中国农业大学有机化学课件第十一章 醛和酮.ppt
Chapter 11 Aldehydes&Ketones11.1 Classification and Nomenclature11.1.1 Classification11.1.2 Nomenclature(1)Common Nomenclature(2)Systemic Nomenclature2-甲基环己甲醛甲基环己甲醛2-甲基丁醛甲基丁醛2-戊酮戊酮3,3-二甲基环己酮二甲基环己酮AldehydeKetoneAlcoholAlkene and AlkynePrecedence order of functional groups as principle part in nomenclature eg.练习：用系统命名法和普通命名法练习：用系统命名法和普通命名法 命名下列化合物命名下列化合物11.2 Physical Properties11.3 Chemical PropertiesReactive centers of aldehyde and ketone reactions on-H attacked by electrophilic reagent attacked by nucleophilic reagentReactions of aldehyde11.3.1 Nucleophilic Addition11.3.1.1 Reaction with hydrogen cyanide11.3.1.2 addition with sodium bisulfite(NaHSO3)11.3.1.3 addition with Grignards reagent11.3.1.4 addition with H2O11.3.1.5 addition with alcoholmechanism：11.3.1.6 addition with amines reaction with primary amineSchiff base reaction with secondary amineenamine11.3.1.7 Wittigs reaction维生素维生素A11.3.1.8 Reaction with Schiffs reagent无色无色红色或紫色红色或紫色11.3.1.9 reaction with aryl hydrocarbons halomethylationmechanism：other reactions11.3.2 oxidative and reductive reactions metal hydrids11.3.2.1 reduction of carbonyl compounds11.3.2.1.1 to alcohol catalytic hydrogenation11.3.2.1.2 to methyleneWolff-Kishners reactionmechanism：Clemmensens reduction desulfur of thioacetal or thioketal11.3.2.2 Oxidation(1)aldehyde(2)ketonemechanism:eg.11.3.2.3 Cannizzaro reactionmechanism：Crossed Cannizzaro reaction：11.3.3 reactions on-HpKa 20enolizationEnolization could be catalyzed by both acid and base：11.3.3.1 Halogenation of-H-H Base-catalyzed halogenationmechanism：Acid-catalyzed halogenationmechanism：Free radical halogenation11.3.3.2 Aldol condensation Base-catalyzed aldol condensationmechanism：Acid-catalyzed aldol condensationmechanism：Crossed aldol condensation11.4 Mechanism of Nucleophilic Addition11.4.1 Simple addition11.4.1.1 mechanism11.4.1.2 Factors affecting the addition Nucleophility of reagent electric factors stereo factors练习：判断下列各组化合物中哪个化合物练习：判断下列各组化合物中哪个化合物 进行亲核加成反应时活性更强，为进行亲核加成反应时活性更强，为 什么？什么？1.4-溴丁酮和溴代丙酮溴丁酮和溴代丙酮2.2,3-丁二酮和丁酮丁二酮和丁酮3.对硝基苯甲醛和对甲氧基苯甲醛对硝基苯甲醛和对甲氧基苯甲醛4.环戊酮和环丙酮环戊酮和环丙酮11.4.2 Complexed Addition11.4.3 Stereochemistry of Nucleophilic Addition11.5.1 From Hydrocarbons (1)Oxidation of side chain of substituted aryl hydrocarbons (2)Ozonolysis-reduction of alkene (3)Hydration of alkynes (4)Formylation of alkenes (5)FriedelCrafts acylation of aryl hydrocarbons11.5 Preparation of Aldehyde and Ketone11.5.2 Oxidation or dehydrogenation of alcohol11.5.3 From carboxylic acid11.5.4 Extracted from animal or plant body(1)Formaldehyde11.6 Representatives11.6.2 Acetaldehyde11.6.3 Benzaldehydemechanism：11.6.4 Acetone11.6.5 cyclohexone11.7 Unsaturated carbonyl compound11.7.1 enone11.7.2,-unsaturated carbonyl compound(1)Nucleophilic AdditionNucleophilic addition of,-unsaturated carbonyl compound(2)插烯规插烯规律律11.7.3 QuinoneRepresentatives：
