The Carbonyl Group

The following sections are included:

• General

  • Aldehydes and Ketones

• Synthesis of Aldehydes

  • Ozonolysis of Alkenes via Ozonide

  • Oxidation of Primary Alcohols

    • Pyridinium Chlorochromate (PCC, C₅H₅NH⁺ CrO₃Cl^-)

    • Pyridinium Dichromate (PDC, (C₅H₅NH)₂Cr₂O₇)

    • Manganese Dioxide

    • Silver(I) Carbonate

  • Hydration of Alkynes

  • From Primary Alkyl Iodides or Tosylates and DMSO

  • Catalytic Hydrogenation of Acyl Chlorides - The Rosenmund Reduction

  • Reduction of Nitriles - The Stephen Reduction

  • Aromatic Aldehydes - The Reimer-Tiemann Reaction

  • Aromatic Aldehydes - The Gattermann-Koch Reaction

  • Industrial Oxidation of Alkenes - The Wacker Process

• Synthesis of Ketones

  • Ozonolysis of Alkenes

  • Oxidation of Secondary Alcohols

    • Pfitzner-Moffatt Oxidation

    • The Swern Oxidation

  • Oxidation of 1,2-Diols

  • Rearrangement of a Strained 1,2-Diol - The Pinacol-Pinacolone Rearrangement

  • Hydration of Alkynes - Formation of Methyl Ketones

  • Thermolysis of Calcium and Barium Dicarboxylates - Formation of Cyclopentanones and Cyclohexanones

  • Aromatic Ketones - The Friedel-Crafts Acylation

• Reactions of the Carbonyl Group

  • Reactions Of Carbonyl Compounds Without Enolisation

    • Addition Reactions

      • With HCN

      • With Organometallics

      • Formation of β-Hydroxy Esters - The Reformatsky Reaction

      • The Stobbe Condensation

      • Reaction of Ketones and Diazomethane

      • With Amines

        • Primary Amines - Imine Formation

        • Secondary Amines - Formation of Enamines

        • Special Cases - Other Amines

          • Hydrazine - Formation of Hydrazones

          • Semicarbazide

          • Hydroxylamine - Formation of Oximes

        • Amine Formation Reactions

          • Reductive Amination

          • Formation of β-Amino Carbonyls - The Mannich Reaction

      • With Alcohols - Formation of Hemiacetals and Acetals

      • With Thiols - Formation of Thioacetals

      • Reduction Reactions With Metal Hydrides

      • Reactions With Phosphorus Ylids - The Wittig Reaction

      • Reaction With Dimsyl Sodium: a Sulphur Ylid

      • Addition of Bisulphite

    • Oxidation Reactions

      • Of Aldehydes

      • Of Ketones

        • Peracid Oxidation to Esters - The Baeyer-Villiger Oxidation

        • Oxidation to 1,2-Diones With SeO₂

    • Reduction Reactions

      • Metal Hydrides

      • Reduction to 1,2-Diols With Metals - The Pinacol Reaction

      • Reduction to Alkanes

        • The Clemmensen Reduction

        • Reduction via the Hydrazone - the Wolff-Kishner Reaction

        • Reductton via Thioacetals

      • Reduction of Aldehydes With No α-Hydrogens - The Cannizzaro Reaction

    • Miscellaneous Reactions

      • With PCl₅

      • Conversion of a Strained 1,2-Dione to an α-Hydroxyacid - The Benzilic Acid Rearrangement

      • Conversion of Aldehydes to Nitrites

  • Reactions Of The Carbonyl Group via Enols

    • Conversion of a Methyl Ketone to a Carboxylic Acid - The Haloform Reaction

    • Formation of α-Hydroxy Carbonyls - The Aldol Condensation

      • Base Catalysed Reaction

      • Acid Catalysed Reaction

      • Use in Synthesis

        • Formation of Carbocyclic Rings

        • Mixed Aldol Reactions - General

        • Mixed Aldol Reactions of Aldehydes - The Claisen-Schmidt Reaction

      • Alkylation of Enolates - O vs. C Attack

    • Special Condensation Reactions

      • The Benzoin Condensation