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Tuesday, June 23, 2015

Organic Chemistry, "Form", Part 16 - Ketones & Nomenclature

Greetings,

This post explores ketones a bit further than the last post.  The "ketyl" functional group is a single carbon atom double bonded to an oxygen atom, with alkyl groups bonded to the ketyl carbon atom.

Ketones are very important compounds in several industries, which include coatings, painting, polymers, and pharmaceuticals.  One could say that a ketone compound is in a "fully oxidized" state.  The ketyl functional group will not readily accommodate the addition of another oxygen atom and there is no hydrogen atom to be lost.  Reduction of a ketone to an alcohol by the addition of hydrogen (Hydrogenation) can be readily performed with a wide array of reducing agents (such as sodium borohydride, NaBH4) or with the aid of a surface catalyst.

Ketones are named according to their carbon chain length and ketyl group position on the carbon chain when IUPAC rules are referenced.  Otherwise, a more common naming convention, using the names of alkyl groups attached to the ketyl group, is generally observed.  Ketone IUPAC names will tend to be used for scientific journal publications and compound-characterization electronic libraries, such as those used with FTIR (Fourier Transform Infrared Spectroscopy) analysis.  The following chart provides a few examples of structures and corresponding names for lower molecular weight ketones.


Note that IUPAC names for the two lightest ketones do not indicate the ketyl group position (Do you know why? See answer below.*)  Also the last two ketones listed are the only structural isomers consisting of a five carbon chain.

That's all for this post.  As always, thank you for reading!
 

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*"The Answer" - Propanone has only one possible location of the ketyl group, otherwise we would have an aldehyde!  Butanone may at first consist of a pair of structural isomers, but the ketyl group is always the second carbon of the chain, therefore no need to indicate its position!

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