STEREOCHEMISTRY

complete notes
by
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STEREOCHEMISTRY
1. General description of stereochemistry.
2. Basic terminology of stereochemistry.
3. Conventions for configurations R– S system.
4. Stereoisomers and interconversion between
i) Enantiomers, (ii) Diasteceoisomers (iii) Homomers.
5. Representation of three Dimensional molecules and interconversion

m
i) Fischer Profections representations.
ii) Flying wedge representation

co
iii) Sowhore representtions
iv) Newmann projection representations.

C.
6. Symmetry element

B
7. Stereoisomerism resulting from more than one stereogenic unit
i) Threo and erythro Nomenclature. yA
ii) Meso and d-l pair system.
iii) Conventions for configuration D and L pair.
tr
8. Chirality
i) Allenes
is

ii) Spirans
m

iii) Atropisomers
iv) Helicity
he

9. Geometrical Isomerism
10. Topicity / Prochirality
.C

i) Enantiotopic.
w

ii) Diastereotopic
iii) Homotopic
w

 Cram’s rule
 Anti Cram’s rule
w

 Prelog’s rule
11. Conformations –
i) Conformation in acyclic system
Ethene , n-propane, n Butane
ii) Conformations of cyclic system
Cyclo propane
Cyclo Butane

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Cyclo pentone
Cyclo hexane
iii) Conformation of cyclohexane derivatvery:-
iv) Factor affeeting the cyclohexane derivatues:-
12. Deealins system and its stability:-
13. Perhydro phenanthrenes and its stability:-
14. Conformation of perbydroanthracenes:-
 Specific rotation and

m
15. General Description of
Stereoselectivity Enantiomeric erces

co
Stereospecipicity
Regioseleitivity

C.
Chemo selectivity
16. Questions for practice

B
17. NET / JRF preleions year Questions.
18. GATE Preleious year Questions.
yA
Stereochemistry
Stereo  Spatial arrangement / 3 D arrangement of atoms or group. It involves
tr
the study of relative 3D arrangement of atoms or go.
is

CH3
CH3

H
m

C HO C
OH
C2H5
H C2H5
he

. 2 D arcengmen
3 d Arrengment / Spatialarrergrrent

ISOMERISM  In Which Different having the same molecule formula

.C

ISOMERS
w

Structural /Constitutional Isomers Ste reoisomers

w

.
Dif f erent sequence of Bonding But redatiue arrengrrent of atoms will be dif f ernt
of their atoms.
Ex.
w

CH3 CH3
H
C C
CH2CH3 OH
H CH3 CH2
OH
- - -
(s) (+) 2 Butanol (R) ( ) 2 Butano

Types of Constitutional isomers

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i) Chain isomerism
ii) Position isomerism
iii) Metamerism
iv) Tautomerism
v) Valenee isomerism
vi) Functional group isomeridm
Stereoisomers

m
Conformational

co
Isomer Configurational
or Isomers

Rotomers

C.
Enantiomers Diastereomers

B
Enantiomers Diastereomers

 Conformational Isomers. yA
Different shapes of molecule by rotation around single bond.
zz
tr
(I) and (II) are not mirrop image to each other so they are conformational
Diastereaisomers.
is

CH3 CH3 CH3 H

m

H H CH3
H (II)
(I)
he

- -
cis 2- Butene
- Trans 2 Butene
.
Diastereomers

Configurational
.C

CH3
CH3
D
w

C
D C
CH2 CH3
HO
CH3 CH2 OH
w

.
There two are enantiomens
w

CH3
CH3 H CH3 CH3 CN R H
C C
H OH H CN
CH3 CH2 CH3 CH2 H H

.
Configurational Diastereoisomers

Some terminology 
Optical activity

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Those compound which rotate the plane polarized light either left Secretion or
right section known as optical active compound and this process as optical
activity.
 Symmetric atoms archival
Compound having minimum any one symmetry.
Object or molecule which are super imposable on their mirror image.
H Br
Cl H Cl
H Cl
H

m
H H H
σ + nt Cl H

co
Plane of symmetry . Br
Atternate axis of Symmetry
i + nt
cantce of symmetry

C.
No any symmetry + nt in the molecule.
CH3

B
CN OH
Cl
C R
C2H5 H
re
H yA
c con t
e tr i
symm COOH
tr
A
H
* OH
Plane of symmetry
is

H
* OH
m

COOH
Assymmetric contre
.
Achiral molecule with two asymmetric contre
he
.C
w
w
w

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Chiral centre
Compound, central atom attached with four different groups and no any symmetry +
not on atom.
OH Chiral centre H Chiral centre
OH
Br H3C C
C
CH3 CH3
Cl H H

achiral centre

m
Stereogenic Centre Stereocentre.
 A stereagenic centre is an atoms having groups of such nature that

co
interchanges of any two groups will produs stereo isomers.
Ex:-

C.
CHO
CHO
H C OH HO C H

B
CH2OH CH2OH
-
D Glyceraldehyde -
yA
L Glyceraldehyde
.
(R)
(S)
tr
A carbon atom that is a steneocenter is also called steneogenic carbon.
R and S Designation from three dimensional Drawing
is

R  Rectus = clockwise
m

S  Sinister = Anticlockwise
Acc. to cip rule (Cohn ingold Grelog’s rule)
he

1) Assign the priority of group attached to stereo cent follow the order of
degreasing atomic number.
.C

2) Lowest priority substituent must be away from obseruen

3) Rotate eyes in the decreasing order of priority
w

 Clockwise –R
 Anticlockwise –S
w

Sequence rule-
w

1) Assign the priority of group Acc. to atomic number of atom directly attached
to the centre atom. Heauer atoms should be assign the highest priority.
(2)
I, Br, Cl, F F
H (4)
(1) (2) (3) (4) C
CH3 3
Cl ( )
1
( )

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2) If isotopes of an elements are +nt assign the priority according to mass

numbers.
1 2 3
1H 1H 1H (3) (2)
D T
(3) (2) (1)
C
37 H CH3
35
17H (4) (1)
17H
(3) (1)

3) It atoms are attached to central atom, then go for the near heaceir atom,

m
(1) CH3 Br
(4) Br
H (2)
CH3 OCH C

co
C Br
C
CH3 CH2 CH CH3 (3)
CH2 I

C.
OH (2) (1)

(1)

B
NO2 HO (4)
H
(2) yA
CH2 CH NH2
(2)
C
OH (3)
CH2 CH CH3
CH3
tr
(1) H

4) If atom attached to double or triple bond, they should be considered as

is

duplicates and triplicates.

CH3 CH3
m

(1)C CH2
C CH
CH3 (4)
C H3C C
he

CH3 C C
CH3 CH2 (3) 2 C CH3
( ) CH3 CH2 OH
CH3
H CH3
.C

C C
C C
w

C C
w

 Double bonded attached carbon Count will be double carbon.

C C
w

CH3 C C H CH3 C C

C C

 Triple bonded Carbon atom count triple carbon.

C C
(3)
CH3 (1) C C H
C C H
C
C C C
CH2 CH3
(4)
H (2)

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O O C C
CH
(4) H
5) C C O CH2 C
H Br
HO CH3 (1)
(3)
(4)

6) Lone pain should be taken as lower priority of subs his

(4)

N (2)
(3)

m
CH3
H
CH2 CH
(1) 3

co
(R)

7) If lowest priority group present on herizentas position, rotation of substituent

will be opposite direction.

