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ISOM RISM
E
A guide for the students
ISOMERISM
CONTENTS
• Prior knowledge
• Types of isomerism
• Structural isomerism
• Stereoisomerism
• Geometrical isomerism
• Optical isomerism
• Check list
ISOMERISM
Before you start it would be helpful to…
• know the functional groups found in organic chemistry
• know the arrangement of bonds around carbon atoms
• know what affects the boiling point of organic molecules
TYPES OF ISOMERISM
CHAIN ISOMERISM

STRUCTURAL ISOMERISM
Same molecular formula but
different structural formulae

POSITION ISOMERISM

FUNCTIONAL GROUP
ISOMERISM

GEOMETRICAL ISOMERISM

STEREOISOMERISM
Same molecular
formula but atoms
occupy different
positions in space.

Occurs due to the restricted
rotation of C=C double bonds...
two forms… E and Z (CIS and
TRANS)
OPTICAL ISOMERISM
Occurs when molecules have a
chiral centre. Get two nonsuperimposable mirror images.
STRUCTURAL ISOMERISM - INTRODUCTION
COMPOUNDS HAVE THE SAME MOLECULAR FORMULA
BUT DIFFERENT STRUCTURAL FORMULA
Chain

different arrangements of the carbon skeleton
similar chemical properties
slightly different physical properties
more branching = lower boiling point
STRUCTURAL ISOMERISM - INTRODUCTION
COMPOUNDS HAVE THE SAME MOLECULAR FORMULA
BUT DIFFERENT STRUCTURAL FORMULA
Chain

different arrangements of the carbon skeleton
similar chemical properties
slightly different physical properties
more branching = lower boiling point

Positional

same carbon skeleton
same functional group
functional group is in a different position
similar chemical properties - slightly different physical properties
STRUCTURAL ISOMERISM - INTRODUCTION
COMPOUNDS HAVE THE SAME MOLECULAR FORMULA
BUT DIFFERENT STRUCTURAL FORMULA
Chain

different arrangements of the carbon skeleton
similar chemical properties
slightly different physical properties
more branching = lower boiling point

Positional

same carbon skeleton
same functional group
functional group is in a different position
similar chemical properties - slightly different physical properties

Functional Group different functional group
different chemical properties
different physical properties
• Sometimes more than one type of isomerism occurs in the same molecule.
• The more carbon atoms there are, the greater the number of possible isomers
STRUCTURAL ISOMERISM - CHAIN
caused by different arrangements of the carbon skeleton
similar chemical properties
slightly different physical properties
more branching = lower boiling point

There are two structural isomers of C4H10. One is a straight chain molecule where all
the carbon atoms are in a single row. The other is a branched molecule where three
carbon atoms are in a row and one carbon atom sticks out of the main chain.

BUTANE
straight chain

2-METHYLPROPANE
branched

C4H10
STRUCTURAL ISOMERISM - CHAIN
DIFFERENCES BETWEEN CHAIN ISOMERS
Chemical

Isomers show similar chemical properties because
the same functional group is present.

Physical

Properties such as density and boiling point show trends according
to the of the degree of branching

Boiling Point

“straight” chain isomers have higher values than branched ones
the greater the degree of branching the lower the boiling point
branching decreases the effectiveness of intermolecular forces
less energy has to be put in to separate the molecules
- 0.5°C
straight chain

- 11.7°C
branched

greater branching
= lower boiling point
STRUCTURAL ISOMERISM - POSITIONAL
molecule has the same carbon skeleton
molecule has the same same functional group... BUT
the functional group is in a different position
have similar chemical properties / different physical properties
Example 1

POSITION OF A DOUBLE BOND IN ALKENES

1

2

PENT-1-ENE
double bond between
carbons 1 and 2

2

3

PENT-2-ENE
double bond between
carbons 2 and 3

There are no other isomers with five C’s in the longest chain but there are three
other structural isomers with a chain of four carbons plus one in a branch.
STRUCTURAL ISOMERISM - POSITIONAL
molecule has the same carbon skeleton
molecule has the same same functional group... BUT
the functional group is in a different position
have similar chemical properties / different physical properties
Example 2

POSITION OF A HALOGEN IN A HALOALKANE

1

1-CHLOROBUTANE
halogen on carbon 1

2

2-CHLOROBUTANE
halogen on carbon 2

BUT

2

is NOT
3-CHLOROBUTANE

Moving the chlorine along the chain makes new isomers; the position is measured from
the end nearest the functional group... the third example is 2- NOT 3-chlorobutane.
There are 2 more structural isomers of C4H9Cl but they have a longest chain of 3
STRUCTURAL ISOMERISM - POSITIONAL
molecule has the same carbon skeleton
molecule has the same same functional group... BUT
the functional group is in a different position
have similar chemical properties / different physical properties
Example 3

RELATIVE POSITIONS ON A BENZENE RING

1,2-DICHLOROBENZENE
ortho dichlorobenzene

1,3-DICHLOROBENZENE
meta dichlorobenzene

1,4-DICHLOROBENZENE
para dichlorobenzene
STRUCTURAL ISOMERISM – FUNCTIONAL GROUP
molecules have same molecular formula
molecules have different functional groups
molecules have different chemical properties
molecules have different physical properties

