I.c.tl
=
te
Cos = ✗

H
④
Pos = I
C
Br
Cos = ✗
ce Rog
Br

a
①
Pos = ✗ chiral molecule

C
µ
Cos = ✗ (o A
- - C- I

B.
Br
f
 Br H

④
Br ce ⑤

te ce
te ti
Trans I
cist
✗
Pos = ✗
Pos =

Cos = ✗
Cos = ✗

Cl U
④ Pos =/ Meso compounds

l
cos = ✗ (o -
I C - -

ti 17
Achiral molecule

with chiral atom

a
U

H te

⑦ me
me
④ me
te

te te te me

O' A- c.
Ccésl ( Trans )
(chiral
1
Pos __ ✗
Pos =

Compound )
cos Cos = ✗
= ✗
④ "
" " " -
U
Pos __ 2
sic =c=c
cos ✗
EBS ice
-_

ce

② Cl
" " " -
° Pos = ✗
No chiral
"
c=c=c atom
cos ✗
Eto
☐~ Br
Chiral
molecule

⑨ - A. c)

④ Alternating Axis of Symmetry = Rotation

Reflection axis
of symmetry : -

possesses n fold
of alternating
an
A molecule
-

axis ( Sn) when molecule

of symmetry -

rotated through an
angle of 3[ about

the axis and then

neglected across a

plane perpendicular to the axis ,

an

identical structure is obtained .

 180°
µ
cook

0 a
E - "

te
ce
th ce ,

te COOH
C te
te 00

h H
co
Sz
-

H ce

" ' ' " ' " ' ' ' ' "' " ''

H
↳ cook

Cae
H
ce
te ce

COOH 17

Asymmetric compounds ! -

Compounds in which all

elements
of symmetry
( Except C ,
axis ) do not exist .

Dissy metric Compound ! -

Compound in which Pos ,

Cos and alternating axis of symmetry

are absent -
 #
All Assymetric Compounds are dissy metric but

its reverse is not always true .

(☒ 1 Some Important definitions related to

optical Isomerism : -

A Enantiomers : - ① ftercoisomcrs which are

mirror image of each other but

they are not superimpose on each other .

② Enantiomers are
always optically Active .

③ Enantiomers have identical physical properties

like M.P. , B. P .

, solubility , density etc .

Except direction
of rotation of light -
( PPH

④ Both Enantiomers can rotate the vibrational

plane of PPL with 5am @ magnet dude in

direction
opposite .
⑤ Enantiomers have identical chemical properties

inactive oeeagent but

with optical they have

different chemical properties with optical

Active reagent -

⑥ Enantiomers have different biological

properties in biological system .

a
EE -

c,

Br Br
(Enantiomers )
D ☐
D H H

H
ce ce
te
② (Enantiomers )
ce te te ce

COOH COOH
③
H OH Ho H

cuz CH3
(Lactic Acid )
⑨ Dia stereo mess : -
① Stereoisomers which are

not mirror image of each other and non

super imposable .

② Dia stereo mess

may be optically active and

may not be active .

③ Dia stereoisomers have different physical

properties .
So
they can be separated by
normal physical separation methods .

( like fractional distillation , Recrystallisutiou )

it
E¥
- ① Hi
, = ,
the =,
ie geometrical
\ diastercomers
6 he £ µ

( Trans )
fist

② ce ce
H
a

diaster comers
te te ce te

Cisl Transl
 COOH

[
° "
③
H OH H Oh

H Oh OH H

COOH COOH

( Diastereomers )

② Meso compounds ! -
A Meso compound is a

non -
optically active member of

a set of stereoisomers .

E ① Pos =L
-

chz CH3
Achiral molecule

17 H O -
I C
- .

Chiral atom =L

Meso compound

co -
H

②
H OH
- - - - - -
Meso tartaric Acid .

It 0h

Cook
 me me
Pos = ✓
③
H H Optically Inactive

No chiral atom

No meso

⑦ Racemic mixture = Racemic modification

=
⇐I =
(diet : -

① A mixture which contain equal amount

of

enantiomers .

② A pure Racemic mixture is optically Inactive

due to presence External compensation

of
.

