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Chem 120 Reaction of Alcohols

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Information about Chem 120 Reaction of Alcohols
Education

Published on September 29, 2008

Author: cpesison

Source: authorstream.com

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Slide 1: Reactions of Alcohols Slide 7: Reaction of Alcohols Reactions which favors Tertiary Alkyl halides Slide 8: Practice on the Reaction of Alcohols with HBr Reaction of Alcohols Reactions which favors Tertiary Alkyl halides Reaction with HBr Slide 9: Chloride is a weaker nucleophile than bromide. Add ZnCl2, which bonds strongly with -OH, to promote the reaction. The chloride product is insoluble. Lucas test: ZnCl2 in conc. HCl 1° alcohols react slowly or not at all. 2 alcohols react in 1-5 minutes. 3 alcohols react in less than 1 minute. Reaction of Alcohols Reactions which favors Tertiary Alkyl halides Reaction with HBr Reaction with HCl (Lucas Reagent) Slide 10: Reaction of Alcohols Reactions which favors Tertiary Alkyl halides Reaction with HBr Reaction with HCl (Lucas Reagent) Reaction which favors Primary and Secondary Alcohols Reaction with Thionyl Chloride Primary and Secondary Alcohols react easily with thionyl chloride Slide 11: Practice on Reaction of Alcohols with Thionyl Chloride Slide 12: Reaction of Alcohols Reactions which favors Tertiary Alkyl halides Reaction with HBr Reaction with HCl (Lucas Reagent) Reaction which favors Primary and Secondary Alcohols Reaction with Thionyl Chloride Reaction with Phosphorus Trihalide Primary and Secondary Alcohols react easily with Phosphorus trihalide Slide 13: Practice on Reaction of Alcohols with Phosphorus trihalide Slide 14: Reaction of Alcohols Reactions which favors Tertiary Alkyl halides Reaction with HBr Reaction with HCl (Lucas Reagent) Reaction which favors Primary and Secondary Alcohols Reaction with Thionyl Chloride Reaction with Phosphorus Trihalide Dehydration Tertiary ROH and Saitsev's Rule Slide 15: Practice on Dehydration Reaction which favors Tertiary Alcohols Saitsev’s Rule states that the double bond would attach to the more substituted carbon Slide 16: Reaction of Alcohols Reactions which favors Tertiary Alkyl halides Reaction with HBr Reaction with HCl (Lucas Reagent) Reaction which favors Primary and Secondary Alcohols Reaction with Thionyl Chloride Reaction with Phosphorus Trihalide Dehydration (Elimination Reactions) Tertiary ROH and Saitsev's Rule Primary and Secondary ROH Slide 17: Reaction of Alcohols Reactions which favors Tertiary Alkyl halides Reaction with HBr Reaction with HCl (Lucas Reagent) Reaction which favors Primary and Secondary Alcohols Reaction with Thionyl Chloride Reaction with Phosphorus Trihalide Dehydration (Elimination Reactions) Tertiary ROH and Saitsev's Rule Primary and Secondary ROH Oxidative Cleavage of Vicinal Diols Slide 18: Same products formed as from ozonolysis of the corresponding alkene. Slide 19: Practice on Cleavage of Vicinal Diols Slide 20: Practice on Cleavage of Vicinal Diols Slide 21: Reaction of Alcohols Reactions which favors Tertiary Alkyl halides Reaction with HBr Reaction with HCl (Lucas Reagent) Reaction which favors Primary and Secondary Alcohols Reaction with Thionyl Chloride Reaction with Phosphorus Trihalide Dehydration (Elimination Reactions) Tertiary ROH and Saitsev's Rule Primary and Secondary ROH Oxidative Cleavage of Vicinal Diols Oxidation Primary ROH Mild Oxidizing agents convert primary alcohols to aldehydes Strong oxidizing agents convert primary alcohols directly to carboxylic acids Slide 22: List of common oxidizing agents for alcohols Slide 23: Practice on Oxidation of Primary Alcohols Slide 24: Practice on Oxidation of Primary Alcohols Slide 25: Practice on Oxidation of Primary Alcohols Slide 26: Practice on Oxidation of Primary Alcohols Slide 27: Practice on Oxidation of Primary Alcohols Slide 29: Practice on Oxidation of Primary Alcohols Slide 30: Reaction of Alcohols Reactions which favors Tertiary Alkyl halides Reaction with HBr Reaction with HCl (Lucas Reagent) Reaction which favors Primary and Secondary Alcohols Reaction with Thionyl Chloride Reaction with Phosphorus Trihalide Dehydration (Elimination Reactions) Tertiary ROH and Saitsev's Rule Primary and Secondary ROH Oxidative Cleavage of Vicinal Diols Oxidation Primary ROH Secondary ROH Slide 31: Even with strong oxidizing agents, secondary alcohols cannot be converted to carboxylic acids. Slide 32: Practice on Oxidation of Secondary Alcohols Slide 33: Practice on Oxidation of Secondary Alcohols Slide 34: Tertiary Alcohols cannot be oxidized. Reaction of Alcohols Reactions which favors Tertiary Alkyl halides Reaction with HBr Reaction with HCl (Lucas Reagent) Reaction which favors Primary and Secondary Alcohols Reaction with Thionyl Chloride Reaction with Phosphorus Trihalide Dehydration (Elimination Reactions) Tertiary ROH and Saitsev's Rule Primary and Secondary ROH Oxidative Cleavage of Vicinal Diols Oxidation Primary ROH Secondary ROH Tertiary ROH Slide 35: Reaction of Alcohols Reactions which favors Tertiary Alkyl halides Reaction with HBr Reaction with HCl (Lucas Reagent) Reaction which favors Primary and Secondary Alcohols Reaction with Thionyl Chloride Reaction with Phosphorus Trihalide Dehydration (Elimination Reactions) Tertiary ROH and Saitsev's Rule Primary and Secondary ROH Oxidative Cleavage of Vicinal Diols Oxidation Primary ROH Secondary ROH Tertiary ROH Conversion to Ethers Acid-Catalyzed Condensation of Alcohols to Ethers Slide 36: Practice on Acid Catalyzed Condensation of Alcohols to Ethers Slide 37: Reaction of Alcohols Reactions which favors Tertiary Alkyl halides Reaction with HBr Reaction with HCl (Lucas Reagent) Reaction which favors Primary and Secondary Alcohols Reaction with Thionyl Chloride Reaction with Phosphorus Trihalide Dehydration (Elimination Reactions) Tertiary ROH and Saitsev's Rule Primary and Secondary ROH Oxidative Cleavage of Vicinal Diols Oxidation Primary ROH Secondary ROH Tertiary ROH Conversion of Alcohols to Ethers Acid-Catalyzed Condensation of Alcohols to Ethers Williamson Ether Synthesis Slide 38: Reaction of Alcohols Reactions which favors Tertiary Alkyl halides Reaction with HBr Reaction with HCl (Lucas Reagent) Reaction which favors Primary and Secondary Alcohols Reaction with Thionyl Chloride Reaction with Phosphorus Trihalide Dehydration (Elimination Reactions) Tertiary ROH and Saitsev's Rule Primary and Secondary ROH Oxidative Cleavage of Vicinal Diols Oxidation Primary ROH Secondary ROH Tertiary ROH Conversion of Alcohols to Ethers Acid-Catalyzed Condensation of Alcohols to Ethers Williamson Ether Synthesis

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