Is There a Better Way to Add Water to Synthesize an Alcohol From an Alkene?
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16-7-2019
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Is There a Better Way to Add Water to Synthesize an Alcohol From an Alkene?
A more efficient pathway does exist: see Oxymercuration - Demercuration: A Special Electrophilic Addition. Oxymercuration does not allow for rearrangements, but it does require the use of mercury, which is highly toxic. Detractions for using electrophilic hydration to make alcohols include:
- Allowing for carbocation rearrangements
- Poor yields due to the reactants and products being in equilibrium
- Allowing for product mixtures (such as an (R)-enantiomer and an (S)-enantiomer)
- Using sulfuric or phosphoric acid
Oxymercuration is a special electrophilic addition. It is anti-stereospecific and regioselective. Regioselectivity is a process in which the substituents choses one direction it prefers to be attached to over all the other possible directions. The good thing about this reaction is that there are no carbocation rearrangement due to stabilization of the reactive intermediate. Similar stabilization is also seen in bromination addition to alkenes.
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