nextweek bawan

->

polisits 3 jaumn peniti

 =

->
Mananb hiri

seimbang
 I
S
N
Y
M
N
M
A
E
T
T
U
R
R
Y
E
 I
S
N
Y
M
N
M
A
E
T
T
U
R
R
Y
E
 I
N
S
Y D
M E
M C
E O
T R
R A
Y T
I
O
N
 I
N

S A
Y R
M C
M H
E I
T T
R E
Y C
T
U
R Leaning tower of Pisa, Leaning tower of Teluk Intan,
E Italy Malaysia
 Taj Mahal, India Ancient Greek architecture, Greece
I
N

S A
Y R
M C
M H
E I
T T Egyptian pyramids

R E
Y C
T
U
R
E
Cambodian Angkor Wat
 I Sydney
N Opera House

S A
Y R
M C
H Eiffel Tower
M Paris
E I
T T
R E
Y C
T
U
R KLCC Petronas Twin Tower
Malaysia Atomium
E
Brussel
 THE CONCEPT OF SYMMETRY IN
CHEMISTRY
What are symmetry
-

operations for
-

WATER compound?
https://elements.envato.com
/water-molecule-QXCKMC
Observe the movement of
atoms or molecules
from one point to the
AMMONIA other point in the
https://elements.envato.com/
ammonia-molecule-9DAHRH compound (Not
METHANE through a reaction)
https://elements.envato.com/

Ipart
in
methane-molecule-RJNXR2
 THE CONCEPT OF SYMMETRY IN
CHEMISTRY
The result of the
movement of the
WATER atoms/molecules upon
https://elements.envato.com a symmetry operation
/water-molecule-QXCKMC
is then compared to
that before the
compound undergoes
AMMONIA the symmetry
https://elements.envato.com/
ammonia-molecule-9DAHRH operation.
METHANE
https://elements.envato.com/
methane-molecule-RJNXR2
Why do chemists care about symmetry
and point groups?

Symmetry helps to understand molecular

structure, some chemical properties, and
characteristics of physical properties
(spectroscopy).

Therefore a theoretical approach must be

provided to observe symmetry in molecules
 OTHER LEARNING SOURCES

https://youtube.com/@noorshidamohdali
↳ tengon video
ni ti meada https://symotter.org/
masa
 TABLE OF CONTENTS

03
SYMMETRY ELEMENTS MULTIPLICATION
& OPERATIONS OF SYMMETRY
POINT ELEMENTS &
GROUPS OPERATIONS
 SYMMETRY SYMMETRY
ELEMENTS OPERATIONS

A symmetry operation is An operation perform on an object

carried out with respect to which leaves it in a configuration

a
LINES, POINTS or PLANES that is indistinguishable from and
superimposable on the original
- configuration
of
types
 n-fold
improper
rotation Sn

n-fold Plane of
axis of symmetry
rotation σ
Cn SYMMETRY
ELEMENTS &
OPERATIONS
Centre of
Identity symmetry i
E
 IDENTITY (E)
A no change

All molecules possess the identity element of

symmetry, E that is rotation of the
molecule through⑧ 0° leaves the
configuration unchanged
 n-FOLD AXIS OF ROTATION Cn
lines
I Clockwise rotation
A molecule having a Cn
axis can be rotated-by
360°/n about the oaxis and
↳ s dia
the configuration will lines
remain unchanged
Cnn = n(360°/n) = C1
e.g. C44 = 4 (360°/4)
= 360° = C1
Cn = 360°/n
about axis C1,C2,…Cn e.g. C2 = 360°/2 = 180°
CnOtanticlockwise
clockwise
Cn6m = m (360°/n) -m = m (360°/n)
e.g. C4Oberapavali
3 = 3 (360°/4) e.g. C4-3 = 3 (360°/4)
O
angle = 270° C4-3 = 270° = C41
Rotate three times in Rotate three times in a
a clockwise direction anticlockwise direction
of 90° of 90°
-
1. Axis is lying in the plane 2. Axis is passing
of the paper through the central
C3
e.g : H2O C2 atom and
C2 = 360°/2 = 180° perpendicular to
-

the plane of the

paper From front / side view
e.g : BF3
bend shape C3 = 360°/3 = 120°

3. Axis is passing
through the centre
C6
C3
of the ring and
perpendicular to
- C6
the plane of the
paper From top view
From front / side view
e.g : benzene
From top view C6 = 360°/6 = 60°
4. Axis is passing through 5. Anticlockwise rotation
the whole linear molecule e.g : BF3
e.g : HCN -

