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Halohydration of Alkenes

Article ID: 86
Last updated: 22 Jul, 2011
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 This reaction proceeds via cyclic halonium ion (compare with halogenation of alkenes). However, the alternate nucleophile, water opens the halonium ion (instead of the halide ion).
Regioselectivity: X reacts as the electrophile so the C-O bond forms at the more stable cation center, or the alcohol adds to the more substituted side.
Stereoselectivity: anti since the two new sigma bonds form in separate steps on opposite alkene faces.
Step 1:
Same first step as for the reaction of Br2/CH2Cl2
The π electrons act as a nucleophile, attacking the bromine, displacing a bromide ion but forming a cationic cyclic bromonium ion as an intermediate.  All atoms in the bromonium maintain their octet.
Step 2:
Attack of the nucleophilic water molecule from the side away from the bromonium center in an SN2 like fashion opens the cyclic bromonium ion to give overall trans or anti addition
Step 3:
An acid / base reaction converts the oxonium into the alcohol.  The base would most likely be another molecule of water.


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Department of Chemistry & Chemical Biology