1) Only one compound with the general formula CH 3 X is ever found.
2) Only one compound with the formula CH 2 X 2 or CH 2 XY is ever found.
3) Two enantiomeric compounds with the formula CHXYZ are found.
H
HH
H
C H
H H
C H H
H H
H
C
Planar Pyramidal Tetrahedral
H
HH
X C H X
HH
C Y
H Y
C H
Cis Trans
Cis Trans
X X
H H
C Y H
H H
C H
H Y
C H
YX H X
H
C H Y
H
rotate 180 C
o
Y
X Z X
H
C Z Y
H
C
5.5 TESTS FOR CHIRALITY: PLANES OF SYMMETRY
- Superposibility of the models of a molecule and its mirage:
- If the models are superposable, the molecule that they represent is achiral.
- If the models are nonsuperposable, the molecules that they represent are chiral.
- The presence of a single tetrahedral stereocenter ⇒ chiral molecule.
- The presence of a plane of symmetry ⇒ achiral molecule
- A plane of symmetry (also called a mirror plane) is an imaginary plane that
bisects a molecule in such a way that the two halves of the molecule are mirror