Robinson Annulation

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The Robinson Annulation is really neat, you guys. It's a Michael Addition followed by an intramolecular Aldol Condensation, and it makes a ring! Contain your excitement, you don't want a public disturbance violation.
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Опубликовано:

22 сен 2024

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Комментарии : 113

@kristinakafle4249 2 года назад

Studying the day before my mcat, and this was the easiest and quickest explanations I could find and understand. Thank you SO much!

@andy0695 2 года назад

How was the exam????

@kristinakafle4249 2 года назад

@@andy0695 killed the chemistry/physics section! can't speak so much for the rest LOL

@CloudyGumption 9 лет назад

I am a great fan of this reaction mechanism, I do believe the OH is eliminated after electrons are pushed to the carbonyl oxygen in that last step. Like an E1cB

@ProfessorDaveExplains 9 лет назад

David Wells yes indeed, the last part of an aldol condensation is an elimination, as shown here!

@Mary-cv2fm 8 лет назад

Professor Dave!!!!! I love your videos. They are extremely helpful, thank you for making them!!

@ProfessorDaveExplains 8 лет назад

+Mary Bass my pleasure! spread the word!

@tyedyegurl1999 5 лет назад

T-5hr until my orgo exam and Dave out here saving my ass once again... not the hero I deserved, but the hero I needed.

@pierce1234567891 4 года назад

2020 coronavirus pandemic-sees professor dave cough-NO

@thirishar1237 3 года назад

We got more information with less span of time....thank you very much prof.dave 🤗

@nouralzahraafawaz8860 6 лет назад

I have to thank you from the bottom of my heart 💜 I have been studying through your amazing videos since 3 weeks! My exam is on Monday and I hope to do well! Wish me luckkk🤞🏻

@PunmasterSTP 2 года назад

I know it's been awhile, but how did your exam go?

@YuliyaTsishchanka 5 лет назад

I have never left a comment on a video before but you are literally the best ever teacher on youtube and I wish you were my teacher-which you kind of are! Thank you so much for this!

@ProfessorDaveExplains 5 лет назад

thanks kindly :)

@sevgiarslan1827 4 года назад

@@ProfessorDaveExplains Can I have your email

@thebilla6568 9 лет назад

One of the best on RU-vid. Thanks.

@sydneyesposito8572 6 лет назад

Thank you so much for all your videos! You explain concepts so well, I always look for your videos before anything else when I need help. :)

@shrishtibhattarai8319 6 лет назад

Thanks for making it so simplistic.

@sudhagupta5719 4 года назад

Easy and good explanation

@mshisha 9 лет назад

This is wonderful. Thank you so much for your time!

@omayma3542 8 лет назад

Thank you for that simple explanation !

@Kittendu18 7 лет назад

OMG thank you so much ! This video is very useful, and it's short, effecient. Thank you Prof

@shaikhfirdousmuskanR 8 лет назад

awesome teaching ...thanku so much professor u have helped me alot for my xams.

@quentinmcilvaine4447 4 года назад

you're a solid guy, Dave.

@giulialanza-billetta8133 8 лет назад

You're honestly the greatest! Thank you :)

@Emma-js7ui 9 лет назад

Thanks! This was super helpful

@drgracional 9 лет назад

Thanks from Brasil. Great job, Professor.

@Hauskkia 7 лет назад

Awesome tutorial! It is a very cool reaction indeed.

@momijidoll13 9 лет назад

WHERE were your videos when I was in first year?? Your videos are so effective and your style of simplifying complicated concepts is beyond brilliant. Would it be possible for you to make some videos on retrosynthesis? and maybe the organic chemistry of palladium? Thank you

@ProfessorDaveExplains 9 лет назад

momijidoll13 I will absolutely add retrosynthesis to the list of next topics! Thanks for watching!

@suhaibaziz4597 11 месяцев назад

Thank you Pro.

@PunmasterSTP 2 года назад

Robinson annulation? More like "This is some great knowledge and information!" Thanks again so much for making and sharing such amazing videos.

@elifacet3809 5 лет назад

Thank you very much for your effort

@chemicalscience2445 3 года назад

Really so helpful

@KoolViking3 8 лет назад

Brilliant! Thanks!

@nouryassin7721 6 лет назад

Thank you professor 🤓

@kirubabowneeth3928 7 лет назад

thank you sir.

@christinamelita2412 6 лет назад

sir how do we know whether the product will form ring or not. why can't it remain linear sir.

@christinamelita2412 6 лет назад

sir I mean that how do we know for given two reagents, Robinson annulation will take place.

@alaanader9913 4 года назад

Thanks so much you really helped me 🖤

@simonbedenbender3087 5 лет назад

Just watched two of your videos. They are very good and well explained. I was looking for some explanation for some name reactions during studying for my organic chemistry II examn. The script was very bad but just spending five minutes on your video gave me all explanation i needed thanks!! Just giving the links of your vids to the students would be better than reading the scrpit ;) Thanks from Germany!