↳en
·inder

Sprintre
C∞ C3 C3

Linear asymmetrical
C31 = C3-2 C32 = C3-1
wedatare
↳
e.g : ethyne e.g : XeF4

C∞ C4 C4
C4
Linear symmetrical

C41 = C4-3 C42 = C4-2 = C21 C43 = C4-1

 n-FOLD IMPROPER ROTATION Sn
->
depends
rotation
Ca ↓
ada (2
02 reflection by across a
plane perpendicular to
reflect I axis
90

rotate

C2 and passing
through the
clockwise ⑳
rotation by centre of the
360°/ 2 about the axis molecule
-trigonal
planar 02
reflection by across a and passing
ada plane perpendicular to through the centre
of the molecule
axis

C3
clockwise
rotation by
360°/ 3 about
the axis
-> tetrahedral 02
ada reflection by across a and passing
plane perpendicular to through the centre
axis of the molecule
C4

clockwise
rotation by
360°/ 4 about

Potato
the axis
 From
02
top view
reflection by across a and passing
plane perpendicular through the centre
From front / side to axis of the molecule
view

C10
clockwise
rotation by
360°/ 10 about
the axis
 benzene ertstaggered
⑱ ecliples
1,2-dibromo-1,2-dichloroethane
(staggered)
↳
a
i ⑤

I
itI!
③

trans-N2F2
i
- I contra edudunan
=> tapi Repanjangan
i stills amd

i
i
trans-1,2-dichloroethene
xenon tetrafluoride ethyne
 PLANE OF SYMMETRY σ
A molecule having a plane symmetry σ is unchanged in C2
configuration if all the atoms are reflected across the plane σd
besar
parai C4
principal σv C2

e
axis

8
C4 C4 σd
σv ③ Dihedral / diagonaldivide
paper
σσ reflection plane rela
->

h ② Passing through origin & axis with

④
Horizontal reflection plane
Passing through origin &
perpendicular to axis with the
highest symmetry (main axis)
Vertical reflection plane
-
Passing through the origin
& axis with the highest
symmetry (main axis)
the highest symmetry (main axis).
Bisecting the angle between two
-C2 axes (two C2 axes are
perpendicular to the main axis)
 Vertical reflection plane Dihedral / diagonal reflection plane

•Passing through the origin & •Passing through the origin & the axis with
the axis with the highest the highest symmetry
symmetry •Bisecting the angle between the two-fold
C4
d
axes perpendicular to the symmetry axis
C2
v
F C
F 2
h
d
Xe C2
Horizontal reflection plane

F F •Passing through the

origin
v C2
•Perpendicular to the axis 29

with the highest symmetry

 POINT GROUPS
Groups with
low symmetry 01
under a ada C1 , Cs , C i Groups with an n-
sangat terhad
02 fold rotational axis
Dihedral groups Cn, Cnh, Cnv
X
same a da Dn, Dnh , Dnd 03
22 perpendicular
Groups with
yg

04 high symmetry
Td, T, Oh, O, D∞h, C∞v
https://pxhere.com/en/photo/49899
 POINT GROUP: POINT GROUP: POINT GROUP:
bentuk
C1 aplain
aU
Cs Ci
a
man
puting bromodifluoroiodomethane CHClBr-CHClBr (staggered)
I lowsymetry
▪ C1 = E -> identity
Total symmetry elements = 1 i
Has only C1
rotation
▪ C1 = E i
▪ σ sigma
->

bromochlorofluoromethane Total symmetry elements = 2

Contain a plane of
symmetry
i
▪ C1 = E
▪ i = S2 -> ret
Total symmetry elements = 2
Contain a centre of inversion i
Apple / Armando
▪ C1 = E ● e.g : hydrogen peroxide (H2O2) POINT GROUP:
▪ C21 = 180° = C2-1
Total symmetry C2 C2
elements = 2

