SN1 Reaction

[@ProfessorDaveExplains]

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[@becomingvoid3084]

but for sn1 100% racemization is not observed practically because nucleophile starts attacking the substrate before the formation of carbocation therefore we get more no. of inverted product( stearically unhindered ) may be regioselective be the reason...

[@becomingvoid3084]

sir please correct me if I'm wrong

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[@ProfessorDaveExplains]

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more clear and concise in 3min than my profs' multiple hour long lectures.

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Hi Professor Dave, I'm Student Dave. Thanks for making these short and sweet. Appreciate the knowledge! Might just pass O-chem now!

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@@PunmasterSTP Yep, and with a solid B thanks in part to these videos! The professor I had believed in the "flipped classroom" method, which has little direct instruction. And that is what I needed. These videos helped break down difficult concepts and get me through O-chem!

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@@PunmasterSTP Long journey. Still going. Love learning science stuff!

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@@maximussarcasticus1312 I'm glad to hear it, and personally I'll always love learning science stuff!

[@becomingvoid3084]

but for sn1 100% racemization is not observed practically because nucleophile starts attacking the substrate before the formation of carbocation therefore we get more no. of inverted product( stearically unhindered ) may be regioselective be the reason...

[@ivkoklbik]

As being physicist, I appreciate that molecular geometry approach.

[@PunmasterSTP]

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[@PunmasterSTP]

SN1? More like "Great content? This is definitely some!" Thanks again for making so many videos that convey so much knowledge and understanding.

[@Rudra-c3t]

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[@seanc.reynolds8829]

In this reaction though, wouldn't the chloride leaving group shield one side of the carbocation as it leaves? If that's the case, once water attacks the carbocation one side of attack will be preferential due to the shielding from the leaving group. I think this means that a SN1 substrate that generates a chiral product actually wouldn't form a racemic mixture (50/50 mix of enantiomers), but would instead form more of the product that results from addition of water to the unshielded side of the carbocation and much less of the product resulting from addition to the shielded side. In the example in the video, though, it wouldn't matter because a tert-butyl chloride shouldn't form a chiral molecule in SN1.

[@ProfessorDaveExplains]

Shizzan Reynoodles i'm not aware of any such shielding effects, i only know SN1's to be completely unspecific in terms of stereochemistry. for the carbocation to be completely planar, there must be no remaining interaction with the leaving group, so it must be equally available on both sides for substitution, otherwise if there was still interaction with the leaving group it would have some SN2 character. of course there are many reactions that are truly somewhere in between SN1 and SN2, it gets a little messy.

[@tenorosmanaj5588]

+Shizzan Reynoodles yeah I agree with you

[@tinasayari716]

You are completely right Sean, it wouldn't be a complete 50%/50% racemic mixture! Rather that the product is approximately 80% racemized and 20% inverted

[@tinasayari716]

The leaving group shields one side of the carbocation intermediate from reaction with the nucleophile, thereby leading to some net inversion of configuration rather than complete racemization

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[@smolcryingpepo]

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[@jocelynnemarie806]

So the example reaction shown in this video doesnt produce a pair of enantiomer because its leaving group is not attached to a chiral center right? (since the C atom at center is not attached to 4 DIFFERENT substituents)

[@evelineberg4764]

I thought so too! In his example there's no stereocenter but he's telling us that in general you should see if the reaction has produced a stereocenter and if so, there would be a 50/50 mix of the products. Important note for this video..

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[@ProfessorDaveExplains]

Kyle K in my next update I plan to include tutorials for NMR spectroscopy, and possibly IR and mass spectroscopy as well. Thanks for watching!

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[@tomau3946]

Sn1: One reaction has happened. Two more to go. SN2: Two reactions have happened. One more to go.

[@AhnafAbdullah]

I find it funny how Sn1 reactions are in my syllabus but I don't understand half of the words you said.

[@ProfessorDaveExplains]

watch the SN2 video first, i define the terms

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It feels illegal to understand something in under 5 mins than my professor does in 90 minutes

[@ruerue0066]

I have a question sir! can you please tell, how is %age racemisation depending on the leaving grp. ability and stability of carbocation! waiting for your answerb

[@Johnnymemories]

The ending of the song was wicked!

[@Thaumius]

Is it always true that SN1 will undergo an acid base reaction or is only for solvolysis? ex: Tertbutyl Bromide + OH- -> ?

[@ProfessorDaveExplains]

we can't make such generalizations, SN1 is just a mechanism, many different reactions follow this mechanism

[@aidat7657]

Dear Professor , I have a question. Why negative charge stabilizes the carbocation? Isnt this negative charge a trouble for nucleophile itself carrying a negatie charge with electrons? what is actually meant by "stability" of carbocation? thanks for your video!!!

[@Snakesake2099]

I'm sorry mate, I know it's too late! Carbocation is stabalized by electron donating groups via eitger of one of the process such as Inductive effect,Hyperconjugation and offcourse the Mesomeric effect. Coming to your question A negative charge would never stabalize a Carbocation till it is not in conjugated system! Which is one of the conditions for Resonance effect! Hope this helps

[@CliffStamp]

Why does the Chlorine just leave? What is the solvent doing specially which causes that?

