Lecture 23Outline of Last Lecture I. Halogenation of Alkanesa. Radicalb. Br2 vs. Cl2c. Mechanismd. Hammond PostulateI. Allylic HalogenationCHEM 333 1st EditionII. Radical Addition of HBr to Alkenes: anti-Markovnikov additionOutline of Current LectureI. Alcoholsa. Nomenclatureb. Common alcoholsc. Classificationd. Physical PropertiesII. Synthesis of Alcohols (Review)III. Reactions of Alcoholsa. 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 CatalyzedCurrent LectureI. Alcoholsa. Nomenclature: suffix is -olb. Common alcohols:c. Classification: 1° 2° 3°d. Physical Properties:i. Polarii. Hydrogen bonding - increase boiling point over hydrocarbons of same sizeiii. Low molecular weight alcohols = H2O solubleiv. High molecular weight alcohols = not H2O solubleII. Synthesis of Alcohols (Review)III. Reactions of Alcoholsa. Acid Catalyzed Dehydration of Alcohols (Review)b. PBr3 (mild)i. 1° or 2° alcohol ---> bromoalkaneii. Mechanism:c. Thionyl chloride or bromide (SOCl2 or SOBr2)i. Mechanism:IV. Aryl/Alkyl Sulfonates (Create good leaving groups)a. Example:V. Ethersa. Nomenclature: select longest chain and name -OR bonded to it = alkoxyi. Example: 2-methoxy-2-methylpropaneb. Common ethers: THF diethyl etherVI. Preparation of Ethersa. Williamson Ether Synthesis (SN2 reaction)b. Acid Catalyzed Addition to Alkenesc. Epoxides: 3 membered ring ethersi. Wants 109.5° angles, but is at 60°ii. Strained and reactiveVII. Synthesis of Ethersa. Oxidation of Alkenes with Peroxycarboxylic Acidsb. Internal Nucleophilic SubstitutionVIII.Reactions with Epoxidesnucleophile attacks and opens ringa. Acid Catalyzedi.
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