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ISOMERISM A guide for A level students. 2008 SPECIFICATIONS. KNOCKHARDY PUBLISHING. KNOCKHARDY PUBLISHING. ISOMERISM. INTRODUCTION

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slide1

ISOMERISM

A guide for A level students

2008 SPECIFICATIONS

KNOCKHARDY PUBLISHING

slide2

KNOCKHARDY PUBLISHING

ISOMERISM

INTRODUCTION

This Powerpoint show is one of several produced to help students understand selected topics at AS and A2 level Chemistry. It is based on the requirements of the AQA and OCR specifications but is suitable for other examination boards.

Individual students may use the material at home for revision purposes or it may be used for classroom teaching using an interactive white board.

Accompanying notes on this, and the full range of AS and A2 topics, are available from the KNOCKHARDY SCIENCE WEBSITE at...

www.knockhardy.org.uk/sci.htm

Navigation is achieved by...

either clicking on the grey arrows at the foot of each page

or using the left and right arrow keys on the keyboard

slide3

ISOMERISM

  • CONTENTS
  • Prior knowledge
  • Types of isomerism
  • Structural isomerism
  • Stereoisomerism
  • Geometrical isomerism
  • Optical isomerism
  • Check list
slide4

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
slide5

TYPES OF ISOMERISM

CHAIN ISOMERISM

STRUCTURAL ISOMERISM

POSITION ISOMERISM

Same molecular formula but different structural formulae

FUNCTIONAL GROUP ISOMERISM

GEOMETRICAL ISOMERISM

Occurs due to the restricted rotation of C=C double bonds... two forms… E and Z (CIS and TRANS)

STEREOISOMERISM

Same molecular formula but atoms occupy different positions in space.

OPTICAL ISOMERISM

Occurs when molecules have a chiral centre. Get two non-superimposable mirror images.

slide6

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

slide7

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

slide8

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
  • FunctionalGroup 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
slide9

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

slide10

STRUCTURAL ISOMERISM - CHAIN

DIFFERENCES BETWEEN CHAIN ISOMERS

ChemicalIsomers 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

slide11

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

2

3

PENT-1-ENE

double bond between carbons 1 and 2

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.

slide12

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

BUT

1

2

2

1-CHLOROBUTANE

halogen on carbon 1

2-CHLOROBUTANE

halogen on carbon 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

slide13

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

slide14

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

MORE DETAILS FOLLOW

slide15

STRUCTURAL ISOMERISM – FUNCTIONAL GROUP

ALCOHOLS and ETHERS

NameETHANOL METHOXYMETHANE

ClassificationALCOHOLETHER

Functional GroupR-OHR-O-R

Physical propertiespolar O-H bond gives rise No hydrogen bonding

to hydrogen bonding. low boiling point

get higher boiling point insoluble in water

and solubility in water

Chemical properties Lewis base Inert

Wide range of reactions

slide16

STRUCTURAL ISOMERISM – FUNCTIONAL GROUP

ALDEHYDES and KETONES

Name PROPANAL PROPANONE

ClassificationALDEHYDEKETONE

FunctionalGroupR-CHOR-CO-R

Physicalpropertiespolar C=O bond gives polar C=O bond gives dipole-dipole interaction dipole-dipole interaction

Chemical properties easily oxidised to acids of undergo oxidation under

same number of carbons extreme conditions only

reduced to 1° alcohols reduced to 2° alcohols

slide17

STRUCTURAL ISOMERISM – FUNCTIONAL GROUP

CARBOXYLIC ACIDS and ESTERS

NamePROPANOIC ACID METHYL ETHANOATE

ClassificationCARBOXYLIC ACIDESTER

Functional GroupR-COOHR-COOR

Physical propertiesO-H bond gives rise No hydrogen bonding

to hydrogen bonding. insoluble in water

get higher boiling point

and solubility in water

Chemical properties acidic fairly unreactive

react with alcohols hydrolysed to acids

slide18

STEREOISOMERISM

Molecules have the SAMEMOLECULARFORMULAbut 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

slide19

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...
slide20

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

slide21

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

slide22

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.

slide23

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) higher priority groups / atoms on

OPPOSITE sides of C=C bond

E / Z

slide24

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) higher priority groups / atoms on

OPPOSITE sides of C=C bond

E / Z

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

eg C2H5 > CH3 > H and I > Br > Cl > F > C > H

slide25

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) higher priority groups / atoms on

