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Bonding in Carbonyl Compounds

  • Page ID
    3641
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    The simple view of the bonding in carbon - oxygen double bonds

    methanal.GIF

    Where the carbon-oxygen double bond, C=O, occurs in organic compounds it is called a carbonyl group. The simplest compound containing this group is methanal. We are going to look at the bonding in methanal, but it would equally apply to any other compound containing C=O. The interesting thing is the nature of the carbon-oxygen double bond - not what it's attached to.

    Note

    Methanal is normally written as HCHO. If you wrote it as HCOH, it looks as if it contains an -O-H group - and it doesn't. Methanal is an aldehyde. All aldehydes contain the CHO group.

    An orbital view of the bonding in carbon - oxygen double bonds

    The carbon atom

    Just as in ethene or benzene, the carbon atom is joined to three other atoms. The carbon's electrons rearrange themselves, and promotion and hybridisation give sp2 hybrid orbitals. Promotion gives:

    promoteline.GIF

    Hybridization of the 2s orbital and two of the 2p orbitals means that the carbon atom now looks like the diagram below. Three sp2 hybrid orbitals are formed and these arrange themselves as far apart in space as they can - at 120° to each other. The remaining p orbital is at right angles to them. This is exactly the same as in ethene or in benzene.

    sp2.GIF

    The oxygen atom

    Oxygen's electronic structure is 1s22s22px22py12pz1. The 1s electrons are too deep inside the atom to be concerned with the bonding and so we'll ignore them from now on. Hybridisation occurs in the oxygen as well. It is easier to see this using "electrons-in-boxes".

    oxboxes.GIF

    This time two of the sp2 hybrid orbitals contain lone pairs of electrons.

    oxorbs.GIF

    The carbon atom and oxygen atom then bond in much the same way as the two carbons do in ethene. In the next diagram, we are assuming that the carbon will also bond to two hydrogens to make methanal - but it could equally well bond to anything else.

    methanalbits.GIF

    End-to-end overlap between the atomic orbitals that are pointing towards each other produce sigma bonds. Notice that the p orbitals are overlapping sideways.

    methanalorbits.GIF

    This sideways overlap produces a pi bond. So just like C=C, C=O is made up of a sigma bond and a pi bond. Does that mean that the bonding is exactly the same as in ethene? No! The distribution of electrons in the pi bond is heavily distorted towards the oxygen end of the bond, because oxygen is much more electronegative than carbon.

    methanalpi.GIF

    This distortion in the pi bond causes major differences in the reactions of compounds containing carbon-oxygen double bonds like methanal compared with compounds containing carbon-carbon double bonds like ethene.

    Contributors

    Jim Clark (Chemguide.co.uk)


    This page titled Bonding in Carbonyl Compounds is shared under a CC BY-NC 4.0 license and was authored, remixed, and/or curated by Jim Clark.

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