C.
(2)COOH

B
(3)
H D
(4)
OH 'S'
yA
(1)

In that care fourth clowej priority group +nt on horizontal position, direction
tr
of rotation taken opposition.
Rotation arice ‘R’ But actual contusion is ‘S’.
is

8) If open chain and ring having identical atom then prefer gives to ring always.
m

2
(3) O
he

(4)
1
O (4)
O (2)
(1) 3
'R'
.C

lowest Priority on hozizontal positoin So 'R'

4 O
3
w

O
O 2 2
1
w

'S' 1
3
w

1
O OH Cl O
O Br
3 4 3 4
2 2

Br 'R'
'S' NO2
'S'

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In fuced ring system, assign the configuration Acc. To above or below the plane
of group. Firstly pertinence the group attael to stereagenic centre then follow as
trick.
1 2 3 4 (+) = as it is
Above the plane (+) (-) (+) (-) (-) = opposite
Below the plane (-) (+) (-) (+)
.
Q
N N
NO2 Br NO2 Br
B CA = S
CB = R

m
H H H H

co
.
Q
Br
Br

C.
CA = R
B
OH C A CB = R
H OH CC = R

B
O H
O H O
yA
In this case view from the cavity, so carbons towards the observer and endo bond
away from the obscure.
O CH3
(1) (2) H3C CH3
tr
C H (2) (2)
H OH (1)
is

(4) H C C C C H
CH2OH (3) (1)
(3) (4)
m

(S)
H3C CH3
CH3
(3)
he

H3C CH3
(4)
4
C ( ) CHO (4)
(3)
N C C C H NH2OC COOH
(1) (3) (2)
.C

COOR
(2) (S) (1) (S)
w
w

(5) NHR
(6) CH3 CH2 CH2 CH2 CH3
O C (3) 3
( )
O
w

HS C NR2 C N
HO
(2) (1) (2)
C H (S) (S)
(4) (4) CH2 CH3
O
(7)
H OH O
(8)

H
(R)
(R)

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(9) O
CH3 (10) H CH3
NH2
I
II

H
(R) Is , II R (R)

H
(11) Me H (12) (13) H
(14) H
I I
II
II II
(R) H H I

m
IS, IIS IS, II S
[ ] H
IR, IIS

co
(15)
(16) H H
Cl OH HO
H Cl Br

C.
5 3 1 II II
7
6 4 2
8 III III
H
Br Cl

B
H
IR, IIR, IIIS
Is , II S III R
yA
(17) (18) H3C HO CH3
H H OH
Me
tr

HOOC OH
is

COOH H
HO H
'R'
m

'S'

(17) HO
he

H H3C CH3
H OH
Me

HOOC OH H
.C

HO COOH H
'S' 'R'
(19)
w

H3C (20) CH3

CH3 H3C H
w

I I 3 4
O
O
II II 2 1
w

CH3 H3C H3C

CH3 H H
OH
H3C OH H3C H3C CH3 CH3
H3C
IS, IIS IR, IIR

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(21) (22)
CH3 CH3 (23) CH3

HO H
HO
HO
H3C CH3 H3C CH3
Isomenthol
Neomenthol Neoiso menshol
, , , ,
(1S RS 5S) (1R 2R 5R)
(24)

m
CH3 CH3
H

co
H

HO OH
HO H

C.
H3C CH3 H3C CH3

Menther I R, 2S, 5R

B
CH3
(25) H Br

I
H
yA I
H
II III II III
H Cl H NO2
tr
O2N Cl
IR, IIR , III R IS, IIS, IIIS
is

(26)
(27)
m

NH3 NH3
Br Br Cl
CH3 Cl
he

H H H
H
.C

Cl
Cl
CS'
CR'
w

(28) Br
Br (29) HO H
H OH
w

Br H H Br
H OH
OH H
H IR, IIR
w

H IS, IIS IS, IIS

IR, IIR

(30) H
H
O O

H
H
IR, IIS

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(31)
H3C CH3 (32)
CH3 H
H CH3 H
H
O I I
O I O II
I
II II
II
H
H
H H IS, IIR
IR, IIS
IS, IIS IS, IIS

(32) H (33)
H H
H
I O

m
I
II II
H

co
H H
H O
IR, IIS IS, IIR IS, IIR
IR, IIS

C.
CH3 CH3
(34) H3C
H H CH3

B
I I
II III III II
OH yA
OH
H H H
H H
IS, IIS, IIIS
IR, IIR, IIIR
tr
(35) (36) CHO
CHO
CHO S
HO OH
H
is

OH
H OH R
H OH
HO OH
H OH S H
m

HO
H OH
H OH S H
HO
H OH
he

CH2OH CH2OH
CH2OH -
- L glucocl
D glucecl
(36)
.C

OH

O OH
w

H (5)
H
(6)
(4) OH H
w

HO
(3) (2) H
H OH
w

1R , IIR , IIIS, IV S, V R
( )

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Symmetry with molecular f ormula

Yes No

Homomers Isomers
some bonding Coonnectivity

Yes No

Stereoisomers Constitutional isomer

(Onisometric)

m
object and mirror
image

co
No
Yes
Diastereomers
Enantiomers
(anicometric)

C.
(Isometric) Energy barrier
Energy barrier

B
High low
High low yAConf igurational Conf ormational
Conf igurational Conf ormational Diastereomer
Diasteceomers
Enantiomers Enantiomers
tr
Enantiomers 
is

Enantiomers are structures that are Non – sperimposable. But they are mirror image to
each other.
m

Br Br * A pair Enontiomers are mirror image f orm of some

compound and have opposite absolute Steceochemistry.
Cl Cl F
he

F
* The physical and chemical Properties of enantiomers are
.
I I identical
A
( ) (B)
.C
w

 These structure (A) and (B) mirror image to each other but they are Non
sperimposable to each other. So they are enantiomers.
w

mirror me = CH
3
CN -
HO CN OH Et = CH2 CH3
w

Et Me Me Et

.
Enantiomers
mirror

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mirror

H H
H H
C O O C
C O O C
H C OH HO C H
H C OH HO C H
HO C H H C OH
CH2OH CH2OH
- C HO C H
D Glycoraldehyde -
L Glyceraldehyde
H OH

H C OH H C OH

Enantiomers CH2OH
mirror CH2OH
-

m
- ucos L Glucos
D Gl

co
Enantiomers,

COOH COOH

C.
H C OH HO C H
HO C H H C OH

B
COOH COOH

(Tartaric acid)
(Apair of Enantiomers)
yA
Diastereaisomers:-
tr
Diastereaisomers are stereoisomers that are not mirror image to each other.
OR Stereoisomers other than enantiomers.
is

* Two chastreoisomers are dif f erent Compound and have

m

Br CH3 CH3
Br .
dif f eretn relative stereochemistry
* The physical and chemical proporties of diastereoisomers
he

HO D HO D .
dif f er
* Diastereoicomers may be chiral or achiral.
.
Diastereoisomers
.C

Me Me Me H
w

H H H Me
- -
w

cis 2 Butene - -
Trans 2 Butene

.
Diastereoisomers
w

Note Steneocenter is not necessary condition for dastercoiom

HOOC H H H

COOH HOOC COOH

H
(f umaric acid) (maleic acid)
(Trans) (cis)
Butanedioic acid

.
Diastereoisomers

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Ar CO2Me Ar CO2Me

O
O
Trans eposide Cis eposide

.
Diastereoisomers
OH
OH

m
Pair of achrial
Plone of

co
.
symmetry. Diastoreoisomers

C.
.
Diastereoisomers

Note:- Conversion of enantiomers and Diastereaisomers.