ALCOHOLS and ETHERS

ALDEHYDES and KETONES

ACIDS and ESTERS
STRUCTURAL ISOMERISM – FUNCTIONAL GROUP
ALCOHOLS and ETHERS

Name

ETHANOL

METHOXYMETHANE

Classification

ALCOHOL

ETHER

Functional Group

R-OH

Physical properties

polar O-H bond gives rise
to hydrogen bonding.
get higher boiling point
and solubility in water

Chemical properties

Lewis base
Wide range of reactions

R-O-R
No hydrogen bonding
low boiling point
insoluble in water
Inert
STRUCTURAL ISOMERISM – FUNCTIONAL GROUP
ALDEHYDES and KETONES

Name

PROPANAL

Classification

ALDEHYDE

KETONE

R-CHO

R-CO-R

Functional Group

PROPANONE

Physical properties

polar C=O bond gives
dipole-dipole interaction

polar C=O bond gives
dipole-dipole interaction

Chemical properties

easily oxidised to acids of
same number of carbons

undergo oxidation under
extreme conditions only

reduced to 1° alcohols

reduced to 2° alcohols
STRUCTURAL ISOMERISM – FUNCTIONAL GROUP
CARBOXYLIC ACIDS and ESTERS

Name

PROPANOIC ACID

Classification

CARBOXYLIC ACID

Functional Group

R-COOH

METHYL ETHANOATE
ESTER
R-COOR

Physical properties

O-H bond gives rise
to hydrogen bonding.
get higher boiling point
and solubility in water

No hydrogen bonding
insoluble in water

Chemical properties

acidic
react with alcohols

fairly unreactive
hydrolysed to acids
STEREOISOMERISM
Molecules have the SAME MOLECULAR FORMULA but the atoms are
joined to each other in a DIFFERENT SPACIAL ARRANGEMENT - they
occupy a different position in 3-dimensional space.
There are two types...

• GEOMETRICAL ISOMERISM
• OPTICAL ISOMERISM
GEOMETRICAL ISOMERISM IN ALKENES
Introduction
•
•
•
•

an example of stereoisomerism
found in some, but not all, alkenes
occurs due to the RESTRICTED ROTATION OF C=C bonds
get two forms...
GEOMETRICAL ISOMERISM IN ALKENES
Introduction
•
•
•
•

an example of stereoisomerism
found in some, but not all, alkenes
occurs due to the RESTRICTED ROTATION OF C=C bonds
get two forms...

CIS (Z)
Groups/atoms are on the
SAME SIDE of the double bond

TRANS (E)
Groups/atoms are on OPPOSITE
SIDES across the double bond
GEOMETRICAL ISOMERISM
RESTRICTED ROTATION OF C=C BONDS
Single covalent bonds can easily rotate. What appears to be a different structure is
not. It looks like it but, due to the way structures are written out, they are the same.

ALL THESE STRUCTURES ARE THE SAME BECAUSE C-C BONDS HAVE ‘FREE’ ROTATION

Animation doesn’t
work in old
versions of
Powerpoint
GEOMETRICAL ISOMERISM
RESTRICTED ROTATION OF C=C BONDS
C=C bonds have restricted rotation so the groups on either end of the bond are
‘frozen’ in one position; it isn’t easy to flip between the two.
Animation doesn’t
work in old
versions of
Powerpoint

This produces two possibilities. The two structures cannot interchange easily
so the atoms in the two molecules occupy different positions in space.
GEOMETRICAL ISOMERISM IN ALKENES
E/Z or CIS-TRANS

E/Z

Z (zusammen)

higher priority groups / atoms on
the SAME side of C=C bond

E (entgegen)

higher priority groups / atoms on
OPPOSITE sides of C=C bond
GEOMETRICAL ISOMERISM IN ALKENES
E/Z or CIS-TRANS

E/Z

Z (zusammen)

higher priority groups / atoms on
the SAME side of C=C bond

E (entgegen)

higher priority groups / atoms on
OPPOSITE sides of C=C bond

To determine priority, the Cahn, Ingold and Prelog convention is used.
eg

C2H5 > CH3 > H

and

I > Br > Cl > F > C > H
GEOMETRICAL ISOMERISM IN ALKENES
E/Z or CIS-TRANS

E/Z

Z (zusammen)

higher priority groups / atoms on
the SAME side of C=C bond

E (entgegen)

higher priority groups / atoms on
OPPOSITE sides of C=C bond

To determine priority, the Cahn, Ingold and Prelog convention is used.
eg

C2H5 > CH3 > H

and

I > Br > Cl > F > C > H
GEOMETRICAL ISOMERISM IN ALKENES
E/Z or CIS-TRANS
Z (zusammen)

higher priority groups / atoms on
the SAME side of C=C bond

E (entgegen)

E/Z

higher priority groups / atoms on
OPPOSITE sides of C=C bond

To determine priority, the Cahn, Ingold and Prelog convention is used.
eg

E

C2H5 > CH3 > H

Z

and

I > Br > Cl > F > C > H

Z

E
GEOMETRICAL ISOMERISM IN ALKENES
E/Z or CIS-TRANS

CIS /
TRANS

Should only be used when there are two H’s and two
non-hydrogen groups attached to each carbon.
cis

non-hydrogen groups / atoms on the
SAME side of C=C bond

trans

non-hydrogen groups / atoms on
OPPOSITE sides of C=C bond
GEOMETRICAL ISOMERISM IN ALKENES
E/Z or CIS-TRANS

