Timeline for Would the carbocation intermediate undergo rearrangement?
Current License: CC BY-SA 3.0
9 events
| when toggle format | what | by | license | comment | |
|---|---|---|---|---|---|
| Jul 12, 2021 at 9:40 | comment | added | napstablook | @AS_1000 I agree with zhe wagner would have occured before elimination only if nirogen was not already protonated by conc. H2SO4. Infact it get's protonated before alcohol group | |
| Jun 30, 2017 at 14:06 | comment | added | AS_1000 | In this scenario, there are two different Meerwein rearrangements (contracting the ring vs. moving the bridgehead) that can take place, he mentioned one of them in the question, I mentioned the other in my response. Both are possible, and due to the answers being what they are on the answer key, I conclude that his rearrangement won't occur and rather the one I suggested will. | |
| Jun 30, 2017 at 14:01 | comment | added | Zhe | Yes, that's the whole point. The nitrogen would ordinarily stabilize a cation to form an iminium but it can't if it's fully protonated from sulfuric acid. You do not place an fully substituted, electron withdrawing nitrogen next to carbocation for a rearrangement. That rearrangement will not occur. And if you disagree, then we're not talking about the same thing. I suggest reading the OP's question again. | |
| Jun 30, 2017 at 13:53 | comment | added | AS_1000 | You do not understand the mechanism of a Wagner-Meerwein rearrangement, the resulting carbocation is beta to the nitrogen, and the degree of substitution on the nitrogen wouldn't rule out the possibility of a rearrangement. | |
| Jun 30, 2017 at 13:46 | comment | added | Zhe | It absolutely rules out rearrangement because it would put the carbocation next to a fully substituted nitrogen. | |
| Jun 30, 2017 at 13:45 | comment | added | AS_1000 | Straightforward elimination could occur, but that does not rule out the possibility of Wagner-Meerwein rearrangements. In more complex orgo problems, there are numerous possibilities. There is no way to prove either of us right or wrong without experimental evidence. | |
| Jun 30, 2017 at 13:31 | comment | added | Zhe | This is not correct because compound (a) does not undergo rearrangement. It also does not really answer the OP's question... | |
| Jun 30, 2017 at 10:26 | review | Late answers | |||
| Jun 30, 2017 at 10:54 | |||||
| Jun 30, 2017 at 10:11 | history | answered | AS_1000 | CC BY-SA 3.0 |