1

Elements of Chirality (Chiral 3 Cl F 4 clockwise rotation so 'R'

and lowest priority group
centre) and CIP Nomenclature Br
2
is at horizontal line so
change the result means
'S'
Absolute configuration = S
By Rajeev Gupta R
COOH pseudo chiral centre
H OH

H OH R>S
H OH

S COOH

8 Aug 2020
SP University, Anand, Gujarat, India
 Chirogenic or Chiral centre: A tetrahedral site or atom (generally
carbon atom) around which all the four attached groups are
different is called chiral centre.

COOH interchange of two groups COOH chirogenic centre

as well as
HO H stereogenic
CH3 CH3
H HO
new stereoisomer

Configuration: It is the 3-D arrangement of atoms or groups around

the stereocentre.

By Rajeev Gupta
 Configuration

Representation Assignment

wedge-desh

saw-horse cis/trans
fischer
representation D/L or
projection
newmann's R/S E-Z
projection (CIP or
Nomenclature) syn-anti
Absolute Configuration:
R/S Configuration

CIP rule Chirality rule

OR
Cahn-Ingold-Prelogs Rule
OR
Sequence rule
OR
Priority rule

By Rajeev Gupta
 To find out R/S configuration of a chiral centre, first we are to apply CIP rule to
give priority to all the four different groups. Then we apply second rule which is
chirality rule to finally assign R/S.
CIP rules:
1. Higher the atomic number of directly attached atom to the chiral centre has
higher the priority.
4
3 CH3
Cl 3
Br F 4 1F NH2
2
I 1 OH
2
priority order is I>Br>Cl>F priority order is F>OH>NH2>CH3

By Rajeev Gupta
 2. Heavier the isotope more will be the priority.

2
F
3
1 Cl D
H 4
priority order is Cl>F>D>H

By Rajeev Gupta
3. If directly attached atoms to the chiral centre are same then move
towards next atom and check its atomic number.
3 3
CH2CH3 CH2Cl
4H3C OH 1 4 F3C OH 1
2 NH2 2 NH2
priority order is priority order is
OH>NH2>CH2CH3>CH3 OH>NH2>CH2Cl>CF3
B A
4. Multiple bonds are treated as follows: A B A B

B A

A B A B

B A

By Rajeev Gupta
 1
F F O COH

H 2N COOH H2N C OH
2 3
CHO H C O
HC O O
4

Q. Arrange the following in decreasing order of priority according to

CIP rules.
-Cl, -CH2Cl, -CH2-CI3, -tbu

Answer: -Cl > -CH2Cl > -tbu > -CH2-CI3

By Rajeev Gupta
 ‘R’ configuration has more priority on ‘S’ as shown in the following
molecule,
R
COOH pseudo chiral centre
H OH

H OH R>S
H OH

S COOH

By Rajeev Gupta
 Lone pair gets lowest priority.
4 C2H51
N
H CH3
3
2

Chirality rule:
We make a arc in the direction as 1→2→3. If it is clockwise then
assign ‘R’ and if it is anticlockwise then assign ‘S’.
We can observe or apply chirality rule in following given Fischer
Projections:

By Rajeev Gupta
Fischer Projection:

4 4
4

away from viewer towards the viewer

result as it is change the result

R R R S
S S S R

By Rajeev Gupta
 Examples:
4
F
1 I Cl 3
anticlockwise rotation so 'S'
Br and lowest priority group
2 is at vertical line so result
as it is
Absolute configuration = S

1
I
3 Cl F 4 clockwise rotation so 'R'
and lowest priority group
Br is at horizontal line so
2 change the result means
'S'
Absolute configuration = S

By Rajeev Gupta
Q. What is the absolute configuration of the following given molecule:
F

OHC OH

H3C Br

COOH

(a) RR (b) SS (c) SR (d) RS

Answer: second and third number carbons are chiral
4
F for second number: for third number:
3 2 1
OHC OH

2 4 1 4 2
H3C Br

3 3
COOH S but reverse then R R but reverse then S
1
Answer: (d) RS
By Rajeev Gupta
Thank You