1,1-Dihydroxyethene

1,1-Dihydroxyethene.png 100px Ethene-1,1-diol 1,1-Dihydroxyethene 1,1-Ethenediol Ketene hydrate 10375-04-9 101752 91938 C=C(O)O 1S/C2H4O2/c1-2(3)4/h3-4H,1H2 LONYOMRPNGXPGP-UHFFFAOYSA-N 2 4 2 1,1-Dihydroxyethene is an organic compound consisting of two hydroxy groups as substituents on the same carbon atom of an ethene chain. The chemical is also called ketene hydrate because it is the carbonyl hydrate of ketene. Its structure can also be considered as the enol form of acetic acid. This compound is likely a key intermediate in the hydration reaction that converts ketene into acetic acid. Can. J. Chem. 77 817–829 1999 The hydration mechanism of ketene: 15 years later Minh Tho Nguyen Greet Raspoet 5–6 10.1139/v99-090 The analysis of the possible pathways for this reaction has been cited as an example of the importance of considering activation energy of each mechanistic step. Advances in Physical Organic Chemistry 45 John P. Richard No barrier theory and the origins of the intrinsic barrier J. Peter Guthrie 205–208 Academic Press 2011 9780123860477 The hydration of the carbonyl of ketene, which formally involves an addition reaction of one water molecule onto the carbonyl group, is likely catalyzed by a second water molecule. Theoretical Study of Reaction of Ketene with Water in the Gas Phase: Formation of Acetic Acid? Thanh Lam Nguyen Bert C. Xue G. Barney Ellison John F. Stanton J. Phys. Chem. A 2013 117 43 10997–11005 10.1021/jp408337y 24087932 2013JPCA..11710997N The compound has now been synthesized and identified spectroscopically. 1,1-Ethenediol: The Long Elusive Enol of Acetic Acid Artur Mardyukov André K. Eckhardt Peter R. Schreiner Angew. Chem. Int. Ed. 2020 59 14 5577–5580 10.1002/anie.201915646 31899845 7154680 free References Category:Enols Category:Geminal diols Category:Organic compounds with 2 carbon atoms