Sciencemadness Discussion Board

Regarding Basic Acetic / Ethanol / Acid / Metal Chemistry

crestind - 25-9-2015 at 21:20

Acetic
+ Sulfuric -> Seemingly no reaction despite various claims to the contrary...
+ Nitric -> ?
+ Hydrochloric Acid -> ?
Seemingly no reaction for all.
+ Metal -> Corresponding acetate

Ethanol (Can react with either anions or cations?)
+ Sulfuric Acid -> Ethyl Sulfate
+ Nitric Acid -> Ethyl Nitrate
+ Hydrochloric Acid -> Ethyl Chloride
+ Metal -> Corresponding Ethoxide

1. So given that a metallic sulfate, nitrate or chloride reacted with ethanol can form an ethoxide + acid, does this mean that the above ethyl compounds can react with metal directly to form the corresponding ethoxide and acid? So Fe + Ethyl Chloride -> FeR + HCl?

Ethanol + Acetic Acid -> Ethyl Acetate
2. Does this react with metals at all?

3. If we have a dry metal acetate and combine with excess ethanol, does it react to form an ethoxide + acetic acid? Likewise if we have an ethoxide and combine with an excess of acetic acid, does it convert it to the acetate + ethanol?

My questions are based on a somewhat old German text I've been studying, and I've been trying to figure what they are doing. It is from the 1700s. If you're interested in the text just PM me for it.

It says to dissolve Hg in nitric acid and then to mix that with acetic acid to "extract" a new salt. Then once you have this you mix with ethanol to get another salt. It would seem that this would form Hg ethoxide, but I'm slightly confused about why they need the acetic acid step. I'm guessing it might be a way to avoid the formation of Hg fulminate, but I thought that couldn't form without both nitric and ethanol at the same time.

http://www.sciencedirect.com/science/article/pii/S0277538700...
This text suggests an acetate can be a foundation to form an ethoxide of Pb.
https://books.google.com/boaoks?id=qxRhA3MZg6AC&pg=PA226...

gdflp - 26-9-2015 at 08:11

Quote: Originally posted by crestind  
Acetic
+ Sulfuric -> Seemingly no reaction despite various claims to the contrary...
+ Nitric -> ?
+ Hydrochloric Acid -> ?
Seemingly no reaction for all.
+ Metal -> Corresponding acetate

Ethanol (Can react with either anions or cations?)
+ Sulfuric Acid -> Ethyl Sulfate
+ Nitric Acid -> Ethyl Nitrate
+ Hydrochloric Acid -> Ethyl Chloride
+ Metal -> Corresponding Ethoxide

1. So given that a metallic sulfate, nitrate or chloride reacted with ethanol can form an ethoxide + acid, does this mean that the above ethyl compounds can react with metal directly to form the corresponding ethoxide and acid? So Fe + Ethyl Chloride -> FeR + HCl?

Ethanol + Acetic Acid -> Ethyl Acetate
2. Does this react with metals at all?

3. If we have a dry metal acetate and combine with excess ethanol, does it react to form an ethoxide + acetic acid? Likewise if we have an ethoxide and combine with an excess of acetic acid, does it convert it to the acetate + ethanol?

My questions are based on a somewhat old German text I've been studying, and I've been trying to figure what they are doing. It is from the 1700s. If you're interested in the text just PM me for it.

It says to dissolve Hg in nitric acid and then to mix that with acetic acid to "extract" a new salt. Then once you have this you mix with ethanol to get another salt. It would seem that this would form Hg ethoxide, but I'm slightly confused about why they need the acetic acid step. I'm guessing it might be a way to avoid the formation of Hg fulminate, but I thought that couldn't form without both nitric and ethanol at the same time.

http://www.sciencedirect.com/science/article/pii/S0277538700...
This text suggests an acetate can be a foundation to form an ethoxide of Pb.
https://books.google.com/boaoks?id=qxRhA3MZg6AC&pg=PA226...

Acetic acid will not react with any of those acids.

Ethanol will only react with a few metals to form ethoxides(namely group I and some group II metals). It will also not directly react with acids; catalysts, heat, or other conditions are needed to get a reaction to occur. Organic chemistry is not as simple as inorganic chemistry. Also beware that alkyl nitrates are extremely explosive.

1.You cannot form an ethoxide with any of those anions. This is because the pKa of the corresponding acids is significantly lower than that of ethanol. Thus, the ethoxide ion is a stronger base than sulfate, chloride, and nitrate and will preferentially stay protonated. Alkyl halides are only reactive with certain metals and only under strictly anhydrous conditions. Some examples of these metals include lithium, magnesium, aluminum(amalgam), and zinc. And the product is not an acid, it is the metal salt along with the alkyl metal, e.g. 2Li + MeBr --> LiBr + MeLi

2. No, esters are unreactive towards metals.

3. No, for the same reason above. Ethanol has a significantly higher pK<sub>a</sub> than acetic acid, so ethoxide is a stronger base and thus acetates will not be protonated by ethanol. The reverse will happen quite quickly though, the acetic acid will protonate ethoxide ions to produce ethanol and acetate ions.

Finally, I wouldn't trust any information from a book from the 1700's, especially when using it as a source for information of mercury chemistry. They had very little understanding of the chemistry and toxicity of the various mercury salts at this point, use the information on this forum and more recent books to make sure that the information is reliable and the procedure is safe.

MeshPL - 26-9-2015 at 23:46

Estrers are reactive towards alkali metals and will undergo acyloin condensation, when treated with some.

I suspect ethanol and acetic acid will react with fuming (>90%) nitric acid to rorm nitro compounds. But such a concentrated acid is hard to buy or obtain. And dangerous. And such reactions are hard to describe or use to form specific compounds but nitromethanes.

Amos - 27-9-2015 at 06:55

Chemistry isn't this simple. No two compounds or reagents will react the same way as another two; for example, yes, ethanol will react with sodium to form sodium ethoxide due to the extreme reactivity of sodium metal, but absolutely nothing is going to go on if you drop a piece of copper into ethanol. Reactions of ethanol with acids depend highly on concentration of the reagents and whether or not water is present, not to mention temperature, pressure, phase, etc.

I think you should learn some more about chemical reactions in the most basic sense before you deal with the potentially explosive chemistry of a volatile element widely regarded for its toxicity and debilitating effects.