Видео

If Nitrogen was doing 1,2 addition (attacks on carbonyl carbon), followed by proton transfer, then N atom attacks on carbon 4, to expel OH group (just like E1cb) to form a ring. The OH group gets a proton from N atom to form H2O as the side product., For this mechanism, why 1, 4 addition is more likely to occur?

I love pericyclic reactions, especially DIels-Alder, because how efficient and beautiful to draw they are. For the next reaction, the mitrile is hydrolyzed to a carboxylic acid, which then forms the lactone. For this hydrolysis, the acid protonates the nitrogen, making the carbon highly electrophilic. Here, a water molecule could attack the nitrile and form a C-OH and a C=NH bond; however, the intramolecular attack of the alcohol is probably more favored here. Then, the imine bond is hydrolyzed to a carbonyl (protonation of nitrogen, attack from water, proton transfer and removal of ammonia), which eventually forms the lactone.

Super underrated channel holly

Pinner reaction for next week

neat mechanism! i really like diels alder reactions

Hello! I have a proposal for next weeks reaction. Hydrolysis of the cyano group will lead to formation of a carboxylic acid . And then the acid and alcohol groups undergo esterification reaction to produce a ester (I think its a lactone in this case)

For next week, after protonation of nitrile we have an intramolecular nucleophilic attack from the alcohol, then hydrolysis of the resulting imine yields the product

for next week, hydrolysis of nitrile via amide then to RCOOH, followed by fischer esterification

How did you do? I'd love to hear your proposals for next week's mechanism so drop them down below! Subscribe for more chemistry content, and hit the notification bell to stay updated! #ScienceCommunity #MechanismMonday #OrganicChemistry

Wtf?? The first reagent is not a byciclo

carboxylic acid acting as a nucleophile burnt my eyes

i got the frist step correct but i got studk after i used OMDM in the 2nd step as there was no way to add NMe2 after that

So I think this is more tricky than one might initially think because of the aldol condensation step. 1.) Form the enolate of ethyl butyrate and react it with the SM, yielding a beta-ketoester 2.) Deprotect the enolether 3.) Oxidize the alcohol 4.) With mild base - like KCarb in DMF - as to not enolize the aldehyde, form the enolate of the 1,3-dicarbonyl. Attack at the aldehyde carbonyl yield a 6-membered ring. The resulting aldol is stable, since there's no alpha-H available. 5.) Hydrolyze the ketoester. Acidic workup releases CO2, tautomerization of the enol back to the ketone. Now, there is an alpha-H available 6.) Acid or base with mild heating form the alpha-beta unsaturated ketone. 7.) Michael addition with nitromethane 8.) wittig reaction with ethyl triphenylphosphonium iodide to install the olefin 9.) Reduction of the nitroalkane using Pd/C H2 I think the installation of a simple alkyl chain in the first step will lead to problems in the aldol reaction step: The aldehyde is going to be more reactive than the ketone. If the base enolizes the aldehyde, it can either attack at the ketone carbonyl intramolecularly (would form a 4-membered ring, equilibrium would probably favor the backwards reaction) or at the aldehyde carbonyl on another equivalent of the SM (this leads to dimerization and seems like, if reaction is not performed at high dilution) So, while my route is longer, I think it will be easier to achieve good yields that way.

Thanks really easy to understand explanation

Thank you for making this series!!! I watched every single video in it, and I've never understood Inorganic Chemistry better! I would love to see more in this series if you do have plans on continuing it in the future, especially more complex examples of molecular orbitals :D Have a fantastic new year!

I tried to figure out the Propranolol synthesis with an epoxide route but I couldn't think on the allyl bromide so i got stuck :/ About the next reaction, I am thinking on this sequence: 1) Addition of a propyl chain to the acyl chloride, with an organometalic compound and a Weinreb amide or adding some copper (I) salt to prevent further addition to ketone; 2) TBAF or CsF for alcohol deprotection; 3) DMP or PCC to oxidize alcohol to aldehyde; 4) LDA to deprotonate the alpha position to the ketone, intramolecular aldol condensation to form the enone (as the nucleophilic attack on aldehyde is more favored); 5) Conjugate addition of nitromethane anion; 6) Wittig/Horner-Wadsworth-Emmonds reaction with an ethyl derivative to form the double bond; and 7) Fe + HCl to reduce nitro groupto amine Maybe it is too long for a synthetic route, and there will surely be a better option, but this is my bet and I will stick with it

Let me suggest this option: 1. Reaction with EtMgBr. 2. Deprotection TBSO to alcohol. 3. Oxidation alcohol to aldehyde.(PCC) 4. Aldol condensation. 5. Michael addiction of MeNO2. 6. Wittig olefination with EtP(Ph)3. 7 Reduction NO2 group to amino group.