Enantiomeric Excess ( ee ) : -
When Enantiomers

are
present in unequal amount in a mixture ,

then Excess -1 .

of prodominant Enantiomer
is called Enantiomeric Excess . Its value

is equals to value of optical purity for

mixture .
 Id -
el
✗ 100
@ e =

dye

[ ✗]mi×
optical purity =
✗ too

(d) pure

ofdentify [a> mix for given

¥ values of
.

compositions , if G) pure
= -180

¥
•
1. d '
lol e. e- -1 - Racemic [2) mix .

Mixture

65% 35 -
to 304 .
70.1 . +24°

30 -1 . 70-1 .
40 -1 .
Got . -32°

80-1 20^1 Got

.

. . -
40-1 . +48

25 75-1 . 50 -1 . 50T . -
40°
⑤ Resolution ! -
① We know Enantiomers can't

be separated by normal physical separation

methods from a racemic mixture because

enantiomers have identical physical properties .

② Separation method enantiomers from a mixture

of
enantiomers is called Resolution
of
.

③ Enantiomers are also known as Resolvable

compound .

Mechanical Resolution

Biological Resolution

Resolution
Chromatography Resolution

Chemical Method

( )
= Dia stereo manic method
Dia stereo Merrie Resolution ! -

gu this method

Racemic mixture is treated with pure

optical Active compound ( Reactant) form

mixture of diastereomeric products ,

these

diastereomeric products are e- Soluble .

This

isolated diastercorner may be regenerate

and isolate parent enantiomer .

CRI CSI ⑨
)
(
'
'
B A A -13
CA + A + > -
B +

④ ⑨ ⑤ ③
Pure
(Racemic Active
optical mixture of
mix ) .

compound diastercomers

( optically Active mix )

.

/
chemical

B < "→
A +
F" "" " "
R× "
⑨ ⑨
distillation

chemical
A' + B < A '
- B
Rxw
⑤ ⑨
EE:-O
Me
me
H Coote = A

Esterification
Et Ho -

µ
+

Et Et

te Coote = A
'
(pure optical
-1120
Me Active Compound )

Racemic mix .
(B)

me me Et me
o

É
f
11

µ
-

-0 in + te E- o H

Me
Et Et Et

mixture of diastercomers

fractional distillation

me me Et Me
i 0

Bl
f
11
µ
-
C -0 H (A -

te c- o H

Et Me
Et Et
1A '
-
B)
 Hydrolysis Hydrolysis
u u

me Et

Gott ti Gott
ti

Me
Et
+
+
me
me

to -

H
Ho -

Et
Et

molecules :
(E) Three dimensional Representation
-

of

( 3D Projection
-

formula )

④ wedge dash
projection formula .

⑤ Fischer projection formula

② Saw horse Projection formula not applicable

for only one

④ Newmann Projection formula chiral carbon

④ wedge -
dash Projection formula ? -

FÉÉ : -

Bonds side of
on below
> Bond
the plane ~
C
the Plane of paper
µg
of paper fr
(away from

observer )
Bond above

side of the plane

of paper

( towards observer )

for more chiral carbons ! -

As
By qq

Ba

B
(B) Fischer Projection formula : -

Carbon

µ
l
( on plane of
HZ 172
og
paper)

Vt .

Horizontal lines : - Bonds are on above side of

plane of paper .

( Towards observer )

vertical lines : -
Bonds are on below side of

plane of paper
( Away from observer )

① we obtain identical structure by 180 rotation

Fischer formula in plane

of of paper .

② we obtain enantiomeric structure by 90

'

rotation of
formula in the plane of paper .
 ③ we obtain identical configuration on chiral

carbon by even no simultaneous Exchanges

.

of

of group .

④ we
get Inversion of configuration of
chiral carbon
by odd no .

of simultaneous

Exchanges of groups on same chiral carbon .

'

180 Br
Ex : - ① f
=
a
① 7
ce ce
Oceano <
g.
defied
H Br
\ '

¥
Exchanges F Br µom°m•
Enantiomer
(
p
)
"
"
H
Even 290 F
.

