Structural Isomerism

Isomerism
LOs:
To be able to define isomerism
To be able to define stereoisomerism
To be able to assign priority on C=C using Cahn-Ingold-
Prelog rules.
Starter:
1)Draw the displayed formula for butan-2-
ol.
2)What is the difference between ethanol
and ethanal? Draw the skeletal formulae of
both.
3)Can different structures have the same
molecular formula? Give as many
examples as you can.
Isomerism
Isomerism is where 2 (or more) compounds
have the same molecular formula (e.g. C6H12)
but different arrangement of their atoms;
Isomers have different physical and chemical
properties (depending on the type of
isomerism)
•TASK: HOW MANY DIFFERENT DISPLAYED

FORMULA OF C5H10 CAN YOU DRAW?
Types of Isomerism
Isomerism
Structural Stereoisomerism
Functional
Chain Position Geometrical Optical
Group
Structural Isomerism
Same molecular formula but different structural formula.
Three ways this happens:
1.Chain: Alkyl groups in different places
2.Positional: Functional groups are in different places
3.Functional group: Functional groups are different.
Task: Draw the skeletal formula of the following and state
what type of isomerism are the following:
1)Butane and 2-methyl-propane
2)Ethanol and Methoxymethane
3)2-methylpentane and 2,2-dimethylbutane
4)Propanone and Propanal
5)Butanoic acid and 1-hydroxybutan-2-one
Physical and chemical
properties.
In which are the chemical and properties
the same or different?
Alkyl groups  similar chemical, different physical.

Functional groups in different position  similar
chemical, different physical.
Functional Groups are different  different chemical,
different physical.
Starter:
• For each compound:
• Name it
• Draw its displayed, structural, skeletal and molecular formula
• Draw two isomers of it and name what type of isomerism it is.
Types of Isomerism
Isomerism
Structural Stereoisomerism
Functional
Chain Position Geometrical Optical
Group
Stereoisomerism (Spatial
isomerism)
Same molecular formula, same functional
groups, same bonds, but different
arrangement in space. This often occurs
with a double bond
Geometric Isomerism!
(b) Or..
if a central atom is attached to 4 different groups
Optical Isomerism! (A2)

Stereoisomerism
Geometric Isomerism
• This is covered in AS and needed for A2
• Geometric isomerism occurs where there is a
double bond between 2 carbon atoms which
have 2 different groups on them e.g.
• ..resulting in cis- and trans- isomerism
• Cis and trans isomers may have different
properties e.g. in the way they interact with
biological molecules
Geometric isomerism.
oThis type of isomerism results from restricted rotation
somewhere in the molecule (usually C=C).
oHOWEVER.......
Pi bonds are formed by a sideways overlap
between p- orbitals.
If they are twisted then this overlap is disrupted

and the Pi bond is broken.
So we cant rotate around double bonds.

Cis and trans isomers if the
cis-1,2-dichloroethene same group is on both
carbons.
trans-1,2-dichloroethene
“on this side”
Cis- MP -80ºC, BP 60ºC

Trans – MP -50ºC, BP 48ºC
“across”
Starter
• Are the following compounds cis or trans? – Name them
So what do we call this?
Cahn-Ingold-Prelog
Rules
1. Locate C=C in a molecule and redraw to show
substituents.
2. Focus on one carbon atom, assign the priority

of each substituent. Then do the same for the
second.
1. Higher priority = bigger mass
3. If highest priorities across the double bond are

on the same side its Z and if highest priority are
on opposite sides its E.
So Cis/trans
isomerism is a
special case of E/Z
isomerism.
E-Z isomerism
Z –Zusammen = together
E –Entgegen = opposite
If 2 groups with the highest priority
are on the same side they are a Z
Examples
Which is E,
which is Z?
Now try the
worksheet
Plenary:
1) Draw a molecule of 1,2-dichloroethene. Explain why there
are two possible isomers of this molecule.
1) Why is there only 1 isomer of 1,2-dichloroethane?
a) True or false:
a) Cis/trans is the same as E/Z isomerism.
b) E/Z isomerism is a type of stereoisomerism.
c) E/Z isomerism is a type of structural isomerism.
d) Functional group isomerism is when the functional group appears
in a different place on the molecule.
e) Chain isomerism is when the molecule has an alkyl group in a
different place, changing the chain length.
b) Correct the incorrect statements above.

Answers:
1) There are two isomers of 1,2-dichloroethene as it contains
a double bond which prevents rotation, locking the groups
in their position in space.
a) There is only one isomer of 1,2-dichloroethane as there is no double
bond locking the groups in place so free rotation can occur.
2) True or false:
a) Cis/trans is the same as E/Z isomerism.
c) E/Z isomerism is a type of structural isomerism.
d) Functional group isomerism is when the functional group appears
in a different place on the molecule.
Answers:
3) True or false:
a) Cis/trans is a special case of E/Z isomerism in which the groups
are the same.
c) E/Z isomerism is not a type of structural isomerism.
d) Functional group isomerism is when two molecules have the
same molecular formulae but different functional groups.

Structural Isomerism

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Isomerism

•TASK: HOW MANY DIFFERENT DISPLAYED

Alkyl groups  similar chemical, different physical.

Optical Isomerism! (A2)

If they are twisted then this overlap is disrupted

So we cant rotate around double bonds.

“on this side”

Cis- MP -80ºC, BP 60ºC

2. Focus on one carbon atom, assign the priority

3. If highest priorities across the double bond are

b) Correct the incorrect statements above.

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