Summary of Synthetic Methods

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1、SummaryofSyntheticmethodSSynthesisofAlkanes,Cycloalkanes,andAromaticHydrocarbons1.Catalytichydrogenationofalkenes(5.9,17.7)2.Catalytichydrogenationofalkynes(7.5)3.Catalytichydrogenationofaromaticcompounds(13.11)4.ProtonationofGrignardreagents(9.8)5.Additionofcarbenoidst

2、oalkenes(6.7)6.Friedel–Craftsalkylationofaromaticcompounds(13.2)7.Wolff–KishnerorClemmensenreductionofaldehydesorketones(13.8,18.5)8.Reductionofaryldiazoniumsaltswithhypophosphorousacid(13.8)9.Catalyticreductionofarylketones(13.11)10.Substitutionreactionofalkylhalidewit

3、hlithiumdialkylcuprates(9.8)11.Reductionofthioacetals(19.9)12.Gilmanreagentalkylationofaromaticcompounds(17.2)13.Gilmanreagentalkylationofallylichalides(17.2)14.Heckreactionforsynthesisofarylalkenes(17.3,17.5)15.Suzukicouplingofarylgroupandarylhalides(17.3,17.4)16.Sonog

4、ashirareactionforsynthesisofarylalkynes(17.3,17.6)SynthesisofAlkenes1.Acid-catalyzeddehydrationofalcohols(8.20)2.Catalytichydrogenationofalkynes(7.5)3.Dehydrohalogenationofalkylhalides(9.18)4.Hofmanneliminationofquaternaryammoniumhydroxides(23.9)5.Wittigreactionofaldehy

5、desorketones(19.9)6.AlkenecouplingwiththeGrubbsmetathesisreaction(17.9)7.Heckreactionforsynthesisofarylalkenes(17.3,17.5)8.Gilmanreagentalkylationofallylichalides(17.2)SynthesisofAlkynes1.b-Eliminationofdihaloalkanesorvinylhalides(7.7)2.Alkylationofalkynideswithalkylhal

6、ides(7.7)3.Sonogashirareactionforsynthesisofarylalkynes(17.3,17.6)SynthesisofAlkylHalides1.Polaradditionofhydrogenhalidestoalkenes(7.2)2.Additionofhalogenstoalkenes(7.6)3.Reactionofalcoholswithhydrogenhalide(8.14)4.Reactionofalcoholswiththionylchlorideorphosphorustribro

7、mide(15.3)5.Allylicorbenzylichalogenation(11.5)6.a-Halogenationofaldehydes,ketones,orcarboxylicacids(22.5,22.14)7.Ahalogenationofaldehydes,ketones,orcarboxylicacids(23.5,23.14)SynthesisofArylHalides1.DirecthalogenationusingLewisacidcatalyst(14.2)2.Reactionofaryldiazoniu

8、msaltswithcopper(I)halide(13.8)SynthesisofAlcohols1.Acid-catalyzedhydrationofalkenes(6.5)2.Oxymercuration–deme