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Organic chemistry question


Suggest why C2H3Cl, does not react with warm aqueous sodium hydroxide


The context of the question is the production of PVC but I don't see why the Na+ couldn't act electrophile and electrophilic addition take place?

Any help would be very much appreciated.

Dadeyemi

Edit: corrected neucleophilic subtitution to electrophilic addition
Its the OH part of sodium hydroxide that would react here if anything (as a nucleophile) but you can't do SN2 reactions on alkene carbons (sp2 centre) like you can on alkanes (sp3 centre)
Reply 2
EierVonSatan
Its the OH part of sodium hydroxide that would react here if anything (as a nucleophile) but you can't do SN2 reactions on alkene carbons (sp2 centre) like you can on alkanes (sp3 centre)


sorry I was thinking ellectrophilic addition :p:, but i don't really see what you mean by sp2/sp3/SN2 reactions??
wouldn't the Na+ be attrated to the double bond? and produce the +ve carbocation that would bond with OH?
Ok SN2 just means nucleophilic substitution (2 molecules in the fast step), sp2 and sp3 describe the electronics of the carbons, here you have chloroethene each carbon has two single bonds and one double bond this is called sp2 when a carbon has 4 single bonds (such as in cholorethane) is called sp3. You're right in that that maybe the Na+ would be attracted to the electron rich double bond, but Na doesnt form covalent bonds with carbons. But consider the anion OH - in chloroethane, it would attack (SN2) the partially positive C in the C-Cl bond because Cl is more electronegative and pulls electrons away from the carbon. But in chloroethene the carbon isn't so electrophilic and will not undergo nucleophilic substitution :smile:
Reply 4
EierVonSatan
Ok SN2 just means nucleophilic substitution (2 molecules in the fast step), sp2 and sp3 describe the electronics of the carbons, here you have chloroethene each carbon has two single bonds and one double bond this is called sp2 when a carbon has 4 single bonds (such as in cholorethane) is called sp3. You're right in that that maybe the Na+ would be attracted to the electron rich double bond, but Na doesnt form covalent bonds with carbons. But consider the anion OH - in chloroethane, it would attack (SN2) the partially positive C in the C-Cl bond because Cl is more electronegative and pulls electrons away from the carbon. But in chloroethene the carbon isn't so electrophilic and will not undergo nucleophilic substitution :smile:


Thank you very much
electrophiles have to be able to accept a PAIR of electrons. In the case of Na+ this would form a Na- ion, which just does not exist!
Reply 6
charco
electrophiles have to be able to accept a PAIR of electrons. In the case of Na+ this would form a Na- ion, which just does not exist!

Well, unless you get very fancy with cryptands and all of that crap...
SN2 means both steps happen at the same time.
no, SN2 means that there are two particles involved in the rate determining step of the mechanism.

S= substitution
N = Nucleophilic
2 = bimolecular

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