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HCN and CN – in synthesis Increasing carbon chain length

HCN and CN – in synthesis Increasing carbon chain length. Formation of C–C  N. Reaction of haloalkanes with CN – RBr + CN –  RCN + Br – Reaction of carbonyl compounds with HCN: Aldehydes: RCHO + HCN  RCH(CN)COH Ketones: RCOR’ + HCN  RCR’(CN)COH. Haloalkane  nitrile.

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HCN and CN – in synthesis Increasing carbon chain length

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  1. HCN and CN– in synthesis Increasing carbon chain length

  2. Formation of C–CN Reaction of haloalkanes with CN– RBr + CN– RCN + Br– Reaction of carbonyl compounds with HCN: Aldehydes: RCHO + HCN  RCH(CN)COH Ketones: RCOR’ + HCN  RCR’(CN)COH

  3. Haloalkane  nitrile Reagents and conditions • CN– ions, e.g. KCN(aq) in ethanol solvent Mechanism: • Nucleophilic substitution charge C–C bond forms lone pair

  4. Carbonyl nitrile Reagents and conditions • CN– ions in dilute acid, e.g. KCN(aq)/H2SO4(aq) Mechanism: • Nucleophilic addition charge lone pair C–C bond forms

  5. Nitriles in synthesis Reduction amines • H2 and Ni catalyst Acid hydrolysis carboxylic acids • Aqueous acid, H+/H2O, e.g. HCl(aq) nitrile amine nitrile carboxylic acid

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