The task was less than 3 Carbons, not 3 or less

i finally figured out one! thanks!

Interested in more multi-step synthesis problems? Every month I post 2 exclusive members-only videos for you to test your skills! Join us here: ruclips.net/channel/UCvZXVdaLlO1B6EDdR9s-m6wjoin

On your last problem, how did you determine that the mirror of the screen itself was sigma h, not sigma v? Is there a coordinate axis that tends to be chosen over others for being the principal rotation axis when all rotations are C2?

This is an amazing refresher on org chem theory. I’m a bit out of practice and it’s such a nice and well presented exercise. Thankyou so much, I’m glad to have found your channel!

Marry me.

It must be a diels-alder with the furan ether oxygen eliminating as water?

I love to see this kind of reactions, where a relatively complex reaction can be easily describe with such simple steps. Also, there are some possible side reactions, like the attack of water to the tertiary carbocation to form tertbutanol, so this being the major product is quite impressive. As for the next reaction, I like it a lot because it was something shocking to discover for the first time. The first step is the Diels-Alder reaction between a furan derivative (counts as an electron-rich diene) and maleic anhydride (a great dienophile), which gives the cyclic cyclohexene adduct with a bridging ether. The acidic treatment protonates the brigde oxygen, allowing an elimination reaction which gives a cyclohexadiene and an alcohol which, with sulphuric acid, gives dehydration to form the final product. The reaction is favored by both the formation of an aromatic ring and (i guess) the conjugation with the anhydride group too. This is a great method to form phthalic acid derivatives starting from furan :)

Happy new year, i hv seen H2O attacking as nucleoph.. But hesitated to use H2O here .this mechanism confirms that it will in such cases, now im confident.

Couldn’t the carbon monoxide be protonated first, then nucleophilic attack of the alkene generating a tertiary carbocation and then nucleophilic attack of water to the tertiary carbocation generating an a hydroxy-aldehyde?

for next week, diels alder to form cyclohexene ring followed by one elimination of the bridged O to form an alcohol whoch is also eliminated by E1

Happy new year!

Heyy!! Got something for next week The double bond in the ester acts a nucleophile to cleave the ether . And then shift some pi some bonds to get the positive charge on one of tertiary carbons , a double forms here due to which the adjacent carbon releases a proton . This proton forms a alcohol . Due to the acidic medium the alcohol is eliminated as water and another pi bond is formed to give the final product .

Very nice 🎉

so simple yet so good! thanks!

My answer was same sir

thank you, you're video are very helpful

How did you do? I'd love to hear your proposals for next week's mechanism so drop them down below! Subscribe for more chemistry content, and hit the notification bell to stay updated! #ScienceCommunity #MechanismMonday #OrganicChemistry

Good

i am so motivated by your this playlist that i would like to remake your videos in my native language. will you allow me to do so?

nice

Good video. It would be also very helpful to present the reason for the stereochemistry of this reaction (the chair like conformation of transition state)

Not a chemist , but the was so cool I kinda learn something here

Thank you for all the chemistry videos over 2024, happy new year!! Also, around what level (university?) are these mechanism videos, thanks!

Man that's hard, 😅 it's unpredictable on how this molecule can form to completely different molecule. Even you form this product you can't tell what's the final product unless you have NMR & thing.

Mate huge love from india 🇮🇳❤️✨, thanks for the organic chemistry series

Thank You for the educational videos in Year 2024, keep it going in Year 2025! I hope you will have a Happy New Year!

following this channel hard until i get at the level to understand what you wanna teach. 🤌🫦 . See ya in your pervious videos sooner or later

Intramolecular Diels alder 💀, didn't see it coming. Whenever I see a base I go for aldol and similar XD.

I love watching these videos (am a senior year chemistry student ) but I feel I don’t know enough to do the problems myself. What level of chemistry would you say this would be ? Also what resources should I use to be able to get better at this stuff? Thanks

Cheers

Thanks Please explain Yavari reactions

Very nice explanation sir Can you suggest how to convert exocyclic double bond to dimethylation in simple procedures