From front /
side view C2
C2
C2
H
H
111°

From top view, C2 axis passes through

O−O bond. Rotation can be: C21 = C2-1
▪ C1 = E ● e.g : triphenylphosphine (not planar) POINT GROUP:
▪ C31 = 120°
▪ C32 = 240° = C3-1
C3
C3
Total symmetry
elements = 3

From front / side view

C3
C3
From top view, C3 axis passes
through P atom. Rotation can
be:
1. C31
2. C32 = C3-1
▪ C1 = E
▪ C21 = 180° = C2-1 ● e.g : trans-1,2-dichloroethene POINT GROUP:
▪ σh
▪ i = S2 ● If n is even the point group C2h
Total symmetry necessarily contains a centre of
elements = 4 symmetry (i)

C2

C2
C2
From front / side view
i

From top view, C2 axis passing through C=C bond.

Rotation can be: C21 = C2-1
σh
▪ C1 = E
▪ C31 = 120° -renwise
▪ C3 = 240° = C3
2 -1 ● e.g : Orthoboric acid : B(OH)3 POINT GROUP:
▪ σh memans
C3h
noware
->

▪ S3 e
▪ S3 -1

Total symmetry C3
elements = 6

From front / side view

C3 C3
From top view, C3 axis passing
through B atom. Rotation can be:
1. C31
2. C32 = C3-1
σh
▪ C1 = E
▪ C21 = 180° = C2-1 ● e.g : all bent / V shape such as water POINT GROUP:
▪ σv (H2O), H2S, SO2
▪ σv’ C2V
Total symmetry ● Other example: 1,2-dichlorobenzene
elements = 4
C2
C2
C2 From front /
side view

C2

Goto
σv’ σv’

σv
σv
40

C The plane in which

2 the molecule lies C
2

O O v’
H
H1 H2 H
v’

The plane bisects

C the molecule C
2 v 2

O v’
O H
H1 H2 H
v’
v
 C2
Cl Cl

H H

v’
Cl H
H H
C2
Cl H v’
v
H H
dichlorobenzene
v 41
▪ C1 = E
▪ C31 = 120° ● e.g : all trigonal pyramidal in shape POINT GROUP:
▪ C32 = 240° = C3-1 such as: ammonia (NH3), phosphine
▪ 3σv (PH3), PCl3, arsine (AsH3) C3V
Total symmetry
elements = 6 C3

C3
σv

σv
C3 From front / side view

From top view, C3 axis passes

through N atom. Rotation can be:
1. C31 σv
2. C32 = C3-1
 C3 l
very
stor, m
v-P, m
H N
ammonia
H H

v v
▪ C1 = E
▪ C41 = 90° ● e.g : all the square pyramidal in POINT GROUP:
▪ C42 = C21 = 180° = C4-2 shape such as iodine pentafluoride
▪ C43 = 270° = C4-1 (IF5), BrF5, XeOF4 C4V
▪ 4σv
Total symmetry C2/C4
elements = 8
C2/C4

σv
σv
From front / side view

C2 / C4 From top view, C2 and C4 axes

pass through F−I bond. Rotation
can be: σv
1. C41
2. C42 = C21
3. C43 = C4-1
σv
Photo by Ivo M. Vermeulen
 C1 = E
POINT GROUP:
▪
▪ C31 = 120° (main axis)
● nC2 axes perpendicular to the
principal axes Cn
▪
▪
C32 = 240° = C3-1 (main axis)
3C21 = 180° = C2-1 (3C2 ⊥ C3) ● e.g : tris(ethylenediamine)cobalt(III) D3
cation
Total symmetry
elements = 6