CIS /
TRANS

Should only be used when there are two H’s and two
non-hydrogen groups attached to each carbon.
cis

non-hydrogen groups / atoms on the
SAME side of C=C bond

trans

non-hydrogen groups / atoms on
OPPOSITE sides of C=C bond
GEOMETRICAL ISOMERISM IN ALKENES
E/Z or CIS-TRANS

CIS /
TRANS

Should only be used when there are two H’s and two
non-hydrogen groups attached to each carbon.
cis

non-hydrogen groups / atoms on the
SAME side of C=C bond

trans

non-hydrogen groups / atoms on
OPPOSITE sides of C=C bond

cis

trans

cis

trans
GEOMETRICAL ISOMERISM
GEOMETRICAL ISOMERISM
Isomerism in butene
There are 3 structural isomers of C4H8 that are alkenes*. Of these ONLY
ONE exhibits geometrical isomerism.

but-1-ene

cis but-2-ene
(Z) but-2-ene

trans but-2-ene
(E) but-2-ene

2-methylpropene

* YOU CAN GET ALKANES WITH FORMULA C4H8 IF THE CARBON ATOMS ARE IN A RING
GEOMETRICAL ISOMERISM
How to tell if it exists
Two different
atoms/groups
attached

Two different
atoms/groups
attached



Two similar
atoms/groups
attached

Two similar
atoms/groups
attached



Two similar
atoms/groups
attached

Two different
atoms/groups
attached



Two different
atoms/groups
attached

Two different
atoms/groups
attached



GEOMETRICAL ISOMERISM

Once you get two similar
atoms/groups attached to
one end of a C=C, you
cannot have geometrical
isomerism

GEOMETRICAL ISOMERISM
OPTICAL ISOMERISM
Occurrence

another form of stereoisomerism
occurs when compounds have non-superimposable mirror images

Isomers

the two different forms are known as optical isomers or enantiomers
they occur when molecules have a chiral centre
a chiral centre contains an asymmetric carbon atom
an asymmetric carbon has four different atoms (or groups)
arranged tetrahedrally around it.
OPTICAL ISOMERISM
Occurrence

another form of stereoisomerism
occurs when compounds have non-superimposable mirror images

Isomers

the two different forms are known as optical isomers or enantiomers
they occur when molecules have a chiral centre
a chiral centre contains an asymmetric carbon atom
an asymmetric carbon has four different atoms (or groups)
arranged tetrahedrally around it.

CHIRAL CENTRES

There are four different colours
arranged tetrahedrally about
the carbon atom

2-chlorobutane exhibits optical isomerism
because the second carbon atom has four
different atoms/groups attached
OPTICAL ISOMERISM
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
1-chlorobutane

C
C
C
C

3 H’s around it
2 H’s around it
2 H’s around it
2 H’s around it

NOT chiral
NOT chiral
NOT chiral
NOT chiral


OPTICAL ISOMERISM
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
1-chlorobutane

CH3CH2CHClCH3
2-chlorobutane

C
C
C
C

3 H’s around it
2 H’s around it
2 H’s around it
2 H’s around it

NOT chiral
NOT chiral
NOT chiral
NOT chiral



C
C
C
C

3 H’s around it
2 H’s around it
H, CH3, Cl,C2H5 around it
3 H’s around it

NOT chiral
NOT chiral
CHIRAL
NOT chiral


OPTICAL ISOMERISM
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
1-chlorobutane

CH3CH2CHClCH3
2-chlorobutane

(CH3)2CHCH2Cl
1-chloro-2-methylpropanane

(CH3)3CCl
2-chloro-2-methylpropanane

C
C
C
C

3 H’s around it
2 H’s around it
2 H’s around it
2 H’s around it

NOT chiral
NOT chiral
NOT chiral
NOT chiral



C
C
C
C

3 H’s around it
2 H’s around it
H, CH3, Cl,C2H5 around it
3 H’s around it

NOT chiral
NOT chiral
CHIRAL
NOT chiral



C 3 H’s around it
C 2 CH3’s around it
C 2 H’s around it

NOT chiral
NOT chiral
NOT chiral



C 3 H’s around it
C 3 CH3’s around it

NOT chiral
NOT chiral


OPTICAL ISOMERISM
Spatial differences between isomers
• two forms exist which are NON-SUPERIMPOSABLE MIRROR IMAGES of each other
• non-superimposable means you you can’t stack one form exactly on top of the other
OPTICAL ISOMERISM
Spatial differences between isomers
• two forms exist which are NON-SUPERIMPOSABLE MIRROR IMAGES of each other
• non-superimposable means you you can’t stack one form exactly on top of the other

Some common objects are mirror images and superimposable
superimposable but not mirror images
non-superimposable mirror images

spoons
books
hands
OPTICAL ISOMERISM
Spatial differences between isomers
• two forms exist which are NON-SUPERIMPOSABLE MIRROR IMAGES of each other
• non-superimposable means you you can’t stack one form exactly on top of the other

Some common objects are mirror images and superimposable
superimposable but not mirror images
non-superimposable mirror images
NB

For optical isomerism in molecules, both conditions must apply...
they must be mirror images AND be non-superimposable

spoons
books
hands
OPTICAL ISOMERISM
What is a non-superimposable mirror image?

