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Author: Subject: Ethyl Iodide
Texium (zts16)
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[*] posted on 24-11-2017 at 14:08


Welcome to the forum! You've come to the right place to ask such questions.
Quote: Originally posted by SamuelLFraction  
For a start, there is not much literature on this reaction apart from chemplayer and an erowid text I believe. Chemplayer mentions in the video that the reaction initially starts as thus:
Al + 3I --> AlI3
Am I correct in believing that since Iodine is diatomic, that it should be:
2Al + 3I2 --> 2AlI3?

Secondly, based off of this (if correct) the molar calculations are incorrect and have been calculated via simply the atomic mass of the element Iodine, 126.9 , when diatomic it should be 253.8g/mol, since a molecule, no? This is not in any way, shape or form a way of trying to slate Chemplayer at all, I just want to make sure my knowledge on chemistry is right.
Yes, you're right that the true balanced equation is 2Al + 3I2 --> 2AlI3
However, it doesn't matter which equation you use to calculate the amounts of reagents needed since both equations are still balanced in a 1:3 ratio of Al to I. 50 grams of I and 50 grams of I2 contain the same number of I atoms, you see?

I don't have any other comments to make though as I haven't run this reaction myself.




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[*] posted on 24-11-2017 at 14:32


Saturated primary (eg ethanol) and secondary alcohols (eg isopropanol) are unaffected by aluminum triodide. Allylic, benzylic, and tertiary alcohols are regioselectively converted to the corresponding iodide by the reagent. There is little expectation that ethyl iodide will be formed with aluminium triodide, at least in any useful amount.

Unfortunately, the chemplayer experiment is not useful. The product was not characterized (no boiling point). The identification of the product was based on "it looks like ethyl iodide." Maybe there was some iodide formed but the experiment as it stands is non-informative and unconvincing.

For some useful information please see:

P Sarmah, NC Barua, Tetrahedron 1989, 45, 3569. "Regioselective transformation of allylic, benzylic and tertiary alcohols into the corresponding iodides wrih aluminium triiodide: deoxygenation of vicinal diols"

AvB
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SamuelLFraction
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[*] posted on 24-11-2017 at 14:57


Zts - thank you for your reply, I feel a bit silly now realising this haha!
AvB - I'm glad to have an explanation for the relatively low yield I produced. It did have a boiling point of 73 degrees so at least all hope is not lost with the questionable reaction, shame such a small amount but I'm glad to learn. I really appreciate you including the material of regioselection, I now have something interesting to read and learn, thank you! :)
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[*] posted on 24-11-2017 at 23:00


Quote: Originally posted by AvBaeyer  
Saturated primary (eg ethanol) and secondary alcohols (eg isopropanol) are unaffected by aluminum triodide. Allylic, benzylic, and tertiary alcohols are regioselectively converted to the corresponding iodide by the reagent. There is little expectation that ethyl iodide will be formed with aluminium triodide, at least in any useful amount.

Unfortunately, the chemplayer experiment is not useful. The product was not characterized (no boiling point). The identification of the product was based on "it looks like ethyl iodide." Maybe there was some iodide formed but the experiment as it stands is non-informative and unconvincing.
AvB


@AVBayer, you 're completely right when you say AlI3 doesn't affect primary and secondary alcohols.

Unfortunately many "ChemPlayer" videos at you tube are not trustworthy about the results and yields he claims. In my oppinion, in some experiments he clear did work up mistakes that affected the yields and others experiments clearly suffers from conceptual matters, although his experiments appears to be very instructive and interesting for the amateur chemistry.

I think he needs urgently start to use a LC-MS to make a qualitative and quantitative sample analyze, like "Nurd Rage" does.

@SamuelLFraction, if you intend to sinthesize alkyl iodides easily and with good yields, I suggest you the use of an alkaline iodide, phosphoric acid and the alcohol (or ether, or alkene), at reflux, following the method I posted in the study attached below:

Attachment: Iodides from clevage of ethers or iodination of alcohols and alkenes with KI + H3PO4.pdf (328kB)
This file has been downloaded 94 times
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[*] posted on 25-11-2017 at 01:43


I have occasionally questioned Chem Player's results (such as when I made p-aminophenol and experienced much more rapid decomposition than was apparent in the video), but for the most part I think Chem Player demonstrates good science, and some of Chem Player's stuff is really cutting edge. There is a tendency among YouTube chemists in general to avoid extensive characterization or to show only easy characterizations that support the chemist's conclusion without ruling out impurities or other products. (For example, do you see any YouTube sulfuric acid distillation video that shows an actual titration?) But I don't think that Chem Player is worse than NurdRage or Nile Red or any other YouTube chemist in this regard, and I don't think it's caused by untrustworthiness so much as cognitive bias. There are very good reasons for peer review, after all....

That said, do any of the big box stores carry 85% phosphoric acid?

[Edited on 25-11-2017 by JJay]




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[*] posted on 25-11-2017 at 02:37


@Chemi Pharma, I did originally think it would be a lot easier to avoid the Aluminium route and go with phosporic acid, however, could not think of where to accumulate it.
Luckily I have had an epiphany and realised it's easily found. (Also thank you for the material!)
@JJay phosphoric acid at 85% is available as Ph adjustment for cultivation, if you wanted to know. Perhaps I better not say product name as maybe this is not allowed?
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[*] posted on 25-11-2017 at 05:00


It is permitted, but I don't blast that sort of information on every thread either. It is up to you based on how you feel that information will be used.



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[*] posted on 25-11-2017 at 06:16


Quote: Originally posted by SamuelLFraction  
Perhaps I better not say product name as maybe this is not allowed?


Read the FAQ.

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[*] posted on 25-11-2017 at 07:44


The process is not unlike P and the alcohol is not supposed to be anhydrous, so the water makes HI.