"

Enantiomer
's
Einar
☐s
H a
)
H ce
Cfdentical
Br

F
(E) Interconversion 3D Projection formula :
-

of

④ wedge dash Fischer

for one chiral carbon ! -

w
w

= ✗ Y

✗
Bag z

y
z

short trick : -

① Dashed group on vertical line .

② Remaining group
in same sequence on

remaining positions
 F
ce
Ex : -
①
=

I F = a
BB Br
I
Br

② For Two chiral carbons : -

D
Me H
H
age
D me
=

F Br

oooo Br
Cl
F
ce
④ wedge dash ,
Fischer ,
Newmann 's and Saro

Horse : -

'
I
Method .
-

F
Br U F

ce EY Br

ce f
Br
I
=
It
H Ph
Ph

☐
D
BBB
H ph
D 111

H Ph
U - F
•

Br
☐
 Method I : -
Fischer , Newmann 's and saw Horse : -

Et Ph
me me

Ph me Br
Et Ph
= = Et
F Br
Ce F

U F ce
Br

☒
Br

me Et

U
F

Ph

Fou formation of Identical compounds

'

.
-

Interconversion sequence on front sequence on

side carbon back side carbon

same seaeeeuce
① Fischer ← Fischer same sequence

② Fischer ⇐ saw -
11 -
opposite
Horse sequence .
③ Fischer ← new
-
,, -
opposite
manor
sequence

④ Sawhorse → -11 - Same

sequence
sawhorse

⑤ Newmann ← -11 -
-11 -

Newmann

⑥ Sawhorse → -11 -
-11 -

Newmann
 -

Nomenclature chiral
Configurational of

carbons : -

v
v

④ Relative configuration ④ Absolute configuration

( it D -
L Nomenclature (it R, S Nomenclature

Ciii three -

Erythro

④ is D -
L Nomenclature : -
This nomenclature

is applicable for carbohydrates ,

amino acids

and their derivatives .

Carbohydrates : -

Polyhydroxy carbonyl compounds .

Amino Acid : -
✗ -
Amino Carboxylic Acid

For Identification D L nomenclature draw

of
-

Fischer formula
of given compound in which

first carbon ( most oxidised carbon ) present on

 top of vertical line and last carbon on

bottom of vertical line . then compare with

eeeference compound .

Reference Compounds

For Carbohydrates For Amino Acids

CHO CHO COOH COOH

HO H H
H OH H Nhz Nhz

Chz -0h CHZ-0h

CHz- 0h chz -
oh

L C l D # Serine < c- ) Serine

H
- - -

D - -

Glyceraldehyde
Glyceraldehyde

For Carbohydrates : when OH Highest

groups of
-
-

numbered chiral carbon is

present on RHS then

configuration will be

☐ series .

LHS the L Series .

For Amino Acids : -
when -

Ntez group of d- position

of
-
Cooh group present on

Rhs ☐ series

LHS L -11 -

CHO
H

EE -

① 3 2
"
CHO H
cuz Ho
10h
OH
OH
CHZ -

L -
series

'
CHO

t
②
D- series
H OH

3
( D -

Erythrose)
µ OH

( 2D 3D ) 2,314 -

Tsihydroxye
,

YCHZ -0h
butanol
 Éteo
OH
③

①
"
"
↳ °
" ° "

4 3
I
H
9h2 H
3
OH
OH
OH
↳
cuz →H

(D -
series )

th roose)
(D -

(2L ,
3D / 2,314 - Tri hydroxy
butane

co - H Coote

|
⑨ ⑤
Han te
te
Hzw

CHZ -

Ph
0h
H

L -
Series ( Amino Acid )
OH
Chz
-

C- Phenylalanine C- Amino acid

C- Threonine

OH COOH

⑥
te COOH I 0h te

CH z Ctiz 4- Lactic Acid )