Animation doesn’t
work in old
versions of
Powerpoint
OPTICAL ISOMERS - DIFFERENCE
•
•
•
•
•

isomers differ in their reaction to plane-polarised light
plane polarised light vibrates in one direction only
one isomer rotates light to the right, the other to the left
rotation of light is measured using a polarimeter
rotation is measured by observing the polarised light coming out towards the observer
OPTICAL ISOMERS - DIFFERENCE
•
•
•
•
•

isomers differ in their reaction to plane-polarised light
plane polarised light vibrates in one direction only
one isomer rotates light to the right, the other to the left
rotation of light is measured using a polarimeter
rotation is measured by observing the polarised light coming out towards the observer

• If the light appears to have

turned to the right
DEXTROROTATORY
d or + form

turned to the left
LAEVOROTATORY
l or - form
OPTICAL ISOMERS - DIFFERENCE
•
•
•
•
•

isomers differ in their reaction to plane-polarised light
plane polarised light vibrates in one direction only
one isomer rotates light to the right, the other to the left
rotation of light is measured using a polarimeter
rotation is measured by observing the polarised light coming out towards the observer

• If the light appears to have

turned to the right
DEXTROROTATORY
d or + form

turned to the left
LAEVOROTATORY
l or - form

Racemate

a 50-50 mixture of the two enantiomers (dl) or (±) is a racemic mixture.
The opposite optical effects of each isomer cancel each other out

Examples

Optical activity is common in biochemistry and pharmaceuticals
• Most amino acids exhibit optical activity
• many drugs must be made of one optical isomer to be effective
- need smaller doses (safer and cost effective)
- get reduced side effects
- improved pharmacological activity
OPTICAL ISOMERISM
The polarimeter
A

B
C

D

E
F

A
B
C
D
E
F

Light source produces light vibrating in all directions
Polarising filter only allows through light vibrating in one direction
Plane polarised light passes through sample
If substance is optically active it rotates the plane polarised light
Analysing filter is turned so that light reaches a maximum
Direction of rotation is measured coming towards the observer

If the light appears to have

turned to the right
DEXTROROTATORY

turned to the left
LAEVOROTATORY
OPTICAL ISOMERISM
How optical isomers can be formed
Carbonyl compounds undergo nucleophilic addition. If there are two different
groups attached to the C=O bond, the possibility of forming optical isomers arises.
THE NUCLEOPHILIC ADDITION OF HCN TO ETHANAL
If the nucleophilic cyanide ion
attacks from above one
optical isomer is formed
OPTICAL ISOMERISM
How optical isomers can be formed
Carbonyl compounds undergo nucleophilic addition. If there are two different
groups attached to the C=O bond, the possibility of forming optical isomers arises.
THE NUCLEOPHILIC ADDITION OF HCN TO ETHANAL
If the nucleophilic cyanide ion
attacks from above one
optical isomer is formed

However, attack from below,
gives the non-superimposable
mirror image of the first
OPTICAL ISOMERISM
How optical isomers can be formed
Carbonyl compounds undergo nucleophilic addition. If there are two different
groups attached to the C=O bond, the possibility of forming optical isomers arises.
THE NUCLEOPHILIC ADDITION OF HCN TO ETHANAL
If the nucleophilic cyanide ion
attacks from above one
optical isomer is formed

However, attack from below,
gives the non-superimposable
mirror image of the first

The reaction produces a mixture of the two optical
isomers because both modes of attack are possible
OPTICAL ISOMERISM
How optical isomers can be formed
Carbonyl compounds undergo nucleophilic addition. If there are two different
groups attached to the C=O bond, the possibility of forming optical isomers arises.
THE NUCLEOPHILIC ADDITION OF HCN TO ETHANAL

ANIMATION

The reaction produces a mixture of the two optical
isomers because both modes of attack are possible
OPTICAL ISOMERISM
Synthesis of 2-hydroxypropanoic acid (lactic acid)
LACTIC ACID can be formed from ethanal in a two stage process.
1. Nucleophilic addition of hydrogen cyanide to ethanal
2 Hydrolysis of the nitrile group

HCN

H+ / H2O
OPTICAL ISOMERISM
Synthesis of 2-hydroxypropanoic acid (lactic acid)
LACTIC ACID can be formed from ethanal in a two stage process.
1. Nucleophilic addition of hydrogen cyanide to ethanal
2 Hydrolysis of the nitrile group

HCN

During the first stage, the nucleophilic CN- ion
can attack from below, or above, the aldehyde.
A mixture of the two enantiomers is formed.

H+ / H2O
OPTICAL ISOMERISM
Synthesis of 2-hydroxypropanoic acid (lactic acid)
LACTIC ACID can be formed from ethanal in a two stage process.
1. Nucleophilic addition of hydrogen cyanide to ethanal
2 Hydrolysis of the nitrile group

HCN

During the first stage, the nucleophilic CN- ion
can attack from below, or above, the aldehyde.
A mixture of the two enantiomers is formed.
Acid hydrolysis of the mixture provides a
mixture of the two lactic acid forms.

H+ / H2O
OPTICAL ISOMERISM - THALIDOMIDE
The one obvious difference between optical isomers is their response to plane
polarised light. However, some naturally occurring molecules or specifically
synthesised pharmaceuticals show different chemical reactivity.
The drug, THALIDOMIDE is a chiral molecule and can exist as two enantiomers. 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. The drug was banned worldwide, but not after tens of thousands of babies had been affected.
OPTICAL ISOMERISM – Other points
The following points are useful when discussing reactions producing optical isomers.

