Hazel Chem - 2018-09-27
hello you all this time i am synthesising trans cinnamic acid via the claisen condensation ! this is the first video of two this one deals with the synthesis of cinnamic acid ethylester from benzaldehyde and ethyl acetate catalysed over sodium ethanolate the music is by ChemPlayer (sadly deleted) you inspired !! have fun and do not kill your self !
We need channels like this in the age of youtube "experts"...
Thank you for posting all this interesting content!
thx :D in like 3 weeks i should have some time for a new video
mfg hazelChem
Yet another breath taking video. Amazing chemistry work dude, and hella love for giving that shoutout yo chemplayer. All the love and #staynerdy. Cant wait for the new one
thx dude :D
Amen - Tribute to the fallen - God speed ChemPlayer (now on Bitchute)
I don't know when i subbed to this channel;
I thought NileRed had changed his page name when i first saw the thumbnail.
But I'm glad I've found this channel :)
thanks for the nice feedback :D
mfg hazelChem
Hazel Chem Auch von mir vielen Dank für die Videos. Ist ja alles nicht mehr so einfach heutzutage. Hab gesehen, Du hast einiges an Rasotherm Glas. Hab vor Jahren mal nen halbes ehemaliges DDR-Chemie-Labor gekauft an Glasware usw. Um die 20 Bananenkisten voll für 400 EUR. Glück muss man haben, 1a Qualität. Auch Boral Pula, aber auch einiges an westl. Marken, Duran, Hirschmann usw. Das betreffende Labor bestand bis ca. 2002.
sehr geil ;D muss man halt immer glück haben wobei es leider so ist dass man nur standard sachen findet planschliffe wie ich es brauchen würde bekommst eigentlich nur neu .... ab 130€
mfg hazelChem
@Hazel Chem Ja, versteh schon, aber 60% von dem "Paket" war Normschliff 29 oder 14. Naja, 12 1l Dreihalskolben NS29/NS14 braucht ich dann doch nicht, genausowenig wie 8 30 cm Spiralkühler NS29. Hab dann viel verkauft und das ausgegene Geld sogar wieder reingeholt. Nur eine Reihe Kleinteile mit Schliff 29 oder 14 haben gefehlt, z.B. Destilliationsaufsätze, die musste ich dann auch "teuer" kaufen.
ja eine gute ns 14 vakuum destille sollte man schon haben .... meine wird im nächsten video zu sehn sein wenn ich den zimtsäureethylester hydrolysiere.
mfg hazelChem
good work! like for CP's music and atmosphere! but two errors - suits and four hands in frame ))
Interesting one! I am planning to synthesize trans cinnamaldehyde by the aldol condensation of acetaldehyde and benzaldehyde!
a well known way have fun :D
mfg hazelChem
GREAT VIDEO.............now you got this and the styrene video with an upcoming part 2. Awwwwwwwwwwwwwwwww . Oh well it is worth the wait. Seriously this is a very UNIQUE video. Great job. I surprised myself and actually understood everything on the first watch without having to look anything up. Usually an experiment like this i have to watch a few times and look up a million things before i understand it all. I can not wait till i am up to doing optical isomer chemistry but that seems a long time away from now
cinnamic acid will come in the next two days and one bitchute only video
mfg hazelChem
cool
I also made some cinnamic acid using Benzaldehyde, Acetic anhydride and sodium acetate. For recrystallizing I needed Liters and liters of water, but I finished at some point. Now I have two 1L Bags full of a very fluffy white solid, but don't know what to do with it for the last year. You maybe have an idea?
Chem Player :( oh the good old times :'(
Chemplayer is still on Bitchute. Science is awesome! Gallium forever!
QUESTION...........By making your sodium ethoxide while the ethyl acetate was in the pot do you think during that time some of your ethyl acetate was alpha deprotonated and enolized and then reacted with the positive carbonyl on another ethyl acetate making ethyl acetoacetate?????????????? Or did you add the sodium quick enough and cold enough where it would not make much difference?????????
What purpose does the sodium bicarbonate provide?
HAZEL CHEM............GREAT VIDEO. BUT What the heck made you use sodium carbonate to dry your product??????????????? I mean that seems like something out of left field.
well sometimes one does stupid things XD
mfg hazelChem
@Hazel Chem ............Trust me i get that. My whole life is just a continuous series of stupid things i have done. At least your only doing it once in a while....lol. GREAT VIDEO though. I definitely want to do some enol chemistry this winter. I have known about many enol reactions for years now. But when i watched your video i finally got INSPIRED and took the time to see WHY they are so similar. Before your video i knew they were all similar but never took the time to REALLY compare everything
Du kommst doch aus Deutschland, oder?