C2
3
+
From front / side view
C3 C3 C2
From top view, C3 axis passes
through Co atom. Rotation
can be:
1. C31
2. C32 = C3-1 C2
 C1 = E
POINT GROUP:
▪
● nC2 axes perpendicular to the
▪ C21 = 180° = C2-1 (main axis)
principal axes Cn
▪ 2C21 = 180° = C2-1 (2C2 ⊥ C2)
I D2h M
σh ● if n = even number, has i
8
re
▪
2σv 3σ Total symmetry ● e.g : ethylene N
-

↓mini
▪ i = S2 elements = 8
C2 C2
amike
C2 C2
C2
C2
From front / side view C2
C2 i C2
σ
i From top view, 3C2 axes pass
through C=C bond at x, y and z
axes. Rotation can be: C21 = C2-1 σ
σ
 C1 = E
▪
▪ C21 = 180° = C2-1 (main axis)
● nC2 axes perpendicular to the
principal axes Cn
POINT GROUP:
▪
▪
2C21 = 180° = C2-1 (2C2 ⊥ C2)
σh ● if n = even number, has i D2h
▪ 2σv 3σ Total symmetry ● e.g : naphthalene
▪ i = S2 elements = 8
C2
C2
C2
C2
C2
C2 i C2
From front / side view
C2 i σ
C2 From top view, 3C2 axes pass
through the middle of the two
rings at x, y and z axes. Rotation
σ
can be: C21 = C2-1
σ
▪ C1 = E
▪ C31 = 120° (main axis) ● nC2 axes perpendicular to the POINT GROUP:
▪ C32 = 240° = C3-1 (main axis) principal axes Cn
▪ 3C21 = 180° = C2-1 (3C2 ⊥ C3) ● e.g : phosphorous pentafluoride
D3h
▪ σh
▪ 3σv Total symmetry C3
▪ S3 elements = 12
▪ S3-1 From front /
side view
C2 C3 σv
C2 C2
C2 C2
C3
σh C2
From top view, C3 axis passess
C2 through P−F bond. Rotation can be:
C2 1. C31 C2
2. C32 = C3-1
σv σv
▪ C1 = E
▪
▪
C41 = 90° (main axis)
C42 = C21 = 180° = C4-2 (main axis)
● nC2 axes perpendicular to the POINT GROUP:
principal axes Cn
▪
▪
C43 = 270° = C4-1 (main axis)
4C2 = 180° = C2-1 (4C2 ⊥ C4) ● if n = even number, has i
D4h
▪ σh ● e.g : xenon tetrafluoride
▪ 2σv
Total symmetry
▪ 2σd
elements = 16
C4/C2
▪ i = S2 C2
▪ S4 C2 C2
▪ S4-1 C2 σv
C2
C2 C2
C2 C2 C2
From front / side view C4/C2
i C2
From top view, C4 and C2 axes pass σv
C2 through Xe atom. Rotation can be:
C4/C2 σd
σd
Get
1. C41

σ re
2. C42 = C21 = C4-2 = C2-1
3. C43 = C4-1
h
 C1 = E
▪
▪ C21 = 180° = C2-1 (main axis)
● nC2 axes perpendicular to the
principal axes Cn
POINT GROUP:
▪
▪
2C21 = 180° = C2-1 (2C2 ⊥ C2)
2σd
● S2n D2d
Total symmetry ● n σd plane
▪ S4 X ● e.g : allene
▪ S4-1 elements = 8

C2
C2 C2
From front / side view
σd C2 From this view, 2 dihedral
planes pass through origin
σd & main axis. These 2σd σd C2
bisect the angle between
two C2 axes. Rotation can σd
C2 be: C21 = C2-1
▪ C1 = E
C31 = 120° (main axis)
▪
▪ C32 = 240° = C3-1 (main axis)
● nC2 axes perpendicular to the POINT GROUP:
principal axes Cn
▪
▪
3C21 = 180° = C2-1 (3C2 ⊥ C3)
3σd ● if n = odd number, has i
D3d
▪ i = S2 Total symmetry ● S2n
●
-
▪ S6 n σd plane
elements = 12
▪ S6-1 ● e.g : ethane (staggered)
From front /
side view C3
From this view, 3
C2
σd σd dihedral planes
C2 C2
pass through
origin & main
axis. These 3σd
i
σd bisect the angle
between two C2
C2 C2 axes. Rotation
can be: C21 = C2-1 C2
 SYMMETRY OBJECT
04
Groups with
high
symmetry

https://www.wayfair.com/ https://www.westelm.ca/
 LINEAR
LINEAR LINEAR
SYMMETRICAL ASYMMETRICAL
DGe
∞h Car
∞v
e.g : ethyne e.g : HCN

