Isomers part 2

Geometric Isomers

two molecules with the same molecular formula but different spatial arrangement of
atoms

Geometric isomerism is much easier than structural isomerism. Its all about double bonds and comes
under the heading of stereoisomerism.

Stereoisomerism is category of isomers that looks at how atoms are arranged. Here we are looking at one
part of stereoisomerism (geometric isomers) and there is more to come in A2.

The criteria for geometric isomerism (a favourite exam question):

1. You need a double bond. The double bond means that there is no rotation possible around it
so the atoms are fixed in position.

2. You must have two different atoms attached to each carbon on the double bond. Students
often miss this point. For example:

X
Cis and Trans
Cis and trans are names used to distinguish between two geometric isomers.

You have to imagine a horizontal line running through the carbon-carbon double bond. Then look above
and below this line to see if similar groups are on the same side or not.
In the 1st example above, both the CH3 groups are on the same side of our imaginary horizontal line and
is given the name cis.

The 2nd molecule has the CH3 groups on a diagonal line opposite each other, which is given the name
trans.

same side = cis, different side = trans

Z and E
Z and E and cis and trans are more or less the same thing.but not quite. Cis and trans is seen as the
older system, which works for simple alkenes. You can cis and trans by just looking at it quickly.

if you have 4 different groups attached to the C=C double bond you must use Z and E

With these more complicated examples, cis and trans wont work as you cant tell by just looking at it,
which groups are on the same side. Z and E will work for all examples.

Priority Rules
When there are 4 different groups attached to the C=C, priority must be assigned to each atom by atomic
number.

A lot of students think the priority is based on the molecular weight of each group and this works most of
the time. But the correct method is to look at the atomic number of each atom.

In the example below, if we look at the left hand carbon, we have: F = 9 and Cl = 17: the higher numbered
atom is assigned 1 and the other atom assigned 2.

On the right hand carbon, we look at the C of the CH3 and the H atom. As C has higher atomic number
than H we assign it priority 1.

All we then need to do is look at what side of our imaginary horizontal line the number 1s and 2s are:

1s on the same side = Z, 1s on different side = E

Example

On the left hand side, we look at the first atoms of the CH3 and CH2CH3 group attached to the C=C. Those
are both carbon atoms. We then must look at the next atom.

The CH3 has a H atom, whereas the CH2CH3 has another carbon. As the carbon has higher atomic number
than the H atom, we assign this the higher priority.

Example

To demonstrate the priority rules further, if we look at the molecule below, on first glance students might
assign the CH2CH3 as priority 1 over the OH group, as the CH2CH3 weighs 29 compared to the OH 17. This
is incorrect.

But using the priority rules we again have to look at the first atom attached the C=C and not the whole
group. So it is the O from the OH versus the C from the CH2CH3. O has higher atomic number than C, so O
wins.