Carboxylic Acid and Its Derivatives

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Carboxylic acid and its derivatives A. Introduction The most important functional group in organic compounds Structure: sp2 hybridization, trigonal planar electron-withdrawing group B. Nomenclature Groups Acid Acyl halide Acid anhydride Ester Amide Prefix Carboxy- Alkanoyloxy- Suffix -carboxylic acid -oic acid -oyl halide -oic anhydride Alkyl alkanoate -amide Organic acid/ alkanoic acid/ carboxylic acid: methanoic ethanoic hexane-1,6-dioic benzoic acid trans-butenedioic acid acid acid formic acid acetic acid (vinegar) Acyl halide: ethanoyl chloride benzoyl bromide hexane-1,6-dioyl chloride (a monomer of nylon or polyester) Acid anhydride: ethanoic anhydride butenedioic anhydride butanoic ethanoic anhydride acetic anhydride (starting material to synthesis of heroin) Ester: methyl ethanoate phenyl butanoate 2-ethanoyloxybenzoic acid o-acetylsalicylic acid (aspirin) Amide: pentanamide benzamide N-ethyl-N-methylbutanamide C. Carboxylic acid 1. Preparation (a) Oxidation of primary alkanol or aldehyde Oxidizing agent: acidified potassium permanganate (b) Oxidation of alkylbenzene (c) Hydrolysis of nitriles (d) Iodoform test 2. Physical properties (a) highly polar compounds (b) intermolecular/intramolecular hydrogen bond, high boiling point, high melting point, soluble in water (solubility decreases as molecular mass increasing) (c) In gaseous state, it exists in dimeric form. 3. Chemical properties (a) Acidic Acidity: RCOOH > > ROH Stability: RCOO > > RO Effect of substituents on acidity: CCl3COOH > CCl2HCOOH > CClH2COOH > CH3COOH CFH2COOH > CClH2COOH > CBrH2COOH > CIH2COOH CH3CClHCOOH >> CClH2CH2COOH > CH3CH2COOH Reason: Electron donating group stabilize

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