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Module 6 Chapter 27 (27.1 Amines (Classifying (Primary- 1 Carbon directly…

- - - - -NH2 on end of chain
        
        Suffix- -amine
        
        Prefix- Alkyl (longest carbon chain)
        
        e.g. CH3NH2= Methylamine
      - -NH2 not on end of chain
        
        Prefix- Amino
        
        Suffix- Alkane (longest carbon chain)
        
        e.g. CH3CH(NH2)CH3= 2-aminopropane
        
        Must give it a number
      - Multiple groups
        
        Prefix- amino
        
        Suffix- alkane (longest carbon chain)
        
        Number them and add di, tri etc.
        
        e.g. NH2CH2CH2CH2NH2= 1,3- diaminopropane
    - - Same groups
        
        Suffix- amine
        
        Prefix- dialkyl (longest carbon chain)
        
        e.g. (CH3CH2CH2)2 NH= dipropylamine
      - Different groups
        
        Longest chain= alkylamine
        
        Shorter chain N-alkyl in alphabetical order
        
        e.g. CH3NHCH2CH3= N-methylethylamine
    - - Same groups
        
        Prefix- trialkyl (longest carbon chain)
        
        Suffix- amine
        
        (CH3CH2CH2)2N= tripropylamine
      - Different groups
        
        Longest chain- alkylamine
        
        Shorter chain N-alkyl in alphabetical order
        
        e.g. CH3N(CH2CH3)CH2CH2CH3= N-ethyl-N-methylpropylamine
  - - - Good bases lone pair of N atom of -NH2 can accept protons
      - When they accept a proton, dative covalent bond forms between lone pair of electrons on nitrogen and the proton
      - Amine + H+ -> Alkylammonium ion
      - Amine + Acid -> Alkylammonium Salt
  - - - Primary
        
        1) Add excess ammonia to a haloalkane in an ethanol solvent
        
        2) Add aqueous alkali to liberate amine from salt
        
        Excess ammonia reduces further substitution of amine group to form secondary and tertiary amines
        
        In reaction ammonia acts as nucleophile, replaces halogen on haloalkane with NH2 group
        
        Ethanol Solvent prevents any substitution of the haloalkane by water to produce alcohols
      - Secondary
        
        1) Primary Amine+ Haloalkane -> Dialkylammonium salt (use ethanol solvent)
        
        2) Dialkylammonium salt + Base -> Secondary Amine + Salt + H2O
      - Tertiary
        
        1) Secondary Amine+ Haloalkane -> Trialkylammonium Salt (use ethanol solvent)
        
        2) Trialkylammonium Salt + Base -> Tertiary Amine + Salt + H2O
    - - Made by reduction of nitro-arenes (have nitro (-NO2) group attached to aromatic ring)
      - 1) Heat nitro-arene under reflux with tin metal in conc. HCl
      - 2) Add excess base (aq) to from amine from salt
- - - - Prefix- amino (or diamino) need to number the carbon atom
      - Suffix- carboxylic acid (longest chain)
      - e.g. 2,6-diaminohexanoic acid
  - - - Amino Acid + Acid -> Ammonium Salt
      - Because amine group is basic
    - - Amino Acid + Base -> Salt + Water
      - Amino Acid + Alcohol -> Ester + Water
      - This is done under acidic conditions so ammonium salt of amine made
      - If there are 2 COOH they both react so balance accordingly
  - - - Tertiary
        
        3 Carbon atoms bonded to N
        
        Prefix- Shorter chains N-alkyl
        
        e.g. N-ethyl-N-methylethanamide
        
        Suffix- alkanamide
      - Secondary
        
        2 Carbon Atoms bonded to N
        
        Prefix- shorter chain N-alkyl
        
        Suffix- alkanamide
        
        e.g. N-ethylethanamide
      - Primary
        
        1 Carbon atom attached to N
        
        Prefix- Alkane (no e)
        
        Suffix- amide
        
        e.g. ethanamide
  - - - Found in molecules with chiral centre (carbon atom joined to 4 different atoms or groups of atoms)- leads to existance of 2 non-superimposable moleucles (enantiomers)
      - All amino acids (except glycine H2NCH2COOH) contain a chiral carbon
      - To be chiral they can't have double bond or be in an aromatic ring
      - Chiral Carbon
- - - - Monomer must contain a carboxylic acid (-COOH) and alcohol (-OH) functional group
    - - One monomer is a diol- 2 hydroxyl groups (-OH)
      - One monomer is a dicarboxylic acid- 2 carboxyl groups (-COOH) at either end
    - - ACID
        
        Conditions- H2O/H+ (hot aqueous acid)
        
        Often incomplete- Polyester ⇌ Dicarboxylic acid + Diol
      - BASE
        
        Conditions- H2O/ OH- (hot aqueous alkali)
        
        Polyester-> Diarboxylic acid salt + Diol
  - - - Monomer must be an amino acid (contains an amine (-NH2) and carboxyl (-COOH) functional group)
    - - One monomer is a dicarboxylic acid- 2 carboxyl groups (-COOH) at either end (can be an acyl chloride)
      - One monomer is a diamine (-NH2 group at either end)
    - - Often incomplete-Polyamide ⇌ Dicarboxylic acid + Ammonium Salt
      - Conditions- H2O/H+ (hot aqueous acid)
    - - Polyamide -> Dicarboxylic acid salt + Diamine
      - Conditions- H2O/ OH- (hot aqueous alkali)