有机合成课件第2章基础有机合成.ppt

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1、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-1.Hydrogenation of alkene2.Reduction of alkyl halides a)Hydrolysis of Grignard reagent.Example:b)Reduction b

2、y 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 Exampl

3、es:2.Dehydration of alcoholsExamples: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-d

4、emercurataion2.Hydroboration-Oxidation3.Grignard synthesis4.Hydrolysis of alkyl halidesExamples: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 Hydro

5、gen 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 Eth

6、er-1.Williamson Synthesis2.Alkoxymercuration-Demercuration-Preparation of Ether-1.Williamson synthesisExamples:2.Alkoxymer curation-demercuration-Preparation of Alkylbenzene-1.Friedel-Crafts Alkylation2.Conversion of Side Chain-Preparation of Alkylbenzene-1.Friedel-Crafts alkylationExamples:2.Conver

7、sion 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

8、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 Dia

9、zonium-1.Replacement of Nitrogen2.Coupling1.Replacement of nitrogen-Reaction of Diazonium-a)Replacement by-Cl,-Br,-CNExamples:b)Replacement by-I Example:c)Replacement by-FExamples:d)Replacement by-OHExample:e)Replacement by-HExample:2.CouplingExample:-Preparation of Aldehyde&Ketone-Aldehyde1.Oxidati

10、on of Primary Alcohols2.Oxidation of Methylbenzene3.Reduction of Acid chlorideKetone1.Oxidation of Secondary Alcohols2.Friedel-Crafts Acylation-Preparation of Aldehyde&Ketone-1.Oxidation of primary alcoholsExample:2.Oxidation of methylbenzeneExamples:3.Reduction of acid chlorideExample:1.Oxidation o

11、f secondary alcoholsExample:2.Friedel-Crafts acylationExamples:-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.Oxidationa)AldehydesExampl

12、e:b)Methyl ketonesExamples:2.Reductiona)Reduction to alcoholsExamples:b)Reduction to hydrocarbonsExamples:3.Addition of cyanideExamples:4.Addition derivatives of ammonia5.Addition of alcoholsExample:6.Cannizzaro reactionExamples:7.Addition of Grignard reaction8.Others-Reaction of Carbanion-1.Halogen

13、ation of ketones2.Nucleophilic Additon to Carbonyl Compounds3.Nucleophilic Acyl Substitution1.Halogenation of ketones-Reaction of Carbanion-Examples:2.Nucleophilic addition to carbonyl compoundsa)Aldol condensationExamples:b)Wittig reactionExample:3.Nucleophilic acyl substitutiona)Claisen condensati

14、onExamples:-Substitution on Aromatic Ring-1.Nitration2.Sulfonation3.Halogenation4.Friedel-Crafts Alkylation5.Friedel-Crafts Acylation6.Protonation-Substitution on Aromatic Ring-1.Nitration2.Sulfonation3.Halogenation4.Friedel-Crafts alkylation5.Friedel-Crafts acylation6.Protonation7.Other special rea

15、ctions-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 alcoholsExamples:2.Oxidation of alkylbenzenesExamples:3.Carbonation of Grignard reagentsExamples:4.Hydrolysis of nitrilesExamples: