How E2 Elimination Reactions Work (Animation) | Mechanism & Orbitals | Organic Chemistry

👀 This video explains E2 eliminations: basics of geometries, orbitals, selectivities...
🚀 Thanks to all channel supporters!!!
👉 Follow me on Instagram for updates on random research, chemistry problems and interesting news!

00:00 E2 elimination basics and orbitals
01:14 Ask yourself these questions
01:31 Level 1: 2-Bromobutane elimination and stereoselectivity
02:46 Level 2: Kinetic isotope effects and stereospecificity
04:35 Level 3: Cyclic substrates and A-values
06:25 Level 4: Peterson olefination and Brook rearrangement

The bimolecular elimination (E2 elimination) reaction is a cornerstone of organic chemistry, particularly for synthesis of alkenes. In the E2 mechanism, a base abstracts a proton (H+) from a carbon adjacent to an sp3-hybridized carbon, which is bonded to a leaving group. Simultaneous expulsion of the leaving group, forms a double bond (alkene) - with a concerted mechanism (deprotonation and and leaving group departure occur in a single step). This contrasts with the E1 elimination mechanism, where the leaving group's departure is the rate-determining step and occurs before the deprotonation step.

Some recommended books on organic synthesis:
- Clayden, Greeves, Warren; Organic Chemistry (basic organic chemistry knowledge)
- Wyatt, Warren; Organic Synthesis: The Disconnection Approach (excellent introduction to retrosynthesis)
- Kurti, Czako; Strategic Applications of Named Reactions in Organic Synthesis (extensive toolkit of functional group reactions and applications thereof with common conditions)
- Nicolaou; Classics in Total Synthesis 1-3 (the ultimate total synthesis trilogy)
- Nicolaou; Molecules That Changed the World (the world's most important molecules and their impact on everyday life)
- Carreira, Kvaerno; Classics in Stereoselective Synthesis (compilation of the groundbreaking methods of stereoselective synthesis and application to synthesis of stereochemically complex structures)

[totalsynthesis]

Hello there, thanks for watching! Our next few videos will focus on more complicated molecules and deeper chemistry - but let me know if would like to see more of these 'basic' videos in future! Thanks to all my supporters!

[ommhatre]

Underrated channel and Great videos! We want more such videos that teach reaction mechanisms. It would be great if you cover all types of mechanisms. If possible add animations as well 😊

[gabrielalx]

very nice video, you should try if it's possible to show the orbital interactions (like the bonding/antibonding/lone pair orbitals) that would help a lot of students vizualise what's really happening. Also you could maybe do a video on frontier molecular orbitals of conjugated systems (conjugated unsaturated ketones, conjugated polyenes, enolates / extended enolates etc.), that would be really cool!

[jonathana.]

Love the visuals reprensentation it's a really great to learn at understand the reaction. Please make more of them haha

[matejnastran]

Nice video, I prefer your style to every other theoretical chemistry youtuber, but I think these basics are well covered by others and you should focus on more advanced topics.

[zachlerdahl]

I think it would be really cool if you could animate the bonds forming and unforming when these molecules react with each other. Seeing that happen in 3D space would make this sort of stuff very intuitive. However, that does sound very time consuming. Maybe try just animating 1 reaction forming somewhere in the video. Love this video by the way! Thank you so much!

[amanitaocreata]

They didn't cover that Si stuff in my book, thanks!

[성이름-doo]

But why is resonance so effective in predicting almost all types of reactions? Continue with NBMOs and resonance-type heuristic MO approximations!

[vtncosmiik]

Thanks for this very nice video ! It was very interesting.

I just don't get the example between deuterium and hydrogen, why it should explain that the mechanism is concerted ?

Also at 6:55
You show the energy of C-Si and C-O
But you wanted to show C-Si and Si-O no ??

Thank you again:)

[ChemicaLove]

5:46 wondering if the boat configuration would be significant here, since it would have tBu-equatorial. Boat conformations are usually higher energy but this case may be an exception?

[SharpAssKnittingNeedles]

Very nicely explained! Skilled lecturers who make it interesting and understandable are so rare 😢 I was lucky to have an instructor like you who made ochem fun and a joy to study. Makes me so sad when people say they hate chemistry cuz they had a shitty instructor