Benzaldehyde is very hard to find.
but you can make it from benzyl alcohol that should be easy to get
mfg hazelChem
Or another route is brominating toluene and then hydrolysis. Toluene should be available otc, bromine could be made from sodium bromide/H2SO4 if not available/too expensive.
that is a good way and i allready done this synthesis route but with chlorine because it is way cheaper
mfg hazelChem
@Hazel Chem chlorinating is also possible of course ;-)
In theory, acetophenone can be condensed with nitroethane to form 2-phenyl-3-nitrobutene. This can be reduced to 2-phenyl-3-nitrobutane by sodium borohydride in ethanol. Then the aromatic nitro alkane can be reductive amination with Galinstan aluminum amalgam and tin 2 chloride to speed it along. Thus making 2-phenyl-3-aminobutane. Galinstan is non-toxic and better than mercury.
HAZEL CHEM: So sodium metal does NOT react with esters???????????? In a claisen or an aldol reaction how do you stop the reaction so you do not dehydrate the alcohol and make a double bond ??????????? Every time i read about those reactions i get the impression it is possible BUT VERY VERY VERY HARD to stop it at the alcohol and keep the molecule saturated. But nothing ever says how to stop the reaction and protonate the alcohol without dehydration. I mean would using very dilute acid to make your alcohol stop it from dehydrating and forming a double bond.?????? Man i just spent like 4 hours watching this 15 minute video and posting these post. But it sure was worth it. I got a brain cramp now. THANKS FOR THE GREAT EXPERIMENTS YOU POST. Oh my god it just hit me why the double bond forms so easily. Resonance with the carbonyl. I made propene from isopropanal with a acid catalyzed dehydration and as you know it takes a million degrees to get it to start. I kept wandering why do these reactions dehydrate so much easier. Yeah that was an OBVIOUS reason. Some times things just blow by me sometimes...lol.
Who is Chem Player?
Chem player was a very good chemistry channel which got deleted :/
mfg hazelChem
@Hazel Chem Wish I had seen him, and I'll look for re-uploads - thanks
QUESTION......... I AM ONLY TALKING ABOUT THE REACTION UP TO WHERE HE MAKES A beta hydroxy ester. The CLASSICAL claisen reaction involves ONE ester. And 2 molecules of that same ester react and that will make a symmetrical KETONE. But he used an ester and a ALDEHYDE. And benzaldehyde is NON enolizable. So it is FORCED to be an electrophile. And when the tetrahedral intermediate is formed there is NO alkoxy group from an ester to leave. Because benzaldehyde does not have an alkoxy group on its carbonyl like an ester...it has a hydrogen. So the tetrahedral intermediate can NOT collapse back in to a carbonyl like when using 2 esters for the reaction. So then he acidifies to protonate his tetrahedral intermediate to make a beta hydroxy ester. KEEP IN MIND HE DOES NOT HEAT ANYTHING. In the CLASSIC claisen reaction the tetrahedral intermediate can collapse BACK IN TO A CARBONYL because it has a good leaving group......an alkoxide FROM THE ESTER. So now in the CLASSIC reaction you got a carbonyl beta to the ester/carbonyl instead of like in the video he had a beta ALKOXIDE that used to be a carbonyl but can not collapse. In the CLASSIC reaction when you got a CARONYL beta to an ester and acidify AND HEAT IT UP. The ester will hydrolyze to a carboxy group and since there is a carbonyl beta to the carboxy group then decarboxylation is inevitable. Leaving you with a symmetrical ketone. Since you used 2 identical esters as the reactants the ketone created will be symmetrical.
Now lets compare his reaction to an aldol. He got a beta hydroxy ester. Which means he got a beta hydroxy carbonyl (with a alkoxy group on the carbonyl) In an aldol reaction he would have gotten a beta hydroxy carbonyl ALSO but with no alkoxy group on the carbonyl. Cause in an aldol reaction there is no ester so there is alkoxy group on the carbonyl. It is the same EXACT reaction. if you take the alkoxy group off of the ethyl acetate and replace it with a hydrogen or alkyl group then it would be called an aldol reaction. And they are also similar cause in both reactions after getting the beta alkoxy carbonyl(his carbonyl with an alkoxy group on it) then in both reactions you would protonate the alkoxide anion to make an alcohol and then dehydration is almost inevitible in both reactions to make an alpha beta unsaturated carbonyl compound. But since he started with an ester the carbonyl has an alkoxy group on it making it an alpha beta unsaturated ester.
wow i actually think that is all right. If you made it this far you might as well post me back if you know weather i am right or wrong
Petko Tzvetkov - 2018-09-27
Great, great the Chem Player spirit in me and others lets make it. lets do it...@! Hazel Chem lesten to Eddie Hazel we love you'!