alexleyenda
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organic chemistry suggestion
Hi, for my seconth o-chem class, I have to choose an experiment to replicate and i'm quite sure you could have interesting suggestions for me 
Project specifications:
The school may order special chemicals we need, we have a maximum of 12 hours allowed in labs ( 4x 3 hours). It also must somehow have a link in
theory with one of the following: biology,
maths, physics or geology. The link does not have to be so much stong. A link with biology seems quite easy to make, especially if the molecules are
some kind of drugs.
Some exemples from the past years are isolate caffein from many different drinks like coffee, tea, redbull... There was also change pear aromatic
molecules into bananas aromatic molecules.
Info on the class:
The kind of lab we did is eugenol extraction from the plant by distillation and purification through many aqueous/organic phase extractions, changing
eugenol into it's sodium salt to make it soluble in the aqueous phase when needed and regenerating it ( I have no idea how you would call the salt in
english, in french it is Eugénolate de sodium, please tell me if you know!). We also did Cyclododecanol oxydation into cyclododecanone, changing
maleic acid into fumaric acid by breaking and reforming the double bond...
Some of the labs coming before the project are Dibenzylideneacetone synthesis, acetaminophen (paracetamol) aka tylenol synthesys, transesterification.
So yeah if you have any interesting suggestions go ahead and tell me!
[Edited on 22-1-2014 by alexleyenda]
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alexleyenda
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Just a little bump to say that if anyone have an idea I still search an interesting suggestion. At the moment my plan is wintergreen leaves --->
Methyl Salicylate---->sodium salicylate---->salicylic acid--->acetyl salicyclic acid.
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Mailinmypocket
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How about synthesis of benzocaine? Get PABA (p-aminobenzoic acid) and Recrystallize it from PABA vitamin supplement tablets (very easy) and esterify
with ethanol. You can tie this into biology with how it interacts with the nervous system. It's an easy synthesis and many procedures from o-chem
books are online if you just google "benzocaine synthesis experiment". I always found it fun to make benzocaine!
http://courses.chem.psu.edu/chem36/SynFa06Web/Expt86.pdf
[Edited on 25-1-2014 by Mailinmypocket]
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alexleyenda
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That was a very interesting read and it sounds like a fun synthesis, I will definitly consider this option, thanks. Next time I go to a pharmacy I'll
look for these tablets. If you have any other interesting Idea 
[Edited on 25-1-2014 by alexleyenda]
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Mailinmypocket
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Try looking for PABA in health stores... Around here pharmacies often don't sell it. Scaling up that procedure would be a good idea too!
PABA:
Re crystallized
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S.C. Wack
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Off the beaten path: extraction and separation of harmine and harmaline from Peganum harmala seeds. Bonus: UV fluorescence.
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Zephyr
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Making luminol is a very interesting and challenging synthesis. And you could tie in the physics chemiluminesence.
http://infohost.nmt.edu/~jaltig/Luminol.pdf
http://m.youtube.com/watch?v=58Ve69s0qD0
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alexleyenda
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I must admit that fluorescence/chemiluminescence make a nice bonus.
@ S.C. Wack -> However the extraction of harmaline/harmine is probably too short, extractions and purifications are usually done in 3-6 hours and
we have around 9-10 considering the wash time and other little things. Also the fact that it is off the beaten path makes it interesting to me but I
forgot to mention it, we have to present two versions of protocol found in serious sources to our teacher before we can make our own version and do it
in the lab... and all I found on harmaline/harmine extraction is cooking recipes on recreative drugs forums :p Anyways it is interesting so I'll keep
it in mind for future home experiments.
@Pinkhippo11 -> The luminol synthesis is awesome on many levels, it seems quite long however but I'll write down the principal steps and make a
quick estimation of the time it'll take. I have to take in account the fact that we have 2h20 per lab considering the time it takes to wash everything
and present things to the teacher before the lab starts. I'll also try to fit the evaporations between the lab periods.
My deadline to pick my lab is 3 February (in one week) so if any other good ideas come to your mind until that day suggest them. Anyways all the
projects on this thread atm are really interesting and I'll probably try them all at home when I'll have time.
[Edited on 26-1-2014 by alexleyenda]
[Edited on 26-1-2014 by alexleyenda]
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thebean
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Aspirin to 5-aminosalicylic acid is a pretty simple procedure and 5ASA is a biologically active compound, therefore a drug, used to treat inflammatory
bowel diseases and mild to moderate Crohn's Disease under the name Mesalazine. First hydrolyze your aspirin using sodium hydroxide in excess to
produce sodium salicylate, then acidify using hydrochloric acid to produce the barely soluble salicylic acid. Filter and dry. Then nitrate it using
glacial acetic acid as your solvent and nitric acid to produce 5-nitrosalicylic acid. Here is a 5-nitrosalicylic acid prep procedure. After nitration you can reduce it to 5ASA, I don't remember the reducing agents I've heard of
being used by I know I remember reading about electrolytic reduction and raney nickel catalyzed reduction with hydrazine  which would be a little nuts in my opinion.
"You need a little bit of insanity to do great things."
-Henry Rollins
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alexleyenda
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@ thebean -> I like the idea but the reduction of the nitro into amine causes two problem: all the protocols I have seen talk about 3 to 6 hours
reflux, I have a maximum of 2h20-2h30 manipulation time per lab period. Also, I doubt we have access to Raney nickel which is used in all protocols
I've found as the education system where I live have cut in the highschool and the university time to put a 2-3 years formation in between in which I
am right now so we do have plenty labware and reagents but not as much as universities. I am in the last chemistry class given in this formation and
we have never done catalysed hydrogenations in labs so we probably do not have such catalysts and they are really expensive to order.
@ luminol synthesis -> For the luminol, I checked it again and the synthesis is sadly far too long for the time we're allowed, it contains many
hours long heating/cooling/evaporating moments. It's too bad as it was my favourite suggestion atm.
Atm the synthesys of benzocaine from PABA is the one that I would chose but keep suggesting. By the way, I especially like compounds with little
bonuses such as chemiluminescence and I take at least 30 mins to look at every suggestion and research on them so no matter what you suggest you can
be sure that I'll look at it seriously.
[Edited on 26-1-2014 by alexleyenda]
[Edited on 26-1-2014 by alexleyenda]
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