Optical Isomers

Constitutional Isomers
Have same molecular form but different structural formula Both isomers to the right are C4H10 These have different chemical and physical properties
CH2 H3C CH2
butane
B.P = -0.5rC

CH3

CH3 CH H3 C CH3

isobutane
B.P = -11.7 rC

Stereoisomers
Appear to have same structure in 2D In 3D have different structures Are non-superimposable mirror images of each other

With modeling kit build a model: carbon atom with four different colors attached (use same size bonds!) Look at your model in a mirror, build what you see in the mirror. Are the two superimposable? Animation (watch Chirality)

How to draw 3D: Dash-Wedge Formula

Draw two straight lines about 110 r from each other
Bond angle is 109.5r These represent the bonds in the plane of the page

H Cl OH CH3

Draw dashed line for the bond that extends behind the plane of the page Draw wedge for bond that extends in front of the plane of the page

Drawing Enantiomers
Draw the molecule you built, using the dash-wedge formula and colored pens Use a mirror to see the enantiomer Sketch the mirror image, using the dashwedge formula Draw the two stereoisomers of 1-chloro-1bromo-ethane.
There is no convention for which atom is attached to a wedge.

Chiral centers
Carbon attached to 4 different substituent groups
Even if two substituent groups start with C, they could still be different
H H3CH2C OH CH3

HO H3 C

CH2CH3

C=O, never chiral (C only attached to 3 things) CH3, CH2 groups, never chiral because they are symmetric:

Vocabulary
Stereoisomers have chiral centers. Carbon atoms can be
chiral or achiral Asymmetric or symmetric

If two molecules are stereoisomers, they are also called enantiomers Chiral molecules are optically active Enantiomers are optical isomers

Properties of Optical Isomers

same physical and chemical properties rotate plane polarized light
Each isomer rotates it in a different direction What is plane polarized light?
Animation (watch Optical Activity)

Try polarizers

Optical Activity
Stereoisomers are said to be optically active if the rotate plane polarized light Each type of enantiomer rotates light the same amount, but in different directions. Amount and direction of rotation must be experimentally determined using a polarimeter

Optical Activity
The amount of rotation depends on
Length of sample tube Concentration of enantiomers

Both isomers present, rotation cancels out called: racemic mixture