Advanced Organic Chemistry Reactions

Chemistry Reactions

• Aldol Condensation: Two aldehyde or ketone molecules with α-hydrogens condense in the presence of a base (e.g., dilute NaOH, Na₂CO₃, Ba(OH)₂) to form β-hydroxyaldehydes or β-hydroxyketones (aldols).

• Birch Reduction: Disubstituted alkynes react with sodium metal in liquid ammonia to predominantly form trans-alkenes.

• Beckmann Rearrangement: Oximes treated with catalysts like concentrated H₂SO₄, SOCl₂, or PCl₅ undergo rearrangement to form substituted amides.

• Balz-Schiemann Reaction: Fluorobenzene is prepared from benzene diazonium salt by first converting it to benzene diazonium tetrafluoroborate.

• Clemmensen Reduction: Aldehydes and ketones are reduced to alkanes using Zn-Hg amalgam and concentrated HCl.

• Corey-House Synthesis: An alkyl halide is converted to lithium dialkyl cuprate, which then reacts with another alkyl halide (preferably a primary alkyl halide) to produce an alkane.

• Cope Elimination: Tertiary amine oxides with a β-hydrogen atom form alkenes via Cope elimination.

• Carbylamine Reaction: Primary amines react with chloroform and alcoholic potassium hydroxide to yield isocyanides (carbylamines), characterized by an unpleasant odor.

• Claisen-Schmidt Reaction: Aromatic aldehydes can condense with aliphatic aldehydes or ketones in a base-catalyzed crossed aldol condensation.

• Cannizzaro Reaction: Aldehydes lacking α-hydrogens undergo disproportionation to form an alcohol and the salt of a carboxylic acid in the presence of an alkali.

• Claisen Condensation: β-keto esters are formed through self-condensation of esters with α-hydrogens in the presence of strong bases such as sodium ethoxide.

• Curtius Rearrangement: Acyl azides, derived from carboxylic acids, rearrange in acidic or alkaline media to form primary amines via an isocyanate intermediate.

• Diels-Alder Reaction: A conjugated diene reacts with a dienophile to produce a cyclic system.

• Etard Reaction: Aromatic hydrocarbons treated with a mild oxidizing agent (e.g., chromyl chloride) form aldehydes.

• Frankland Reaction: Similar to the Wurtz reaction, but using zinc instead of sodium. Reacts with tertiary alkyl halides to form hydrocarbons containing quaternary carbon atoms.

• Finkelstein Reaction: Iodoalkanes are produced by reacting alkyl chlorides or bromides with sodium iodide in a solvent like acetone or methanol.

• Friedel-Crafts Reaction: Simple aromatic hydrocarbons form substituted hydrocarbons through reaction with alkyl halides in the presence of Lewis acids like AlCl₃ or FeCl₃.

• Fries Rearrangement: Acyl groups in phenyl esters migrate from the phenolic oxygen to ortho or para positions on the benzene ring upon heating with anhydrous AlCl₃.

• Gabriel Phthalimide Synthesis: Phthalimide reacts with caustic potash, followed by alkyl halide treatment and hydrolysis with hydrochloric acid, to produce primary amines.

• Gattermann-Koch Reaction: Benzene yields benzaldehyde upon reaction with a mixture of CO and HCl in the presence of AlCl₃.

• Hoffmann-Bromamide Reaction: Primary amides treated with bromine and alkali produce primary amines with one fewer carbon atom.

• Hydroboration-Oxidation: Alkenes react with diborane and subsequently with hydrogen peroxide to yield alcohols.

• Hunsdiecker Reaction: Carboxylic acid silver salts react with bromine in refluxing carbon tetrachloride to form alkyl bromides with one fewer carbon.

• Hofmann Mustard Oil Reaction: Only primary amines undergo this reaction; the reaction of primary amines with carbon disulfide and other reagents yields alkyl isothiocyanates.

• Haloform Reaction: Methyl ketones are oxidized by hypohalites to form haloforms and the sodium salt of a carboxylic acid.

• Hell-Volhard-Zelinsky Reaction: Aliphatic carboxylic acids form α-halo acids when treated with bromine or chlorine in the presence of red phosphorus.

• Knoevenagel Reaction: Aldehydes or ketones with reactive methylene compounds (e.g., malonic acid, acetoacetic ester) yield α,β-unsaturated compounds.

• Kolbe's Electrolytic Method: Sodium or potassium salts of carboxylic acids are electrolyzed to produce higher alkanes.

• Leuckart Reaction: The reaction of aldehydes or ketones with ammonium formate or formamide produces an aldehyde or ketone-derived formyl derivative of a primary amine via a reductive amination.

• Meerwein-Ponndorf-Verley Reduction: Ketones are reduced to secondary alcohols using isopropyl alcohol in the presence of aluminum isopropoxide.

• Oppenauer Oxidation: Secondary alcohols are oxidized to ketones using aluminum tert-butoxide in the presence of excess of an aldehyde (or ketone).

• Ozonolysis: Oxidizing alkenes with ozone yields ozonides, subsequently reduced for aldehyde or ketone products.

• Perkin Condensation: Aromatic aldehydes react with acid anhydrides in the presence of sodium salts to produce α,β-unsaturated acids.

• Reimer-Tiemann Reaction: Phenol reacts with chloroform and aqueous alkali to give salicylaldehyde.

• Reformatsky Reaction: α-haloesters and aldehydes/ketones treated with zinc yield β-hydroxy esters

• Rosenmund Reduction: Acid chlorides are reduced to aldehydes via palladized barium sulfate partially poisoned with sulfur.

• Sandmeyer Reaction: Diazonium salts react with copper(I) halides to yield aryl halides.

• Schmidt Reaction: Carboxylic acids react with hydrazoic acid in acidic conditions to yield primary amines.

• Schotten-Baumann Reaction: Aryl halides or alcohols can be benzoylated in the presence of base and acyl halide under neutral conditions.

• Sabatier-Senderen Reaction: Unsaturated hydrocarbons in the presence of a nickel catalyst are reduced to alkanes.

• Stephen's Reduction: Cyanides are reduced to aldehydes through reaction with SnCl₂/HCl followed by hydrolysis.

• Tischenko Reaction: Aldehydes react with aluminium ethoxide to produce esters and alcohols by simultaneous reduction and oxidation.

• Ullmann Reaction: Aryl halides, especially iodides, react with copper to produce biphenyls.

• Wacker Process: Alkenes are directly oxidized to aldehydes or ketones in the presence of air or oxygen and palladium-copper catalysts.

• Williamson Ether Synthesis: Metal alkoxides react with alkyl halides to produce ethers.

• Wurtz Reaction: Alkyl halides react with sodium metal in anhydrous ether to produce alkanes. (Often followed by addition of an alkyl halide)

• Wittig Reaction: Carbonyl groups are converted into alkenes via reactions with ylides.

• Wolff-Kishner Reduction: Aldehydes and ketones give alkanes when heated with hydrazine and a strong base like potassium hydroxide.

• Wurtz-Fittig Reaction: Aryl halides and alkyl halides react with sodium in dry ether to yield alkyl-substituted arenes.

• Wohler's Reaction: Calcium carbide reacts with water to produce acetylene. This is a laboratory preparation method.