The Student Room Group

Isn't this nucleophilic and electrophilic addition? 🧐

Isn't the reaction in the picture I've put into the comments both a nucleophilic and el electrophilic addition reaction because sodium's the electrophile whilst the cyanate ion is the nucleophile? 🙂
59B58417-A94D-406B-BDBA-5A104F80DE60.jpg.jpeg
Yes it's an addition elimination reaction.
it is nucleophilic addition
And the proton, the H+, is an electrophile 😄
Original post by ethancruise15
Yes it's an addition elimination reaction.


Please may you explain why it's an elimination reaction as well? 🙂
Original post by kurro
it is nucleophilic addition


Why isn't it electrophilic addition as well, though? 🙂
can't the cyanate ion also cause the double bond to become a single bond because of dipole interactions - i.e. the cyanate ion gets close to the central carbon and causes the electrons around it to position themselves closer to the more negatively charged oxygen ion and break the polar bond to give oxygen another lone pair of electrons :smile:, I'm just making sure that there isn't something that I don't know here as I understand that, if I do understand everything, this scenario would be less likely as, in order for the cyanate ion to bond to the central carbon, the cyanate ion would have to bump into the central carbon once to change the polarity of the carbonyl and consequently be repelled from the central carbon and then, once the central carbon is positively charged, the cyanate ion would then be attracted to the central carbon and bond with it again. The other scenario being that the hydrogen ion, the proton, is attracted to and bonds with the negatively charged oxygen and that then makes the double bond a single bond and the central carbon ion more positively charged. I'm now, upon going through all of that in my head, I'm not sure which scenario is more likely! 😄

Quick Reply

Latest