Question
Question: What is the product in the hydroxylation of \((z) - 3 - hexene\)with \(Os{O_4}\)?...
What is the product in the hydroxylation of (z)−3−hexenewith OsO4?
Solution
Hint : Hydroxylation is an oxidation reaction in which the carbon-hydrogen (C−H) bond is broken and replaced by the carbon–hydroxyl (C−OH) bond. The hydroxylation reaction is often mediated by catalysts and heat in organic chemistry. Metal ions are sometimes used as catalysts in hydroxylation reactions.
Complete Step By Step Answer:
The OsO4 reaction is a well-coordinated reaction with a cyclic intermediate and no rearrangements. Vicinal syn dihydroxylation is a step in the non dihydroxylation of an alkene that follows the epoxide-hydrolysis series. Stereocenters can form in the glycol substance when an alkene reacts with osmium tetroxide. Trans alkenes produce racemic mixtures, while cis alkenes produce meso materials.
Alkene dihydroxylation with OsO4 is a syn cycloaddition reaction that produces vicinal diols with cis stereochemistry.
The structure of (Z)-hex-3-ene is
Because of the syn addition, all OH groups would be cis.
Note :
The reaction with alkenes has been altered due to the high cost and toxicity of Osmium tetroxide. To reduce some risks, catalytic concentrations of OsO4 and stoichiometric amounts of an oxidizing agent such as hydrogen peroxide are still used. Also, potassium permanganate (KMnO4), an older reagent, was used instead of OsO4.