有機(jī)合成教學(xué)課件第2章基礎(chǔ)有機(jī)合成

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

2、n 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 hali

3、de Examples: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-

4、1. Oxymercuration-demercurataion2. 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 hydr

5、ocarbons3. 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.

6、 Halide exchange-Preparation of Ether-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.

7、Friedel-Crafts alkylationExamples: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. Rea

8、ction 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

9、:5. Hofmann degradation of amides Examples:-Reaction of Diazonium-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 -HExa

10、mple:2. CouplingExample:-Preparation of Aldehyde & Ketone-Aldehyde1. Oxidation 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.

11、Oxidation of methylbenzeneExamples:3. Reduction of acid chlorideExample:1. Oxidation of secondary alcoholsExample:2. Friedel-Crafts acylationExamples:-Reactions of Aldehyde & Ketone-1. Oxidation2. Reduction3. Addition of Cyanide4. Addition Derivatives of ammonia5. Addition of Alcohols6. Cannizzaro R

12、eaction7. Addition of Grignard Reagent-Reactions of Aldehyde & Ketone-1. Oxidationa) AldehydesExample:b) Methyl ketonesExamples:2. Reductiona) Reduction to alcoholsExamples:b) Reduction to hydrocarbonsExamples:3. Addition of cyanideExamples:4. Addition derivatives of ammonia5. Addition of alcoholsEx

13、ample:6. Cannizzaro reactionExamples:7. Addition of Grignard reaction8. Others-Reaction of Carbanion-1. Halogenation of ketones2. Nucleophilic Additon to Carbonyl Compounds3. Nucleophilic Acyl Substitution1. Halogenation of ketones-Reaction of Carbanion-Examples:2. Nucleophilic addition to carbonyl

14、compoundsa) Aldol condensationExamples:b) Wittig reactionExample:3. Nucleophilic acyl substitutiona) Claisen condensationExamples:-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 reactions-Preparation of Acid-1. Oxidation of Primary Alcohols2. Oxidation of Alkylbenzene3. Ca