B
 One enantiomers convert into another enantiomers, both stereagenic canter are
inverted. yA
 One Diastereaisomers convert into another Diastereaisomers only one of the
two is inverted.
tr
Ar CO2Me
Ar CO2Me
S R
is

S R
O
O
enantiomers Diastereoicomers
m

enantiomers

Ar CO2Me
Ar
he

CO2Me
R S RS
RR R R
O
Enantiormers

Diasteroisomers O
Enantiomers
.C
w

SR
SS
w

Homomers
Homo  same or identical.
w

A molecule having more orientation which looks different at first sight but having
some configuration.
B A H B D
E
E D Br
D A c B
(a) (b) ( )

Homomers

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Br
H Br

H Br
H c
(a) (b) ( )

Homomers

Note:- A given compound / molecule can have only one enantiomers, all other
steneomers will be Diastereomers.
Hybridisation

m
Intermixing of atomic orbital to give hybrid orbital of similar size, shape and
energy.

co
For carbon atom for, (CH4 molecule)
CG.S. = 1s 2 , 2s 2 , 2 p 2

C.
6

6 CE.S. = 1s 2 , 2s1 , 2 p3

B
H H H H yA
Sp3
tr
H Sp3 H
090 280
methane
is

C
H H H
H
H H
m

No of
Hybridisation S% geometry anle f igure
P% Covalent bond
he

Sp3 75 4 Tedrahedral A
25 1090 280
Sp2 33 66 3 Trgonal planner E
1200 D
.C

2 C
Sp 50 50 Linear
w

1800 A C 1

Note:- More S character, more bond angle stronger bon N = No. of sigma bond
w

around central atom + No. of localism lave Pair / we charge.

-
Ex: H3C CH CH C C H
w

Sp2 Sp2 Sp Sp
Sp3
O O O
O
C CH3 C CH2 C O H
C N
H R C
R
Sp3 Sp2 Sp3 Sp2
Sp2 Sp2
Sp

Representation of three Dimensional molecules 

1) Fischer Projections representation.

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2) Flying wedge / wedge representation

3) Sawhorse representation
4) Newman projection representation.
1) Fischer Projections representations 
Fischer represent two Dimensional plane Projection formulas.
In sischer projections uses a cross to represent the Stereocetne horizontal lines
represent the Bond points towards observer. Vertical lines represent the bond
point away from observer.

m
CH2OH CH2OH

OH H C OH
H

co
CH3 CH3

C.
e
tc
cen
eo
er Cl Vertical lines (Below plane, aways f rom observer)
St

B
Me OH yA
Br Horizontal line (above the plane, towards obsorcer)
tr
Cl
is

Me C OH
m

Br

Rule
he

1) Odd no. (1, 3, 5, 7) of inter change to give, 1800 rotator out of plane and 900
rotation with in plane to give enantiomers.
.C

Cl Cl
Br I
F Br F I
w

I Br

Cl
w

1800 rotation out of plane Enantiomers

Br F
w

I
900 rotation out in plane F

I Cl

Br

ii) Even number of interchage (2, 4, 6) or 1800 rotation with in plane to give
Homomer / same molecule.

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Cl Cl F
Br F Cl
I
F Br F I Cl I

I Br Br

(A) (B) (C)

A/ C Identical / Homomer
A/ B Enantiomers
A/ C Enantiomers

m
iii) 900 rotation with in plane is not allowed beas above and below plane atom
will be exchanged.

co
Cl F

900
F Br I Cl
A / B Enantiomens

C.
I Br
(A) (B)

B
iv) 1800 rotation with in plane is allowed.

F
Cl

Br
1800
Br
IyA F

I Cl
tr
(A) (B)
- .
A/ B Some / identical
is

v) 1800 rotation out of plane will not allowed, they will give enantiomers.
Cl Cl
m

Br F
F Br Br F
he

I I
(A) (B)
.
A/ B Enantiomers
.C

2) Flying – wedge Representation 

In flying wedge representation, bonds are free to rotate. Solid wedge
w

represent the bonds above the plane (towards) observer) Broken wedge
Below the plane / (away from observer) continuous lines (—) bonds with in
w

plane.
X
w

X
Y
C B X
A B A
C

y A B
Y
Fischer projections .
Flying wedge

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X
Y
C B X
A
C
A B
Y
.
Flying wedge

OH OH
H OH
CH3 CH2 CH3 CH3 CH2 C
C CH3
CH3 CH2 CH3
H
H

m
OR
HO

co
H H
C Rotate OH
C
CH3 CH3 CH2
CH3 CH2 CH3

C.
Me Me
COOH
C NH2 H

B
NH2 H
COOH
f lying wedge yAf ischer

Compound with two chiral centre

A
tr
to wards aboeruev
x y Above x y
y' y1 x
the x1 y
is

x y plane x
A
B B B A
m

with in plane
Flying usedge
f ischer f rond sido
(towards obceruen)
he

CH3
Cl Br H Cl
Cl OH Br H OH OH
.C

Br H
C2H5 CH3 C2H5 CH3
C2H5 f lying wedge
w

f ischer

COOH
w

Cl HO Br Cl
Cl OH HO Br OH OH
w

HO Br CH3 COOH
CH3 COOH
CH3 f lying wedge
f ischer

Note Fischer only represent deiced conformation.

[3] “Sowhorcl” Representation
 In Sowhorcl Representation bond between two carbons is diagonally and
slightly elongated. Which can depleted in elopes or in staggered
conformations. Ex ethane.

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H H
H
H H
H H
H
H
H H (Sawhorcl
staggered)
(Sawhorcl edipced)

C2H5
HO Br H HO
HO H Br Cl OH H

Br Cl
CH3 C2H5 CH3 C2H5

m
CH3
'Sawhorcl' eclipced flying wedge
( )
fischer

co
Br Cl C2H5 Br Cl C2H5

OH
H OH H
CH3

C.
CH3

(Sewhave staggened) slying usedge

B
Newman Projection:-
In Newman projection, molecule is viewed along the bond joining the two carbon yA
atom, front carbon is shown by three in (y) shape, and back carbon is shown by
circle with three bond pointing out from it.
H H
tr
H H H H
H H

H H
is

H H
eeliped Newman projection
sawhorde
m

H H H
H H H
H
he

H
H H H H H
CH3 H OH
Br H H Br H OH
OH
Br
.C

H OH H H

H Br CH3 CH3 CH3

CH3 H CH CH3
3
w

CH3

COOH
COOH
w

OH COOH OH
H COOH
H
HO H H OH
H OH HO
H
w

H
COOH COOH

COOH
COOH
HO H COOH COOH H
HO
H OH H
HO H H OH
HO
COOH COOH

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Interconvession of fisher- sawhorse – Newman and flying wedge

CHO D
Br Cl Br
HO D Cl
HO D
HO
Br Cl CHO
C2H5 CHO
C2H5
C2H5 (Eclipced) Mewmann
Fischer Sawhorse

