1. Learning Objectives (LO)
Optical isomerism
Learning Objectives (LO)
Be able to explain how racemic mixtures are formed
Be able to describe how enantiomers affect plane polarised light
Be able to identify molecules that exhibit optical isomerism
Keywords:
Stereoisomer, chiral, plane-polarised light, enantiomer, racemate, optically-active

2. SHOW CLIP

3. S carvone (caraway seed)
R carvone (spearmint)
The film just showed these molecules in this slide.
These molecules look exactly alike.
They have all the same atoms but they can be different.
They can smell differently.
They taste differently and they rotate light differently.
We say they are optically active or they are stereoisomers
Caraway Seed is peppery and citrusy with
Some liquorice overtones
From the carrot family

4. OPTICALLY ACTIVE CHEMICALS
1-methyl-4-isopropyl-1-cyclohexene.
R limonene (oranges)
S limonene (lemons)

5. PLANE POLARISED LIGHT
Light travels in waves in all directions from the source. It is like
tying a piece of thick string to a hook in a wall, and then shaking the string vigorously; up and down and side to side.
Now, suppose you passed the string through a vertical slit. The string is a really snug fit in the slit. The only vibrations still happening is one direction (up and down). What you have is "plane polarised string“. Well, light does the same thing, after it emerges from such slits it is called PLANE POLARISED LIGHT

6. PLANE POLARISED LIGHT
But if the second slit is at 90° to the first one, the string will stop vibrating entirely. Plane polarized light, like a single directional string, can be stopped or blocked, and all goes dark (or black)
Clockwise is called +
Or dextrorotatory  (d) to the right.
Left is (-) or laevorotatory (l) (anticlockwise)
Optically active chemicals are able to rotate light (that is polarized).
If you shine a beam of polarised light through a chemical that is optically, when the light emerges it will have been rotated.

7. OPTICALLY ACTIVE CHEMICALS
Notice the left has 2 same (pink) atoms, ALL are NOT different so it has a plane of symmetry and is achiral (non handed). You only get optical isomers if all four groups attached to the central carbon are different. When all are different (right side) there will NOT be any symmetry, they are chiral (like your hands) and optically active and are known as enantiomers

8. Chirality
Chiral means handedness. Hands are mirror images and NOT superimposable. Try it. Optical isomers (enantiomers) like hands, are molecules that are mirror images and are non-superimposable
Ask student to explain

9. CHEMICALS and MIRROR IMAGES
All molecules have a mirror image – but they are NOT optically active if they are not ALL different (notice 2 hydrogen's, so all atoms not different)
Ask student to explain

10. OPTICALLY ACTIVE CHEMICALS
Chiral, all 4 groups are different, have mirror images which are not non-superimposable
Ask student to explain

11. Non Superimposable Mirror Image
What is a non-superimposable mirror image?
Wait a few seconds
Animation doesn’t work in old versions of Powerpoint

12. Chirality and mirror images explained
Film clip Khan Video ( 4 min)

13. CHEMICALS and MIRROR IMAGES
Prove all this for yourself, use your molymods to build the following molecules: Build 2 of each
Methane
Bromochloromethane
Bromochlorofluoromethane
Try to superimpose them onto one another, can it be done.
mirror images of the following compounds:
Which ones are superimposable? Which ones aren’t?
What is the difference between them? Which are chiral, which achiral?
Which are optically active?

14. OPTICALLY ACTIVE AMINO ACIDS
Do amino acids (alanine, if R = CH3 ) have 4 different groups? If Glycine, where R = H
Answer : Yes, no
Are they therefore chiral?
Is the amino acid a mirror images?
Are they superimposable?
Are they optically active, or will they rotate plane polarized light?
Answer : Yes,no

15. SUMMARY
These are chiral molecules and so are optically active or are able to rotate light right (+) or left (-). They are called optical isomers or enantiomers
They are asymmetric carbons with four different groups arranged tetrahedrally around it.
A 50/50 mixture of the two enantiomers is a racemic mixture and is NOT optically active as the rotations cancel if present in equal amounts
Students to draw this diagram

