Lecture 24Outline of Last Lecture I. Alcoholsa. Nomenclatureb. Common alcoholsc. Classificationd. Physical PropertiesII. Synthesis of Alcohols (Review)III. Reactions of AlcoholsCHEM 333 1st Editiona. Acid Catalyzed Dehydration of Alcohols (Review)b. PBr3c. Thionyl chloride or bromide (SOCl2 or SOBr2)IV. Aryl/Alkyl Sulfonates (Create good leaving groups)V. Ethersa. Nomenclatureb. Common ethersVI. Preparation of Ethersa. Williamson Ether Synthesisb. Acid Catalyzed Addition to Alkenesc. EpoxidesVII. Synthesis of Ethersa. Oxidation of Alkenes with Peroxycarboxylic Acidsb. Internal Nucleophilic SubstitutionVIII. Reactions with Epoxidesa. Acid CatalyzedOutline of Current LectureI. Acid Catalyzed Reactions with Epoxidesa. H+ expoxide opening is streospecificb. Good nucleophiles also open epoxidesII. Reductiona. NaBH4b. LiAlH4III. Oxidationa. Chromic acid (H2CrO4)b. Pyridinium chlorochromate (PCC)c. Potassium permanganate (KMnO4)IV. OrganolithiumsCurrent LectureI. Reactions with Epoxidesa. H+ expoxide opening is streospecificb. Good nucleophiles also open epoxidesi. Any good nucleophile worksii. Stereospecific reactioniii. Example:1. Nucleophile attacks least substituted side with good nucleophiles2. Nucleophile attacks more substituted side when acid catalyzedII. Reduction: increase in hydrogen or decrease in oxygen contenta. NaBH4 (sodium borohydride): weaker reducing agent, H- sourceb. LiAlH4 (lithium aluminum hydride): stronger reducing agent, H- source III. Oxidation: increase in oxygen or decrease in hydrogen contenta. Chromic acid (H2CrO4): strong oxidantb. Pyridinium chlorochromate (PCC): mild oxidantc. Potassium permanganate (KMnO4): strong oxidantIV. Organolithiums: good nucleophiles that attack carbonyls and
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