hkparker
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Sodium Ethoxide
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!
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"Nothing is too wonderful to be true if it be consistent with the laws of nature." -Michael Faraday
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Magpie
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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.
The single most important condition for a successful synthesis is good mixing - Nicodem
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hkparker
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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]
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"Nothing is too wonderful to be true if it be consistent with the laws of nature." -Michael Faraday
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ThatchemistKid
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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.
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not_important
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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.
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hkparker
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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  which product is that?
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"Nothing is too wonderful to be true if it be consistent with the laws of nature." -Michael Faraday
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Jor
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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.
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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?
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Magic Muzzlet
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http://www.orgsyn.org/orgsyn/orgsyn/prepcontent.asp?print=1&...
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roamingnome
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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
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