[@ProfessorDaveExplains]

a good question! yes it is due to interactions with solvent particles, which is why these kinds of mechanisms are best suited for polar solvents. halogens are quite polarizable, and if they collide with solvent particles in just the right way, the attraction can be enough to break the carbon-halogen bond, but this is an endothermic step, and the rate-determining step, it's very slow and unfavorable.

[@potenzersingh1520]

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[@avantika6077]

Why does the oxygen have positive charge btw? It has two lone pairs on its own.

[@pandaaaaa_official]

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[@RayanMADAO]

Wouldn't the Cl- make HCl from the H20+?

[@ProfessorDaveExplains]

+Mayo taizou HCl is a stronger acid than H3O+, so a chloride ion won't be basic enough to deprotonate hydronium, at least not appreciably.

[@adasulaiman]

Thank you very much, you are really a good teacher

[@kayakalp10]

l and d are 50% 50% in recemic mixture and recemic mixture is not polarise light to right or left and u say 50%/50% R and S confrugration i dont understand professor dave.??

[@ProfessorDaveExplains]

L and D is terminology that specifically applies to sugars, in general stereocenters are either R or S

[@gracerheault4678]

I love you Professor Dave

[@ALIEN-wp9ph]

How is the intermediate so different and why does water attack? Is there an equation or something like a question to show that water has to attack? I don’t understand :(

[@ProfessorDaveExplains]

well it doesn't have to attack, the leaving group could get back on, there could be elimination, it's just one of the things that can happen. and by tweaking reaction conditions you can get it to happen preferentially.

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[@ProfessorDaveExplains]

I said the sign-off once and pasted it at the end of every video. It's called efficiency.

[@changminhaa786]

Rate of sn1 mechanism only depends upon the concentration of substrate ???? Justify

[@danda8019]

what if we had an (Ch3)³C-Oh , It would be possible for an Cl- or any strong base to steal the H from that Oh?

[@danda8019]

please help me, this is the one little thing that keeps annoying me because i can t understand why it wouldn t happen if the oxigen pulls so hard on the shared electrons, maybe it repells the chloride..maybe it s a more stable final product this way, i just can t find the answear. Thank you!

[@ProfessorDaveExplains]

a strong base can deprotonate tert-butanol, sure, but not chloride.

[@danda8019]

Professor Dave Explains Is it because Chloride is stable by itself? And also thank youu very much btw 👌👌

[@ProfessorDaveExplains]

yep, HCl is a strong acid so chloride is an extremely weak base

[@danda8019]

Professor Dave Explains And so if a very strong base would deprotonate the alcohol what would happen next can be a separate reaction from Sn2/E2? I mean it can as well make a Sn2/E2 reaction if the base it s Na Oh, considering oh- wouldn t be hindered by any sterical repulsions because it s so small ,so my question is can there also be a secondary reaction and by 'miracle' form an ether or something, like having the deprotonated alcohol interacting with the alkene in the solution in any strange way.Why isn t that possible professor?

[@ramshaazeem2181]

why carbon changes it's state of hybridization from tetrahedral to planar? 😕

[@ProfessorDaveExplains]

because when the leaving group leaves, it takes the electrons in that covalent bond with it, so carbon loses an electron domain! with only three remaining, trigonal planar is the best geometry. check out my general chemistry tutorial on VSEPR theory for more help with this!

[@braydenhascup1560]

Love these vids!!

[@khanveer7981]

How carbocation has sp2 hybridized orbitals ????

[@ProfessorDaveExplains]

it only has three electron domains

[@sciencenerd7639]

very clear and concise

[@max_maverick]

Wait a minute... I don't get why can't this reaction proceed as Sn2, like in the previous vid?. Or these two are just competing mechanisms?

[@ProfessorDaveExplains]

nucleophile isn't strong enough to attack substrate

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hey cant understand at last how h2o remove H and oH form plz expln

[@ProfessorDaveExplains]

well it's no different from the water on the substrate, they just collide and proton transfer occurs!

[@عباسعمادكاظم]

Thank you man your areal life saver😍

[@ninjaspore]

the carbocation intermediate shouldnt have dashes or wedges, its trigonal planar (flat).

[@ProfessorDaveExplains]

it is drawn in the plane perpendicular to the plane of the board to better show the nucleophile attacking from either side of the intermediate.

[@ninjaspore]

oh i see it now thanks

[@dsir172]

What exactly is the difference between sn1 and E1 ?

[@ProfessorDaveExplains]

One is substitution, the other is elimination! Huge difference.

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[@ProfessorDaveExplains]

just watch all my tutorials! check out the playlists on my home page.

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[@subhabrataghosh3565]

what is racemic mixture

[@ProfessorDaveExplains]

a mixture of stereoisomers

[@rassimsimou1594]

Good

[@HexaneChemistry]

Thanks

[@ranjeetsohanpal752]

Where is SN2?

[@ProfessorDaveExplains]

that's got its own tutorial, check out my organic chemistry playlist for all of them!

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