The formation of racemic mixtures is more likely in a laboratory reaction
than in a chemical process occurring naturally in the body.
If a compound can exist in more than one form, only one of the optical
isomers is usually effective.
The separation of isomers will make manufacture more expensive.
A drug made up of both isomers will require a larger dose and may cause
problems if the other isomer is ‘poisonous’ like thalidomide.
REVISION CHECK

What should you be able to do?
Recall the definitions of structural isomerism and stereoisomerism
Explain and understand how structural, geometrical and optical isomerism arise
Work out all the possible isomers for a given formula
Recall and understand the importance of optical activity in natural product chemistry

CAN YOU DO ALL OF THESE?

YES

NO
ISOMERISM
The End

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Isomerism Power point

  • 1. ISOM RISM E A guide for the students
  • 2. ISOMERISM CONTENTS • Prior knowledge • Types of isomerism • Structural isomerism • Stereoisomerism • Geometrical isomerism • Optical isomerism • Check list
  • 3. ISOMERISM Before you start it would be helpful to… • know the functional groups found in organic chemistry • know the arrangement of bonds around carbon atoms • know what affects the boiling point of organic molecules
  • 4. TYPES OF ISOMERISM CHAIN ISOMERISM STRUCTURAL ISOMERISM Same molecular formula but different structural formulae POSITION ISOMERISM FUNCTIONAL GROUP ISOMERISM GEOMETRICAL ISOMERISM STEREOISOMERISM Same molecular formula but atoms occupy different positions in space. Occurs due to the restricted rotation of C=C double bonds... two forms… E and Z (CIS and TRANS) OPTICAL ISOMERISM Occurs when molecules have a chiral centre. Get two nonsuperimposable mirror images.
  • 5. STRUCTURAL ISOMERISM - INTRODUCTION COMPOUNDS HAVE THE SAME MOLECULAR FORMULA BUT DIFFERENT STRUCTURAL FORMULA Chain different arrangements of the carbon skeleton similar chemical properties slightly different physical properties more branching = lower boiling point
  • 6. STRUCTURAL ISOMERISM - INTRODUCTION COMPOUNDS HAVE THE SAME MOLECULAR FORMULA BUT DIFFERENT STRUCTURAL FORMULA Chain different arrangements of the carbon skeleton similar chemical properties slightly different physical properties more branching = lower boiling point Positional same carbon skeleton same functional group functional group is in a different position similar chemical properties - slightly different physical properties
  • 7. STRUCTURAL ISOMERISM - INTRODUCTION COMPOUNDS HAVE THE SAME MOLECULAR FORMULA BUT DIFFERENT STRUCTURAL FORMULA Chain different arrangements of the carbon skeleton similar chemical properties slightly different physical properties more branching = lower boiling point Positional same carbon skeleton same functional group functional group is in a different position similar chemical properties - slightly different physical properties Functional Group different functional group different chemical properties different physical properties • Sometimes more than one type of isomerism occurs in the same molecule. • The more carbon atoms there are, the greater the number of possible isomers
  • 8. STRUCTURAL ISOMERISM - CHAIN caused by different arrangements of the carbon skeleton similar chemical properties slightly different physical properties more branching = lower boiling point There are two structural isomers of C4H10. One is a straight chain molecule where all the carbon atoms are in a single row. The other is a branched molecule where three carbon atoms are in a row and one carbon atom sticks out of the main chain. BUTANE straight chain 2-METHYLPROPANE branched C4H10
  • 9. STRUCTURAL ISOMERISM - CHAIN DIFFERENCES BETWEEN CHAIN ISOMERS Chemical Isomers show similar chemical properties because the same functional group is present. Physical Properties such as density and boiling point show trends according to the of the degree of branching Boiling Point “straight” chain isomers have higher values than branched ones the greater the degree of branching the lower the boiling point branching decreases the effectiveness of intermolecular forces less energy has to be put in to separate the molecules - 0.5°C straight chain - 11.7°C branched greater branching = lower boiling point
  • 10. STRUCTURAL ISOMERISM - POSITIONAL molecule has the same carbon skeleton molecule has the same same functional group... BUT the functional group is in a different position have similar chemical properties / different physical properties Example 1 POSITION OF A DOUBLE BOND IN ALKENES 1 2 PENT-1-ENE double bond between carbons 1 and 2 2 3 PENT-2-ENE double bond between carbons 2 and 3 There are no other isomers with five C’s in the longest chain but there are three other structural isomers with a chain of four carbons plus one in a branch.
  • 11. STRUCTURAL ISOMERISM - POSITIONAL molecule has the same carbon skeleton molecule has the same same functional group... BUT the functional group is in a different position have similar chemical properties / different physical properties Example 2 POSITION OF A HALOGEN IN A HALOALKANE 1 1-CHLOROBUTANE halogen on carbon 1 2 2-CHLOROBUTANE halogen on carbon 2 BUT 2 is NOT 3-CHLOROBUTANE Moving the chlorine along the chain makes new isomers; the position is measured from the end nearest the functional group... the third example is 2- NOT 3-chlorobutane. There are 2 more structural isomers of C4H9Cl but they have a longest chain of 3
