Addition_to_Alkenes

Addition_to_Alkenes - Spring 2007 RECOGNIZING ORGANIC...

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Spring 2007 CHM 201 RECOGNIZING ORGANIC REACTIONS/MECHANISMS Additions to Alkenes A Look at the Orbitals Alkene the ! -orbitals that make up the double bond The ! -orbitals are "negative" because of the electrons that reside in them; so these negative electrons will grab anything that is positive around (Ex: H + , slightly positive centers, etc) H + H Carbocation X H X X Carbocation X X X X X " - " +
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Spring 2007 CHM 201 RECOGNIZING ORGANIC REACTIONS/MECHANISMS Mechanism of Addition to Alkenes ALL THESE MECHANISMS INVOLVE A CARBOCATION INTERMEDIATE WITH FULL ARROW HEADS IN THE ARROW-PUSHING Hydrohalogenation: General Formula: alkene + hydrogen halide alkyl halide + HCl Cl H alkene (sp 2 hybrid carbons) alkyl halide (sp 3 hybrid carbons) hydrogen halide Example: Mechanism: Formation of a CARBOCATION INTERMEDIATE!!! H + H carbocation intermediate Cl H Cl
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Spring 2007 CHM 201 RECOGNIZING ORGANIC REACTIONS/MECHANISMS Unsymmetrical Alkenes: Follows MARKOVNIKOV’S RULE : The hydrogen from the first step of the mechanism will add to the carbon with the most
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Addition_to_Alkenes - Spring 2007 RECOGNIZING ORGANIC...

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