NurdRage - 2018-02-18
In this video we make tertiary alcohols using the (in)famous Grignard reaction. Briefly, an alkyl halide is reacted with magnesium metal to form an organometallic alkyl magnesium halide. This is the grignard reagent. This reagent is then reacted with a carbonyl containing compound suck as a ketone, an ester or an organic carbonate to form a tertiary alcohol. The mixture is then reacted with water and titrated with acid to dissolve the magnesium hydroxides formed. Finally, the alcohol is purified by a series of liquid extractions and distillations. Related videos: Purifying and drying diethyl ether for use in grignard reactions: https://www.youtube.com/watch?v=EEXqjJd0Bak Making alkyl halides: https://www.youtube.com/watch?v=Ydn1D4FSqkc the dean stark apparatus: https://www.youtube.com/watch?v=jxgpLp279Yc Donate to NurdRage! Through Patreon (preferred): https://www.patreon.com/NurdRage Through Bitcoin: 1NurdRAge7PNR4ULrbrpcYvc9RC4LDp9pS Glassware generously provided by http://www.alchemylabsupply.com/ Use the discount code "nurdrage" for a 5% discount. Social media links: Twitter: https://twitter.com/NurdRage Facebook: https://www.facebook.com/NurdRageYoutube/ Instagram: https://www.instagram.com/nurdrageyoutube/
You always have to be very gentle to your Grignard. My organic chemistry professor recommends gently petting the Grignard before starting, works very well if the moon is in the right position
That comment made my day xD
A method that doesn't use fire is better?
Guess we see things differently here.
As long as you like explosions too :)
Can you turn that into OMgBrO :D
NiCe
ThAt'S PuRe GeNiUS.
medexamtoolsdotcom I'm diene
No I don’t think so, because magnesium is in group two and will attach two groups unlike group one. I think you could make mg(bro2)2 though.
@ecstasy.apostasy r/whoosh
This channel and NileRed should do a crossover episode ~
Caju explosivo just don't that meme is dead and is cringey as fuck.
I think they might be the same person.
I don't believe it. NR aspect is very different from that of NR. OK, NR has never shown his face, but you can see the silhouette in the early QA videos, and after NR did a face reveal, I find it difficult that the two silhouettes coincide.
Abbreviations don't work when they are the same letters.
I actually did that on purpose!
i've been watching your vids for so long and never really understood what you're talking about but since i started college last fall taking gen chem and now organic chem; it feels good know like 1% of what you're talking about.
Rss Reader isnt complicated
I recommend the youtuber, Tyler DeWitt, he (for me anyway) makes things just click and make sense.
Great work, one trick I've learned to get a Grignard started is to add 2ml of your starting alkyl halide then cup the flask in your hand till you feel the flask starting to heat up and you get a very gentle reflux then proceed as normal.
I was wondering where you got those huge chunks of ice from. Then I remembered: canadian winter.
When you take organic chemistry and actually understands what he is doing!!!!
You have some timing. I literally just learned about Grignard reactions in my OChem class.
0:52 did you make that image? Pretty detailed. Very neat.
we used thf, a three arm flask, and a syringe for our setup
I did this in college lab a few months ago, i made 2-methyl-2-hexanol
A way of doing grignard reactions with wet solvent and reagents is to use an ultrasonic bath, but yields are usually lower.
How do you think 2-methoxybenzylmagnesium chloride would react with acetone? I mean the normal way or there will be some rearangment?
oh man I've been waiting for this one, I'm excited
hi i am 13 and when I grow up I want to become an electrochemist so is it ok to do some more videos on electrochemistry?
Right on. I've been waiting for someone to take this on. Perhaps you'll answer all of our speculations once and for all. I'll be looking forward to the alkalai metals video.
For the prodigal Son Returns
DILLY! DILLY!
What is it with youtube chemists and the word anyway?
Anyway, great video.
Even with holding da thing called phd this is always exciting! Wicked!
Wow, that's a LOT of content, could have easily been like three separate less insanely dense videos IMHO. Great stuff!
What about activating magnesium with iodine?
kan petyim i think that iodine would react with the newly formed carbanions.
It's one of the ways
Nile red did that
We used that method in the lab. Certainly works.
What about activating tertiary alcohols with fire?
I remember when you upload a video where you show how to make potassium metal i never know if youtube or you got out the video, regards from Mexico
Dropping tiny bit of iodine seems to activate rxn really well for me, produced so magnesium iodide also removes that last traces of water.
Great vid thanks for posting!
I’ve tried the reaction before wherein KOH in a specific type of oil (I couldn’t afford it so I tried mineral oil) is heated with magnesium and a tertiary alcohol (I used tert-butyl), with slight pressure kept using a balloon on top of a fractional distillation column.
I couldn’t get the reaction to start. I got the idea from the sciencemadness.org forum many years ago and some people appeared to pull it off. A good portion of the posters were suspicious of it being a “troll”.
Good luck!
My pictures are still on that original thread over there I’m sure. But I don’t want to connect the two identities so...
you forgot the most important application of the grignard reagent. Teaching second years to clean their fumehood^^ man we all hated the grignard reaction^^
Quote: "....I'm going to do some amateur research in creating potassium.." - Bro, i get it, you're way smart.
