Timeline for Reaction of nitrobenzene with potassium ferricyanide
Current License: CC BY-SA 3.0
12 events
| when toggle format | what | by | license | comment | |
|---|---|---|---|---|---|
| Feb 2, 2017 at 13:10 | comment | added | Huy Ngo | I think H attached to the carbon which bonds to cyanide group is a $H^-$, which is a base (and even stronger than NaOH), so how can it be taken away? | |
| Feb 2, 2017 at 12:52 | comment | added | Black Jack 21 | @orthocresol My exercise book is the only place where I saw this reaction. Unfortunately I dont know the answer to the question. There is a good possibility that the author just made this reaction up, as it wont be the first time this has happened. ( not mentioning the book and author as its a local book for exam preparation, most probably you wont be able to find it on net) | |
| Feb 2, 2017 at 12:22 | comment | added | Linus Choy | @orthocresol Yes, I don't think this reaction is likely to happen in great amount as I've noted. But there's no possible electrophile to undergo electrophilic substitution either. However, it seems unfair to simply put "No reaction". And I've skimped on the amide part. :P Thanks for pointing that out though. | |
| Feb 2, 2017 at 12:20 | comment | added | orthocresol | Aside from that there are some errors in the mechanisms. In the first mechanism, the first arrow should be a forward arrow $\to$ not a resonance arrow $\leftrightarrow$. The third structure is missing a double bond between C and N. In the second mechanism, the amide has to be protonated first before H2O can attack, and NH2 has to be protonated before it can leave. | |
| Feb 2, 2017 at 12:15 | comment | added | orthocresol | I'm afraid there are some real problems with this loss of a hydride. If CN- attacks nitrobenzene, the subsequent step must expel H- not H+. Do you have any reference for this reaction? Nucleophilic substitution of hydrides is not unknown (Chichibabin reaction), but it doesn't make much sense here. cc @AlphaRomeo | |
| Feb 2, 2017 at 12:05 | vote | accept | Black Jack 21 | ||
| Feb 3, 2017 at 6:39 | |||||
| Feb 2, 2017 at 11:57 | comment | added | Linus Choy | I've edited the mechanism above already, thanks for pointing that out. | |
| Feb 2, 2017 at 11:57 | history | edited | Linus Choy | CC BY-SA 3.0 |
edited body
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| Feb 2, 2017 at 11:53 | comment | added | Linus Choy | While $\ce{CN-}$ is possible to be displaced by $\ce{OH-}$, it is a much stronger ligand. Therefore I suspect that this reaction would not happen to a large extent. What's more, nucleophilic aromatic substitution generally occurs with aryl halides since $\ce{X-}$ is a much better leaving group. | |
| Feb 2, 2017 at 11:51 | comment | added | Black Jack 21 | Btw, you left your mechanism at amide, no need to edit it to acid though. I know the mechanism | |
| Feb 2, 2017 at 11:49 | comment | added | Black Jack 21 | I thought it was tough to remove ligands inside a complex. Can you explain how/why CN- comes out? | |
| Feb 2, 2017 at 11:44 | history | answered | Linus Choy | CC BY-SA 3.0 |