Chem 120 Reaction of Alcohols

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Chem 120 Reaction of Alcohols

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Presentation Transcript

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