Carbocation Rearrangement - Hydride and Methanide Shifts
Hydride and methanide shifts? What are those? Well, I'll tell you. Surely by now you've noticed that's what I'm doing here, no? Carbocation rearrangement is no exception.
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I love you man
@ProfessorDaveExplains
7 жыл бұрын
i love you too, buddy!
true hero right here. You're saving my semester!!!!
this man is a legend... really it's so easy to learn from your videos
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@enochgau1115
3 жыл бұрын
EXACTLY!!!! Thank you so much ! Professor Dave !!!
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I literally only needed to watch 30 seconds of your video and I got it. Thanks bro
Love how your vids are not too long
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What an elegant explanation. Thank you so much 🤩🤩🤩🤩🤩🤩🤩
Amazing. Thank you, Prof. Dave. That helped a lot! :D
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thank you dave good explanation
Nice explanation sir, Thanks a lot.
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Thanks sir helped a lot for me
Would it be also possible for e.g. a chloride shift? Chloride is Electronegative (partial negative) and thus pulled towards the Kation. Shouldn't it be even easier for chloride because the Cl-Ion state is accessed more easily, so lower activation energy?
I don't know how to think you professor This is really helpful with details and great explications I'm writing every single information hhhhh I don't care about being late to study the whole course because I can never forget those chemical reactions Thank you very much 😍😍😊
@MATTicall
2 жыл бұрын
thank* explanations*
@meriembouziani1
2 жыл бұрын
@@MATTicall thank you for correcting me And also reminding me those days of orgo chemistry hhhh
Just like you said rearrangements occur among adjacent carbons, so can a primary carbocation transform itself into a tertiary carbocation? Plz help
PROF DAVE CAN YOU PLEASE EXPLAIN MORE HOW TO PRIDICT THE MAJOR AND MINOR PRODUCT
Good
Thx king
since there is a tertiary and secondary carbon wouldn't the hydride ion stay for longer with the secondary carbon than the tertiary carbon giving it a lower charge than the tertiary carbon?
Hi Dave ! Your YT channel is amazing, really nice job ! Just a quick question : in the methanide shift, right after the rearrangement, is the molecule configuration correct or am I missing something? I mean, after the shift, the new carbocation has 3 bonds (CH3, CH3, R, nothing) and the former carbocation has 4 bonds (CH3, CH3, R, implied H). Thus shouldn't one of the 2 methyl groups on the former carbocation be going towards (or away from) the viewer? Not very important but I want to make sure I don't miss something here. Thanks for enlightening me :)
@ProfessorDaveExplains
6 жыл бұрын
Nope you're absolutely right! Sometimes we write groups as though they are flat to indicate that the stereochemistry is not important, or not known, or even just out of laziness! It is indeed tetrahedral, as opposed to the other carbon, which actually is newly trigonal planar, with a formal charge.
thank you!!!!!!
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You are so awesome. Wish you lived in Tampa, I would totally hire you as a tutor. Just name your price! :-)
Hey ! I was studying the hydration of alkynes, and i wanted to ask if a carbocation rearrangement could happen in a vinyl carbocation (for example with a hydride shift). Thanks a lot !
@ProfessorDaveExplains
5 жыл бұрын
no not for vinyl, because of the resonance!
Love from india🇮🇳🇮🇳
I like your intro
So if a secondary carbocation is not adjacent to a tertiary or quaternary carbon then it most likely does not rearrange?
@ProfessorDaveExplains
4 жыл бұрын
yep!
Life saver 😍
How is a racemic mixture possible at 3:08 even though there were no chiral carbon in that compound formed after hydride shift? Isn't a chiral carbon mandatory in Sn1 reaction for a racemic mixture to be formed?
@ProfessorDaveExplains
3 жыл бұрын
Yes that particular example is achiral, I was just speaking generally.
@Rikka_V1
3 жыл бұрын
@@ProfessorDaveExplains Oh,ok. Sorry about that, I didn't realize it initially, anyways a great tutorial as always!
Zaitsev will dominate over the E1 reaction but will it also dominate over the SN1 reaction?
@ProfessorDaveExplains
6 жыл бұрын
Zaitsev/Hofmann refer to alkene products, so the terminology does not apply to substitution reactions
isn't Sn1 reaction supposed to produce racemic mixture only when there is chiral center?
@ProfessorDaveExplains
6 жыл бұрын
yep
@ayarabie7571
6 жыл бұрын
But in the example the center is achiral because it's connected to 2 identical methyl groups
@ProfessorDaveExplains
6 жыл бұрын
ah yes, so in this case it wouldn't matter, but modify a methyl and the stereochemistry becomes relevant
what drives a hydride over a methanide shift?
trans 2 phenyl 1 bromocyclopentane+alcoholic koh,can you please explain why the carbocation does not rearrange and move on the tertiary carbon attaching the phenyl group to Cyclo Pentane?
@ProfessorDaveExplains
7 жыл бұрын
i would assume that it would rearrange in that way. where are you seeing that it does not?
@rahulsangamker6085
7 жыл бұрын
Professor Dave Explains ,this was asked in the year 2006 in Aieee(all india engineering entrance examination),so according to the key 3 phenyl cyclopentene is being formed whereas if rearrangement would have taken place,the product should have been 1phenyl cyclopentene,could it be that it may have undergone E2 mechanism,if yes,could you please explain why?
@ProfessorDaveExplains
7 жыл бұрын
oh sorry, i didn't fully understand the question, yes i think with hydroxide present there would be no chance for E1 or SN1 to take place, so there would be no carbocation intermediate. E2 is most likely, depending on temperature. however, one might still expect the tertiary proton to be extracted over any secondary ones, so the final product is still a little puzzling.
@rahulsangamker6085
7 жыл бұрын
Yeah,that is true too,I just realised that the tertiary hydrogen could also be extracted, is the phenyl's resonance is affecting this in anyway?
@ProfessorDaveExplains
7 жыл бұрын
i suppose it's possible that a little bit more electron density is getting to the tertiary carbon, not necessarily by resonance but by induction, and this makes its proton slightly less acidic? if the base were bigger i would say sterics were a factor, but its hydroxide.
Does the hydride shift occur more spontaneously than the methanide shift?
@ProfessorDaveExplains
5 жыл бұрын
hmm, i suppose so, since given the option of either it would prefer hydride?
@inarmi7169
5 жыл бұрын
Professor Dave Explains thank you sir
Wouldnt water as a nucleophile react via Sn1 since it a small Nucleophile?
@ProfessorDaveExplains
6 жыл бұрын
Sure it can, and I've shown that possibility here. Temperature would be the main element of control to steer things towards substitution or elimination products.
@justafriendlyhuman1141
6 жыл бұрын
Professor Dave Explains Thx man
The shift is impossible if the Hydroxy is connected to a primary carbon right? Somewhere (on the internet) is saw a guy doing a concerted shift, because the primary carbokation isnt stable, but shouldnt that shift be impossible and therefore solely a Sn2/E2 with no shift(because its a primary substrate)? PS: Substrate was was the same, except one carbon shorter on the right
@ProfessorDaveExplains
7 жыл бұрын
hmm yeah if the alcohol is primary i'm thinking water won't leave, at least not typically
@Crazy2Berry
7 жыл бұрын
ok, thanks for the reply
@cynthiasexton-wilson8962
5 жыл бұрын
As my professor says over and over and over and over and over - No primary carbocations.!!!! 'm thinking that he might mean to not make CarboCations. :-)
Chemistry sucks but you make it better
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