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Derivatives of Carboxylic Acids - Coggle Diagram

- - - - higher than alkanes
        
        polar C=O group
        
        permanent dipole-dipole attractions
        
        Van der Waals attractions
      - lower than carboxylic acids
        
        do not form H bonds with each other
      - increase with increasing C chain length
        
        greater no of electrons
        
        stronger VDW forces
        
        more energy needed
        
        higher BP
    - - SOLUBLE IN WATER
        
        form H bonds
        
        between lone pair of e- on O in polar C=O
        
        and polar δ+ H on water
      - solubility falls with increased C chain length
        
        longer HC chain force themselves between
        water molecules
        
        break H bonds
      - soluble in
        organic solvents
  - - - conditions
        
        heated to reflux
        
        in presence of conc. sulfuric acid - USES:
        
        supplies H+ ions
        
        removes water (drying agent)
        
        increases yield of ester (keeps equilibrium moving towards product)
        
        acts as catalyst
      - REVERSIBLE
        (disadvantage)
      - esterification
        D: contains ester group formed
        from alcohol + CA
      - equation
      - method
        
        mix of alcohol + conc sulfuric acid in pear shaped flask
        
        add mix alcohol + CA slowly from dropping funnel
        
        add anti- bumping granules
        
        heat under REFLUX
        
        DISTILLATION - (rearrange apparatus)
        
        heat mix + collect distillate (2°C either side of BP of ester)
        
        add ester to SEPARATING FUNNEL
        
        shake with sodium carbonate solution (remove acidic impurities)
        
        invert + open tap - release pressure
        
        remove stopper + allow layers to separate
        
        discard aqueous layer (increases in vol when water added)
        
        DRYING STAGE
        
        add spatula of anhydrous calcium chloride to organic layer (drying agent)
        +add stopper
        
        shake
        
        repeat until ester changes colour from CLOUDY TO CLEAR
        
        FILTER to remove drying agent
        
        REDISTILL to remove organic impurities
        
        collect 1°C side of BP
    - - advantages
        
        no catalyst needed
        
        goes to completion/higher yield
        
        less purification
        
        completed @ room temp
      - IRREVERSIBLE
        why?
        
        gaseous HCl leaves system
        
        & removed from equilibrium
      - equation
      - observations
        
        steamy fumes (HCl)
        
        heat
  - - - conditions
        
        heated under reflux
        
        with dilute HCl acid
      - produces
        
        carboxylic acid
        
        alcohol
      - REVERSIBLE
      - SLOW
        
        water is WEAK nucleophile
      - equation
    - - conditions
        
        heated under reflux
        
        with dilute alkali (NaOH)
      - IRREVERSIBLE
        (advantage)
        (gives better yield)
      - FAST
        
        hydroxide is STRONG nucleophile
        
        as has negative charge
      - produces
        
        carboxylates
        
        alcohol
        
        add mineral acid (dilute HCl)
        
        to reform carboxylic acid
        
        'liberate free CA from its Na salt'
      - saponification