Carbonyl compounds

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  • Carbonyl compounds
    • Aldehydes and Ketones
      • Aldehydes are readily oxidised to carboxylic acids
        • Tollens' reagent forms a silver mirror with aldehydes
        • Fehling's and Benedict's solution forms a brick red precipitate
      • Producing a hydroxynitrile
        • HCN is extremely toxic, so KCN is also used
        • Nucleophilic substitution with a CN- ion
          • HCN is extremely toxic, so KCN is also used
        • Mechanism
      • Reduction of aldehydes and ketones
        • Aldehydes are reduced to primary alcohols
          • Reducing agent: NaBH4 or LiAlH4
        • Ketones are  reduced to secondary alcohols
          • Reducing agent: NaBH4 or LiAlH4
        • Mechanism
    • Carboxylic acids
      • Weak acids
        • The carbonyl (-COOH) can donate a H+
      • Will react with carbonates to produce C02.
        • The carbonyl (-COOH) can donate a H+
        • 2(R-COOH) + R2CO3 --> 2(RCOOR) + CO2 + H2O
      • Involved in esterificationwith alcohol
        • A strong acid catalyst (e.g. sulphuric acid) is required
        • RCOOH + ROH --> RCOOR + H2O
    • Esters
      • Esters have pleasant smells
      • Common uses of esters include use in solvents, plasticisers, perfumes and food flavourings.
      • Vegetable oils and animal fats are esters of glycerol
      • Hydrolysis of esters
        • Reverse esterification
        • RCOOR + H20 --> RCOOH + ROH
        • Vegetable oils and animal fats can be hydrolysed to give soap, glycerol and long chain carboxylic acids
          • Esterification of biodiesel
    • Acyl chlorides and acid anhydrides
      • Acyl chlorides/acid anhydrides with  ammonia / primary amines
        • Nucleophilic substitution-elimination
        • Acid chloride mechanism
        • Acid anhydride mechanism
      • Acyl chlorides/acid anhydrides with water, alcohols, ammonia and primary amines.
        • Acid anhydride mechanism
        • Acyl chloride mechanism
          • Nucleophilic substitution-elimination
            • Acid anhydride mechanism
      • Industrial advantages of using acid anhydrides over acyl chlorides
        • Acid anhydride is cheaper
        • Acid anhydride is less vigorously hydrolysed, so is less corrosive
        • Acid anhydride does not produce harmful HCl fumes

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