WHICH OBJECTS ARE SYMMETRIC ?

(mirror image is identical)

sym (outside)
asym

asym
sym
PLANES OF SYMMETRY

asym sym sym

asym

WHICH OBJECTS ARE SYMMETRIC?

( continued )

sym asym
sym

CHIRALITY, SYMMETRY PLANES

AND ENANTIOMERS

asym (due to pattern) asym asym

 IF AN OBJECT HAS A PLANE OF SYMMETRY,
ITS MIRROR IMAGE WILL BE IDENTICAL An object without symmetry is CHIRAL

no symmetry

The mirror image

of a chiral object is
different and will not
superimpose on the
original object.
OBJECTS WHICH ARE CHIRAL
IDENTICAL MIRROR IMAGES WILL SUPERIMPOSE HAVE A SENSE OF “HANDEDNESS”
(MATCH EXACTLY WHEN PLACED ON TOP OF EACH OTHER) AND EXIST IN TWO FORMS

A SYMMETRIC OBJECT HAS A PLANE OF SYMMETRY

- ALSO CALLED A MIRROR PLANE

plane of
symmetry

CHIRALITY

mirror
plane
 ENANTIOMERS
non-superimposable
mirror images
Cl Cl
rotate

H F F
The whole secret of the study of nature lies in
learning how to use ones eye. Br Br H
this molecule
George Sand, author is chiral Cl
note that the fluorine

H Br and bromine have been

interchanged in the

do interchanges in class
F enantiomer

An object with symmetry is ACHIRAL ( not chiral).

The mirror image of an achiral

object is identical and will
superimpose on the original object.

ENANTIOMERS

STEREOISOMERS

plane of
symmetry
 ENANTIOMERS HAVE
EQUAL AND OPPOSITE
STEREOCENTERS
ROTATIONS
One of the ways a molecule can be chiral is to have a
stereocenter.
W Enantiomers W
A stereocenter is an atom, or a group of atoms,
C C that can potentially cause a molecule to be chiral.
X Y Y X
Z Z
stereocenters - can
give rise to chirality
(+)-nno (-)-nno
dextrorotatory levorotatory
ALL OTHER PHYSICAL PROPERTIES ARE THE SAME

STEREOISOMERS

ENANTIOMERS are a type of STEREOISOMER

Stereoisomers are the same constitutional isomer,

but have a difference in the way they are arranged STEREOGENIC CARBON ATOMS
in three-dimensional space at one or more of their
atoms.

and remember …...

 TWO VIEWS OF THE PLANE OF SYMMETRY
F
Cl ACHIRAL plane of
Br
The plane of the paper symmetry
is a plane of symmetry
F F
F F
Cl Cl
Br Cl Cl Br Cl
Cl Cl Br
Br
TWO IDENTICAL GROUPS RENDERS A Cl
F side edge
TETRAHEDRAL CARBON ACHIRAL Cl
Br view view

STEREOGENIC CARBONS ONE PAIR OF ATOMS ATTACHED TO A TETRAHEDRAL

( called “chiral carbons” in older literature ) CARBON IS IN A PLANE PERPENDICULAR TO THE
OTHER PAIR
plane 1

Cl This is one type of ….

stereocenter
…. others are possible

F
plane 2

H
Br Look at your
A stereogenic carbon is tetrahedral
H F model set !
F Cl
and has four different groups attached. Cl Br
Br
 plane of CONFIGURATION
symmetry

Cl Cl
The three dimensional arrangement of the
groups attached to an atom
Cl Cl
Br Cl
Br Stereoisomers differ in the configuration at one or
more of their atoms.
Cl
side view edge view

ACHIRAL
A CARBON ATOM WITH THREE SIMILAR
GROUPS IS ALSO ACHIRAL …..

Cl Cl
CONFIGURATION
Br Cl Cl
Cl Cl Br
ABSOLUTE CONFIGURATION ( R / S )

Cl
Br
 SPECIFICATION OF CONFIGURATION

Enantiomers are assigned a CONFIGURATION

using the same priority rules we developed for
E/Z stereoisomers.

1. Higher atomic number has higher priority.

2. If priority cannot be decided based on the first NUMBER OF

atom attached move to the next atom, following STEREOISOMERS POSSIBLE
the path having the highest prioity atom.
3. Expand multiple bonds by replicating the atoms
attached to each end of the bond.

CAHN-INGOLD-PRELOG
SEQUENCE RULE

CONFIGURATION - relates to the three dimensional Bromochlorofluoroiodomethane

sense of attachment for groups attached to a chiral
atom or group of atoms (i.e., attached to a stereocenter).

1 1
I I
1 2 counter
clockwise 2 1 4 4
clockwise
F C C
C C 2 F
4 4 Cl Br Br Cl
3 3
3 3 2
view with
substituent
of lowest R S
priority in
back
R (rectus) S (sinister)
Enantiomers
 FINDING STEREOCENTERS
(STEREOGENIC CARBONS)
CH2OH OH RR
RS
CH3 *
C CH2 CH CH CH3 SR
* SS O O O
CH3 CH3
22 = 4 stereoisomers CH3 CH3 CH3
CH3 * * *
* *
RRR RSS * CH3 CH3
* RRS SRS CH3
RSR SSR plane
*
* OH SRR SSS ( but only if cis )

CH stereoisomers (max) :
CH3 CH3 23 = 8 stereoisomers
22 = 4 22 = 4 22 = 4

FINDING STEREOCENTERS
(STEREOGENIC CARBONS)

How Many Stereoisomers

Are Possible? O O O
CH3
*
*
maximum number of stereoisomers CH3
CH3
sometimes fewer = 2n,
than this number plane
will exist ( indicates no stereoisomers )

where n = number of stereocenters stereoisomers (max) :

(sterogenic carbons) 20 = 1 21 = 2 21 = 2
 TYPES OF ISOMERS

ISOMERS CONSTITUTIONAL
FINDING STEREOCENTERS (CHIRAL CARBONS) Different compounds ISOMERS
with the same Isomers with a different
molecular formula order of attachment of
the atoms in their
CH3 molecules
* each isomer could
CH3 have stereoisomers
ENANTIOMERS
STEREOISOMERS Stereoisomers whose
* * molecules are non-
CH3 CH3 Isomers with the same order
superimposible mirror
* of attachment, but a different
* images of each other
* configuration (3D arrangement)
* CH3 of groups on one or more of
HO * the atoms DIASTEREOMERS
H Stereoisomers whose
double bond or ring
n=8 molecules are not mirror
with a ring
cis/trans both can apply
images of each other
28 = 256 ISOMERS
(geometric) TYPES OF ISOMERISM