Unit 19: Nitrogen Compounds

Forming amines (-NH₂)
> n__ s__ w/ e__ e__ N__ + h__ + p__ w/ h__ → primary amine + HX
> halogen replaced w/ N__
> if not in e__, amine acts as n__ → m__ of amines made

nucleophilic substitution, excess ethanoic NH3, heat, pressure, halogenoalkane, NH2, excess, nucleophile, mixture

Forming nitriles (-C≡N)
> n__ s__ w/ e__ K__ + r__ w/ h__ → nitrile + __
> extra _ added

nucleophilic substitution, ethanoic KCN, reflux, halogenoalkane, X-, C

Forming hydroxynitriles
> n__ a__ w/ __ + __ catalyst + h__ (KCN + acid → HCN)
> O → __, C≡N added

nucleophilic addition, HCN, KCN, heat, OH

Reactions of nitriles
> h__ w/ d__ a__/alkali (-CN → COOH)
acid:
> nitrile + __ + __ → c__ a__ + N__

hydrolysis, dilute acid, HCl, H2O, carboxylic acid, NH4Cl

Reactions of nitriles
> h__ w/ d__ acid/a__ (-CN → COOH)
alkali:
> nitrile + N__ + __ → s__ c__ + N__
> further acidification → c__ a__

hydrolysis, dilute, alkali, NaOH, H2O, sodium carboxylate, NH3, carboxylic acid