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orgo question-protonation

Discussion in 'Pre-Medical - MD' started by yalla22, Apr 27, 2004.

  1. yalla22

    yalla22 Senior Member
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    what does h30+ do when it reacts with double bonds?(like c=c and c=o)?
     
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  3. Bones2008

    Bones2008 waiting for retirement
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    H30+, like any acid, donates a proton, though you'd have to have more to the reaction than just protonated water and a double bond to get it to do anything at all.
     
  4. liverotcod

    liverotcod Lieutenant Crunch
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    Acid can hydrolyze an alkene to an alcohol, with Markovnikov orientation, but it's not generally used in lab synthesis. Protonation makes a carbonyl more reactive.
     
  5. yalla22

    yalla22 Senior Member
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    what is h3o+ is the only compound shown to be reacting with this gigantic molecule containing a bunch of c=o's, etc...
     
  6. liverotcod

    liverotcod Lieutenant Crunch
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    Need more specifics. What molecule?
     
  7. notJERRYFALWELL

    notJERRYFALWELL Squirrel tactics!!
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    The O of the C=O will be protonated by the H+, and then the H20 will attack the C of the C=O. Depending on the nature of the carbonyl's r group(s), it may or may not undergo elimination (by eliminating an r group, or opening up a ring), as the H2O loses one proton, forming a carboxylic acid.

    It be easier to help if we had specifics, not just a general case, because different conditions warrant different mechanisms, but generally, the above will happen. Simple addition/elimination.
     

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