@PunmasterSTP 2 года назад

I know it's been a long time, but how did your exam go and how have your studies gone since then?

@simonbedenbender3087 2 года назад

The exam went well, I got a pretty good mark in the oral exam. But I havent got much contact with OC since then because I actually studied biochemistry, OC was just a subject we had to do

@PunmasterSTP 2 года назад

@@simonbedenbender3087 I'm glad it went well! How did the rest of biochem go, and where did you end up career or academic-wise?

@heshamnasher4997 2 года назад

Thank you very much for the good and clear effort :)

@AlexzandriaL 4 года назад

What is the overall reaction? I mean what do we write as the reagents for this rxn?

@youssefnaitlaarbi922 6 лет назад

thanks from morocco ... great professor

@buckyrx7 4 месяца назад

So this is kind of similar to a Dieckmann condensation being an intramolecular version of Claisen condensation?

@mariamejaz3429 Год назад

JazaqAllah Sir

@DarlinaLiu 8 лет назад

How do you know which carbon to deprotonate (which enolate to form) during the intramolecular aldol condensation step? Also, at the end, do we really have hydroxide as a leaving group? Not water?

@ProfessorDaveExplains 8 лет назад

+Darlina Liu good questions! first, it's absolutely true that you could enolize on either side of the carbonyl for the second step, but a four-membered ring is much less likely to form, so enolization on the inside of the carbonyl might just be reversed to reform the carbonyl until enolization occurs on the other side, at which point the ring might snap shut to get the six-membered ring. and yes hydroxide is a reasonable leaving group in strong basic conditions, if there's a bunch of hydroxide swimming around in solution one more won't hurt.

@DarlinaLiu 8 лет назад

+Professor Dave Explains Thanks for the thoughtful replies, Professor Dave!! Your videos are so so helpful, wish I discovered them earlier!

@a1738k 5 лет назад

Will you get a racemic micture? The methyl group can be a wedge or a dash correct?

@ProfessorDaveExplains 5 лет назад

oh good question, i suppose so, i would probably have to draw it out with chairs to know for sure

@a1738k 5 лет назад

@@ProfessorDaveExplains Alright, I was thinking the enolate can attack the Michael acceptor from any face (re so si) so you'd get a racemic mixture.

@ProfessorDaveExplains 5 лет назад

well at that stage the molecule would be achiral because its meso, but the product is chiral, so i'm actually not positive if there is anything that would favor one isomer over another, there may be information in the chairs

@a1738k 5 лет назад

@@ProfessorDaveExplains Yeah exactly, thanks!

@Thaumius 2 года назад

4:35, isn't OH- typically a bad leaving group?

@kainatshaikh5781 7 лет назад

you're so amazing!

@korangalalita1229 6 лет назад

Thanks sir

@claudiafeola9215 6 лет назад

In the first step the enolization happens on the more substituted carbon. Why isn't the reaction controlled by a kinetik mechanism in basic conditions? (why not an attac on less substituted carbon?)

@ProfessorDaveExplains 6 лет назад

Like I say in the video it's just because that proton is the most acidic! The conjugate base has resonance across two carbonyls.

@celinekim432 5 месяцев назад

For the step after the tautomerism step, would the base used not have to be an LDA or stronger base to give the kinetic/less substituted product?

@sukainaalherz3554 9 лет назад

I like your way in explanation Is there any video in this account about (syn) and (anti) or (Si/ Ri).

@annagmg230 3 года назад

J'adore merci beaucoup

@dancingdodo2768 6 лет назад

If I pass my organic chemistry exam on Monday, I'll have you to thank!

@PunmasterSTP 2 года назад

I know it's been a while, but did you pass?

@dancingdodo2768 2 года назад

@@PunmasterSTP to be honest, I can't remember if it came up on whatever exam it was for, but I sit here waiting to start a PhD in polymer chemistry in April so I can say the video is at least good enough not to have you fail

@PunmasterSTP 2 года назад

@@dancingdodo2768 That's amazing, and that sounds like an awesome field to do research in! Is your ultimate goal to go into industry, stay in academia, or do something else?

@dancingdodo2768 2 года назад

@@PunmasterSTP the PhD is sponsored by the company I work for but afterwards, I don't really have a preference. I just want to do research. I haven't got the patience for the stupidity of commercialisation

@PunmasterSTP 2 года назад

@@dancingdodo2768 I gotcha. Please forgive my ignorance, but what type (or subtypes) of polymer chemistry are there? Which one(s) would you hope to conduct?

@ruger51995 3 года назад

Isnt OH a bad leaving group though?

