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lecture12_s05 - Lecture 12 Reactions of Alkenes Lecture I...

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Lecture 12: Reactions of Alkenes I. Finish Addition of H-X to an Alkene G. Epoxides 5. Carbocation Rearrangements 1. Acid-catalyzed ring opening 2. Base-catalyzed ring opening II. Preparation of: H. Cycopropane A. Alkyl halides 1. CHCX 3 , strong base 2. Simmons-Smith B. Vicinal Dihalides I. cis -1,2-Diols C. Halohydrins 1. OsO 4 D. Alcohols 2. Cold, dilute KMnO 4 1. Acid-catalyzed hydration J. Ketones, Aldehyes, Carboxylic Acids 2. Oxymercuration-Reduction 1. Alkene cleavage 3. Hydroboration-Oxidation a. KMnO 4 E. Ethers b. O 3 (oxidative and reducing) F. Alkanes 2. Diol cleavage Suggested Reading: Chapter 7, 9.12-9.14 Suggested Problems: 7.23-7.45, 7.48-7.57 Carbocation Carbocation Intermediate Summary Intermediate Summary Stability - the more substituents on the carbocation, the more stable the carbocation, and the faster it can form (Hammond Postulate) Regiospecificity - a reaction will take the path of the more stable carbocation intermediate Markovnikov’s Rule - when adding an electrophile to an alkene, H forms a sigma bond to the carbon with
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