 COOH Cooh
⑦ D L Nomenclature

I
-

H OH Ho -
te
=
is not applicable
H OH HO -

H
for similar Ends

Coon Coote
containing compounds

⑧ Cooh COOH COOH

I OH =
CHZ Ho -

te
Boop OH

CH3 H
H CH
}

2- Lactic Acid

COOH
COOH
⑨
te •

MHz 17
Mhz

H OH
Ho
••-CHz -04
CHZOH
te

( 2- Amino Acid )
 CHO
Cho
④
H
OH H OH

=
Ho te

te 0h
CHZOH
CHz- Oh

C-
carbohydrate

⑨ Ii , Turco -

Erythro Nomenclature :
-

This nomenclature is applicable for 2 chiral

carbon containing compounds in which at

least 2- 2 groups should be same both

of
chiral carbon .

a a a

l f- l
C b C b C b

C b b C d b

a a a

Erythro three Erythno

 Cuz
CH3

Ph

H
f-
0h

OH 4/-04
to

Czts
te

CH3
Three o

Erythro

④ Absolute Configuration : -

(it R -
S Nomenclature : -

R = Rectus =
Right

S = Sinister = left

For Identification of R S Nomenclature

of
-

chiral carbon give priority order four

, of
chiral
different groups of carbon according
to CIP Sequence rule and visualise the

molecule in such a
way that the lowest

is directed away from

priority group ( 4th group )
 the observer and remaining three ( 1 , 2,3 )

groups are
facing towards observer .

off rotation of 1 → 2-33

group ① = R

( clockwise)

off rotation of 1 → 2-33

group A = S

( Anticlockwise)

④
F
Ex : -
①
②

①
= ③ = R
Br ce

I ①

Short trick for R ,

S -
Nomenclature : -

① Draw Fischer projection formula of given

compound .
② Give priority order of
four groups chiral
of

carbon according to CIP Sequence rule .

③ when 4th group is vertical line

present on

and rotation
of
1 → 2 → 3 A = R

I → 2 → 3 G = s

④ when 4th priority group on Horizontal

line and

I → 2 → 3 2 = s

1- 2- 3 G = R

③
CHBRZ
EE : -

H % = s

④
CI
}
②
ii
② C - H

②
H OH =
R
④ ①

③ CHZOH
 ÉHO ② ②

④
R
④ @ ① ⑨
@ ①

H OH ③
z ③
R
H OH
3

ychz OH

Tri hydroxy butane

(2R,3R ) 2,314 -

4h2
-
OH
CHO
⑤ c=o

|
H OH ④ Ho te ④

|
OH H ④ H OH yR☐
on
H OH ④ µ

µ OH
⑤ CHZ -04

ctk -04 D- Fructose )

(
( D-Glucose)
2

COOH
Ph

|
⑥
" ph
= ? 3
(R )
qq.ie
cook OH H
 ② a
" Homem "
⑦ COOH ④
1- ① COOH
③ >
<
3 S
2 R Ho te
H OH

3 S R
HO te
te OH ③ z

④ 1- ①
②
↳ COOH COOH
,

(R> s ) (2R ,
3s ) ( ZR ,3S)
Trans)
(Cis >

Z>
E)
(

Examples of
chiral centres : -

( other than

carbon )

H O

②
EI : -
① ④
p
sp
?

D D
Et OH µ
me

Pos = ✗ Pos = ✗

Cos ✗
Cos = ✗ =

(o -
A -
c.) 6. A- c.)
 • •
OH
③ ⑨ Sp3
As
si
Bo
Et F a
CH3 CD3
Pos _- ✗
Pos _- ✗ ✗
cos =

Cos =
✗
G. A- c.)
@ -
A. c- I

0
⑤ ⑥
↳
Y
- - - -

, pos=✗
I
'
s M 1 Cos -_ ✗

% I
ce35
1
( O .A -
c- I

Ly - - - CI
637

POS -- ✗ ↳
Cos =
✗

(o
-
A - -
c.)
Umbrella 9 nuevsion : -

• • • •
• •

N c
-0 0+0
B£
"" "
"1 ""
Rob
'

pyramidal Pyramidal pyramidal

when N, C and O have three different groups

with one lone pair this type of structures

are optically 9. native ( at eeoom temp / . .

Gt

9hVersion inversion
is due to umbrella , By this

above species form racemic mix .

"
Umbrella H
,
: N D
D 111 111 N ! -
11111111

gnuevsion
Egg BATCH }
113C 50^1 . 504 .

