Ch6 - Chapter 6 Alkenes: Electrophilic Addition Reactions...

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1 Chapter 6 – Alkenes: Electrophilic Addition Reactions 1) Addition of Acids a) Markovnikov Addition ** - (HX) 6.4-6.7 b) Anti-Marknikov Addition - (HBr/ROOR) 6.8 2) Addition of H 2 O or ROH a) Acid-catalyzed hydration 6.10 b) Hydroboration/Oxidation 6.12-6.14 3) Addition of Halogens a) Addition of X 2 ** 6.15-6.17 b) Halohydrin Formation 6.18 4) Reduction 6.3 5) Oxidation H H H H X H H H H H X X H H H H X OH H H H H H OH H H H H * * Know mechanism H H H H H H
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2 The H (E.S.) always connects to the carbon with the most hydrogens 6.4-6.6 Addition of Acids: HX C H 3 C C H 3 C CH 3 H H Br C Br C H 3 C H 3 C H CH 3 H ( Addition of HBr to __________________ ) 2-methyl-2-butene Markovnikov’s Rule (6.5) Mechanism The structure of the transition state resembles that of the nearest stable species. Hammond Postulate (6.6) Try problems 6.4 - 6.6 know regio & stereo chem. of these steps
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3 3 + to CH 3 + (Decreased Stability: Harder to form) CR 3 + CH 3 + Alkyl groups donate e-density 1) Hyperconjugation overlap of C-H sigma bond with an empty p-orbital (or an anti- bonding pi-M.O) . 2) Inductive effect – the positive carbon has an increased electronegativity C H 3 C + C H 3 CH 3 Example Orbital picture
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4 6.7 Carbocation Rearrangement: Hydride or Alkyl Shift C H 3 C C + C H H H H H H Rearrangement "Hydride Shift" Intermediate C H 3 C C C + H H H H H H C H 3 C C C + C H 3 CH 3 H H H H C H 3 C C + C CH 3 H H H H CH 3 Primarily seen with 1° or 2° carbocations and 3 or 4 membered rings (See
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This note was uploaded on 04/15/2008 for the course CHE 3331 taught by Professor Primrose during the Fall '07 term at Baylor.

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Ch6 - Chapter 6 Alkenes: Electrophilic Addition Reactions...

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