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SCAN0025 - electrophflic addition to double bond forms a...

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Unformatted text preview: electrophflic addition to double bond forms a vicinal dihalide \/ ll /C=“\ + _.+ X‘T—T—X Conditions: Brz, CCl4 or Cl:, CCl4 F2 addition proceeds with explosive violence l2 addition is endot hermic: vicinal diiodides dissociate to an alkene and l2 Stereochemistry of Halogen Addition anti addition Know to write the Mechanism : A; More highly substituted double bonds react faster. Akyl groups on the double bond make it more “electron rich.” 6) Halohydrln formation (Addition X and OH! alkenes react with X2 in water to give vicinal halo hydrins \ / 020 + X2 + H20 __..__> l l / \ X*T_T_OH Conditions: Br2,H20 or Clz, H20 Stereospecific: anti addition Regioselective: OH ends up on the most substituted carbon of the double bond. Markov nikov's rule applied to halohydrin formation: the halogen adds to the carbon having the greater number of hydro gens. 7i Egoxidation Epoxide Nomenclature \c=c/ + RCOOH -———> \c—c/ RCOH / \ LI /\/\ * ll peroxy acid Stereospecific syn addition : substituients that are cis to each other in the alkene remain cis in the epoxide. Substituents that are trans in the alkene remain trans in the epoxide. ' ...
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