16. 1-chloro-2-methylpropanane 2-chloro-2-methylpropanane
SPOTTING CHIRAL CENTRES
Look at each carbon atom in the chain and see what is attached to it. For a chiral centre
you need an asymmetric carbon with four different atoms/groups) arranged tetrahedrally around it.
IF A CARBON HAS MORE THAN ONE OF ANY ATOM/GROUP ATTACHED, IT CAN’T BE CHIRAL
CH3CH2CH2CH2Cl
C 3 H’s around it NOT chiral
C 2 H’s around it NOT chiral 
1-chlorobutane
CH3CH2CHClCH3
C 3 H’s around it NOT chiral
C 2 H’s around it NOT chiral
C H, CH3, Cl,C2H5 around it CHIRAL 
2-chlorobutane
(CH3)2CHCH2Cl
C 3 H’s around it NOT chiral
C 2 CH3’s around it NOT chiral
C 2 H’s around it NOT chiral 
1-chloro-2-methylpropanane
(CH3)3CCl
C 3 H’s around it NOT chiral
C 3 CH3’s around it NOT chiral 
2-chloro-2-methylpropanane

17. TASK
10 minutes
Are each of the molecules optically active? Draw them and identify the chiral carbon
a) propan-2-ol
e) butanone
b) 2-chlorobutane
f) 2-methylbutanoic acid
c) 1-chlorobutane
g) butan-2-ol
Questioning activity.
d) 3-methylhexane
h) 1-chloro-3-methylpentane

18. Propan-2-ol
NOT OPTICALLY ACTIVE

19. 2-chlorobutane
OPTICALLY ACTIVE

20. 3-methylhexane
OPTICALLY ACTIVE

21. butanone
NOT OPTICALLY ACTIVE

22. Propan-2-ol
NOT OPTICALLY ACTIVE

23. 2-methylbutanoic acid
OPTICALLY ACTIVE

24. Butan-2-ol
OPTICALLY ACTIVE

25. 1-chloro-3-methylpentane
OPTICALLY ACTIVE

26. SUMMARY The optical isomers are called enantiomers.
They have identical chemical and physical properties, except:
Their effect on plane polarised light
Their reaction with other chiral molecules
Ask student to explain

27. OPTICAL ISOMERISM - THALIDOMIDE
The drug, THALIDOMIDE is a chiral molecule and can exist as two enantiomers, a racemic mixture. In the 1960’s it was used to treat anxiety and morning sickness in pregnant women. Tragically, many gave birth to children with deformities and missing limbs.
It turned out that only one of the enantiomers
(the structure on the right) was effective and safe;
its optically active counterpart was not.
The major problem was that during manufacture
a mixture of the isomers was produced.

28. Thalidomide (2min)

29. (illegal psychotic drug)
S methamphetamine
(illegal psychotic drug)
R methamphetamine
(nasal decongestant)

30. ALAN BAXTER Winter Olympics 2002 in USA won silver in skiing
stripped of medal after failed drugs test
had used US Vicks inhaler
contained R-methamphetamine (not in UK version) – but original test did not distinguish this from enantiomer (which is stimulant & illegal)
despite the R-methamphetamine having no stimulant effect, he lost his medal

31. Spot the chiral carbon (there may be one, none or many)

32. Check your answers… *
2-bromobutane

33. Check your answers…
Aspirin
No chiral carbon atoms

34. Check your answers… * *
Aspartame

35. Check your answers…
Chloroethanoic acid
No chiral carbon atoms

36. Check your answers… *
2,3-dimethyl pentane

37. Check your answers…
Propene
No chiral carbon atoms

38. Check your answers… *
Thirosine

39. Check your answers…
Binol
No chiral carbon atoms

40. Check your answers… *
Thalidomide

41. Check your answers… * * * * *
Glucose

42. Check your answers… *
Phenylalanine

43. Check your answers…
Glycine
No chiral carbon atoms

44. ∆ 9-tetrahydrocannabinol
Check your answers… * *
∆ 9-tetrahydrocannabinol

45. Check your answers… * * *
Cytosine

46. Check your answers… *
Methionine

47. Check your answers…
Glycerol
No chiral carbon atoms

48. Check your answers… * * * * * * *
Cholesterol