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Polymerization of acetone

  1. Mar 19, 2010 #1
    What follows is a suggested mechanism for base catalyzed acetone polymerization which is based on simple nucleophilic addition series. I have divided the mechanism into three steps, shown below.

    In step 1, the reaction is initialized by a base catalyzed initiation into ketone-enolate resonance. From here, two reactions are possible.

    The first, step 2a, is that the karboanion takes back the H+ and we end up with the original reactant which can enter into ketone-enolate resconance again through step 1.

    The second, step 2b, is that the enolate attacks another acetone molecule at the electrophilic center (the carbonyl group carbon atom) and start a chain on similar addition reactions and make a polymer. The figure shows the first two of these addition reactions.

    Step three is then the termination reaction where the base gives back the hydrogen kation. We gat a hydroxy group at the end, and the end product is shown below.

    Is this a plausible mechanism? If not, where did I make a mistake?

    All feedback is appreciated.

    http://img441.imageshack.us/img441/5240/polyaceton.png [Broken]

    EDIT: The following polymer could also be formed:

    http://img168.imageshack.us/img168/8738/polyaceton2.png [Broken]
    Last edited by a moderator: May 4, 2017
  2. jcsd
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