INTRODUCTION

OF STEREOCHEMISTRY

PRESENTED BY

SUYATNO

DEPARTMENT OF CHEMISTRY
STATE UNIVERSITY OF SURABAYA

2018
 ISOMER
 Isomer  Compounds that have the same molecular
formula but are not identical
 Isomers fall into two main classes: constitutional isomers and
stereoisomers.
 Constitutional isomers differ in the way their atoms are
connected.
 Stereoisomers (Configurational isomers) differ in the way
their atoms are arranged in space. Stereoisomers are
different compounds that do not readily interconvert.

 Therefore, they can be separated. There are two kinds of

stereoisomers: cis–trans isomers and isomers that contain
chirality centers.
 GEOMETRIC ISOMER
 CIS-TRANS ISOMERS (GEOMETRIC ISOMERS) RESULTED
FROM RESTRICTED ROTATION CAUSED EITHER A DOUBLE
BOND OR BY CYCLIC STRUCTURE

A COMPOUND HAS GEOMETRIC ISOMER IF :

1. IT HAS DOUBLE BOND OR RING
2. EACH OF CARBON FORMING THE DOUBLE BOND
BOND TWO DIFFERENT ATOM OR GROUP

 THERE ARE TWO KIND S OF GEOMETRIC ISOMER, NAMELY:

1. CIS-TRANS ISOMER
2. E-Z ISOMER
 CIS-TRANS ISOMER

IF A COMPOUND WHICH HAS GEOMETRIC

ISOMER:
1. TWO THE SAME GROUP LOCATED AT THE
SAME SIDE OF DOUBLE BOND  CIS ISOMER

2. TWO THE SAME GROUP LOCATED AT THE

OPPOSITE SIDE OF DOUBLE BOND  TRANS
ISOMER
EXAMPLES
EXAMPLES

PROBLEMS
PROBLEMS

WHICH OF THE FOLLOWING COMPUNDS HAVE

CIS-TRANS ISOMER ?

1. 1-PENTENE
2. 1,1-DIBROMO-1-BUTENE
3. 2-METHYL-2-BUTENE
4. 3,4-DIMETHYL-3-HEXENE
5. 1,3-CHLORO CYCLOHEXANE
E-Z ISOMER

A COMPOUND WHICH HAS GEOMETRIC ISOMER

IF :
1. TWO THE SAME PRIORITY GROUP LOCATED
AT THE SAME SIDE OF DOUBLE BOND 
Z ISOMER

2. TWO THE SAME PRIORITY GROUP LOCATED

AT THE OPPOSITE SIDE OF DOUBLE BOND 
E ISOMER
DETERMINATION OF THE GROUP PRIORITY

CHAN-INGOLD-PRELOG RULE

Rule 1. The relative priorities of the two groups depend

on the atomic numbers of the atoms that are
bonded directly to the carbon. The greater the
atomic number, the higher is the priority.

PRIORITY OF : 1H  6C  8O  17Cl
Rule 2. If the two substituents bonded to an carbon
start with the same atom (there is a tie), you
must move outward from the point of
attachment and consider the atomic numbers
of the atoms that are attached to the “tied”
atoms.
Rule 3. If an atom is doubly bonded to another atom,
the priority system treats it as if it were singly
bonded to two of those atoms. If an atom is triply
bonded to another atom, the priority system
treats it as if it were singly bonded to three of
those atoms.
Rule 4. In the case of isotopes (atoms with the same
atomic number, but different mass numbers),
the mass number is used to determine the
relative prioritie

PRIORITY OF : 1H1  1D2  1T3

PRIORITY OF : 1H  6C  8O  17Cl
 CHIRALITY
 An object with a right-handed and a left-handed form is
said to be chiral. “Chiral” comes from the Greek
word cheir, which means “hand.” Example: hand, feet,
gloves, and shoes

 A chiral object has a nonsuperimposable mirror image. In

other words, its mirror image is not the same as itself.

 While an achiral object has a superimposable mirror image.

Some other achiral objects would be a table, a fork, and a
glass.
 THE OPTICAL ISOMERS
 The feature that most often is the cause of chirality in a
molecule is an asymmetric carbon

 Compound that has the optical isomer is characterized by

by the presence chiral carbon atom or asymetric carbon

 Chiral carbon is carbon atom which bond four different

atom or group

CH3
CHIRAL CARBON
HO C C2H5

C3H7

 SUM OF OPTICAL ISOMER IS FORMULATED  2n

n = NUMBER OF CHIRAL ATOM
PROBLEMS
PROBLEMS

1. Which of the following compound have optical isomer

and determine sum of the optical isomer:
a. 2-butanol
b. 2-methyl-pentane
c. 2,3-dihydroxypentanal
d. 3-ethyl-3-methyl hexane

2. Show the asymetric carbon in the following compounds and

determine sum of the optical isomer:
ABSOLUTE CONFIGURATION

 Arrangement (configuration) of atoms around the chiral carbon

 A system of nomenclature that indicates the configuration

(arrangement) of the atoms or groups about the asymmetric
carbon. Chemists use the letters R and S to indicate the
configuration about an asymmetric carbon.

 Steps to determine the R and S confuguration:

1. Rank the groups (or atoms) bonded to the asymmetric

carbon in order of priority using the Chan – Ingold - Prelog
2. Orient the molecule so that the group (or atom) with the
lowest priority (4) is directed away from you. Then draw an
imaginary arrow from the group (or atom) with the highest
priority (1) to the group (or atom) with the next highest
priority (2).
If the arrow points clockwise, the asymmetric carbon has
the R configuration (R is for rectus, which is Latin for
“right”). If the arrow points counterclockwise, the
asymmetric carbon has the S configuration (S is for sinister,
which is Latin for “left”).
EXAMPLES
PROBLEMS
Determine the absolute configuration of the following
compunds:
 ENANTIOMER, DIASTEREOISOMER, AND MESO

 Enantiomer  Pair of stereoisomers which are superposable

mirror image

 Diastereoisomer  Pair of stereoisomers which are not

superposable mirror image

 Meso Compound  Compound which has asymetric carbon

but it is achiral compund because it superimposable on its
mirror image
 1 and 2 ; 3 and 4  Enantiomers
 1 and 3; 1 and 4; 2 and 3; 2 and 4  Diastereoisomer

Meso Compounds
PROBLEMS

Draw the stereosiomers of the following compounds:

O COOH

H2 HC OH
C C OH
H3C CH
HC OH

NH2
COOH
(a) O (b)

C H

HC Br

HC OH

CH3

(c)
PROBLEMS

Draw the stereosiomers of the following compounds:

O COOH

H2 HC OH
C C OH
H3C CH
HC OH

NH2
COOH
(a) O (b)

C H

HC Br

HC OH

CH3

(c)