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CH 8-3: Electrophilic Addition of Br 2 and Cl 2

Explore the electrifying world of electrophilic addition reactions including HX, H2O, ROH, Br2, and Cl2, with a focus on carbocation intermediates, regioselectivity, stereospecificity, and the intriguing halonium ion mechanism. Understand the intricate pathways, reaction specifics, and potential rearrangements for a comprehensive grasp of these fundamental organic chemistry reactions.

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CH 8-3: Electrophilic Addition of Br 2 and Cl 2

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  1. 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

  2. Electrophilic Addition of Br2 or Cl2 to Alkenes Part I: Dihalide Products (no other nucleophile) Stereospecific Anti-Addition of Electrophile and Nucleophile

  3. 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!

  4. 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.

  5. Electrophilic Addition of Br2 or Cl2 to Alkenes Part II: “Second” Nucleophile • Anti-Addition of electrophile and a second nucleophile.

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