Sciencemadness Discussion Board

Sodium Ethoxide

hkparker - 10-1-2011 at 17:12

Hey everyone!

So ive always found organometallic chemistry really cool but never done many reactions with it. So today I started to synthesis sodium ethoxide and I was wondering if theres anything cool I can do with it. Anything it reacts with thats interesting or a good demonstration of its properties. Thanks!

Magpie - 10-1-2011 at 17:27

I suggest making an ether with a Williamson synthesis. Perhaps pick one that is a solid so you can get experience with crystallization, and washing and drying of the crystals. Then do a mp to determine purity of the product.

If you make a liquid ether pick one that smells good. You may have to do fractional distillation to isolate it, however.

hkparker - 10-1-2011 at 17:44

Do you think it would react with DCM? if so, what products would form?


----------Tried to work out the mechanics----------


According to what I got on wiki about the mechanics I should get C3H7OCl if the ethyl ether group pulls off only one of the chlorine atoms of the DCM, if it pulls off both it would look like C5H12O2, for the reaction:

2NaC2H5O + CH2Cl2 --> C5H12O2 + 2NaCl


Hows that sound... should I post this in organic?

[Edited on 11-1-2011 by hkparker]

ThatchemistKid - 10-1-2011 at 19:28

You could use it for a claisen condensation with for example ethyl acetate to make ethyl acetoacetate

http://en.wikipedia.org/wiki/Claisen_condensation

the ethoxide should only be used with ethyl esters to prevent the formation of mixed esters.


not_important - 10-1-2011 at 20:02

It won't react readily with DMC, but it will react as you illustrated to form ethylal - diethoxymethane or formaldehyde diethyl acetal. Chloroform reacts similarly to form ethyl orthoformat, triethoxymethane, useful for turning Grignard reagents into aldehydes one carbon larger.

hkparker - 10-1-2011 at 20:09

Great information, thanks! So my product that would form with DCM would be ethylal - diethoxymethane or ethylal formaldehyde diethyl acetal? I'm sorry, my organic nomenclature is lacking :P which product is that?

Jor - 10-1-2011 at 20:22

Quote: Originally posted by not_important  
It won't react readily with DMC, but it will react as you illustrated to form ethylal - diethoxymethane or formaldehyde diethyl acetal. Chloroform reacts similarly to form ethyl orthoformat, triethoxymethane, useful for turning Grignard reagents into aldehydes one carbon larger.


I think it would be interesting to make some triethyl orthoformate!
Can I just dissolve sodium in ethanol, add a slight excess of chloroform, reflux for 1-2 hours, distill of most ethanol, add cold water, and extract with ether, followed by evaporation of the ether? Or is the triethyl orthoformate quickly hydrolysed in water (a MSDS says 'decomposes', but how fast?...).
If it quickly reacts with water/hydroxide, do I need to dry ethanol by refluxing over some Mg turnings and distilling it?

Magic Muzzlet - 10-1-2011 at 20:45

http://www.orgsyn.org/orgsyn/orgsyn/prepcontent.asp?print=1&...
:)

roamingnome - 11-1-2011 at 18:11

i believe sodium ethoxide can make a good proton abstracter .

Proton-Transfer Reactions. 1. Partitioning of Carbanion ...
by HF Koch - 1981
In this paper, we deal with carbanions generated by an alkoxide-promoted hydrogen abstraction from. LGAH, Scheme I. After an intermediate, INT-“H”, ...
pubs.acs.org/doi/abs/10.1021/ja00408a023




ew carbanions i can think of a few carbanions I would like to form