Addition of H2O to a double bond (alkenes) is occuring :
1. In the presence of Sulphuric acid (H2SO4).
The initial protonation can occur on either face of the double bond and addition of water can occur on either side of the carbocation, so there is no stereoselectivity in this reaction (form a mix of stereoisomers)
2. In the presence of Borane(BH3) and Hydrogen peroxide(H2O2) , Sodium hydroxide (NaOH).
This is syn addition due to the 4-centered transition state, but it can happen on either face of the double bond, so a mixture of enantiomers forms if there are no other stereocenters in the molecule
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