AMINES AMIDES C27

    Cards (30)

    • Amines
      Derived from ammonia in which 1 or more H atoms is replaced by a carbon chain or ring
    • Amines
      • Serotonin
      • Pseudoephedrine
    • Amines
      • Neurotransmitter
      • Used in medicines
    • Amine classification
      • Primary
      • Secondary
      • Tertiary
    • Primary amine

      N atom is attached to 1 alkyl/aryl group
    • Secondary amine
      N atom is attached to 2 alkyl/acyl groups
    • Tertiary amine

      N atom is attached to two alkyl/acyl groups
    • Amine naming examples
      • N-methylpropylamine
      • N-ethyl, N-methyl propylamine
    • Amines act as bases
      Their lone pair of electrons on the N atom can accept a proton (H+) which can then form a dative covalent bond between the lone pair and the proton
    • Base strength of amines
      Increases if lone pair of electrons on the nitrogen atom are more readily avalible, which depends on the group attached to the N atom
    • Preparation of aliphatic primary amines
      1. Ammonia + HaloalkaneAmmonium salt
      2. Ammonium salt + Alkali (aq) → Primary amine
      ethanol = prevent haloalkane being substituted by h20 to create alcohol
      NH3 in excess = to reduce further substitution
    • Preparation of secondary and tertiary amines
      1. Primary amine + HaloalkaneSecondary salt
      2. Secondary salt + AlkaliSecondary amine
      3. Secondary amine + HaloalkaneTertiary salt
      4. Tertiary salt + AlkaliTertiary amine
    • Preparation of aromatic amines
      1. Nitrobenzene + 6 [H] →(1=tin/reflux & 2= excess NAOH)phenylamine + H2O
      A) nitrobenzene + reflux of Hcl/Tin = phenylammoniumchloride
      B) phenylammoniumchloride + excess NAOH = phenylamine
    • Amino acids
      Have both amine and carboxylic acid groups, so can act as both acids and bases (amphoteric)
    • Amine group reactions
      Amine group (NH2) + AcidSalt
    • Carboxylic acid group reactions
      • COOH group + Alkali (aq) → Salt + H2O
      • COOH group + AlcoholEster + H2O
    • Amides
      Derivatives of carboxylic acids and have a N atom bonded to one side
    • Types of amides
      • Primary amide = one C bonded to N atom
      • Secondary amide = two C bonded to N atom
      • Tertiary amide = three C bonded to N atom
    • Preparation of primary amides
      Ammonia + Acyl chloridePrimary amide
    • Preparation of secondary amides
      Primary amine + Acyl chlorideSecondary amide
    • Stereoisomerism
      Compounds with the same structural formula but a different arrangement of atoms
    • Optical isomerism

      Found in molecules with a chiral centre (C atom attached to 4 different atoms/groups)
    • Amino acid chirality
      All amino acids contain a chiral α-carbon atom except glycine
    • Test for optical isomers
      Optically active isomers will rotate plane polarised light, one enantiomer rotates clockwise (D) and one rotates anticlockwise (L)
    • Condensation polymerisation
      The joining of monomers with the loss of a small molecule (H2O or HCl)
    • Condensation polymers

      • Polyesters
      • Polyamides
    • Polyester formation-COO-

      1. Short chain ester monomers are joined to make ester linkages
      2. Can be made from one monomer with two different functional groups or two different monomers each with two functional groups

      COOH&OH MONOMER X2 = POLYESTER
      DIOL MONOMER+ DICOOH ACID MONOMER= POLYESTER + H20
      DIOL MONOMER+ DIACYL CHLORIDE MONOMER= POLYESTER + HCL
    • Polyamide formation-CONH-

      1. Short chain amide monomers are joined together to make amide linkages/peptide bonds
      2. Can be made from one monomer with two different functional groups or two different monomers each with two functional groups
      COOH&NH2 MONOMER X2 = POLYAMIDE
      DIAMINE + COOH ACID = POLYAMIDE + H20
      DIAMINE + DIACYL CHLORIDE = POLYAMIDE + HCL
    • Polyesters and polyamides can be hydrolysed using hot alkali (aq) or hot acid (HCl)
    • Types of polymerisation
      Addition: Monomer has C=C double bond
      Condensation: Two monomers each with different functional groups or one monomer with 2 different functional groups
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