CHO 1
y
Br
Cl Cl x1 y x y x1
y1
Br CHO x

m
OH B
OH D A
D
C2H5 C2H5
Wedge representation B A

co
Staggened Mewmann Mewmann
Sawharcl

Newnann to fisher

C.
CH3
OH
HO HO NO2 NO 2 OH NO2

B
NO2 OH
NO2
HO NO

C2H5
CH3 C2H5
yA CH3
C2H5

Staggered Newmann to eclipsed

tr
COOH
COOH 1800 Br
Br Br H
H H Br
is

Br H COOH Br H
H
m

COOH COOH COOH

H
he

Br
Me Cl H ? ?
? ?
.C

COOH COOH Me
Flying wedge f iscter
w

rotation
w

OH H
CO
COOH Br Br
w

Cl HOOC

Cl COOH
Me H
Flying wedge Me
Fiseher

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OH CHO
H Br
NO2

Cl D Cl
CHO CHO
Staggered Newmann Fiseter

H Br Cl Br
D H CHO
CHO 1800 rodution out of H Br

m
H
plane Cl
CHO CHO D
Cl D

co
CHO
eclipsedmewmann
Staggered Newmann

Relationship between diff molecule/ compound

C.
Enantiomers / Diastereaisomers / Homomers
(B) (C)
(A)

B
OH OH
Me
Br H H yA Br
H Br

Me Me
OH
tr
Me
Me A/ B = ?
H Br
Br H A/ C = ?
is

B/C=?
OH OH
(B)
m

(A)
Enontiomers

A/B are enantiomers because they are mirror image and non super imposable to
he

each other.
A /C
.C

Me

H Br (A) A/ C = Enantiomer
w

OH
mirror (Bothom side)
w

OH
Br (C)
w

H
Me
- Me OH
B/C Me
Br H OH Me Br
Br H H Br H

OH Me
OH
(B)

Even number of interchange to give Homomers

B/C = Homomer.

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CH3 CH3 OH
CN HO OH
NO2 CH3

NO2 Cl
CH3 NO2 NC NO2
HO CN
(A) (C) (D)
(B)
-
A / B Enontiomer
- omomer
A/C H
-
B/C Enontiomer
-
B/D Homomer

m
(A) NO2 (B) NO2
+S +R
HO CH3 CH3 OH

co
CN CN
.
Enantiomers

C.
A/C

NO2 NO2

B
HO CH3 HO CH3

CN CN
yA
(A) (C)

A/C Identical / Homomer

tr
is

B/C
mirror
NO2
m

NO2

CH3 OH HO CH3
he

CN CN
(B) (C)
Enantiomer
.C

NO2 CN
w

CH3 OH HO CH3 (Homomer due to 2 interdarnge)

NO2
w

CN
(B) (D)
w

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H
Q H NO2 NO2 F
F NO2
CH3
F CH3 H
CH3
(A) (B)
- (C)
A/C Homomer

A/C = Homomer
A/B = Homomer
B/C = Homomer

m
A/C

co
H H
-
F NO2 F NO2 A/ C Homomer

C.
CH3 CH3
(A) (C)

B
A/B
H F

F
*
R
NO2 NO2
*R H
yA A/B = Homomer
due to 2 interction
(A) CH3 (B)
CH3
tr
F H
is

F
m

F
R NO2 H
H NO2 NO2 H
he

CH3 CH3
(B)
F
.C

B/C H

NO2
*R H F
*R NO2 B /C = Homomers
w

CH3 CH3 (C)

(B)
w

H H
F NO2
w

NO2 F F NO2

CH3 CH3

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Two chiral centre

Br H Br H
COOH COOH
HOOC OH HOOC
H HO H

(A) (B)
rotation rotation

Br H H Br H OH
HO H

COOH COOH COOH

COOH

m
COOH
COOH
S
R H H

co
HO H
Br S H
Br R
H

COOH

C.
COOH
(B)
(A) - nan omers.
t
A/ B E i

B
D Cl HO CN
D Cl Cl D HO CN
CN OH

F C2H5 F
yA C2H5
F C2H5

(A) (B) (C)

A/ B = Enantiomers
tr
A/C = Diastereoicomers
B/C = Diastereoicomers
is

mirror
C2H5
C2H5
m

S A/B mirror image / non suprium Enantiomer

HO CN
CN OH
Cl S D
D
he

Cl
F
F
(B)
(A)
.C

A/C C2H5 B/C C2H5

C2H5 C2H5
S S
HO CN HO CN
NC OH HO CN
w

D S Cl D S
D Cl
Cl Cl D
F F
F F
w

(C)
(A) - (B)
A/C Diasteneoisomens -
B/C Diasteneoisomens
w

O NC CN
NC CN
OH
HO O
HO OH
(A) (B)
1800 rotation with in plane

A/ B = Homomers

Symmetry element

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A symmetry element is geometrical entities such as alin a plane or a point with

respect to which one or more symmer operation may be carried out.
Symmetry operations 
A Symmetry operations is the monument of a molecule about symmetry element
in such a manner that the resulting configuration of the molecule is
indistinguishable from the airing molecule. The molecule may assume an
equivalent configured or on identical configuration.
Symmetry element
a) Axis of symmetry (Cn)

m
b) Plone of symmetry ( σ )

co
c) Centre of symmetry (i)
d) Alternate axis of symmetry (Rotation – Reflection axis (Sn)

C.
a) Axis of symmetry An imaginarge axis passing through the molecule,
rotation on which by O0 gives an equivalent orientation of molecule.

B
1800 O
1800

H1
H2
yA H1
H1 H2

H2

360
tr
Order of axis = Cn =
Q
is

360
Ex:- = 2= C2 axis
180
m

Axis of Symmetry
he

Principal axis Subsidiary axis

.C

(Axis of highest order) (axis other than principle axis)

- F1
Ex: BF3 - F3
w

B
F2
w

In BF3 one C3 axis passing through B atom which is perbeding to the

molecule plane.
w

F1 F3 F2 F1
C3 1 2
B C3 C33
B B
F2 B
F1 F3
F3 F2
F1 F2
Identice

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BF3 molecule has also 3C2 axis

1) Passing through B –F1 bond and interchange F2/ F1
2) Passing through B-F2 bond and interchange F1/ F3
3) Passing through B – F3 bond and interchange F1 / F2

F1 F1
-
C2(B F1)
B B
F3
F2

m
F3 F2
F3
F1

co
-
C2(B F2)
B
B
F2
F2

C.
F1
F3

B
F1 F2
-
C2(B F2) yA
B B
F2 F1
F3 F3
tr
4) Plane of symmetry it is an imaginary axis passing through a molecule
which can dived / biseet the molecule into two hale which are mirror image.
is
m
he

Plane
σ
O
Biceet
.C

H1 H2 o atom H2 H1
Resleet
Bisect
w

O Poseect
O
H2 all three atoms H2
H1 H1
w

RO OH
Mirror Bisect above (OH) and Below (OR) group and reflect Cl1 and Cl2
w

2Cl Cl1

H O
H
H H

Br Br
Cl Cl mirror
mirror σ + nt
σ + nt achral
achral

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Br Br Br Br

Cl Cl
Cl Cl
σ tnt achiral σ not + tnt chiral
( ) ( )

O
COOH
Cl
OH σ not + not chiral OH
( ) H
σ tnt
OH
Cl
H OH

m
O
COOH
meso Compound

co
5) Cenacle of symmsrey (i) A centre of symmetry is a point from which lines

C.
when down on one side and produced an equal distance on the other side will
meet identical point in the molecule.

B
CH3
Cl COOH
Br yA H
H H

H C C
H
HOOC H
Br Cl
tr
CH3 i tnt achiral
is tnt
achiral
is

CH3
COOH
OH H
m

Cl

H OH σ tnt
he

COOH Cl
i tnt i tnt
achiral CH3 achiral
.C

Cl H

i tnt H3C O
w

HOOC COOH achiral CH3

O
H
w

Cl
i t n t ( hiral)
ac
w

Cl H Br Cl OH
H
HOOC
H F COOH
F
H
i tnt HO
achiral i tnt
H Cl Cl Br achiral
i tnt
achiral

