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Hydrohalogenation
Hydrohalogenation reactions:
- occur in multiple steps and are classified as an "ionic" reactions
- proceed via a carbocation intermediate
- have Markovnikov addition for a regiochemical outcome (Markovnikov addition has the higher priority group added to the more substituted carbon atom)
- have addition at the carbocation intermediate from top and bottom face with 50/50 distribution to give mixed sterechemical distribution (a racemic mixture if there is only one stereocentre)
Steps of a hydrohalogenation:
- addition of the hydrogen atom to the alkene to generate a carbocation
- there may be carbocation rearrangement
- nucleophilic attack of the halogen anion onto the carbocation
Mechanism:
Watch Out!
Beware the carbocation rearragement! Remember that the more substituted the carbon atom, the more stable the carbocation!
Example: predict the product of the following hydrohalogenation reactions below.
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Example: Hydrohalogenation
Draw a mechanism for the hydrohalogenation reaction below.
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Example: Hydrohalogenation
Predict the product(s) of the following hydrohalogenation reactions.
