Symmetry and Stereochemistry

There are three elements of symmetry

that a molecule may possess…
 Symmetry Operations: Reflection
Symmetry operations are spatial transformations (rotations,
reflections, inversions). A molecule is said to possess a symmetry
element if the molecule is unchanged in appearance after applying
the symmetry operation corresponding to the symmetry element.

H O H The blue plane is a plane of symmetry of A.

A H
C C
H The operation of reflection (σ) involves
projection of each atom onto the plane,
H followed by movement through the plane to a
H distance equal to the projection distance.

H O H H O H
σ
H H H H
C C C C

H H H H
Reflection through the plane is a
symmetry operation on A. Although the
σ red and magenta H’s have changed places,
H O H H O H
H H H H the molecule looks the same. We say that
C C C C A possesses reflection symmetry.

H H H H Animations of the reflection process

 Symmetry Operations: Rotation
Symmetry operations are spatial transformations (rotations,
reflections, inversions). A molecule is said to possess a symmetry
element if the molecule is unchanged in appearance after applying
the symmetry operation corresponding to the symmetry element.

Animations of the rotation process The red axis is an axis of symmetry of A.

O The operation of rotation (Cn) involves rotation
A H H of the molecule 360/n degrees about an axis.
The axis shown is a “C2” axis.
H HH H

Rotation about the axis is a symmetry

O O operation on A. Although the red and
H H H H magenta H’s have changed places, the
molecule looks the same. We say that A
H HH H H HH H possesses 2-fold rotational symmetry.

180°
 Symmetry Operations: Inversion
Symmetry operations are spatial transformations (rotations,
reflections, inversions). A molecule is said to possess a symmetry
element if the molecule is unchanged in appearance after applying
the symmetry operation corresponding to the symmetry element.

H3C H The blue point is an inversion center of G.

Br The operation of inversion (i) involves the
G projection of each atom onto a point at the
center of the molecule, followed by movement
Br through the point to a distance equal to the
H CH3 projection distance.

H3C H H3C H Inversion through the point is a symmetry

Br Br operation on G. Although inversion
exchanges all three groups attached to the
Br Br
H H central carbon, the molecule looks the same.
CH3 CH3
We say that G possesses inversion
symmetry.
Animations of the inversion process