NITRILES AND ISOCYANIDES - PowerPoint PPT Presentation

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NITRILES AND ISOCYANIDES

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  1. NITRILES AND ISOCYANIDES ethannitrile, acetonitrile phenylisocyanide butannitrile benzonitrile, benzoic acid nitrile 3-oxo-pentannitrile 3-methylcyclopentane carbonitrile 4-isocyanobenzoic acid thiazole-2-carbonitrile 3-cyano-pentanoic acid

  2. NITRILES AND ISOCYANIDES • REACTIVITY: • activation of the triple bond by the attack of electrophile at N atom followed by nucleophilic attack at carbon atom • a strong nucleophile is able to attack carbon atom directly • acidic hydrogen atom in a-position carboxylic acid carboxylic acid amide hydrolysis is carried out at higher temperature mostly by conc. H2SO4

  3. NITRILES AND ISOCYANIDES • REACTIVITY: • activation of the triple bond by the attack of electrophile at N atom followed by nucleophilic attack at carbon atom • a strong nucleophile is able to attack carbon atom directly • acidic hydrogen atom in a-position

  4. NITRILES AND ISOCYANIDES • REACTIVITY: • activation of the triple bond by the attack of electrophile at N atom followed by nucleophilic attack at carbon atom • a strong nucleophile is able to attack carbonatom directly • acidic hydrogen atom in a-position

  5. NITRILES AND ISOCYANIDES • REACTIVITY: • activation of the triple bond by the attack of electrophile at N atom followed by nucleophilic attack at carbon atom • a strong nucleophile is able to attack carbon atom directly • acidic hydrogen atom in a-position pKa = 25 condensation with aldehydes and ketones Knoevenagel condensation condensation with another nitrile Thorpe-Ziegler reaction

  6. NITRILES AND ISOCYANIDES poisons and teribly smelling compounds react with electrophiles at carbon atom formic acid derivatives „isonitril“ test – a proof of amino group in biological material