Chem 120 Reaction of Alcohols

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