  • 12. STRUCTURAL ISOMERISM - POSITIONAL molecule has the same carbon skeleton molecule has the same same functional group... BUT the functional group is in a different position have similar chemical properties / different physical properties Example 3 RELATIVE POSITIONS ON A BENZENE RING 1,2-DICHLOROBENZENE ortho dichlorobenzene 1,3-DICHLOROBENZENE meta dichlorobenzene 1,4-DICHLOROBENZENE para dichlorobenzene
  • 13. STRUCTURAL ISOMERISM – FUNCTIONAL GROUP molecules have same molecular formula molecules have different functional groups molecules have different chemical properties molecules have different physical properties ALCOHOLS and ETHERS ALDEHYDES and KETONES ACIDS and ESTERS
  • 14. STRUCTURAL ISOMERISM – FUNCTIONAL GROUP ALCOHOLS and ETHERS Name ETHANOL METHOXYMETHANE Classification ALCOHOL ETHER Functional Group R-OH Physical properties polar O-H bond gives rise to hydrogen bonding. get higher boiling point and solubility in water Chemical properties Lewis base Wide range of reactions R-O-R No hydrogen bonding low boiling point insoluble in water Inert
  • 15. STRUCTURAL ISOMERISM – FUNCTIONAL GROUP ALDEHYDES and KETONES Name PROPANAL Classification ALDEHYDE KETONE R-CHO R-CO-R Functional Group PROPANONE Physical properties polar C=O bond gives dipole-dipole interaction polar C=O bond gives dipole-dipole interaction Chemical properties easily oxidised to acids of same number of carbons undergo oxidation under extreme conditions only reduced to 1° alcohols reduced to 2° alcohols
  • 16. STRUCTURAL ISOMERISM – FUNCTIONAL GROUP CARBOXYLIC ACIDS and ESTERS Name PROPANOIC ACID Classification CARBOXYLIC ACID Functional Group R-COOH METHYL ETHANOATE ESTER R-COOR Physical properties O-H bond gives rise to hydrogen bonding. get higher boiling point and solubility in water No hydrogen bonding insoluble in water Chemical properties acidic react with alcohols fairly unreactive hydrolysed to acids
  • 17. STEREOISOMERISM Molecules have the SAME MOLECULAR FORMULA but the atoms are joined to each other in a DIFFERENT SPACIAL ARRANGEMENT - they occupy a different position in 3-dimensional space. There are two types... • GEOMETRICAL ISOMERISM • OPTICAL ISOMERISM
  • 18. GEOMETRICAL ISOMERISM IN ALKENES Introduction • • • • an example of stereoisomerism found in some, but not all, alkenes occurs due to the RESTRICTED ROTATION OF C=C bonds get two forms...
  • 19. GEOMETRICAL ISOMERISM IN ALKENES Introduction • • • • an example of stereoisomerism found in some, but not all, alkenes occurs due to the RESTRICTED ROTATION OF C=C bonds get two forms... CIS (Z) Groups/atoms are on the SAME SIDE of the double bond TRANS (E) Groups/atoms are on OPPOSITE SIDES across the double bond
  • 20. GEOMETRICAL ISOMERISM RESTRICTED ROTATION OF C=C BONDS Single covalent bonds can easily rotate. What appears to be a different structure is not. It looks like it but, due to the way structures are written out, they are the same. ALL THESE STRUCTURES ARE THE SAME BECAUSE C-C BONDS HAVE ‘FREE’ ROTATION Animation doesn’t work in old versions of Powerpoint
  • 21. GEOMETRICAL ISOMERISM RESTRICTED ROTATION OF C=C BONDS C=C bonds have restricted rotation so the groups on either end of the bond are ‘frozen’ in one position; it isn’t easy to flip between the two. Animation doesn’t work in old versions of Powerpoint This produces two possibilities. The two structures cannot interchange easily so the atoms in the two molecules occupy different positions in space.
  • 22. GEOMETRICAL ISOMERISM IN ALKENES E/Z or CIS-TRANS E/Z Z (zusammen) higher priority groups / atoms on the SAME side of C=C bond E (entgegen) higher priority groups / atoms on OPPOSITE sides of C=C bond
  • 23. GEOMETRICAL ISOMERISM IN ALKENES E/Z or CIS-TRANS E/Z Z (zusammen) higher priority groups / atoms on the SAME side of C=C bond E (entgegen) higher priority groups / atoms on OPPOSITE sides of C=C bond To determine priority, the Cahn, Ingold and Prelog convention is used. eg C2H5 > CH3 > H and I > Br > Cl > F > C > H
  • 24. GEOMETRICAL ISOMERISM IN ALKENES E/Z or CIS-TRANS E/Z Z (zusammen) higher priority groups / atoms on the SAME side of C=C bond E (entgegen) higher priority groups / atoms on OPPOSITE sides of C=C bond To determine priority, the Cahn, Ingold and Prelog convention is used. eg C2H5 > CH3 > H and I > Br > Cl > F > C > H
  • 25. GEOMETRICAL ISOMERISM IN ALKENES E/Z or CIS-TRANS Z (zusammen) higher priority groups / atoms on the SAME side of C=C bond E (entgegen) E/Z higher priority groups / atoms on OPPOSITE sides of C=C bond To determine priority, the Cahn, Ingold and Prelog convention is used. eg E C2H5 > CH3 > H Z and I > Br > Cl > F > C > H Z E
  • 26. GEOMETRICAL ISOMERISM IN ALKENES E/Z or CIS-TRANS CIS / TRANS Should only be used when there are two H’s and two non-hydrogen groups attached to each carbon. cis non-hydrogen groups / atoms on the SAME side of C=C bond trans non-hydrogen groups / atoms on OPPOSITE sides of C=C bond
  • 27. GEOMETRICAL ISOMERISM IN ALKENES E/Z or CIS-TRANS CIS / TRANS Should only be used when there are two H’s and two non-hydrogen groups attached to each carbon. cis non-hydrogen groups / atoms on the SAME side of C=C bond trans non-hydrogen groups / atoms on OPPOSITE sides of C=C bond