@ProfessorDaveExplains 3 года назад

in strongly basic conditions it's no problem

@lyzzts 8 лет назад

Hi, sir. In regards to your mechanism at around 3:51 , I was wondering if there should be an arrow showing the movement of the bonding pair of electrons to the oxygen that will later have the negative charge?

@ProfessorDaveExplains 8 лет назад

+Alyaa Hakim ah yes, you're right, it seems i've omitted an arrow!

@sciencenerd7639 2 года назад

fascinating

@ayoub4144 5 лет назад

merci beaucoup

@ismailsarenkapic485 5 лет назад

Very helpfull tnx, can u pls next time film tje whole rection when u are done so we can see it

@niranjanpradhan1252 6 лет назад

nice video sir

@shanemichael9404 5 лет назад

Hey Prof. Dave. Me again. Pestering you by now probably. But, will be happy to donate by next month hopefully as I do deeply appreciate you answering my ridiculous questions. On the tauteromerization part (probably spelled it wrong) why does the OH grab that hydrogen on Carbon 4 shortly before the ring is made? I believe it's Carbon 4, it appears to be primary with 3 hydrogens. Anyway why that Carbon and not any on the other Carbons? Not surprised that curiosity hasn't killed me yet !

@ProfessorDaveExplains 5 лет назад

so it's the pi bond that grabs the hydroxyl proton, whereas the OH sigma bond because a CO pi bond. check out my tutorial on michael addition, i more thoroughly discuss tautomerization!

@minakshibanerjee3732 5 лет назад

sir i love chemistry and also you

@claudiafeola9215 6 лет назад

sei un mago

@kusalseven3563 6 лет назад

i think it doesnt stop there

@jasonhowe5006 5 лет назад

beast.

@GingerRootss 9 лет назад

Why doesn't the Robinson Annulation always happen because the product of a michael addition creates two carbonyl groups that could react as such?

@ProfessorDaveExplains 9 лет назад

Eva C well it depends on the structure of the electrophile, it needs to be able to form a six-membered ring in the transition state of the second step, so if there is a phenyl or tert-butyl group alpha to the carbonyl it won't work. there could also be issues due to sterics. but fundamentally you are correct that many michael additions could result in subsequent robinson annulation.

@you-ik4oc 5 лет назад

Nice

@msathishkumar1159 6 лет назад

Sir, it's very useful learns organic chemistry mechanism sir. I have one question about the Robinson annulation reaction sir. That is what is the stereo chemistry behind in the last water molecule elimination step sir

@ProfessorDaveExplains 6 лет назад

hmm, no stereochemistry that i can think of, it's just an E2

@abdulbasit-qf7bb 9 лет назад

nice sir

@caseyhagg2657 7 лет назад

Thanks for the clear explanation! I am curious what the significance of your tattoo is?

@ProfessorDaveExplains 7 лет назад

it's the diagram from which the parsec is derived!

@SkudzYNBuddies 8 лет назад

how come you use hydroxide as a base? i've been taught to always use sodium ethoxide for these mechanisms and michael addition itself

@ProfessorDaveExplains 8 лет назад

+its Skudzy hydroxide is the classic, that's what i typically see. methoxide or ethoxide are fine too. kind of arbitrary i think.

@SkudzYNBuddies 8 лет назад

okay thank you for the answer!

@patmahgroyn6868 9 лет назад

can you do a robinson annulation without a di-carbonyl reagent?

@ProfessorDaveExplains 9 лет назад

steven schulster I wouldn't think so, as you need one carbonyl to enolize for the first step, and the other to act as the electrophile in the second step.

@pavanivishnoi5851 3 года назад

Hindi please🙏

@ruger51995 3 года назад

Moves a bit fast

@n.s.1496 8 лет назад

I gotta tell my university about you...

@ProfessorDaveExplains 8 лет назад

+Nickolai indeed you must! spread the good word.

@n.s.1496 8 лет назад

Any chance you could post organic chem videos on phenols, amines to amide conversion and Mass spect? :)

@n.s.1496 8 лет назад

Oh and you are absolutely wonderful. The text book is way to thick in its terminology to understand

@ProfessorDaveExplains 8 лет назад

+Nickolai i will add to the list! i definitely plan to do all forms of spectroscopy/spectrometry.

@kaustavdas6829 8 лет назад

hi, i really like your videos and i am having a hard time understanding Hofmann exhaustive methylation . Could you please upload a video explaining it's mechanism and everything.

@ProfessorDaveExplains 8 лет назад

+Kaustav Das nitrogen lone pair does SN2 on methyl iodide until no more methyls can be accommodated!

@kaustavdas6829 8 лет назад

+Professor Dave Explains if the nitrogen lone pair is in resonance with the ring then what happens?

@ProfessorDaveExplains 8 лет назад

+Kaustav Das it can still be methylated, it will just probably be less kinetically favorable and also bear a formal positive charge in the product.