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[*] posted on 25-11-2017 at 08:36


@S.C Wack, this may well explain why low yield then, since anhydrous ethanol was used. I will try the reaction again, this time with more elemental iodine and dilute anhydrous ethanol until about 85%. I will report back with some figures if all goes to plan :)
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[*] posted on 25-11-2017 at 09:06


The reaction is probably unlike P as now I look it up and see that calls for anhydrous alcohol. 85% you say have you read the original literature calling for 84% ethanol.



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[*] posted on 25-11-2017 at 09:49


@ S.C Wack, oh well, I suppose in chemistry not everything works out to how you expect. Yes I have read the literature regarding 84% alcohol. So far, the mixture is a dark grey to black with a little undissolved aluminium. There was a sudden exothermic reaction which occurred roughly 20 minutes after mixture of Iodine, Al and EtOH and began to froth after some initial heating. This died down after 10 minutes as the literature suggested and then continued to reflux for further 1.5 hours. Smells very ether-like but this of course is no certain indication of EtI. The additional water in the mixture has changed the mixture grey rather than the deep red that anhydrous ethanol made it go before. Distillate is not very miscible with water. I wonder, does the additional water create more Aluminium oxide/hydroxide? Following this reaction's results, I will attempt the Phosphorous acid KI Ethanol reaction.

[Edited on 25-11-2017 by SamuelLFraction]
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[*] posted on 26-11-2017 at 07:22


The procedure above with the aluminum is sort of bullshit and should not be performed, because the scale was changed by the dickface who originally posted this version that has been copied many times. The reactions may be rather too exothermic to proceed as written and deep unpleasantness beyond low yield could result. Weights and volumes were originally 20x less, and a final weight was not given, but the words otherwise remain the same. You want to test this on the smaller scale.

https://www.sciencemadness.org/whisper/viewthread.php?tid=65...
Both of these are short, thus are free to save as .gif from the RSC, until they change that




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[*] posted on 28-11-2017 at 03:37


Finishing the procedure calling for 84% alcohol has resulted in a cloudy distillate with a boiling point of 50-60. Bare in mind this distillate was then further distilled once more and resulted the same end product. Immiscible with water, denser than water also. Aroma of sulphur/pickles, not very pleasant. The procedure was followed exactly, however, resulted in everything but ethyl iodide. The product was immediately appropriately discarded. Perhaps adding the H2SO4 and ethanol to the residue remaining from first distillation to then further distill had ruined this reaction entirely, however, i am not going to attempt this reaction again to find out. Despite the 84% alcohol, iodine and aluminium method resulting in entire disappointment, I have yet to test the suspected ethyl iodide produced (Silver Nitrate test) from anhydrous ethanol, of which is clear and denser than water. Ether aroma present with this substance.

SLF

[Edited on 28-11-2017 by SamuelLFraction]
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[*] posted on 28-11-2017 at 07:18


The low yield in the reaction of iodine with aluminum and ethanol is because aluminum likes to keep some of the iodine for itself, and forms combination hydroxide-iodide species, much like iron forms iron oxide-hydroxide species in the presence of water and oxygen. If you insist on doing something more fun than H3PO4 + ethanol + iodide, you can always react iodine with elemental silicon to form SiI4, which will do just about anything to swap those iodine atoms for oxygen atoms. It's 95% iodine by mass, and can be treated as though it were anhydrous HI for most practical purposes.



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[*] posted on 28-11-2017 at 13:12


Thank you Melgar, Silicon would most certainly be an interesting reagent to use. I'll be adding elemental silicon to my shopping list. I don't mind the idea of using H3PO4, but as you quite rightly connotated, something more fun is... well, more fun ;)

Following on from reaction involving anhydrous ethanol with aluminium and iodine, the distillate was tested with a silver nitrate solution of ethanol, water and NaOH and produced a yellow precipitate. At least the product is actually formed in this synthesis, so not entirely a waste of my time.
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[*] posted on 28-11-2017 at 13:56


Nicoderm's procedure using HCl looks quite easy if you have reagent grade hydrochloric acid on hand. I wonder if potassium iodide would work as well as sodium iodide.



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[*] posted on 12-12-2017 at 06:09


If someone wants to buy us a LC-MS for Christmas then hey, just tell us where to pick it up!

Seriously though, we don't try to produce scientific papers. We do it to learn and to have fun.




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[*] posted on 12-12-2017 at 20:15


Quote: Originally posted by chemplayer...  
We do it to learn and to have fun.


AMEN!




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[*] posted on 13-12-2017 at 03:36


Quote: Originally posted by JJay  
Nicoderm's procedure using HCl looks quite easy if you have reagent grade hydrochloric acid on hand. I wonder if potassium iodide would work as well as sodium iodide.


Did I miss something........?

@JJay - Can you link me please



/CJ

[EDIT] - Pardon my laziness. 7 and a half seconds of UTFSEing yielded this -

"Iodomethane Via the HCl Method" - https://www.sciencemadness.org/whisper/viewthread.php?tid=23...

Excellent......... :D

[Edited on 13-12-2017 by Corrosive Joeseph]




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[*] posted on 18-7-2018 at 11:25


I didn't have any luck getting it to work when I tried it a few months ago (and this was for methyl iodide, not ethyl iodide), but I'm not exactly sure how strong my HCl was. I produced it by gassing azeotropic HCl with HCl gas until it appeared that very little was being dissolved. The amount of iodine recovered after the experiment was far less than the amount of iodide that went into the experiment, so I think that a reaction happened, but I didn't see an organic layer. I'm reluctant to believe that the methyl iodide simply escaped. My potassium iodide was granular, like table salt; it could be that I should have used more finely powdered potassium iodide, but that doesn't explain what happened to the iodine.



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