Amides and Chirality

Amides: Amides are products of reactions of acyl chlorides with ammonia/ amines.
 Stereoisomerism: Remember stereoisomerism are compounds with same structural formula but
different arrangement of atoms in space. Types of stereoisomerism are optical isomerism and E/
Z isomerism.
 Optical Isomerism: Optical isomerism is found in molecules with any chiral centre. For example
in organic a chiral carbon that is attached to four different groups. For each chiral carbon, there
is two non- superimposable mirror image about a chiral centre structures known as optical
isomers or enantiomers.
 Not immediate group but overall group e.g. if were to name them, would they be different. If
not symmetrical, then a chiral. Alkene may count as a different group.
 Alkenes count as different group. But don’t look at the carbon in the double bond as has 3 not 4
groups attached.
 When carbon part of benzene- decide if go in both directions from that carbon, is it exactly the
same/ symmetrical? If it is, then it is in chiral carbon.
 Amino Acids: Chiral carbon in almost all α amino acids.
 Drawing Optical Isomers: Optical isomers drawn in the 3D tetrahedral arrangement to show
four different groups around chiral carbon- the four bonds attached to C. Draw second isomer as
mirror image.
Learn this diagram. Remember mirror
image. Keep the things same distance from mirror line etc.
Chiral carbon are marked below. With skeletal, remember the H atoms.

All are chiral apart from 9.
3, 4, 5 and 7 are chiral because have H and then 3 different bits of ring. 1, 2 and 6 have H, a
functional group and 2 different bits of ring.
Ignore double bond as not 4 different groups.