Further organic chemistry: Carboxylic acids -4

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  • Created by: Shannon
  • Created on: 07-04-15 10:11
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  • Carboxylic acids
    • Functional group -COOH
    • Physical properties
      • Boiling temperatures
        • Polar molecules, so high boiling point
        • Boiling point even higher than expected due to the formation of diemers
          • H bonding between carboxylic acids
      • Solubility
        • Small chain molecules very soluble due to ability to H bond with water
        • Solubility decreases as chain length increases - stronger intermolecular forces at hydrophilic end of molecule
    • Preparation
      • Oxidation of alcohols
        • Primary alcohol -> Aldehyde -> Carboxylic acid
        • Heated under reflux with potassium dichromate and H2SO4
      • Hydrolysis of nitriles
        • Reflux nitrile with dilute HCl
          • Carboxylic acid distilled off
    • Reactions
      • With LiAlH4 in dry ether
        • Reduction reaction
        • Formation of primary alcohol
      • Neutralisation
        • Production of a salt
        • Reaction with a base e.g NaOH
      • with PCl5
        • Formation of acyl chloride
        • -OH replaced with -Cl
        • Steamy fumes of hydrogen chloride given off
      • Esterification
        • Addition of alcohol and an acid catalyst, warmed under reflux
        • Condensation reaction
        • Alcohol responsible for first part of name, e.g pentanol = pentyl
        • Carboxylic acid responsible for second part of name, e.g methanoic acid = methanoate


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