✔ C∞ Total symmetry ✔ C∞ Total symmetry

✔ C∞ -1
elements = ∞ ✔ C∞ -1 elements = ∞
✔ ∞C2 C2 ✔ ∞C2
✔ σh σ⑧
h ✔ ∞σv
✔ ∞σv σv σv
8
✔ i =S2
✔ S∞ i
O CO
∞ C∞
✔OS∞ -1
↓
↓ ↓
principle
rotate B Sebab axis
reflection
d49
belan
balance
 cassignment)
TETRAHEDRAL Td
Total symmetry
C3 C3 TETRAHEDRAL T
elements = 24 Total symmetry
✔ C1 = E elements = 12
✔ 4C31 = 120°
C3 C3 ✔ C1 = E
✔ 4C32 = 240° = 4C3-1 ✔ 4C31 = 120°
✔ 3C21 = 180° = 3C2-1 ✔ 4C32 = 240° = 4C3-1
✔ 6σd ✔ 3C21 = 180° = 3C2-1
✔ 3S4 C3
O
✔ 3S4-1 ↓ https://symotter.org/

pote
From front / side view

C3 4C3 axes pass through four C−H bonds. Rotation can be:
1. C31
2. C32 = C3-1
From top view and thus 4C31 and 4C32 = 4C3-1
 TETRAHEDRAL Td slat Look this molecule
from top view

Total symmetry
elements = 24
✔ C1 = E
C2
jepopha
C2
C2
✔ 4C31 = 120°
✔ 4C32 = 240° = 4C3-1
✔ 3C21 = 180° = 3C2-1 bottom to top front to back left to right
faces faces faces
C2
✔ 6σd
✔ 3S4
✔ 3S4-1
From top view:
C2 axes passess
through C atom
from left to right
faces
 TETRAHEDRAL Td Look this molecule
from top view

