Welcome Guest Search | Active Topics |

Tag as favorite
Nucleophile and electrophile
Aida_5230
#1 Posted : Sunday, June 07, 2020 9:19:43 PM
Rank: Newbie

Groups: Registered
Joined: 6/5/2020
Posts: 2

Thanks: 0 times
Was thanked: 0 time(s) in 0 post(s)
Hi, just wanted to know why an amine is considered a nucleophile (I know it has an electron pair on the nitrogen which can "attack"), while a carbonyl is considered an electrophile, even though the oxygen also has lone electron pairs around it? How can you tell if it will donate or accept electrons?
INSTR_Katerina_102
#2 Posted : Sunday, June 07, 2020 9:27:29 PM
Rank: Advanced Member

Groups: Registered
Joined: 6/24/2019
Posts: 250

Thanks: 0 times
Was thanked: 0 time(s) in 0 post(s)
Great question!

I look at this sort of thing based on the stability of products formed - technically a carbonyl has some nucleophilic character at its oxygen lone pairs, but if you think about the product formed with that attack, you'll have a formal positive on an oxygen which cannot get dissipated by deprotonation, because there are no protons to pluck.

With an amine or an alcohol, you will have that same transient formal positive after nucleophilic attack, but you can deprotonate to stabilize the product formed. You don't have that ability for a carbonyl, so it doesn't act as a nucleophile (it'll tend to leave right after it attacks if it ever does).

Hopefully that isn't too confusing, please let me know if a picture would help.
Users browsing this topic
Guest
Tag as favorite
You cannot post new topics in this forum.
You cannot reply to topics in this forum.
You cannot delete your posts in this forum.
You cannot edit your posts in this forum.
You cannot create polls in this forum.
You cannot vote in polls in this forum.

Clean Slate theme by Jaben Cargman (Tiny Gecko)
Powered by YAF | YAF © 2003-2009, Yet Another Forum.NET
This page was generated in 0.115 seconds.