page_title: Compounds of oxygen
section_title: Organic compounds
hierarchical_section_title: Compounds of oxygen / Organic compounds
caption_attribution_description: Space-filling model of the acetone molecule, C3H6O. Bond lengths and angles from CRC Handbook, 88th edition. Image generated in Accelrys DS Visualizer.
context_page_description: The oxidation state of oxygen is −2 in almost all known compounds of oxygen. The oxidation state −1 is found in a few compounds such as peroxides. Compounds containing oxygen in other oxidation states are very uncommon: −​¹⁄₂, −​¹⁄₃, 0, +​¹⁄₂, +1, and +2.
  Oxygen is reactive and will form oxides with all other elements except the noble gases helium, neon, argon, and krypton.
context_section_description: Among the most important classes of organic compounds that contain oxygen are (where "R" is an organic group): alcohol (R-OH); ethers (R-O-R); ketones (R-CO-R); aldehydes (R-CO-H); carboxylic acids (R-COOH); esters (R-COO-R); acid anhydrides (R-CO-O-CO-R); amides (R-C(O)-NR₂). There are many important organic solvents that contain oxygen, among which: acetone, methanol, ethanol, isopropanol, furan, THF, diethyl ether, dioxane, ethylacetate, DMF, DMSO, acetic acid, formic acid. Acetone ((CH
  ₃)
  ₂CO) and phenol (C
  ₆H
  ₅OH) are used as feeder materials in the synthesis of many different substances. Other important organic compounds that contain oxygen are: glycerol, formaldehyde, glutaraldehyde, citric acid, acetic anhydride, acetamide, etc. Epoxides are ethers in which the oxygen
  atom is part of a ring of three atoms. 
  Oxygen reacts spontaneously with many organic compounds at or below room temperature in a process called autoxidation. Alkaline solutions of pyrogallol, benzene-1,2,3-triol absorb oxygen from the air, and are used in the determination of the atmospheric concentration of oxygen. Most of the organic compounds that contain oxygen are not made by direct action of oxygen. Organic compounds important in industry and commerce are made by direct oxidation of a precursor include:
  Ethylene oxide (used to make the antifreeze ethylene glycol) is obtained by direct oxidation of ethylene:
  C
  ₂H
  ₄ + ½ O
  ₂ + 
  ———→ C
  ₂H
  ₄O
  Peracetic acid (feeder material for various epoxy compounds) is obtained from acetaldehyde:
  CH
  ₃CHO + O
  ₂ + ᶜᵃᵗᵃˡʸˢᵗ
  ———→ CH
  ₃C(O)-OOH
caption: Acetone is an important feeder material in the chemical industry.
  (oxygen is in red, carbon in black and hydrogen in white)
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