Timeline for Carbonyl oxygen as nucleophile
Current License: CC BY-SA 3.0
13 events
| when toggle format | what | by | license | comment | |
|---|---|---|---|---|---|
| Nov 18, 2021 at 13:50 | comment | added | orthocresol | @SasQ Yes. But there's nothing wrong with that, is there? [Heads up: You need to tag me if you want me to get a notification.] | |
| Nov 18, 2021 at 2:06 | answer | added | Oscar Lanzi | timeline score: 4 | |
| Nov 18, 2021 at 1:17 | comment | added | SasQ | Well, in that case we would have to treat the entire conjugate base as a leaving group that leaves the proton, wouldn't we? | |
| Nov 18, 2021 at 0:50 | comment | added | orthocresol | @SasQ Those labels aren't mutually exclusive. H+ is an electrophile, and anything that gets protonated is acting as a nucleophile towards it. | |
| Nov 18, 2021 at 0:49 | comment | added | SasQ | @orthocresol Isn't protonation of the carbonyl an acid-base reaction though? (i.e. not a nucleophile-electrophile reaction) | |
| Apr 2, 2018 at 3:03 | history | tweeted | twitter.com/StackChemistry/status/980641827018756096 | ||
| S Oct 16, 2015 at 18:44 | history | suggested | Mithoron |
added tag
|
|
| Oct 16, 2015 at 18:08 | review | Suggested edits | |||
| S Oct 16, 2015 at 18:44 | |||||
| Sep 27, 2015 at 20:57 | comment | added | permeakra | >Is there any reason for the low reactivity of the oxygen? || Yes. It is in $sp^2$ hybridization state, meaning it binds its lone pairs extremely strong. It seems, however, that it can react with strong electrophyles like proton. It also should act as one in synthesis of pyrilium salts, but I was unable to find a proposed mechanism. Also, technically the nucleophilic oxygen in Wittig synthesis is derived from carbonyl oxygen, but is not one at the moment of attack | |
| Sep 27, 2015 at 19:38 | history | edited | bon | CC BY-SA 3.0 |
edited body; edited tags; edited title
|
| Sep 27, 2015 at 19:37 | answer | added | bon | timeline score: 6 | |
| Sep 27, 2015 at 14:23 | comment | added | orthocresol | It does react, for example in the formation of enol ethers, and technically the protonation of a carbonyl group is also an example. It's a much harder nucleophile than the alpha carbon and therefore reacts with different things. | |
| Sep 27, 2015 at 14:14 | history | asked | Charles | CC BY-SA 3.0 |