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Rotation Reflection axis of symmetry (Sn)

[Sn= Cn + σn ]
It the molecule turned 3600/n about an axis followed by reflection in a plane
perpendicular to that axis bring the molecule in a position indistinguishable from
the original.
Cl H H F

H 1800 rotation about axis H Cl Cl

F H
H F Cn
F H
H

m
Cl σn mirror
sam
e Cl H

co
F H
H F
Rotate through the axis H Cl

C.
by 900

B
H CH3
H
CH3 S4 axiD tnt
H3C
H
CH3

N
yA H achiral

N
CH3 CH3
H
tr
H
H
H3C H CH3
is

F F
m

rotate 1200
B F F B
F mirror
F
he

Some F
F B
F
achiral
.C

Some examples
O
w

Cl
CH3
w

Cl
Cl Cl

H H
H
w

chiral No symmel
achiral
H
CH3 H
HO
OH
mirro H

H H
CH3
Plane of symmetry tnt
meso (σ tnt) H achiral

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H OH H H

H Br
HO H

Cl Br
CH3 H H
Chiral achiral (σ tnt)
(σ tnt) achiral (meso)

Br Cl Br Cl
Cl
Br
H

m
H
σ tnt achiral
H ( )
achiral

co
Cl Cl

C.
CH3 CH3 σ t nt
Br Br

B
(achiral
COOH Br
achiral (σ tnt) yA
Stereoisomerism resulting from more then one stereagenic unit THREO and
ERYTHRO Nomenclature 
tr
THREO AND ERYTRO  (Cabx – Caby)
is

In which molecule, with two adjacent stereo centre having two similar group and
one different group on each carbon. These designations applied on these
m

molecules which do not have symmetric ends.

Erythro  If similar compound on some side.
he

Threo = (trans) if similar compound on apposite side.

H H
A A
.C

x y x Me Cl Me Cl
y

y x x y Me Cl Me Cl
w

Br Br
B B
threo
w

Erytro
E ytro
r threo

CH2CH3 CH2CH3
w

H Br H Br

H Br Br H

CH3 CH3
E ytro
r threo

Note:- Erythiro and threo are dastercoisome having similar physical and chemical
properties.
Meso and d pair (Cabx – Caby)

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In fischer projector (like Erythro, through advent carbon having two similar and
one group) Ends are symmetric
If similar group on same side = meso
If similar group on apposite side = dl pair (enantiomer)
CH3 Me Me

H Br H Br Br H

H Br Br H H Br

CH3 Me Me

m
meso
Plane of Symmtry tnt

co
COOH COOH COOH
H OH
H OH COOH
HO H Tartaric acid

C.
OH a pair of
H H OH H enantiomer
HO
COOH

B
COOH

COOH
yA
COOH
H
COOH
OH
COOH
HO H
H OH OH
tr
H H
H OH HO
COOH
is

COOH
,
(25 35)
m

COOH COOH
COOH
he

H OH
H OH

H OH H OH
.C

COOH
meso Compound

CH3
w

7 CH3
OH
4 OH
3
w

5
OH
3 OH
w

HO OH
1 meso no t meso
2 ( )
6 2R , 6S Bicyclo
( )
, , ,
[2 2 1] heptane 2 6 dil
(meso C omp oun d )

Conventions for Configuration D and L pair

The former D/L system to denote absolute configuration used for Carbohydrate
and amino acid.
If OH group in fischer projection on RH.S.

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(D – Configuration) (+ Enantiomer)
if OH group in fischer proj on L.H.S – (L- Configuration) or (-) Enantiomers
CH2OH CHO
OH RHS)
H OH ( H
HO
(OH LHS)
CHO CH2OH
- -
D Glyceraldehyde L Enantiomers

Enantiomers

m
CHO CHO
H OH H OH

co
HO H HO H
H OH H OH

C.
H OH HO H
CH2OH CH2OH

B
- - ucoce
D Glyceraldehyde L Gl

Diasereoicomers
yA
D- Series, L-Series
tr
D – series of sugar are thoce in which OH group RHS of bottom stereo centre.
L- series of sugar are those in which OH group LHS of bottom stereo center
is

Amino acid
m

In amino acid if NH2 group in RHS of bottom stereo cent –Desires

If NH2 group in LHS of bottom steneocenter = L Series.
he

COOH
COOH
NH2 H
H NH2
.C

CH2OH
CH2OH -
L Serine
w

d or (+) = dextrorotatory (R. H. S) clockwise

w

d or (-) = Levorotatory (L. H.S) Anticlockwise

Racemic mixture  ( ± )
w

Racemic mixture or a racemate is an equinolar mixture of two enantiomers (dorl)

net rotation is zero. Do not rotate plane polarized light in either diretio also meso
compound are optically inactive
Allenes --- ( C = C = C = C = C) –
Allenes means carbon - carbon double bond. (C = C = C)
Central carbon having sp hybridization and linear stauncher terminal atom having
Sp2 (Trigonal planner structure.)

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H R
C C C
R H

Sp2 Sp Sp2

Orbital description
H
H H R
C C C C C
H H H
H

m
In allene, terminal carbon atom are perpendicular to each that

co
R R R R
C C C C C C C
H H H
H

C.
B
Note  In Allene
If odd. Number of double bond present they show geometrical isomerism.
Because terminal atom in some plane. They are achiral in nature.
yA
If number of double bond present, terminal atom are perpendicular to each other.
tr
Are chiral.
-
Eg:
is

Me H
H H
C C C C C C
m

Me Me CH3 CH3
σ abcent chiral
(actiral) σ present
( )
he

due to chiral axis

.C

H H H H
C C C C
C C
w

CH3 CH3 CH3 CH3

.
Enantiomers
w

3
Me 2 3 NO NO2 1
2 F
w

C C C = identical
C C C
F 4 C2H5 C2H5 Me
1 (A) 4 (B) 2

(actiral) σ present

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4 4

2 1 2 1

3 3
'S' 'S'

.
Q
Cl Cl Cl COOH
C C C C C C
F Me

m
F Cl
(actiral) σ present achiral ( σ tnt)

co
Me

C O

C.
OH H3C
C
CH3
CH3 H

B
Chiral

For R/S Momendatune

H yA
In allene, view near to palmer atom and prefer the higher priority then prefer
tr
above / below the planer group
Ph 4 Cl H
2 Cl
is

C C C C C C C

Br 1 C O CH2 COOH F
(3) Cl Achiral
m

O
Chiral optically actue
'S'
he

2 1
.C

3
(1)
CH3
(1) (3) H
CH3
w

(3) F
C C C
C C C
H (2) (4) CH3
H (2) (4) OH
w

Chiral optically actiue

Chiral optically actiue
4
w

4 'R' 2
1

1 2
3
'S'
3

Hemispiranes
The replacement of one double bond in an allene by a ring gives alkylidene
cycloalkanes.
Hemispiranes does not charge the basic geometry of system of allene.

