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Nitrile Synthesis: Carbon Chain Lengthening Reactions and Mechanisms

Learn about methods to increase carbon chain length using reactions involving C-H bonds, haloalkanes, carbonyl compounds, and nitriles. Understand the formation of C-C≡N bonds and conversion pathways. Detailed mechanisms and reagents are provided for nitrile synthesis, reduction to amines, and hydrolysis to carboxylic acids. Enhance your knowledge of important chemical transformations for organic synthesis.

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Nitrile Synthesis: Carbon Chain Lengthening Reactions and Mechanisms

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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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