Thursday, October 23, 2014

IUPAC Nomenclature and Organic Compounds

Imagine you are sitting a Chemistry exam.
The first question on the exam paper reads,
"Name the molecule shown below:"

How would you answer this question?

My first response is to name it Molly, short for molecule ofcourse. Not a very useful name, especially if I'm asked to name another molecule later on. It might get a bit confusing if I name every molecule Molly, even when the molecules are very different from each other.

So, the International Union of Pure and Applied Chemistry (IUPAC) has developed systems for naming compounds.
For this reason, you probably won't be asked to "name" the molecule, but you might be asked to "systematically name" the molecule, or to give the "systematic IUPAC name" for the molecule.

Even for the relatively simple molecule shown above, there is more than one way to systematically name the molecule using IUPAC nomenclature rules!

You could give a systematic IUPAC name based on the functional class of the compound. This molecule belongs to the functional class known as ketones (non-terminal C=O), two methyl (CH3) groups are attached to the carbonyl carbon atom, so, according to the IUPAC rules for functional class nomenclature, I could systematically name it as dimethyl ketone.

I could give the same molecule a different systematic IUPAC name by applying the rules of substitutive nomenclature. In this case I name the parent hydride, propane, drop the final "e" and add a suffix denoting the non-terminal C=O functional group so that I get propanone, then I add in an infix which locates the functional group along the carbon chain, with the final name propan-2-one.

Because this is a simple molecule with just one functional group, I could use the infix as a prefix, so that the systematic IUPAC name would become 2-propanone. Or, because there is only one position for the C=O functional group to be in if this molecule is to be a ketone, I could drop the infix altogether and just systematically name the molecule as propanone.

So, some of the possible systematic IUPAC names for this molecule are:
  • dimethyl ketone
  • propan-2-one
  • 2-propanone
  • propanone
Because molecules can be named systematically in more than one way, there is a recommendation to adopt "preferred IUPAC names", or PINs. Usually the Preferred IUPAC Name is arrived at by using one of the recognized IUPAC systems for nomenclature, but not always.

If you were asked to give the Preferred IUPAC Name for the molecule shown above, the correct answer would be acetone ("Preferred names in the nomenclature of organic compounds" (Draft 7 October 2004) page 9), or, possibly propan-2-one ("Preferred names in the nomenclature of organic compounds" (Draft 7 October 2004) page 374). Acetone is the traditional name for this compound, literally meaning 'derived from acetic acid', and has been in use for more than 200 years, which is probably why the IUPAC would consider retaining the name "acetone" as the Preferred IUPAC Name for this compound.

Further Reading:
Introduction to Naming Organic Compounds

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