课件columbia大学有机化学有机化学课件05.html.pptxVIP

Chapter 15Alcohols, Diols, and Thiols;15.1Sources of Alcohols;Methanol is an industrial chemical end uses: solvent, antifreeze, fuel principal use: preparation of formaldehyde;Methanol is an industrial chemical end uses: solvent, antifreeze, fuel principal use: preparation of formaldehyde prepared by hydrogenation of carbon monoxide;Ethanol is an industrial chemical Most ethanol comes from fermentation Synthetic ethanol is produced by hydrationof ethylene Synthetic ethanol is denatured (madeunfit for drinking) by adding methanol, benzene,pyridine, castor oil, gasoline, etc.;Isopropyl alcohol is prepared by hydration of propene. All alcohols with four carbons or fewer are readily available. Most alcohols with five or six carbons are readily available.;Hydration of alkenes Hydroboration-oxidation of alkenes Hydrolysis of alkyl halides Syntheses using  Grignard reagents organolithium reagents;Reduction of aldehydes and ketones Reduction of carboxylic acids Reduction of esters Reaction of Grignard reagents with epoxides Diols by hydroxylation of alkenes;15.2Preparation of AlcoholsbyReduction of Aldehydes and Ketones;; ;; ;;Sodiumborohydride; ;Lithium aluminum hydride; ;neither NaBH4 or LiAlH4reduces isolateddouble bonds;15.3Preparation of Alcohols By Reductionof Carboxylic Acids and Esters;lithium aluminum hydride is only effective reducing agent;Example: Reduction of a Carboxylic Acid;Lithium aluminum hydride preferred forlaboratory reductions Sodium borohydride reduction is too slowto be useful Catalytic hydrogenolysis used in industrybut conditions difficult or dangerous to duplicate in the laboratory (special catalyst, hightemperature, high pressure;Example: Reduction of a Carboxylic Acid;15.4Preparation of Alcohols From Epoxides;Reaction of Grignard Reagentswith Epoxides;CH3(CH2)4CH2MgBr;15.5Preparation of Diols;Diols are prepared by...;;vicinal diols have hydroxyl groups on adjacent carbons ethylene glycol (HOCH2CH2OH) is most fa