What does OsO4 do to an alkene?
OsO4 For The Formation Of Vicinal Diols From Alkenes Osmium tetroxide (OsO4) is a volatile liquid that is most useful for the synthesis of 1,2 diols from alkenes. (Side note: another name for 1,2 diols is vicinal diols, or vic-diols). The reaction is very mild, and usefully leads to the formation of syn diols.
Is osmium tetroxide an oxidizing agent?
Specialized use in Organic Chemistry. Osmium tetroxide was first given this use back in 1936 by Criegee and a good source of information on this powerful oxidizing agent is to be found in Schroder, Chem. Rev. 80, 187-213 (1980).
What is the oxidation state of osmium tetroxide?
+8
The oxidation state of Os in OsO₄ is +8. The electron configuration of Os is [Xe]6s²4f¹⁴5d⁶. The 4f electrons are inner electrons, so Os has eight valence electrons — 6s²5d⁶.
Is OsO4 an oxidizing agent?
Osmium tetroxide is an osmium coordination entity consisting of four oxygen atoms bound to a central osmium atom via covalent double bonds. It has a role as an oxidising agent, a poison, a fixative and a histological dye.
What is oxidation of alkenes?
Alkenes undergo a number of reactions in which the C=C double bond is oxidized. An oxidation reaction increase the number of C–O bonds or decrease the number of C–H bonds. On the other side a reduction reaction increase the number of C–H bonds or decrease the number of C–O bonds.
What is the formula of osmium tetroxide?
OsO4
Osmium tetroxide/Formula
How does osmium tetroxide oxidize alkenes to give glycol?
Osmium tetroxide oxidizes alkenes to give glycols through syn addition. A glycol, also known as a vicinal diol, is a compound with two -OH groups on adjacent carbons. Dihydroxylated products (glycols) are obtained by reaction with aqueous potassium permanganate (pH > 8) or osmium tetroxide in pyridine solution.
What kind of compound is osmium tetroxide?
Osmium tetroxide oxidizes alkenes to give glycols through syn addition. A glycol, also known as a vicinal diol, is a compound with two -OH groups on adjacent carbons.
Where does the addition of osmium take place?
Addition occurs on the same side of the ethene molecule to give a syn -addition. Work-up with water gives the syn -diol and reduced Osmium (VI). Osmium (VIII) is reduced to Os (VI) over the reaction which is an oxidation. T. Strassner, in Advances in Physical Organic Chemistry, 2003, vol. 38, pp. 131–160.
What is the result of oxidation of an alkene?
Oxidation-hydrolysis gives a vicinal diol, a molecule with OH groups on neighboring carbons. For this reaction, the dihydroxylation is anti since, due to steric hindrance, the ring is attacked from the side opposite the existing oxygen atom. Thus, if the starting alkene is trans, the resulting vicinal diol will have one S and one R stereocenter.