Advices For Studying Organic Chemistry

5.17 CHIRAL MOLECULES THAT DO NOT POSSES A

TETRAHEDRAL

ATOM WITH FOUR DIFFERENT GROUPS

1. Allenes:

CCC

CCC

R

R' R'

R

CCC

Cl

H H

Cl

C C C

Cl

H H

Cl

Mirror

Figure 5.22 Enantiomeric forms of 1,3-dichloroallene. These two molecules are
nonsuperposable mirror images of each other and are therefore chiral.
They do not possess a tetrahedral atom with four different groups,
however.

Binaphthol

OH

OH

HO

HO

O

O

H

H

O

O

H

H