When methyl methacrylate undergoes free radical addition polymerisation, the C=C pi bond is broken during the process:

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I'm wondering why the C=O pi bond doesn't get broken during the polymerisation. I suspect it may be because the C=O bond is stronger than the C=C bond, but are there any other ways to rationalise this?

  • 1
    $\begingroup$ Compare radicals involved. $\endgroup$
    – Mithoron
    Sep 12 '17 at 19:30

C=O bond is strongly polar, and the cleavage of the double bond would rather involve heterolytic breaking with ions formed than homolytic with radicals.


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