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ORGANIC CHEMISTRY Alkyl Halides and Aryl Halides Dr. Anju Srivastava Dept. of Chemistry Hindu College Delhi (29.09.2006) CONTENTS Alkyl Halides Introduction Structure of Alkyl Halides Classification and Nomenclature of Alkyl Halides Preparation of Alkyl Halides Preparation Method I: Halogenation of Alkanes Mechanism : Free Radical Subtitution Disadvantage of Halogenation Reaction Halogenation of Higher Alkanes : Chlorination Bromination Reactions of Methane with Other Halogens Radical Substitution of Benzylic and Allylic Hydrogens Stereochemistry of Radical Substitution Reactions Preparation Method II : Addition of Halogen Acid To Alkene Rearrangement of Carbocations Preparation Method III : Addition of Hbr : Peroxide Effect Preparation Method IV: Addition of Halogen To Alkenes. Stereochemistry of Addition Of Halogens Preparation Method V : Reaction Of Alcohols With Hydrogen Halides. Preparation Method VI : Alkyl Halides From The Reaction Of Alcohols With Phosphorus Trihalides, Thionyl Chlorides, P-Toluenesulphonyl Chloride. Preparation Method VII: Hunsdiecker or Borodine Hunsdiecker Reaction Preparation Method VIII : Preparation of Alkyl Fluorides And Alkyl Iodides Physical Properties Reactions of Alkyl Halides Substitution Reactions SN2 Reaction SN2 Reaction : Mechanism Stereochemistry Of SN2 Reaction Characteristics Of SN2 Reaction SN1 Reaction SN1 Reaction : Mechanism Stereochemistry Of SN1 Reaction Characteristics Of SN1 Reaction SN1 Vs. SN2 : Comparison And Competition Elimination Reactions Type Of Elimination Reactions E2 Reaction Regioselectivity Of E2 Reactions. E1 Reaction Rearrangements In E1 Reaction Orientation In E1 Reaction E1cb Mechanism Competition Between E2 And E1 Summary Of Reactivity SN1, SN2, E1, E2 E1cb Mechanism Formation of Organo Metallic Compounds Grignard Reagents Organo Lithium Reagents Reduction of Alkyl Halides Miscellaneous Reactions ARYL HALIDES Introduction Bonding In Aryl Halides Preparation Methods Direct Halogenation Of Benzene Decomposition of Aryl Diazonium Salts Physical Properties Reactions of Aryl Halides Lack of Reactivity For SN2 and SN1 Substitution (SNAR) : Addition - Elimination Mechanism Elimination Addition Mechanism: Benzyne Substitution In The Ring : Electrophilic Aromatic Formation of Grignard Reagents Some More Reactions Ulmann Reaction Wurtz Fittig Reaction Hydrogenation Heck Reaction POLYHALOALKANES Preparation Properties And Uses Fluorinated Hydrocarbons Substitution