有机合成课件第2章基础有机合成.ppt
Chapter 2Basic of Organic Synthesis,-Preparation of Alkane-1.Hydrogenation of Alkenes 2.Reduction of Alkyl Halides3.Coupling of Alkyl Halides with Organometalic Compounds,-Preparation of Alkane-Hydrogenation of alkene,2.Reduction of alkyl halides a)Hydrolysis of Grignard reagent.,Example:,b)Reduction by metal and acid.,Example:,3.Coupling of alkyl halides with organometalic compounds.,Example:,-Preparation of Alkene-,1.Dehydrohalogenation of Alkyl Halide2.Dehydration of Alcohols3.Dehalogenationof Vicinal Dihalides4.Reduction of Alkynes,-Preparation of Alkene-,1.Dehydrohalogenation of alkyl halide,Examples:,2.Dehydration of alcohols,Examples:,3.Dehalogenation of vicinal dihalides,Example:,4.Reduction of alkynes,-Preparation of Alcohol-,1.Oxymercuration-Demercuration2.Hydroboration-Oxidation3.GrignardSynthesis4.Hydrolysis of Alkyl Halides5.Hydroxylation of Alkenes,-Preparation of Alcohol-,1.Oxymercuration-demercurataion,2.Hydroboration-Oxidation,3.Grignard synthesis,4.Hydrolysis of alkyl halides,Examples:,5.Hydroxylation of alkenes,6.Aldol condensation7.Reduction of carbonyl compounds8.Reduction of acid and esters,-Preparation of Halide-,1.From Alcohols2.Halogenationof Certain hydrocarbons3.Addition of Hydrogen Halide to Alkenes4.Addition of Halogen to Alkenes and Alkynes5.Halide Exchange,-Preparation of Halide-,1.From alcohols,Examples:,2.Halogenation of certain hydrocarbons,Examples:,3.Addition of hydrogen halide to alkenes,4.Addition of halogen to alkenes and alkenes,5.Halide exchange,-Preparation of Ether-,1.Williamson Synthesis2.Alkoxymercuration-Demercuration,-Preparation of Ether-,1.Williamson synthesis,Examples:,2.Alkoxymer curation-demercuration,-Preparation of Alkylbenzene-,1.Friedel-Crafts Alkylation2.Conversion of Side Chain,-Preparation of Alkylbenzene-,1.Friedel-Crafts alkylation,Examples:,2.Conversion of side chain,-Preparation of Phenol-,1.Hydrolysis of Diazonium Salts2.Alkli Fusion of Sulfonates,-Preparation of Phenol-,1.Hydrolysis of diazonium salts,Example:,2.Alkali fusion of sulfonates,-Preparation of Amine-,1.Reduction of Nitro Compounds2.Reaction of Halides with ammonia or Amines3.Reductive Amination4.Reduction of Nitriles5.Hofmann Degradation of Amides,-Preparation of Amine-,1.Reduction of nitro compounds,Examples:,2.Reaction of halides with ammonia or amines,Examples:,3.Reductive amination,Examples:,4.Reduction of nitriles,Examples:,5.Hofmann degradation of amides,Examples:,-Reaction of Diazonium-,Replacement of Nitrogen2.Coupling,1.Replacement of nitrogen,-Reaction of Diazonium-,a)Replacement by-Cl,-Br,-CN,Examples:,b)Replacement by-I,Example:,c)Replacement by-F,Examples:,d)Replacement by-OH,Example:,e)Replacement by-H,Example:,2.Coupling,Example:,-Preparation of Aldehyde&Ketone-,Aldehyde,1.Oxidation of Primary Alcohols2.Oxidation of Methylbenzene3.Reduction of Acid chloride,Ketone,1.Oxidation of Secondary Alcohols2.Friedel-Crafts Acylation,-Preparation of Aldehyde&Ketone-,1.Oxidation of primary alcohols,Example:,2.Oxidation of methylbenzene,Examples:,3.Reduction of acid chloride,Example:,1.Oxidation of secondary alcohols,Example:,2.Friedel-Crafts acylation,Examples:,-Reactions of Aldehyde&Ketone-,1.Oxidation2.Reduction3.Addition of Cyanide4.Addition Derivatives of ammonia5.Addition of Alcohols6.Cannizzaro Reaction7.Addition of Grignard Reagent,-Reactions of Aldehyde&Ketone-,1.Oxidation,a)Aldehydes,Example:,b)Methyl ketones,Examples:,2.Reduction,a)Reduction to alcohols,Examples:,b)Reduction to hydrocarbons,Examples:,3.Addition of cyanide,Examples:,4.Addition derivatives of ammonia,5.Addition of alcohols,Example:,6.Cannizzaro reaction,Examples:,7.Addition of Grignard reaction,8.Others,-Reaction of Carbanion-,1.Halogenation of ketones2.Nucleophilic Additon to Carbonyl Compounds3.Nucleophilic Acyl Substitution,1.Halogenation of ketones,-Reaction of Carbanion-,Examples:,2.Nucleophilic addition to carbonyl compounds,a)Aldol condensation,Examples:,b)Wittig reaction,Example:,3.Nucleophilic acyl substitution,a)Claisen condensation,Examples:,-Substitution on Aromatic Ring-,1.Nitration2.Sulfonation3.Halogenation4.Friedel-Crafts Alkylation5.Friedel-Crafts Acylation6.Protonation,-Substitution on Aromatic Ring-,1.Nitration,2.Sulfonation,3.Halogenation,4.Friedel-Crafts alkylation,5.Friedel-Crafts acylation,6.Protonation,7.Other special reactions,-Preparation of Acid-,1.Oxidation of Primary Alcohols2.Oxidation of Alkylbenzene3.Carbonation of Grignard Reagent4.Hydrolysis of Nitriles,-Preparation of Acid-,1.Oxidation of primary alcohols,Examples:,2.Oxidation of alkylbenzenes,Examples:,3.Carbonation of Grignard reagents,Examples:,4.Hydrolysis of nitriles,Examples:,