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H H
H H H H C
C C C
C C C C C
R R
R R R R
. Hemispiranes
Allenes Hemispiranes

-
Eg: COOH
COOH HOOC
NO2 C C
Me
Me
Me
F

Enantiomers

m
4

co
'R'
Br
H
N N 1 2
H Cl
OH OH 3

C.
σ tnt
achiral

B
Sqiranes The replacement of both double bon in an acnes by ring sustem gives a
spiran. yA
H3C CH3
CH3 CH3
C C C C C C
tr
H H H H
allene spiranes
is

H H
m

H H
C C C
he

OC COOH HOOC COOH

Allenes spiranes

O O
.C

4 O O
4 'S'
2 'R'
1
O 2 1
w

O O
3 O
3
Enantiomers
w

- Me
Eg:
C
w

OH
H3C O
Tautomerisation C
H3C
H CH3

H (Chiral) (achiral ketone)

.
(exist in this) Enantiomeric f orm

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H H
O O
N 3
N
1 2 'S'

N N 4
H H
O O
Chiral Compound

OPTICAL ISOMERISM IN BIPHENYLS  ATROPISOMERIS

m
Atropisomerism means ‘without turning’

co
Isolable steceaisomers resulting from restricted rotation about single bonds are
called Atropisomerism.
Criteria for Chirality = / Reasons—

C.
i) Rotatoin about the bond linking the two phenyl ringd not occers due to
steric hindcance between the bulky ortho substituents.

B
ii) Boht ring lie in different plane which are pependicular on. Eahc other.
yA
iii) Biphenyl must contain two different orho substituents on eahc ring.
H H

H = Smaller group (Ho restriction)

tr
rotation Possible
is

H H
m

NO2 COOH
Due to the tnll of Bulky ortho Substituent create
steric hinderence. So Both phenyl ring are pependicular to eahc
otherand chiral in nature.
he

COOH
NO2
NO2
.C

COOH
NO2 HOOC
w

NO2 HOOC
COOH
w

NO2
morror
.
Enantiomers (chiral) optically actue
w

Cl NO2 COOH COOH H group (no restriction)

rotation possible

NO2 H COOH
COOH
Achiral (σ tnt) Achiral

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NO2 NHAC CO NH

Hydrilysis

NHAC COOH NH CO
Chiral i tnt
achiral.
(optically achile)
-
Eg:
F COOH
COOH F COOH
F

m
HOOC OC F
COOH F F HO
Chiral

co
chiral Achiral (tnt)

6, 6 – Difluorobiphenyl -2.2’ dicarboxylic acid is chiral buracemizes readily,

C.
since molecule can attain a plane scram easly.
Buttering effect In the tece of bulky ortho substituent as well as substituent

B
present on meta position enhance the recemisation barrier, known as Butters in
yA
effect. Due to the tnce of meta substituent, ortho substituent slip past each
other more readily. They are chiral, Duo to restricted rotation around the bond
joins the aromatic ring. They are perpendicular to each other and exist in two
enantiomeric form.
tr
CH3 Br OH
CH3 Br OH CH3
is
m

HO Br CH3
HO Br
-
he

Chiral Plane Meso Compound i tnt

Chiral plane
.C

Steneocenter Not present. But molecule is optically active due to the

presence of chiral plane.
w

NO2

CH2 CH2
w

Me COOH σ tnt
Achiral
w

CH2
CH2
COOH
COOH Br
t ca
Op i lly acetive
OPtically active
(chiral plane) (chiral plane)

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COOH COOH OMe

OMe
NO2

H NO2
CO H CO
OH OH
' Buttersing ef f ect'

Order of steric hindrance Produced by different group.

 Br CH 3 Cl NO 2 COOH OCH 3 F H 

m
Bridged Biphenyls-
a

co
b If = n = L = Planner not resovable, active

n = 2 = Non planner, resovable chira

Morethan 2 (n > 2) Non planner Resovable, chirol

C.
(CO2)n

B
Cl Me
Me
Br
yA
CH2 CH2
σ tnt achiral
( )
Chiral
tr
, na
2 2 Bi bthol COOH
view Chiral
is
m

OH
HO
OH
he

HO
.C

3 3
'S'

2 'R'
w

1 2 1
Chiral Compound

4 4
w

Trans cyclo octane 

w

H
H
H
H
cis Cyclooctene
Achiral -
Trans cyclo octene
chiral.

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6) Trans cyclo octane in chiral due to the presence of a stereo plan (Planar
Chirality), Constituted by two Trigonal carbons, the two hydrogen atoms on
these and two direetly adjacent carbon the four methylene bridge is skewed in
the third dimension
HELICAL CHIRALITY
Helices are chiral molecules.
Righ – handed holix (clockwise)  P (plus)
Left handed helix (Antidockwice)  M (minus)

m
Due to the crowdies of six membered ring in chain forces them out of
planarity. One of the terminal rings lines about or below the other. So that the
molecule adopt a helical shape.

co
C.
B
chiral
achiral
yA Mirror
tr
is

- -
m

M Mins P Plus (+)

- .
() Hexahelicene
he

Me
e Me Me
M

CH2
.C

COOH
Me -
w

M( )
P (+)
w

E/Z Momenclature (Geometrical Isomerism)

E = Entegegen meaning opposite.
w

Z = Zusammen meanig together.

For E/Z nomenclature four group attached on alkene must different.
If Two tgpes group present on alkene then assing Cis / Trans isomerism.
For E/Z – If Higher prority group attached on alkene on some side then
prefer Z.
For If higher priority group attached on alkene on some side then prefer z.
If Higher priority group attached carbone on opposide side then preter E.

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It some gorup attached on alkene on either side knonw as cis and opposite
side knonw as frons.
OH
Ph 2 NH3 1
H Ph
H C C C
C C H
Me H
Me 1 2
Me
cis
cis 'E' anti

(2) (1)
OH
Me H Me Ph

m
C C N
C C
Me H
Ph (2) C (1)
H Trans
Trans

co
H

- 'Z' Pyn
E/Z

C.
H H L
H
C C C C
L H
L L

B
'Z' 'E'

F
(2) Br
(2) F
C
yA C
I CH3CH2
C N
OH
C C Br
I 1 Cl 'E' H3C 'Z'
Cl 'Z' ( )
(1)
tr
Ph
Cl Cl Cl Br N N
is

C C C C Ph
Br 'E'
H 'E' Cl H
m

No Stereoisomer
H3C
CH3
he

Z R E CH3

S cis / S trans
.C

S cis  If some side double bond along single bond.

S – trans  If trans double bond along single bond.
w

Type – A = CH – CH = B folly eclipsed conformation with a dihedral angle of 00

is termed S – cis while the conformation with the dihedral angle of 1800 is called s
w

– trans.
w

cis -
S trans

- - .
Note In DIels elder Reaction the diene must be able to reaet in the S cis conf ormation

- -
- S cis - S Cis
S trans S trans

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NMe2
NMe2

rotation due to
not rotation carbon - carbon single bond.

O O
Me Me
C N N
C
H H
Ph rotation Ph
No ro a
t tion

m
co
, - , , - ,
(1E 5E) 1 5 cyclodeedione (12 5E) 1 5 Cyclodedine , -
(12 5z) 1 5 cyclodindiene
O Me
HO Me OH

C.
meny MemgI C
C C
H3O H3O
H H H
H H
H

B
Homotopic f aces

HO H
yA
C C C2 Homotopic
H H
tr
Me O
Me
is

C2
H
H
Me Me
m

C C C2 Homotopic
H H
Me Me
he

H
H
O
.C

CH2OH O
C2 H
HOmotopic H
w

CH2OH H
H
w

C2 axis
C2 Homotopicf aces
w

H C1 Homotopicf aces
C1 H

Symmetry Criterion 
 Ligands are hemitropic if they can interchange position by rotation around a
simple axis Cn.
 Two faces of double bond are hemitropic proceeded addition to either face
gives the same product.

