Nucleophiles, Electrophiles, Leaving Groups, and the SN2 Reaction

[@ProfessorDaveExplains]

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[@RKN786]

it is not always the case that if SN2 occurs on the chiral center it will necessarily invert the steriochemistry there. Because if the incoming nucleophile has a different Cahn-Ingold-Prelog priority from the leaving group.

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[@zahranoor4130]

My teacher took 2 hour to explain SN2 and u make it clear in 6 mints

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[@harpreetk2006]

Amazing video on explaining SN2 reaction! Just a question, at 2:27, surely you must mean the oxygen atom is the electron-rich atom? Not oxygen-rich atom? Keep up the great work Professor Dave :D

[@ProfessorDaveExplains]

Whoops! Haha, yes.

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[@cdaug28]

Hi there! First off, your videos are amazing and so helpful. Thank you so much for helping students like me understand difficult concepts! Secondly, you mentioned that an inversion happens at a stereocenter but the compound drawn doesn't have a stereocenter. Just wondering why it had an inversion? Thank you!

[@ProfessorDaveExplains]

well it will always invert, but if it's not a chiral center it won't matter!

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Perfect explanation. I do think it would be helpful to show another rxn to more clearly depict the inversion of stereochemistry

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Prof Dave Explains thanks for your help!! I remembered what attacks what !!

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100000000000000000000000000000000 time better than my lecturer😮.. i did not understand what my lecturer was preaching

[@seanyboyblu]

Awesome video. One question; you say that "the lowest unoccupied molecular orbital is 180 degrees from this carbon chloride bond". How are there any unoccupied orbitals? The carbon has four bonds already, and therefore a full valence shell, sp3 hybridized. So aren't all of the orbitals filled?

[@ProfessorDaveExplains]

So when a nucleophile attacks an electrophile it has to put that electron density somewhere, and it can't put it in any of the ones that are full of electrons, so it goes to the orbital with the lowest possible energy that doesn't have any electrons in it yet. All chemical reactions are HOMO-LUMO interactions in that way! Check out my tutorials on molecular orbitals for more information, preferably the newer one.

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Really well explained! Very thankful to all the KZbin educators like yourself :) One question I have regarding this: what property of the leaving group or incoming nucleophile enables the reaction to proceed forward? (i.e. allows the carbon to dissociate from the Cl- and form a bond with OH- instead) Is there a way of theoretically determining which form (OH bound vs Cl bound) is likely to be in higher concentration in a solution that has been allowed to reach equilibrium?

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i've just been here working hard! i've made a lot of stuff since these first tutorials.

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[@jonathanstevens1917]

Hi Dave and thank you!! What do R and S stand for please?

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awesome video!!!

[@MrPaintballfanatic]

Sn2 does not always cause inversion of absolute configuration; that was incorrect. R does not always change to S, and the other way around too. What he meant is Sn2 causes inversion of stereochemistry, meaning the 'wedges and dashes', or position of bonded atoms in space change due to the nucleophile sterically pushing the other groups away to 'make room'

[@ProfessorDaveExplains]

well, yes, the specifics of R and S depend entirely on the groups present on the molecule and whether the electrophilic carbon is even a chiral center to begin with. but the point that was to be driven home is that the orientation of the groups always inverts due to the backside attack.

[@ΒασίλειοςΑλεβίζος]

Can you tell us an example of SN2 where R remains R or S remains S? Thanks from Greece!

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[@courageojo4769]

Sorry mistake pls professor why is SN1 reaction called unimolecular

[@ProfessorDaveExplains]

check the SN1 tutorial

[@KanishALevels]

numbers in SN2 / SN1 are based on the total number of molecules present in the slowest step. Here, first step is the slowest and it contains two molecules (1 OH- and CH3Cl) so it's SN2. In SN1 the slowest step has only one molecule involved which is, lets say C(CH3)3Cl. The slowest step is C(CH3)3Cl ---> [C(CH3)3]+ + Cl- The reactant in the slowest step is unimolecular so it's SN1

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[@AwaisKhan-mh6cd]

Love you jesus😊 of science. This matures sn2 soooo much simpler

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I just noticed all the new topic you're taking on. Quite like Michael Van Biezen here on YT. Dude is driven , you are too. How is this even remotely humanly possible to understand that many topics?? To a degree where you can fluently teach others. Your parents must truly be brilliant. Good genetics I think plays a big part in people's intellect, and their ability to just devour massive amounts of knowledge like it were a walk in the park. I have to ask have you ever struggled with any subject or has everything pretty much been cake?? Or do you have the MENSA thing going on?? That would explain a lot.

[@ProfessorDaveExplains]

Oh plenty of struggle. I got straight B's in college. The upper level chemistry classes were difficult, especially quantum chemistry. I became better at these subjects later, by virtue of having to teach them to make a living, especially organic chemistry, and I had enough practice at it that I became good at explaining these concepts. But to say that I'm an expert in all of these fields would be a dramatic exaggeration, there are some areas in which I know very little, I just work out of textbooks to write the scripts. But as a generalist, I have a solid knowledge base, and I can consume new information and compartmentalize it rather easily, so learning biology and anatomy & physiology is much easier for me than it is for a person who knows very little science to begin with.

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@@ProfessorDaveExplains one thing for sure brother you were made for this. Teaching , whether it be in the classroom, lecture hall, social media platform or through the airwaves via streams and podcasts. That gift you have, there's no downplaying that. From what I understand teaching and to be successful at it, you have to have such a fine balance between so many things. You got to be well-rounded you have to know your curriculum inside and out. You have to be able to express yourself fluently, got to be able to keep a cool head about you. Because you know there's always going to be a few smart asses intent on making your job that much harder. The most important is to have, and keep a sense of humor throughout it all. That's gold standard brother.. That's a hard job not many willing to tackle. Them cats working at them crab boats or working on them oil rigs are physically tough cookies, but they wouldn't last a week teaching at some suburbian High School.

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[@johnregis1289]

Loved the video, but I have 1 question... At 5:33, you said that an inversion would happen at a chiral center, but wouldn't the molecule you are referring to be achiral? It is attached to 3 identical hydrogens.

[@ProfessorDaveExplains]

yep! so the groups will invert no matter what, but yes you only invert the stereochemistry if it was a chiral center to begin with.

[@johnregis1289]

Professor Dave Explains Okay, but if it was an achiral center, it wouldn't need to be inverted?

[@ProfessorDaveExplains]

well the inversion will still occur, there just won't be any stereochemistry to speak of.

[@johnregis1289]

Professor Dave Explains Ah, okay. Thank you, this makes more sense :)

[@watching4410]

Sn2, Sn1, E2, E1 id NEL/NALGa, LasaGNA/LGNA-deprotonateByWater=racemic, betaTransfer pi-pi LG TP&LG, LGNA p+/pi-pi 2-1, 1-3, 3-1, 3-2 arrows-steps 2,1,3 3distrib 1 step, 2 step LG first

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Ahhh got it ! Sinister and Rectus :)

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Sir please do some video on crystal field theory and isomerism in coordination compounds. their are many in channel but doesn't provide the extent of satisfaction that you give.

[@preetibaghel9698]

**Doubt Professor can you explain why you have shown a reversibility sign in the SN2 reaction Plz reply

[@vipforlyf]

SN2 reactions are generally reversible reactions, but their leaving groups affect how reversible they are