  • 28. GEOMETRICAL ISOMERISM IN ALKENES E/Z or CIS-TRANS CIS / TRANS Should only be used when there are two H’s and two non-hydrogen groups attached to each carbon. cis non-hydrogen groups / atoms on the SAME side of C=C bond trans non-hydrogen groups / atoms on OPPOSITE sides of C=C bond cis trans cis trans
  • 29. GEOMETRICAL ISOMERISM GEOMETRICAL ISOMERISM Isomerism in butene There are 3 structural isomers of C4H8 that are alkenes*. Of these ONLY ONE exhibits geometrical isomerism. but-1-ene cis but-2-ene (Z) but-2-ene trans but-2-ene (E) but-2-ene 2-methylpropene * YOU CAN GET ALKANES WITH FORMULA C4H8 IF THE CARBON ATOMS ARE IN A RING
  • 30. GEOMETRICAL ISOMERISM How to tell if it exists Two different atoms/groups attached Two different atoms/groups attached  Two similar atoms/groups attached Two similar atoms/groups attached  Two similar atoms/groups attached Two different atoms/groups attached  Two different atoms/groups attached Two different atoms/groups attached  GEOMETRICAL ISOMERISM Once you get two similar atoms/groups attached to one end of a C=C, you cannot have geometrical isomerism GEOMETRICAL ISOMERISM
  • 31. OPTICAL ISOMERISM Occurrence another form of stereoisomerism occurs when compounds have non-superimposable mirror images Isomers the two different forms are known as optical isomers or enantiomers they occur when molecules have a chiral centre a chiral centre contains an asymmetric carbon atom an asymmetric carbon has four different atoms (or groups) arranged tetrahedrally around it.
  • 32. OPTICAL ISOMERISM Occurrence another form of stereoisomerism occurs when compounds have non-superimposable mirror images Isomers the two different forms are known as optical isomers or enantiomers they occur when molecules have a chiral centre a chiral centre contains an asymmetric carbon atom an asymmetric carbon has four different atoms (or groups) arranged tetrahedrally around it. CHIRAL CENTRES There are four different colours arranged tetrahedrally about the carbon atom 2-chlorobutane exhibits optical isomerism because the second carbon atom has four different atoms/groups attached
  • 33. OPTICAL ISOMERISM 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 1-chlorobutane C C C C 3 H’s around it 2 H’s around it 2 H’s around it 2 H’s around it NOT chiral NOT chiral NOT chiral NOT chiral 
  • 34. OPTICAL ISOMERISM 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 1-chlorobutane CH3CH2CHClCH3 2-chlorobutane C C C C 3 H’s around it 2 H’s around it 2 H’s around it 2 H’s around it NOT chiral NOT chiral NOT chiral NOT chiral  C C C C 3 H’s around it 2 H’s around it H, CH3, Cl,C2H5 around it 3 H’s around it NOT chiral NOT chiral CHIRAL NOT chiral 
  • 35. OPTICAL ISOMERISM 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 1-chlorobutane CH3CH2CHClCH3 2-chlorobutane (CH3)2CHCH2Cl 1-chloro-2-methylpropanane (CH3)3CCl 2-chloro-2-methylpropanane C C C C 3 H’s around it 2 H’s around it 2 H’s around it 2 H’s around it NOT chiral NOT chiral NOT chiral NOT chiral  C C C C 3 H’s around it 2 H’s around it H, CH3, Cl,C2H5 around it 3 H’s around it NOT chiral NOT chiral CHIRAL NOT chiral  C 3 H’s around it C 2 CH3’s around it C 2 H’s around it NOT chiral NOT chiral NOT chiral  C 3 H’s around it C 3 CH3’s around it NOT chiral NOT chiral 
  • 36. OPTICAL ISOMERISM Spatial differences between isomers • two forms exist which are NON-SUPERIMPOSABLE MIRROR IMAGES of each other • non-superimposable means you you can’t stack one form exactly on top of the other
  • 37. OPTICAL ISOMERISM Spatial differences between isomers • two forms exist which are NON-SUPERIMPOSABLE MIRROR IMAGES of each other • non-superimposable means you you can’t stack one form exactly on top of the other Some common objects are mirror images and superimposable superimposable but not mirror images non-superimposable mirror images spoons books hands
  • 38. OPTICAL ISOMERISM Spatial differences between isomers • two forms exist which are NON-SUPERIMPOSABLE MIRROR IMAGES of each other • non-superimposable means you you can’t stack one form exactly on top of the other Some common objects are mirror images and superimposable superimposable but not mirror images non-superimposable mirror images NB For optical isomerism in molecules, both conditions must apply... they must be mirror images AND be non-superimposable spoons books hands
  • 39. OPTICAL ISOMERISM What is a non-superimposable mirror image? Animation doesn’t work in old versions of Powerpoint
  • 40. OPTICAL ISOMERS - DIFFERENCE • • • • • isomers differ in their reaction to plane-polarised light plane polarised light vibrates in one direction only one isomer rotates light to the right, the other to the left rotation of light is measured using a polarimeter rotation is measured by observing the polarised light coming out towards the observer
  • 41. OPTICAL ISOMERS - DIFFERENCE • • • • • isomers differ in their reaction to plane-polarised light plane polarised light vibrates in one direction only one isomer rotates light to the right, the other to the left rotation of light is measured using a polarimeter rotation is measured by observing the polarised light coming out towards the observer • If the light appears to have turned to the right DEXTROROTATORY d or + form turned to the left LAEVOROTATORY l or - form
