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What are the products formed when vinyl chloride reacts with dimethyl copper?

I thought the product formed would be propene. But answer given is PolyVinylChloride. How does polymerization take place?

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  • $\begingroup$ I thought Gilman Reagent is lithium dialkyl copper. I would expect propene to be formed too. $\endgroup$ – shre_sudh_97 May 20 '16 at 11:07
  • $\begingroup$ en.wikipedia.org/wiki/Anionic_addition_polymerization $\endgroup$ – orthocresol May 20 '16 at 11:41
  • $\begingroup$ @orthocresol so the reaction will start with a nucleophilic attack by a methyl carbanion on vinyl chloride. Will this nucleophile attck the anti-bonding pi orbital? $\endgroup$ – Aditya Dev May 20 '16 at 11:45
  • $\begingroup$ Yes. You can't make propene - that would involve a SN2 (which organometallics are notoriously bad at) at a sp2 centre (which is extremely rare to begin with) $\endgroup$ – orthocresol May 20 '16 at 11:57

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