OPPOSITE sides of C=C bond

E / Z

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

eg C2H5 > CH3 > H and I > Br > Cl > F > C > H

slide26

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) higher priority groups / atoms on

OPPOSITE sides of C=C bond

E / Z

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

eg C2H5 > CH3 > H and I > Br > Cl > F > C > H

Z

E

E

Z

slide27

GEOMETRICAL ISOMERISM IN ALKENES

E/Z or 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

slide28

GEOMETRICAL ISOMERISM IN ALKENES

E/Z or 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

slide29

GEOMETRICAL ISOMERISM IN ALKENES

E/Z or 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

cis

trans

slide30

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

2-methylpropene

cis but-2-ene

(Z) but-2-ene

trans but-2-ene

(E) but-2-ene

* YOU CAN GET ALKANES WITH FORMULA C4H8 IF THE CARBON ATOMS ARE IN A RING

slide31

GEOMETRICAL ISOMERISM

How to tell if it exists

Two different atoms/groups attached

Two different atoms/groups attached

GEOMETRICAL ISOMERISM

Two similar atoms/groups attached

Two similar atoms/groups attached

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

Two similar atoms/groups attached

Two different atoms/groups attached

Two different atoms/groups attached

Two different atoms/groups attached

GEOMETRICAL ISOMERISM

slide32

OPTICAL ISOMERISM

Occurrenceanother 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.

slide33

OPTICAL ISOMERISM

Occurrenceanother 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

slide34

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

C 3 H’s around it NOT chiral

C 2 H’s around it NOT chiral

C 2 H’s around it NOT chiral

C 2 H’s around it NOT chiral

CH3CH2CH2CH2Cl

1-chlorobutane

slide35

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

C 3 H’s around it NOT chiral

C 2 H’s around it NOT chiral

C 2 H’s around it NOT chiral

C 2 H’s around it NOT chiral

CH3CH2CH2CH2Cl

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

C 3 H’s around it NOT chiral

2-chlorobutane

slide36

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

C 3 H’s around it NOT chiral

C 2 H’s around it NOT chiral

C 2 H’s around it NOT chiral

C 2 H’s around it NOT chiral

CH3CH2CH2CH2Cl

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

C 3 H’s around it NOT 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

slide37

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
slide38

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 aremirror images and superimposable spoons
  • superimposable but not mirror images books
  • non-superimposable mirror images hands
slide39

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 aremirror images and superimposable spoons
  • superimposable but not mirror images books
  • non-superimposable mirror images hands
  • NB For optical isomerism in molecules, both conditions must apply...
  • they must be mirror images AND be non-superimposable
slide40

OPTICAL ISOMERISM

What is a non-superimposable mirror image?

Animation doesn’t work in old versions of Powerpoint

slide41

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
slide42

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 haveturned to the rightturned to the left
  • DEXTROROTATORY LAEVOROTATORY
  • d or + form l or - form
slide43

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 haveturned to the right turned to the left
  • DEXTROROTATORY LAEVOROTATORY
  • d or + form l or - form
  • Racematea 50-50 mixture of the two enantiomers (dl) or (±) is a racemic mixture.
  • The opposite optical effects of each isomer cancel each other out
  • ExamplesOptical 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
slide44

A

B

D

C

E

F

OPTICAL ISOMERISM

The polarimeter

A Light source produces light vibrating in all directions

B Polarising filter only allows through light vibrating in one direction

C Plane polarised light passes through sample

D If substance is optically active it rotates the plane polarised light

E Analysing filter is turned so that light reaches a maximum

F Direction of rotation is measured coming towards the observer

If the light appears to have turned to the rightturned to the left

DEXTROROTATORYLAEVOROTATORY

slide45

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

slide46

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

slide47

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 reactionproduces a mixture of the two optical isomers because both modes of attack are possible

slide48

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 reactionproduces a mixture of the two optical isomers because both modes of attack are possible

slide49

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

H+ / H2O

HCN

slide50

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

H+ / H2O

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.

slide51

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

H+ / H2O

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.

slide52

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 world-wide, but not after tens of thousands of babies had been affected.

slide53

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.

slide54

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

Recalland understand the importance of optical activity in natural product chemistry

CAN YOU DO ALL OF THESE? YES NO

slide55

You need to go over the relevant topic(s) again

Click on the button to

return to the menu

slide56

WELL DONE!

Try some past paper questions

slide57

ISOMERISM

The End

© 2004 JONATHAN HOPTON & KNOCKHARDY PUBLISHING