⑨
(A1 )
#
loot . Racemic mix .
( optically 9h active

mixture )
 # Umbrella 9h version not possible for 3rd and

Higher period Elements at room temp .

# when Asymmetric nitrogen is present in

small rings ( upto 5 membered ring )

then Umbrella Inversion not possible due to

in gentes mediate ( T.si

thigh angle strain .

So Such type of compounds are

optically
active .

Active
Examples of optical compounds

without chiral atom : -

(A) Cumueenes = Allenes : -

← 1 Terminal
☐ I •
. G. I .

N ,Y groups
Ex : -
① z
=
soak
c=c=c
1- Pos-_ ✗ ✓ ✓

y ,

y cos -_×
 Gn same
② "
✓
\c=c=c=c→Bok Plane ✗

' "'" ✓
" Pos __
y y

Conditions for optical Activity in cumueenes

it Terminal R #y

(Iit Even no .
of c=c double Bond .

④ Spiro compounds : -

②
'
O'I
1=91 -
G.I.

K Pos ✗ ✓ ✗
1- -_

E① n
'
N
Cos __ ✗
EE
y y

9h
✗ ✓
same
② %, nun
Hi plane
y
.

M→Gy pos=✓
② IÉY :
-

CH } -
Alkyl

Chz -

CHI Alkylidene

K
Ex : -

① K
,,
= ,
c @ 1=91 Pos -_ ✗
BA
y y cos -_ ✗

@ -
A - C- )

②
K
&
/ Pos __ ✓
C= c
y \y ( o I C- )
-
-

④ ortho substituted biphenyl ( Ph -

Ph ) : -

EE: -
①

a
 N
n

be -1kg 72.9 A°
②
No free rotation

Y &
( Restricted Rotation 1
y
@ 1=9+-4+-13 f- Fete ) .

][
Pos -_ ×
o.A.cl
Cos = ✗

( Atrop isomerism I

Br
Br
③
No free rotation

Pos = ✓

Br
& (o . I. c.)
Br

Br
Br
④ Pos = ✗

Cos = ✗

( o -
A -

c.)
Br B
COOH Coon
By
# Short trick for Identification of

Meso compounds : -

For Fischer formula : -

a
n

EE : -
① ②

C b z
① y

c b k
@ 2

a
y
[Meso ) (Meso )

For Sawhorse and Newmann : -

n
a

y
2
⑨y a
b

② b
z
c
z

C
cresol (meso)
 Calculation of Number of Stereoisomers : -

no optical no -
of optical
M no stereo centres
.
of
= .

of
ActiveIsomers gnuctiue Isomers

for dissimilar Ends In Zero

② For Similar Ends In -1 21--1

n = Even no .

③ For Similar Ends 2h

-1
- z
2¥
n= odd no .

with Psuedo stereo

centres

In 2m¥
'
⑨ For
-

Similar Ends

N = odd no .

without Psueclo

stereo centre
 Br

EE:-(i , ① Dissimilar Ends

② 21=2

③ no -

of 0 A I. - -
= 22=4
a
⑨ no .
Of 0 -
I. I .
= 0

⑤ no -

of Enantiomeric pair = 2

⑥ fractional distillations
no
of fractions on

all mixture of stereoisomers

of
= 2

ce Br

cii , ① dissimilar Ends

② n =3

Cl A 23=8
③ no
of 0 I. =
-
-
.

No
⑨ .
of 0 - I - I . = 0

⑤ pair of Enantiomers =
4

⑥ no .
of fractions on
=
y
fractional distillation
 ce
Similar Ends
Ciii , ①

2
② n=

③ no .
of 0 . A. I. = 2h -1--22-1=2
ce

⑨ no -

of 0 -
I - I -
= 2¥ -1--2%-1--20=1
( Meso )

⑤ Total no .
of stereoisomers =3

⑥ no .
of pair of Enantiomer = I

⑦ fractions on fractional distillation

no .

of
= 2

(d) e) ( meso )

ce ce

Civ , I

ce

(E) CH } Ch
GH
- =
CH - -
CH
}

Br