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Published byIrwan Hamdani Hartanto Modified over 6 years ago
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CH 8-3: Electrophilic Addition of Br2 and Cl2
(1) Electrophilic Addition of HX (HCl & HBr) -Carbocation mechanism -Regioselective: Markovnikov’s Rule -Non-stereospecific reaction -Rearrangements possible (2) Electrophilic Addition of H2O and ROH -Acid catalysis -Carbocation mechanism -Rearrangements possible (3) Electrophilic Addition of Br2 and Cl2 to alkenes -”Halonium ion” mechanism -No carbocation!!! -Stereospecific reaction – Anti-Addition
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Electrophilic Addition of Br2 or Cl2 to Alkenes
Part I: Dihalide Products (no other nucleophile) Stereospecific Anti-Addition of Electrophile and Nucleophile
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Electrophilic Addition of Br2 or Cl2 to Alkenes
The mechanism for halogen addition involves a new intermediate, the “halonium ion” (no carbocation): bromonium ion Since there is no carbocation, there are no rearrangements!
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Electrophilic Addition of Br2 or Cl2 to Alkenes
The mechanism for halogen addition involves a new intermediate, the “halonium ion” (no carbocation): The nucleophile must add anti = stereospecific.
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Electrophilic Addition of Br2 or Cl2 to Alkenes
Part II: “Second” Nucleophile Anti-Addition of electrophile and a second nucleophile.
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