Advices For Studying Organic Chemistry

images of each other.

2) The plane may pass through atoms, between atoms, or both.

Figure 5.8 (a) 2-Chloropropane has a plane of symmetry and is achiral. (b)
2-Chlorobutane does not possess a plane of symmetry and is chiral.

4. The achiral hydroxyacetic acid molecule versus the chiral lactic acid molecule:
   
   
   1. Hydroxyacetic acid has a plane of symmetry that makes one side of the
      molecule a mirror image of the other side.
   
   
   2. Lactic acid, however, has no such symmetry plane.
   
   
   
   

H C

OH

H

COOH

CH 3 CH(OH)COOH

Lactic acid

(chiral)

H C

HO

CH 3

COOH

HO−CH 2 COOH

Hydroxyacetic acid

(achiral)

Symmetry plane NOymmetryplane

5.6 NOMENCLATURE OF ENANTIOMERS: THE (R-S) SYSTEM