Radical Copolymerization

5
(2)

Click the structures and reaction black arrows in sequence to view the 3D models and animations respectively

Radical chain reactions are particularly suited to the synthesis of polymers – this copolymerization demonstrates the effect of electron-withdrawing or donating substituents on radical reactivity.

When a mixture of vinyl acetate and methyl acrylate is treated with a radical initiator, polymerization takes place. The polymer produced contains alternating vinyl acetate and methyl acrylate monomers along its chain.

The animated mechanistic sequence above shows why – the nucleophilic radical from vinyl acetate (adjacent to filled n orbital of OAc; high energy SOMO) prefers to add to the electrophilic alkene (acrylate). The new radical (adjacent to the empty pi* orbital of CO2Me; low-energy SOMO) is electrophilic and prefers to add to the nucleophilic alkene (vinyl acetate). This produces a new nucleophilic radical, the cycle then occurs repeatedly until the desired chain length is produced.

How useful was this page?

Click on a star to rate it!

Average rating 5 / 5. Vote count: 2

No votes so far! Be the first to rate this page.

As you found this page useful...

Follow us on social media!

We are sorry that this page was not useful for you!

Let us improve this page!

Tell us how we can improve this page (in your own language if you prefer)?

Provided by the