RASHTRSANT TUKDOJI MAHARAJ NAGPUR UNIVERSITY

DEPARTMENT OF CHEMISTRY

CAHN-INGOLD-PRELOG
NOMENCLATURE

GUIDED BY: Prof. Mrs. J.S. MESHRAM

PRESENTED BY: BIJI SARO VARGHESE

DATE: 4 OCT 2017
 ACKNOWLEDGEMENT

I would like to thank Dr. Mrs. J.S. Meshram mam for

her constant guidance and support throughout the
completion of my presentation. I would like to thank
my seniors of their support. I would also like to thank
my friends and colleague who helped me directly and
indirectly. I would also like to thank my parents who
provided me all the facilities for completion of my
presentation.

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 The Cahn-Ingold-Prelog (CIP)
Nomenclature

The system that we use

was devised by
R. S. Cahn
Sir Christopher Ingold
Vladimir Prelog
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RULE 1:If four atoms attached to the
stereocenter are different ,priorities depend on
atomic numbers.

(S)-2-BROMOBUTANE
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Higher atomic number outranks lower
atomic number

Br > F Cl > H

higher Br Cl higher

C C

F H lower
lower

(Z )-1-Bromo-2-chloro-1-fluoroethene
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RULE 2:If two atoms are isotopes of the same
element, the atom of higher mass number has
the higher priority

1
F H4
C 2

3 D CH3

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 C bonded to O and 2 H’s
C bonded to 3 H’s

C bonded to 2 C’s
and one H

C bonded to C and 2 H’s

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Evaluate substituents one by one.
Don't add atomic numbers within groups.

—CH2OH outranks —C(CH3)3

—C(O,H,H) —C(C,C,C)

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RULE 4:If two carbon chains are attached to the
stereogenic carbon the chain with a secondary
carbon is of higher priority than the one with
primary carbon.

3 2

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 O C
C O C O
H H

C C
C C H C C H
C C

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RULE 6:To assign R and S configuration the
molecule has to be viewed with the lowest
priority group at the back.
H H
CH3CH2 CH2CH3
C OH HO C

H3C CH3

(S)-2-Butanol (R)-2-Butanol

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 Absolute Configuration
The R,S system of nomenclature
Rank the 4 groups (atoms) bonded to the chirality center

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 Naming Enantiomers -R,S System
Assigning Priorities to Groups

1. Oxygen (from CH2OH) = 16

2. Carbon (from CH2CH3) = attached to carbon
3. Carbon (from CH3) = attached to hydrogen
4. Hydrogen = 1

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RULE 7:When the lowest priority group is
towards eyes interchanging of the position of
any two groups twice at stereocenter retains its
configuration and also puts group of lowest
priority away from the viewer.
2 2

First interchange Second interchange

H and CH3 CH3 and NH2

3 4 4
1 1
3 3 1
4

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 1 1 1 1
OH OH OH
2 3 orient lowest priority OH
orient lowest priority H
CO2H 4H CH3 H
4H group away group away
CH3 H3C CO2H 2 CO2H HO2C CH3 3
3 2 2
3

clockwise = R counter clockwise = S

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 1 1

Br OH
2 Cl H 4 4 H CH3 3
F CH2Br
3 2
3
CH2CH3
1 Br CH=CH2 2
H
4
1 2 2 1

3 3

R S

R-RECTUS S-SINISTER 16
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 CIS-TRANS NOMENCLATURE

RULE 8:In case of compounds of the type abC=Cab,

the isomer in which the identical groups are on the
same side of the double bond is called cis and if they
are on the opposite sides then they are called trans .

Cis-2-bromobut-2-ene Trans-2-bromobut-2-ene

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 The E-Z Notational System
• E :higher ranked substituents on opposite sides
• Z :higher ranked substituents on same side

higher lower higher higher

C C C C

lower higher lower lower

Entgegen Zusammen
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C has higher Cl has higher
priority than H priority than F

(Z)-1-chloro-1-fluoro-1-propene

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This is the Z-stereoisomer.

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IMPORTANCE OF
ENANTIOMER

S-enantiomer is teratogenic and R-enantiomer is sedative

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 IBUPROFEN

ONLYS-ENANTIOMER
ONLY S-ENANTIOMER ISIS
ANTI INFLAMATORY
ANTI BUT R-
INFLAMATORY BUTENANTIOMER
R- IS NON TO
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AND INACTIVE
ENANTIOMER IS NON TOXIC AND INACTIVE
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TARTARIC ACID

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eferences
Stereochemistry by P.S. KALSI, seventh
edition,2008
Organic chemistry by Morrison and Boyd, sixth
edition,2007
Structures drawn by CHEM4WORD software
Web sources-
 https://pubchem.ncbi.nlm.nih.gov/compound/ibuprofen ,
 https://pubchem.ncbi.nlm.nih.gov/compound/thalidomide ,
 www.chemspider.com/Chemical-Structure.852.html ,
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 https://chem4word.codeplex.com ,
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