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					  5.4.2 Organic nitrogen
compounds: amines, amides,
  amino acids and proteins
           Diazo formation
• 1o, 2o and 3o aromatic based amines.

Video 1o amine undergoing decomposition
 T>10oC
 Methyl orange via diazo coupling




http://www.science.cmu.ac.th/educate/
couresware_chem/203204/Arputtinan6.htm
The colours of Methyl Orange




• Other Azocompounds (salters chem)
                Polymers




• Video of polymer – ‘bubblegum’ a.k.a.
  Plastics, rubber, food colouring, sucrose
  and dextrose – yum huh?
               Nylons…
• Video 1 – intro to polymers
• Video 2 – nylon – brave? no glasses guy
• Video 3 – specific chemicals used nylon
• Product name : SAP-Super Absorbent
  Polymer
• Chemical name : Sodium polyacrylate
• Monomer Molecular formula : C3H4O2

    monomer                        Many COOH (or COONa)
                                   groups allow for widespread
                                   large amount of interaction
                                   with water molecules


   ? = addition polymer repeating unit of sodium poly(acrylate)
Super Absorbent Polymers for Diaper




      http://www.made-in-china.com
Video
 Other water interacting polymers
• Propeneamide
                                           Dissolving Plastics
                                              Poly(ethanol)




  Propeneamide



                                   •Webpage: DissolvingPolymers.mht



   ? = addition polymer repeating unit of poly(propeneamide)
Polyurethane formation (isocyanate with polyol)




                                                                PU video

    http://ec.gc.ca/substances/nsb/images/Polyurethane_S1.gif
     Condensation polymers
• Terylene is used to make
  fishing nets
  clothes (quick-dry, non-iron)
  cassette and video tapes
Condensation polymers: There are two main types of condensation
polymer made from carboxylic acid derivatives: polyesters and polyamides.

i) Polyesters: A well-known polyester, Terylene, is made by heating
ethane-1,2-diol with dimethylbenzene-1,4-dicarboxylate (dimethyl terepthalate):




The dimethlybenzene-1,4-dicarboxylate is obtained via the following reaction
pathway:




The manufacture of ethane-1,2-diol has already been described in section 26.4.2.
   Or simpler rxn (more edexcel
 friendly) not using the diester as
previously, but the dicarbox acid…
                            Kevlar




Poly(N-substituted amide)
Kevlar again.
        Synthesis of Kevlar




Should be familiar with monomers and
polymer requirments now.

         Poly(N-substituted) amide – similar to Nylon
             Amino acids.
• Naturally occurring ones are L acids
  (laevorotatory)

• Strecker synthesis give L and R (next
  slide)
The amino acids vary
in their side chains
(indicated in blue in
the diagram).


The eight amino
acids in the orange
area are nonpolar
and hydrophobic.
The other amino
acids are polar and
hydrophilic ("water
loving").


The two amino acids
in the magenta box
are acidic ("carboxy"
group in the side
chain).


The three amino
acids in the light
blue box are basic
("amine" group in the
side chain).
Amino acids – Ninhydrin rxn and
             test
     Ninhydrin rxn with amino acids.
Procedure
Add about 2 mg of the sample to 1 mL of a solution of 0.2 g of ninhydrin
(1,2,3indanetrione monohydrate) in 50 mL of water. The test mixture is
heated to boiling for 15-20 sec; This reaction is important not only because it
is a qualitative test, but also because it is the source of the absorbing
material that can be measured quantitatively by an automatic amino acid
analyzer. This color reaction is also used to detect the presence and position
of amino acids after paper chromatographic separation.

Positive Test
A blue to blue-violet color is given by a-amino acids and constitutes a
positive test. Other colors (yellow, orange, red) are negative.

Complications
Proline, hydroxyproline, and 2-, 3-, and 4-aminobenzoic acids fail to give a
blue color but produce a yellow color instead.

Ammonium salts give a positive test. Some amines, such as aniline, yield
orange to red colors, which is a negative test.
Amino acids – analysis with
        ninhydrin
                     chromatography
  Protein synthesis (biological)
• Video (real time)
• Video 2
• Salters Organic Toolbox
• Salters Organic Reactions.mht

				
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