lecture15_s05

lecture15_s05 - Reactions of Alkenes: Summary Intermediate:...

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Reactions of Alkenes: Summary Intermediate: Carbocation Radical 3-Membered Ring None or Cyclic (concerted) Regiochemisty: Markovnikov* Anti-Markovnikov* Markovnikov-like N/A Addition: Syn & Anti Syn & Anti Anti Syn Rearrangements? yes no no no *the reaction goes through the pathway of the most stable intermediate; the more substituents on an electron deficient carbon (carbocation or radical), the greater its stability Stereochemistry: If the reactants are optically inactive (achiral), the products will be optically inactive (achiral, racemic or meso) If the reactants are optically active (chiral), the products will be optically active (unequal mixture of enantiomers, unequal mixture of diastereomers, or 1 enantiomer) Use 2 n of the product to predict the maximum number of stereoisomers (if just anti or just syn addition, divide the maximum number of stereoisomers by 2) Predicting the type of intermediate: Carbocation - H is the electrophile (no lone pair to share with the empty p orbital)
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lecture15_s05 - Reactions of Alkenes: Summary Intermediate:...

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