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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

All molecules have a mirror image

but for most molecules it is the same
molecule.

H
F

H
F

fluoromethane

For some molecules the mirror image

is a different molecule (the mirror
image is non-superimposable).

OH

OH

COOH
CH3

(-) lactic acid

in sour milk

HOOC
H3C

(+) lactic acid

in muscles

Left and right hands are an example

of non-superimposable mirror images.

 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.

The optical isomers are called enantiomers.

These are distinguished by +/-, D/L or more correctly R/S.
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 its name below and decide whether it is optically active or not.
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

propan-2-ol

CH3

CH

CH3

OH

NOT OPTICALLY ACTIVE

Click here to go back to the optical isomerism task

2-chlorobutane

CH3

CH

CH2

CH3

Cl

CH2CH3

CH2CH3

CH3
Cl

H3C
Cl

OPTICALLY ACTIVE
Click here to go back to the optical isomerism task

1-chlorobutane

CH2

CH2

CH2

Cl

NOT OPTICALLY ACTIVE

Click here to go back to the optical isomerism task

CH3

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3-methylhexane

CH3 CH2 CH CH2 CH2 CH311

CH3

CH2CH 2CH 3

CH2CH2CH 3

CH3
CH2CH 3

CH3
CH3CH2

OPTICALLY ACTIVE
Click here to go back to the optical isomerism task

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butanone

CH3

CH2

CH3

NOT OPTICALLY ACTIVE

Click here to go back to the optical isomerism task

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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

CH

CH2CH3

CH2CH3

H
COOH

H
HOOC

OPTICALLY ACTIVE
Click here to go back to the optical isomerism task

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OH

CH3

OH

butan-2-ol
CH3

CH3

CH2

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CH

CH3

CH2CH3

CH2CH3

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

H
CH2CH2Cl

H
CH2ClCH2

OPTICALLY ACTIVE
Click here to go back to the optical isomerism task

CH3

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Molecules that are optical isomers are

called enantiomers.
Enantiomers have identical chemical
and physical properties, except:
Their effect on plane polarised light;
Their reaction with other chiral molecules

 Light is a form of electromagnetic

radiation.

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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

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Optical isomers rotate the plane of

plane polarised light.

(-)-enantiomer
(anticlockwise rotation)

(+)-enantiomer
(clockwise rotation)

()-racemate
(no overall effect)

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.hw.ac.uk/site/chemistry/activity5.asp?outline

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 Chiral molecules often react differently with

other chiral molecules.
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.
Many natural molecules are chiral and most
natural reactions are affected by optical
isomerism.

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 For example, most amino acids (and

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

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 Many drugs are optically active, with

one enantiomer only having the
beneficial effect.
In the case of some drugs, the other
enantiomer can even be harmful, e.g.
thalidomide.

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 In the 1960s thalidomide was given

to pregnant women to reduce the
effects of morning sickness.
This led to many disabilities in babies
and early deaths in many cases.

The photographs are both from Molecule of the Month at Bristol University:
http://www.chm.bris.ac.uk/motm/thalidomide/start.html

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NH

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.

CH2

H2C

H
O

R thalidomide (dangerous drug)

 Thalidomide was banned

worldwide when the effects were
discovered.

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Your nose is chiral too!

CH3

CH3

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CH2

H3C

S carvone (caraway seed)

Caraway Seed has a warm, pungent,

slightly bitter flavour with aniseed overtones.

H2C

CH3

R carvone (spearmint)

CH3

CH3

CH2

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CH2

CH3

H3C

S limonene (lemons)

R limonene (oranges)