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- COOH
Eg:
Reblaceble D OH
with D
COOH HO HO

Hb OH COOH
HO HO Ident due to rotated
COOH 1800 in plane of paper
COOH
Reblace Ha
with D D OH
HO D
(C2)
1800 COOH

m
- COOH
Eg:

co
Two hydrogens Ha, Hb are Homotopic through
Ha OH rotation around C axis.
2
HO Hb

C.
COOH 1200
-
Eg: 1200
1200

B
COOH
COOH COOH

C C
yA C
Hc
Hb Hb
Ha Ha
Hc Ha
Hb Hc
tr
is

Homotopic

H H H
H
m

H H H
H
H H
H H H H H H
H H H H
he

H H H H
H
H H H
H
H H H H

Note:-
.C

Prochirality and Prostereoisomerism 

w

Prostereocenter may not necessary be a parochial centre. Cis – Trans isomers of

alkenes and certain cyclones dispel Stereo chemical difference without being
chiral.
w

CH3 CH3 CH3 CH3 CH3 Cl

H replacewith D Hreplacewith D
C
w

C
D H H I
H H

Note- In cyclobutene C3 centre bearing HC and Ht hydro is prostereogenic (a

Prostereocenter) and not procures thus C3 in cyclobutanol exhibit
Prostereoisomerism and n prochirality.
Homotopic Ligands and faces
Two hemitropic ligands are Homotopic if replacement of each one of them by
another atom or group leads to some structure.

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Ha X
- a
H
Hb Cl +x Hb Cl

HC HC

Ha Ha
-
Hb
Hb Cl +x X Cl Homotopic

HC HC

m
Ha Ha
- a
H
Hb Cl +x Hb Cl

co
X X

Prochirality / Prostereoisomerism

C.
Prochirality  Pro  precious position of Chirality.

B
Prochirality is the properties of certain molecule due to which these can be
concerted into stereoisomers.
yA
A Tetrahedrally bonded atom (Cabc2) become chiral on replereme of one of
identical group with different group (d) called prochain centre.
a a
tr
C e Replace b'
with d C d
is

b b' b d
chiral
m

Prochiral Center
(achiral)
he

OH OH

CH3 Replaced with Br

CH3 CH3 CH3 Br
.C

NO2 NO2
Chiral
Topicity
w

(1) Homotopic or Homomorphic f aceand ligan

(2) Heterotopic f ace and ligands
w

Enantiotopic Diastereotopic
w

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Heterotypic Ligands and faces

Enantiotopic:- Two heterotypic ligands are Enantiotopic if their replacement in turn
by a different achiral ligand gives rice to Enantiotopic faces.
Or
If their position in the molecule are related in their mirror image fashion.
Symmetry criterion:- Heterotopic ligards are Enantiotopic if they are inter
changeable through operation of symmetry σ planes and Sn axes.
COOH COOH COOH

m
x +X +X
HB - HA HB - HA X
HA HB

co
Me Me Me
I II
-
I, II Enantiomer
-
HA, HB Enantiotropic

C.
Cl HA H2C CH2

B
C C C
HB σ Plane
H σplane
-
HB
HA/ HB Enantiotopic
yA CH2
Chiral
plane
H2O

HB
tr
Enantiotopic
COOH
is

COOH COOH

D C OH
Replace H1 H1 OH Replace H2 with H1 OH
m

C C
D C OH With D H2 D
C OH D C OH
he

COOH
COOH COOH
(A) -
Meso f artaric acid (B)
A/ B enantototric
.C

H
H H
H
w

H
H H
O HD H
O O
H H H H
w

H H

H HD H
Enantiotopic lcgnde
w

Cl
HO2CH2C H

Cl C
H H OH
HO2CH2C

Cl
Cl Ehantiotopic ligands

Enantiotopic ligande

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H HA Ph Me
Ph Me
C H H
C C

Cl HB O H
HO
(A) - .
A/ B Enantiotopic f aces
H H CO2H
HD
HA
H3C H
Ph Ph
CH3

m
H HC
Homo t o pic HB
due to C2 Symmetry

co
COOH
Enantiotopic ligands
S4 (C2)

C.
HD
F
F
HA HD
HC

B
900
F HA
HB 7

HC
HB yA F
F

F
HA
tr
.
Enantiotopic ligonds erchangeble through Sn axis
is

Diastereotopic ligands and faces:-

When the replacement of either of two ligands by a different achier test ligand
m

gives Diastereomers then such ligand are termed Diastereotopic.

Symmetry criterions Heterotopic ligands are Diastereotopic, if germinal group
he

are bidet by an angle known as Diastereotopic ligands.

Replace Ha CH3 Cl
with Cl C C
.C

H Hb
CH3 Ha cis (z)
Diastence
C C topic
Hb
w

H
H3C Ha
Replale Hb
with Cl C C
w

H Cl
Trans (E)
w

H OH Replace He OH Replace He HO OH
HO H Hf with OH with OH
Hf H H H
trans
Diastereortopic Cis

FC3 in cyclobutanol is not a prochiral center but a prostreo center (in

prostereogenic center)
Note:- Chirality is neither a necessary nor a sufficient conditions for the presence
of Heterotopic ligand.

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CH3
H Cl
CH3 Z
Ha
H Cl
Cl
Diastereotopic
Ha Hb Hb
CH3
H Cl
Cl
H Z

Cl
CH3
CH3 CH3
Cl

m
H OH OH
HCN CN CN
a
H Hb CH3 H CH3 H

co
Cl C6H5 C6H5

Diastereomers

C.
H H

HA HA Replace

B
Br Br D Br Br
with D
HB H yA
HB

H
H

Diastereomer

HA Replace HA Br Br
tr
with D

D H
is

H
m

O
OH
(H3C)3 C
(H3C)3 C H - - Diastereotopic
he

Trans 4 t Butylcyclohexanol
(achiral)
OH
.C

H
(H3C)3 C

cis - 4 -t Butylcyclohexanol
w

(achiral)
H3C X
w

H3C
w

H3C Top H
H
Replace with
H3C H3C H
H
Botter X Diastereoison

H3C

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Nomenclature of Enantiotopic ligand

Nomenclature of Enantiotopic ligand at Prochiral Center e.g. Ha and Hb in
ethanol, ligand is laballed is arbitrarily assigned a higher c1P priority over the
other if Ha is arbitrarily preffered over Hb in the sequence rule the is OH > CH3 >
Ha > Hb and the hypothetically cofigurational symbol to the prochirality center in
ethanol will be R, thus Ha is designated pro –R and by defaces Hb because pro –S.
the same answer would have come out if Hb was given precedence over Ha, in that
care the sequence would have been OH > CH3 > Hb > Ha. The hypothetically
configuration symbol for ethanol is then S, hence Hb is pro –S.
2

m
2 Me
Me
- - 3

co
3 4 Pro R Clockwise HA HB
HA - -
HB Pro S Anticlockwics 4 Pref f ered Atoms
Pref f ered Atoms
OH

