Isomers part 1

What are isomers?

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

At AS level you need to know about structural and geometric isomers.

Below is a diagram that shows the different types of isomers and what categories they come under:

Isomers

Structural Stereoisomers

Geometric More in A2

Structural Isomers

two compounds with the same molecular formula but different structural formula

A lot of students find this difficult as they think that they need to invent something. However, there are 3
different methods that you can use that will stop it seeming like guess work: chain isomers, positional
groups isomers and functional group isomers.

1. Chain isomers
If given a straight chain alkane, then create a side group by moving a CH3 group from the end to
somewhere in the middle of the molecule. We are trying to create something different in the structure
by disrupting the longest chain.

Starting with pentane on the left, we have simply taken the CH3 group from one end and put it on the
second carbon of the molecule. Then repeated the process:
 some students ask, for example, how do you go from pentane 2-methylbutane? The answer is
you cant! We are not saying there are reactions to go from pentane to 2-methyl butane to 2,2-
dimethylpropane. Isomers are just a theoretical thing.

Remember to check that the molecular formula is the same in both cases: we have C4H10 for both
structures.

This is quite a simple example with only one possible structure that we could draw. Depending on the
length of the carbon chain you could draw several structures by this method.

This can of course be reversed. If given a branched molecule, you could create a straight chain
instead.

2. Positional isomers
This is very simple. It just involves moving functional groups from one part of a molecule to somewhere
else in the chain.

In the example below we have moved the OH group to the only 2 positions that it can go to give different
molecules.

3. Functional Group isomers

This time you actually change the functional group.

In this example, the aldehyde (propanal) and the ketone (propanone):

A very common but not so obvious example is going from an alkene to a cycloalkane (or vice-versa) e.g.
hexane and cyclohexane:

Problems

A common problem is that students draw structures that they think are isomers but they are actually
identical structures. You need to be check for this every time you draw an isomer.

One way to do this is to name the molecules:

if they are isomers then they will have different names

Or if you dont like naming molecules, you can look to see if there is anything different about the
structures.

For example, from the positional isomer example above:

pentan-2-ol has a CH3 next to a CH

pentan-3-ol has a CH between 2 x CH2 groups

pentan-1-ol has the OH group bonded to a CH2 group

All these features are unique for these molecules and are therefore different structures.

Also, remember to make sure the molecular formulas are the same: C5H12O