Orthoacetic acid

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
Orthoacetic acid
Skeletal formula of orthoacetic acid with all implicit hydrogens shown
Names
Systematic IUPAC name
Ethane-1,1,1-triol[1]
Identifiers
  • 463-83-2 ☑Y
3D model (JSmol)
  • Interactive image
ChemSpider
  • 9128639 ☒N
PubChem CID
  • 10953422
Properties
C2H6O3
Molar mass 78.07 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is ☑Y☒N ?)
Infobox references

Orthoacetic acid or ethane-1,1,1-triol is an hypothetical organic compound with formula C
2
H
6
O
3
or H3C-C(OH)3. It would be a triple alcohol with the ethane backbone. Since the hydroxyl groups could lose protons, it can also be viewed as an ortho acid.

Orthoacetic acid is believed to be impossible to isolate, since it would readily decompose into acetic acid and water. It may have a fleeting existence in aqueous solutions of acetic acid.[2]

Orthoacetate anions

In theory, removal of one to three protons from the hydroxyls would produce the anions H
5
C
2
O
3
(dihydrogenorthoacetate), H
4
C
2
O2−
3
(hydrogenorthoacetate), and H
3
C
2
O3−
3
(orthoacetate). One author claims that sodium orthoacetate is formed by reaction of acetylene and sodium hydroxide at 220 °C:[3]

C2H2 + 3 NaOH → Na3CH3CO3 + H2

Orthoacetate esters

There are many stable organic compounds with the trivalent moiety H3C−C(−O−)3, which are formally esters of orthoacetic acid and therefore called orthoacetates. They include trimethyl orthoacetate and triethyl orthoacetate, which are commercially available.

See also

References

  1. ^ "Ethane-1,1,1-triol - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information.
  2. ^ Yamabe, Shinichi (2003). "A computational study of interactions between acetic acid and water molecules". Journal of Computational Chemistry. 24 (8): 939–947. doi:10.1002/jcc.10178.
  3. ^ Heinrich Feuchter (1914). "Reactions in Molten Alkali Hydroxides". Chem. Zeit. 38: 273–274.
Retrieved from "https://en.wikipedia.org/w/index.php?title=Orthoacetic_acid&oldid=855336054"
This content was retrieved from Wikipedia : http://en.wikipedia.org/wiki/Orthoacetic_acid
This page is based on the copyrighted Wikipedia article "Orthoacetic acid"; it is used under the Creative Commons Attribution-ShareAlike 3.0 Unported License (CC-BY-SA). You may redistribute it, verbatim or modified, providing that you comply with the terms of the CC-BY-SA