The legend is back!
#NurdrageforpresidentofEarth make it happen, Earth.
Great chemistry! Thank you!
This episode was amazing. Glad to see that you have been actively making videos since the last episode. You sure put a lot of work into this one.
I think it would be great if you could do a video with illustrations explaining for dummies how the laboratory glassware you use work. Also a "ELI5" on chemical notation or at least color code your illustrations so I have a chance of understanding what squiggly line is what compound. :D
Can Grignard Reaction Can happened when using Akyl Iodide & Zinc but I don't know what solvents should be used
Still working on knowing enough to understand the entirety of your videos... seems it'll take me a while
The best Grignard video I've seen in years! Here in Argentina it is almost impossible to make Grignards, so I have seen such an incredible video that it almost makes me feel what it is to make one,i whanted to do these reaction for years now !! But the research lab where im added does not do these reaction so often. Thanks for this super long and amazing chemistry video :)
Why doesnt magnesium react with 2 bromohexane to make duodecane and magnesium bromide
Alperen Bırçak it does actually its just very very slow unless theres catalyst, usually iirc a Copper(I) salt, this is becuase the carbon in a alkyl halide doesn't have a partial positive charge on it like a carbonyl does making it much less reactive
It does have a partial positive charge and it is used in Wurtz reaction, which is almost the same but uses sodium instead of magnesium, so the organometalic reagent is more reactive.
Distilling for a week? That is the new definition of "dedication". GET ON IT, WEBSTER!!!
Great video. I know that the vapor pressure of these large alcohols should be low but do they smell like something at all?
Very very good to see you posting tutorials again. Missed you man, missed you
Tertiary alcohols?
Is that booze you drink at university?
Yes. You can drink 2-methyl-2-butanol.
It's better than ethanol because it doesn't give you a hangover.
2m2bOH is smoother than EtOH!
Get a 10ml borosilicate/pyrex graduated cylinder, and measure out 2ml to 10ml.
Then add it to a glass of water.
Then add 20ml of vodka(40% ethanol).
Mix and drink!
https://psychonautwiki.org/wiki/2M2B
https://www.youtube.com/watch?v=OaI1PjForUc
https://www.youtube.com/watch?v=YhpPTDVss7M
how do you get good yield of a ketone reacting a Grignard with an acid halide, avoiding a second equivalent giving a tertiary alcohol?
I love these videos.
Greetings, fellow nerds.
I always sublime Iodine with the Magnesium turnings. Was suprised you Skipped that.
Make a video on how to recover all the bromine...
not really worth it. it's cheaper just to buy more sodium bromide.
Why not use a brine wash followed by mag/sodium sulphate to dry your ether once the workup is done? Dean-Stark seems a little overkill.
I though the same, but i suppose it is connected with waste production: remember, brine, sulphate, anything like that generate cost, cost for disposal of chemical waste. With Dean-Stark it uses energy, but without generating wastes, especially on this nice, big scale. From my view, vacuum distillation would be more effective than steam one, but besides that, this was pretty green chemistry from waste point of view.
the Dean-Stark seems more to remove water during the distillation to ensure the product / ether distillate has reduced water content. Additionally the use of washing steps produces Aq. waste which builds up pretty quick on scale.
I love this channel. I'm not a chemist but seeing the science in action is mesmerizing.
Really putting that heating element to work there!
Amazing video , nurdrage is back !
Hey what ever happened to your video on making potassium metal. I remember it was KOH, Mg, some type of solvent and a tertiary alcohol. Youtube flag that one or something? I found another video of someone using lamp oil, but there video isn't as good as yours was.
I love your channel. Nilered and ChemPlayer are fantastic, but I love how you explain things practically. Would you consider doing a whole video devoted to workup schema, especially when one is going into uncharted territory?
NurdRage - 2018-02-18
Next big project will likely be on making fuels.
Jason Enns - 2018-03-02
NerdRage what kind of fuels? What inspired you to be a chemist? Can you do a video about chlorine salts? I have not found a way how to electroplate aluminium please tell me.
Micheal Rachid - 2018-03-05
Do a burn test
BLUEBLADE NINJA - 2018-03-09
.. IamTheDark borneSo I've got 1000 apple seeds arriving some time next week I'm blots the shit out of them in water and lemon juice then I'm gonna boil them and reduce them then add more water blits the shit out of them again then reduce the water down as much as I can then I'm going to add methonol bring to the boil and simmer then add bicarbonate of soda and simmer for another while then blits again then I'll strain it through filter paper 3 times and reduce 1 more time until hope fully all I'm left with is cyanide carbonate will this work let me know1 hour ago• IamTheDark borneSorry sodium cyanide????
Eric Mueller - 2018-05-11
MrAntivirusxp Add water to the fuel. The ethanol will follow the water and you can seperate with a sep funnel. Add back a bit of isopropanol to make any left over water miscible with the gasoline.
Blim The Toolman - 2019-06-28
I'm from 2019 here, he's serious about making gasoline from tetirary alcohols, infact just in the recent video he said it's almost ready. Could this be the newest way to make renewable gas...? Or is it going to be a NFL play by play. Find out next time, same bat place, same bat channel!