C.
OH 1
1 -
- HB = Pro S
HA = Pro R

B
yA H
CH3
Cl

Ha Z
tr
Cl
Diastereotopic
Hb
CH3
is

H Cl

H Z
m

Cl
he

CH3 CH3 H
H Cl H C Cl CH3 C COH
.C

Cl H D
-
Ethanol
-
R Ethanol S Ethanol
w

Prochiral

1
1 1 ClA
Br
w

Br
3 2
HB C HA HB C HA HOOC ClB
4 3 3 4
w

Me Me 4
2 2 CH3
-
- -
HA Pro R
- -
HB Pro S ClB = Pro S

COOH R
HA HB
H C OH -
- Pro R
Pro S HB C HA
ClB
ClA
CHO H C HO

COOH S
CHO

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2 HB Me Br
4

3 4 1 2

1
HA Me NO2
3
- -
ClA = Pro R =
HA Pro R

1 Br
4

3 4 2 HB HA
1 -
Pro R

m
-
Pro S
2 3 NO2

co
-
ClS = Pro S = -
HA Pro S

Enantiotopic faces of Carbonyl Compound

C.
Re – Rectus – Clockwise
Si – Sinister – Anti clockwise

B
If three ligands arranged in priority order opera clockwise in a face, the face is Re. if
they oppear Anti dock wise face is Si.
1
yA
1 O
O
tr
C C CH3
2 H 2
H 3
CH3 3
is

Ref ace
Si f ace
1
m

O 1
O
O 3
C 2
2 C 3 Et
he

CH3 CH3

Sif ace
Ref ace
Si f ace
.C

Note:- Re face attack  Attack side from the closet to the eg thick wedge
w

Si face attack = Attack side from the away from the eyes, hetch wedge.
OH
w

1 C
O CH2 CH3
H3C
2 - -
w

C
CH2 CH3 (S) 2 Butonol
CH3
3 -
Re f ace OH Enantio
H
C
H3C
CH2 CH3
- - u ona
(R) 2 B t l

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Face of Alkenes (Re, Si nomenclature)

In the case of Alkenes- Carbon have sp2 hybridisation with Trigonal planner
structure with two different face. Because Trigonal planner structure views two
side. Top side as well as Bottom side.
Top f ace
H 2
( ) H COOH H COOH
C2H5
C C C C C C
H H H HOOC H
HOOC
- Bottom f ace
Top f ace -
- Re Re
Si Si

m
-
Pro cis -
Si R COOH
O

co
HOOC
H
-
Pro trans e-
H R Si

C.
Enzyme Mediated Reduction – Bakers yeast
- -
Pro S Pro R

B
H B
H H H H
O yA O O
O
H2N C H2N CH3
H
H CH3
N H
N
-
tr
Pro R
R R
is

During the reduction of acetaldehyde the pro R H from NADH is trans furred only
to the Re face of acetaldehyde.
m

Crom’s rule – Felkin – Ahn modifications

1. Label the largest, medium and smallest group to the four group attached to stereo
he

canter.
2. Place the largest group perpendicular to the carbonyl in Newnan projection. The
.C

two remaining group on the steneocenter can then be arranged in two ways (1) the
smaller group towards or away from carbonyl group.
w

3. The nucleophilic addition to the carbonyl group at an optimum angle of around

1070 the attack of nucleophilic occurs from the face of carbonyl group from the
small sized groups, since it will be hindered by the medium sized group.
w

O
M M OH
w

L Nu L

Nu R
S S
R
ro uc
Majer P d t

O H3C O
CH3 . HO H
1 LiAlH4 . H
. C6H5 1 LiAlH4
H C6H5 2 H3O H .
2 H3O
CH3 C6H5
H CH3
H CH3 H3C
,
(2R 3s) mojor - -
(2S 3S) Minor

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Crom’s rule is applicable for Aldehyde and ketonic group.

IInd method 
 Labelled the Largest medium and smaller group attached to streocenter.
O
 These three groups, attached on carbon atom arranged in such a way that,
largest group must trans to group. C
O
 Attack the Nucleophilic to C group from the of smaller group.
O O
(L) H
CH3

m
H CH3 (M)
(3)

co
Nu attack f rom
Nu attack f rom Back side
Back side

C.
Nu O
H O Nu
CH3 H

B
CH3
.
Minor product

O
yA mejor Product

H CH3 O
CH3MgBr H
tr
Ph CH3 CH3
H3O
CH3 Ph
is

CH3 OH
m

OH CH3
CH3
CH3 CH3
he

CH3
H
H Ph
Ph
CH3 OH
.C

OH CH3
Diastereomers H
CH3
H Ph
w

CH3
Ph
CH3
CH3
w

CHO Me
Me
w

HO C Me
Me D meMgBr Me C OH
Me D
H3O Me D
Ph H
Ph H Ph H
CH3
CH3 CH3
minor
Major
Diastereomers

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Me D

H
Ph CHO

CH3 Me
Me OH
Me D
D
H D
Me
H Ph
CHO H
Ph CHO Ph
Ph
CH3
CH3 H CH3
H CH3

m
major minor

Me

co
Me H
Me H H
.
1 Phmg Br H
. H HO C2H
2 H3O Ph CHO

C.
OHC C2H5
H
H

B
Anti cram’s rule
 This rule is applicable due to the Presence of chelating group like Li, mg, Zn
yA
and more electronegative group like OH, Cl etc. Carbonyl group act as a
conformational locked structure.
tr
Li
O
LiAlH4 H
OH O O
is

M Hydrolysis
Me
L
m

L M Me

OH H OH
H
he

HO HO
Me Me
L L Me
Me
minor
.C

Major

H3AlH Li
w

CH3 O Li
O
LiAlH4 O
w

O O CH3 O
H C6H4CH3
C6H5
H C6H4CH3 HCl
w

C6H5
Back side C6H5 C H
6 4
attack.

OH H
H OH
CH3O CH3O
C6H4CH3 C6H4CH3
H C6H5 H C6H5
Major minor

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 If more electronegative element Cl and oxygen and present they Cl exist in

trans position due to more electronegative create Repulsion.
Cl O
CH3 . CH3 O
1 MemgCl C2H5
.
2 Hydrolysis
C2H5 CH3
Cl CH3

attack f rom f rantside attack f rom back sic

CH3 HO
CH3 Me
C2H5 Me C2H5 OH

m
Cl CH3 Cl CH3

co
Major minor

Cram’s cyclic (chelate) model

C.
Me
Me
O O OMe OMe
HO HO

B
R R

RS RL Rs RL Rs
RL
R R
major
yA R
miner

Li CH3
tr
O
OH
Ph O O HO
C CH3
CH3Li
is

Ph C

CH3 OH RS CH3
RL Ph
m

Ph Ph
Meso (92%)

Prelog’s rule  Prelog’s rule is applicable for α - ketoester. This rule is applied for
he

chiral alcohol with these of α - hydroxyacid prelog’s rule cordite’s the

configurations of hydroxy acid in atrolactic acid with that of alcohol as follow.
The ester of phenylglyoxylic acid is written that two carbonyl group are
.C

antiperiplenner to each other. Larger group at the chiral canter on the same side of
the ketonic carbonyl group.
w

O
L
C O
w

C
R S OH
M Me
O
C O
w

Ph
O C
o Ph C
B
emg O
C O m CH3 C2H5
Ph O
C H3 major
Ph C
O C2H5 memgBr
CH3 Me
H3O OH
C O Ph
C
Ph C
O C2H5
CH3
minor

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Nu Θ attack on electrophilic centre from less hindered side.

O
S O
L
C O C Nu Rotation
C L C O C
R C
M R M
O S
O
Nu attack f rom f ront side
Nu attack f rom f rom back side

O Nu
O Nu L

m
S
C O C
C O C C M
C L R
R S

co
M O
O
Rotation
Rotation

C.
O Nu
O S
Nu

B
S C O C
C O C C L
R
R
O
C
M
L
yA O
M

minor
major
tr
is
m
he
.C
w
w
w

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