You are on page 1of 30

1

OPTICAL ISOMERISM
R W Grime

Ripon Grammar School

Molecular mirror images
Optical isomerism and chirality

Enantiomers and racemates

Self-Test: recognising optical isomers from structural formulae
Polarimetry: recognising optical isomers by experiment
Examples of optical isomers and their importance
thalidomide

carvone

limonene

2

• All molecules have a mirror image –
but for most molecules it is the same
molecule.

H

H

H

C

C

H
F

H
F

fluoromethane

H

3

• For some molecules the mirror image
is a different molecule (the mirror
image is non-superimposable).

H

OH

OH

C

C

COOH
CH3

(-) lactic acid
in sour milk

HOOC
H3C

H

(+) lactic acid
in muscles

.4 • Left and right hands are an example of non-superimposable mirror images.

b a a C C c d d c b 5 .• This usually happens when a molecule contains a C atom with four different groups attached (chiral / asymmetric C). • Such molecules are said to be chiral or optically active.

D/L or more correctly R/S.6 • The optical isomers are called enantiomers. • These are distinguished by +/-. • A 50/50 mixture of the two enantiomers is called a racemic mixture or a racemate and shows no optical activity .

TASK Some of the following molecules are optically active. For each one. Click again to see if you are correct. a) propan-2-ol e) butanone b) 2-chlorobutane f) 2-methylbutanoic acid c) 1-chlorobutane g) butan-2-ol d) 3-methylhexane h) 1-chloro-3-methylpentane 7 . click its name below and decide whether it is optically active or not.

propan-2-ol CH3 CH CH3 OH NOT OPTICALLY ACTIVE Click here to go back to the optical isomerism task 8 .

2-chlorobutane CH3 CH CH2 CH3 Cl H CH2CH3 CH2CH3 C C CH3 Cl H3C Cl OPTICALLY ACTIVE Click here to go back to the optical isomerism task H 9 .

1-chlorobutane CH2 CH2 CH2 Cl NOT OPTICALLY ACTIVE Click here to go back to the optical isomerism task CH3 10 .

3-methylhexane CH3 CH2 CH CH2 CH2 CH311 CH3 H CH2CH 2CH 3 CH2CH2CH 3 C C CH3 CH2CH 3 CH3 CH3CH2 OPTICALLY ACTIVE Click here to go back to the optical isomerism task H .

12 O butanone CH3 C CH2 CH3 NOT OPTICALLY ACTIVE Click here to go back to the optical isomerism task .

13 propan-2-ol CH3 CH CH3 OH NOT OPTICALLY ACTIVE Click here to go back to the optical isomerism task .

2-methylbutanoic acid CH3 CH3 CH2 CH3 O CH C CH2CH3 CH2CH3 C C H COOH H HOOC OPTICALLY ACTIVE Click here to go back to the optical isomerism task 14 OH CH3 .

OH butan-2-ol CH3 CH3 CH2 15 CH CH3 CH2CH3 CH2CH3 C C H OH H HO OPTICALLY ACTIVE Click here to go back to the optical isomerism task CH3 .

CH3 1-chloro-3-methylpentane CH3 CH3 CH2 CH Cl CH2 CH2 CH2CH3 CH2CH3 C C H CH2CH2Cl H CH2ClCH2 OPTICALLY ACTIVE Click here to go back to the optical isomerism task CH3 16 .

• Their reaction with other chiral molecules . • Enantiomers have identical chemical and physical properties.17 • Molecules that are optical isomers are called enantiomers. except: • Their effect on plane polarised light.

18 .• Light is a form of electromagnetic radiation.

19 • The wave vibrations are perpendicular to the direction of travel of the wave. normal light (waves vibrate in all directions) plane-polarised light (vibrates in only one direction) plane-polarised light after clockwise rotation .

20 • Optical isomers rotate the plane of plane polarised light. (-)-enantiomer (anticlockwise rotation) (+)-enantiomer (clockwise rotation) (±)-racemate (no overall effect) .

hw.ac.POLARIMETERS can be used to analyse the effect optical isomers have on plane polarised light: Heriot Watt University has a web page with an interactive tutorial and self-test questions about this topic: http://scholar.asp?outline 21 .uk/site/chemistry/activity5.

• This is like the idea that a right hand does not fit a left handed glove – the molecule must be the correct shape to fit the molecule it is reacting with.• Chiral molecules often react differently with other chiral molecules. • Many natural molecules are chiral and most natural reactions are affected by optical isomerism. 22 .

• For example. only one enantiomer usually occurs (e. • In nature. all natural amino acids rotate polarised light to the left). along with many other molecules. most amino acids (and so proteins) are chiral. 23 .g.

with one enantiomer only having the beneficial effect. 24 . thalidomide. e. the other enantiomer can even be harmful.• Many drugs are optically active. • In the case of some drugs.g.

ac.bris.uk/motm/thalidomide/start. • This led to many disabilities in babies and early deaths in many cases.chm.html 25 . The photographs are both from ‘Molecule of the Month’ at Bristol University: http://www.• In the 1960’s thalidomide was given to pregnant women to reduce the effects of morning sickness.

26 O NH O O O H2C NH O C C N CH2 H O S thalidomide (effective drug) The body racemises each enantiomer. so even pure S is dangerous as it converts to R in the body. O N CH2 H2C H O R thalidomide (dangerous drug) .

27 .• Thalidomide was banned worldwide when the effects were discovered.

28 Your nose is chiral too! .

H2C C H CH3 R carvone (spearmint) .CH3 CH3 29 O O H C CH2 H3C S carvone (caraway seed) Caraway Seed has a warm. pungent. slightly bitter flavour with aniseed overtones.

CH3 CH3 CH2 C H H 30 C CH2 CH3 H3C S limonene (lemons) R limonene (oranges) .