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IR6. Carbon Oxygen Double Bonds

  • Page ID
    4173
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    The largest class of oxygen-containing molecules is carbonyl compounds, which contain C=O bonds. A C=O stretch is normally easy to find in an IR spectrum, because it is very strong and shows up in a part of the spectrum that is not cluttered with other peaks. Examples of carbonyl compounds include 2-octanone, a ketone, and butanal, an aldehyde. In an aldehyde, the carbonyl is at the end of a chain, with a hydrogen attached to the carbonyl carbon.

    2octanone.gif butanal.gif

    If you look at the IR spectrum of 2-octanone:

    • IRFig10.gif

      Source: SDBSWeb : http://riodb01.ibase.aist.go.jp/sdbs/ (National Institute of Advanced Industrial Science and Technology of Japan, 14 July 2008)

      Even though there is just one C=O bond, the carbonyl stretch is often the strongest peak in the spectrum. That makes carbonyl compounds easy to identify by IR spectroscopy.

      If you look at the IR spectrum of butanal:

      • IRFig11.gif

        Source: SDBSWeb : http://riodb01.ibase.aist.go.jp/sdbs/ (National Institute of Advanced Industrial Science and Technology of Japan, 14 July 2008)

        The aldehyde C-H bond absorbs at two frequencies because it can vibrate in phase with the C=O bond (a symmetric stretch) and out of phase with the C=O bond (an asymmetric stretch), and these vibrations are of different energies. The probability of the symmetric stretch and the asymmetric stretch are about equal, so the two peaks are always about the same size. This unusual C-H peak can often be used to distinguish between an aldehyde and a ketone.


    This page titled IR6. Carbon Oxygen Double Bonds is shared under a CC BY-NC 3.0 license and was authored, remixed, and/or curated by Chris Schaller.

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