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

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

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

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

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

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