Total symmetry
elements = 24 σd C2
C2
✔ C1 = E C2
✔ 4C31 = 120° σd σd σd σd
✔ 4C32 = 240° = 4C3-1 σd σd
✔ 3C21 = 180° = 3C2-1 C2
✔ 6σd left to right front to back bottom to top
✔ 3S4 faces faces faces
✔ 3S4-1 σd
 TETRAHEDRAL Td
Total symmetry
C4
elements = 24
✔ C1 = E
✔ 4C31 = 120°
✔ 4C32 = 240° = 4C3-1
✔ 3C21 = 180° = 3C2-1 1. Rotate 90° at C4 axis passes
✔ 6σd through C atom from:
✔ 3S4 a. top to bottom face of cube.
✔ 3S4-1 b. front to back face of cube
c. right to left face of cube
Rotation can be: C41 = C4-1
2. Reflect through plane
perpendicular to C4 axis.
3. Therefore, improper rotation
can be: 3S41 and 3S4-1
 Cassignment)
OCTAHEDRAL Oh
Total symmetry C4/C2 OCTAHEDRAL O
elements = 48 Total symmetry
✔ C1 = E elements = 24
✔ 3C41 = 90° = 3C4-1 ✔ C1 = E
✔ 3C21 = 3C42 = 180° = 3C2-1 = 3C4-2 ✔ 3C41 = 90° = 3C4-1
✔ 3C43 = 270° = 3C4-1 ✔ 3C21 = 3C42 = 180°
✔ 3σh C4/C2 = 3C2-1 = 3C4-2
✔ 4C31 = 120° ✔ 3C43 = 270° = 3C4-1
✔ 4C32 = 240° = 4C3-1 ✔ 4C31 = 120°
✔ 6C21 = 6C42 = 180° = 6C2-1 = 6C4-2 C4/C2
✔ 4C32 = 240° = 4C3-1
✔ 6σd From front / ✔ 6C21 = 6C42 = 180°
✔ i =S2 side view = 6C2-1 = 6C4-2
✔ 3S4
✔ 3S4-1 3C2 and 6C4 axes pass through the S
https://symotter.org/
✔ 4S6 atom at x, y and z axes. Rotation can be:
✔ 4S6-1 C41, C21 and C43
 OCTAHEDRAL Oh
Total symmetry C4
elements = 48
✔ C1 = E
✔ 3C41 = 90° = 3C4-1
✔ 3C21 = 3C42 = 180° = 3C2-1 = 3C4-2
At each of the x, y,
✔ 3C43 = 270° = 3C4-1
and z axes, σh is
σh
✔ 3σh C4
perpendicular to the
✔ 4C31 = 120°
C4 main axis.
✔ 4C32 = 240° = 4C3-1 C4
✔ 6C21 = 6C42 = 180° = 6C2-1 = 6C4-2 σh
✔ 6σd
✔ i =S2 σh
✔ 3S4
✔ 3S4-1
From front / side view
✔ 4S6
✔ 4S6-1
 OCTAHEDRAL Oh
Total symmetry Look this molecule
elements = 48 from top view
✔ C1 = E
✔ 3C41 = 90° = 3C4-1
✔ 3C21 = 3C42 = 180° = 3C2-1 = 3C4-2
✔ 3C43 = 270° = 3C4-1
✔ 3σh
✔ 4C31 = 120° C3
✔ 4C32 = 240° = 4C3-1
✔ 6C21 = 6C42 = 180° = 6C2-1 = 6C4-2
✔ 6σd
✔ i =S2
✔ 3S4 C3
✔ 3S4-1
✔ 4S6
✔ 4S6-1
 C2
OCTAHEDRAL Oh σ d C2
σh
C2
σd
Total symmetry C2
elements = 48
✔ C1 = E
✔ 3C41 = 90° = 3C4-1 σh
✔ 3C21 = 3C42 = 180° = 3C2-1 = 3C4-2
✔ 3C43 = 270° = 3C4-1
✔ 3σh σd
σd
✔ 4C31 = 120°
✔ 4C32 = 240° = 4C3-1
C2
✔ 6C21 = 6C42 = 180° = 6C2-1 = 6C4-2 σd
✔ 6σd C2
✔ i =S2
✔ 3S4 Each σh has two σd and σh
✔ 3S4-1 two C2 axes. All of the C2
✔ 4S6 axes are parallel to σd. σd
✔ 4S6-1
 OCTAHEDRAL Oh
Total symmetry
elements = 48
✔ C1 = E
C4
✔ 3C41 = 90° = 3C4-1
✔ 3C21 = 3C42 = 180° = 3C2-1 = 3C4-2
✔ 3C43 = 270° = 3C4-1 rotate clockwise about the C4 axis and reflect in a plane
✔ 3σh perpendicular to the C4
✔ 4C31 = 120°
✔ 4C32 = 240° = 4C3-1
✔ 6C21 = 6C42 = 180° = 6C2-1 = 6C4-2
✔ 6σd C6
✔ i =S2
✔ 3S4
✔ 3S4-1 i rotate clockwise about the C6 axis and reflect in a plane
✔ 4S6
perpendicular to the C6
✔ 4S6-1
 >
buat
dull baruFatbdulbar
o of
There are four symmetry operations which are : A, B, C and D
A x B = C x D
then the right and left operations are said to
Carry out operation
commute or to be commutative B first, then A.
Carry out operation
But if A x B ≠ C x D
D first, then C.

then the right and left operations are said to

do not commute or are non-commutative #every A,B, C, D
are different
 at

②
geclogwatrayrosanta
C31 x σv(H(2)-N) = S31 x σh
commutative and non-commutative ?
e.g: NH3
C3
σv C 31
1
2 3
3
2 1 C
2
1 3

σh
C3 trotate
S 31
retection
Sommutate)
&queen
1 1 3 2
2 3 2 3 1

C31 x σv(H(2)-N) ≠ S31 x σh

non-commutative
THE END