Triple bond on a carbon atom?

Discussion in 'Chemistry' started by jakebarrington, May 3, 2013.

  1. jakebarrington Registered Member

    Messages:
    9
    I was looking at a drug called methylphenidate, and I noticed that it has a triple bond instead of the typical quadruple bond. Here is an image:

    View attachment 6253

    How is this possible? Wouldn't some other atom (maybe a hydrogen or a fluoride) be inclined to bond with it?

    Would this change the properties of the molecule?
     
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  3. leopold Valued Senior Member

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    when molecules are presented like your picture all carbon bonds that aren't shown are assumed to be hydrogen bonds.
    ALL of the carbon in your picture has 4 bonds.

    molecules with a carbon-carbon triple bond are members of the acetylene series and are very unstable.
    they also might be called fulminates but not sure.
     
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  5. jakebarrington Registered Member

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    But in the center of the molecule I see three lines going to an intersection. Here is what I'm talking about, circled:
    View attachment 6254
     
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  7. leopold Valued Senior Member

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    read my previous post.
    this is done for simplicity.
     
  8. exchemist Valued Senior Member

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    Jake, Leopold is right. It is a convention sometimes in organic chemistry not to show the C-H bonds, since they can be assumed by default everywhere that is not bonded to something else. It makes it easier to see (a) the carbon backbone of the molecule and (b) the various "hetero" atoms (i.e. those that are neither C nor H) and "functional groups" that may be present, as these are responsible for the distinctive chemistry of the molecule. The C atom you circle will also be bonded to a hydrogen atom that is not shown, the 4 bonds pointing towards the vertices of a tetrahedron, as normal for an sp3-hybridized C atom. This is automatically understood by any organic chemist reading such a diagram.
     
  9. jakebarrington Registered Member

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    Thanks guys.
     
  10. arauca Banned Banned

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    If you look at C14H19NO2 there will be one Hydrogen at the carbon which connect the benzene ring to the methyl acetate and the cycloamine
    apparently they don't put any Hydrogen on a skeletal molecule
     
  11. sideshowbob Sorry, wrong number. Valued Senior Member

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    2,851
    Just a terminology nitpick: a triple bond would be three bonds between the same two carbon atoms - e.g. in acetylene. You should be saying "three bonds".

    Of course, a "quadruple bond" (between the same two carbon atoms) is not stereochemically possible - go ahead, prove me wrong

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    - but "four bonds" on each carbon attom is the rule.
     
  12. exchemist Valued Senior Member

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    Yes. Though there are one or two intriguing anomalies, such as the norbornyl cation.....:http://en.wikipedia.org/wiki/Non-classical_ion

    .....in which carbon appears to participate in 3-centre bonding, a bit like boron I suppose, thus giving an appearance of forming 5 bonds. Just goes to show all rules have their exceptions, rare though they may be.
     

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