  • 42. OPTICAL ISOMERS - DIFFERENCE • • • • • isomers differ in their reaction to plane-polarised light plane polarised light vibrates in one direction only one isomer rotates light to the right, the other to the left rotation of light is measured using a polarimeter rotation is measured by observing the polarised light coming out towards the observer • If the light appears to have turned to the right DEXTROROTATORY d or + form turned to the left LAEVOROTATORY l or - form Racemate a 50-50 mixture of the two enantiomers (dl) or (±) is a racemic mixture. The opposite optical effects of each isomer cancel each other out Examples Optical activity is common in biochemistry and pharmaceuticals • Most amino acids exhibit optical activity • many drugs must be made of one optical isomer to be effective - need smaller doses (safer and cost effective) - get reduced side effects - improved pharmacological activity
  • 43. OPTICAL ISOMERISM The polarimeter A B C D E F A B C D E F Light source produces light vibrating in all directions Polarising filter only allows through light vibrating in one direction Plane polarised light passes through sample If substance is optically active it rotates the plane polarised light Analysing filter is turned so that light reaches a maximum Direction of rotation is measured coming towards the observer If the light appears to have turned to the right DEXTROROTATORY turned to the left LAEVOROTATORY
  • 44. OPTICAL ISOMERISM How optical isomers can be formed Carbonyl compounds undergo nucleophilic addition. If there are two different groups attached to the C=O bond, the possibility of forming optical isomers arises. THE NUCLEOPHILIC ADDITION OF HCN TO ETHANAL If the nucleophilic cyanide ion attacks from above one optical isomer is formed
  • 45. OPTICAL ISOMERISM How optical isomers can be formed Carbonyl compounds undergo nucleophilic addition. If there are two different groups attached to the C=O bond, the possibility of forming optical isomers arises. THE NUCLEOPHILIC ADDITION OF HCN TO ETHANAL If the nucleophilic cyanide ion attacks from above one optical isomer is formed However, attack from below, gives the non-superimposable mirror image of the first
  • 46. OPTICAL ISOMERISM How optical isomers can be formed Carbonyl compounds undergo nucleophilic addition. If there are two different groups attached to the C=O bond, the possibility of forming optical isomers arises. THE NUCLEOPHILIC ADDITION OF HCN TO ETHANAL If the nucleophilic cyanide ion attacks from above one optical isomer is formed However, attack from below, gives the non-superimposable mirror image of the first The reaction produces a mixture of the two optical isomers because both modes of attack are possible
  • 47. OPTICAL ISOMERISM How optical isomers can be formed Carbonyl compounds undergo nucleophilic addition. If there are two different groups attached to the C=O bond, the possibility of forming optical isomers arises. THE NUCLEOPHILIC ADDITION OF HCN TO ETHANAL ANIMATION The reaction produces a mixture of the two optical isomers because both modes of attack are possible
  • 48. OPTICAL ISOMERISM Synthesis of 2-hydroxypropanoic acid (lactic acid) LACTIC ACID can be formed from ethanal in a two stage process. 1. Nucleophilic addition of hydrogen cyanide to ethanal 2 Hydrolysis of the nitrile group HCN H+ / H2O
  • 49. OPTICAL ISOMERISM Synthesis of 2-hydroxypropanoic acid (lactic acid) LACTIC ACID can be formed from ethanal in a two stage process. 1. Nucleophilic addition of hydrogen cyanide to ethanal 2 Hydrolysis of the nitrile group HCN During the first stage, the nucleophilic CN- ion can attack from below, or above, the aldehyde. A mixture of the two enantiomers is formed. H+ / H2O
  • 50. OPTICAL ISOMERISM Synthesis of 2-hydroxypropanoic acid (lactic acid) LACTIC ACID can be formed from ethanal in a two stage process. 1. Nucleophilic addition of hydrogen cyanide to ethanal 2 Hydrolysis of the nitrile group HCN During the first stage, the nucleophilic CN- ion can attack from below, or above, the aldehyde. A mixture of the two enantiomers is formed. Acid hydrolysis of the mixture provides a mixture of the two lactic acid forms. H+ / H2O
  • 51. OPTICAL ISOMERISM - THALIDOMIDE The one obvious difference between optical isomers is their response to plane polarised light. However, some naturally occurring molecules or specifically synthesised pharmaceuticals show different chemical reactivity. The drug, THALIDOMIDE is a chiral molecule and can exist as two enantiomers. 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. The drug was banned worldwide, but not after tens of thousands of babies had been affected.
  • 52. OPTICAL ISOMERISM – Other points The following points are useful when discussing reactions producing optical isomers. The formation of racemic mixtures is more likely in a laboratory reaction than in a chemical process occurring naturally in the body. If a compound can exist in more than one form, only one of the optical isomers is usually effective. The separation of isomers will make manufacture more expensive. A drug made up of both isomers will require a larger dose and may cause problems if the other isomer is ‘poisonous’ like thalidomide.
  • 53. REVISION CHECK What should you be able to do? Recall the definitions of structural isomerism and stereoisomerism Explain and understand how structural, geometrical and optical isomerism arise Work out all the possible isomers for a given formula Recall and understand the importance of optical activity in natural product chemistry CAN YOU DO ALL OF THESE? YES NO