Chapter 12 Notes - CHAPTER 12 OXIDATION AND REDUCTION 12.1...

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CHAPTER 12 OXIDATION AND REDUCTION 12.1 Definition Recall that oxidation is loss of electrons and reduction is gain of electrons. Remember the concept of oxidation and reduction by the phrase: LEO the lion says GER . Oxidation and reduction reactions are recognized by balancing half reactions A. Rules for Balancing Oxidation-Reduction Reactions: Example: For the reactions below, determine if the reaction is oxidation , reduction , or neither . OH OH OH CH 3 CH=CH 2 B. Recognizing Oxidation-Reduction Reactions in Organic Compounds: Oxidation and reduction reactions can be recognized without balancing half reactions. Oxidation: increasing bonds to O (gain of O), decreasing bonds to H (loss of H). Reduction: increasing bonds to H (gain of H), decreasing bonds to O (loss of O). Example: Created by Dr. Felix N. Ngassa for CHM 242: Organic Chemistry for Life Sciences 2, GVSU, Spring/Summer 2011. 1
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12.2 Oxidation of Alkenes In the presence of suitable reagents, alkenes can be oxidized to epoxides and diols. A. Epoxidation of Alkenes: Epoxidation is when a single oxygen atom is added to an alkene to form an epoxide. Epoxidation of alkenes can be accomplished by the use of peroxycarboxylic acids (RCO 3 H) . In the laboratory, the most common peroxycarboxylic acid used is m - chloroperoxybenzoic acid ( MCPBA ). In the epoxidation reaction with MCPBA, the stereochemistry of the groups in the alkene is retained. Examples: B. Anti Dihydroxylation of Alkenes: The epoxidation of alkenes give a highly reactive product (epoxide) because the three- membered ring has considerable bond angle strain. Epoxide rings can be opened by nucleophiles under acidic or basic conditions.
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Chapter 12 Notes - CHAPTER 12 OXIDATION AND REDUCTION 12.1...

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