HCN and CN– in synthesis

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Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University.

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Presentation transcript:

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

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

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