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5.4.2 Organic nitrogen compounds: amines, amides, amino acids and proteins

5.4.2 Organic nitrogen compounds: amines, amides, amino acids and proteins. Benzene Reaction summary. http://en.labs.wikimedia.org/wiki/ A-level_Chemistry/OCR_%28 Salters%29/Reactions_of_arenes. Burning Benzene – Smokey flame http://www.youtube.com/watch?v=XhRHk4zLR8A.

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5.4.2 Organic nitrogen compounds: amines, amides, amino acids and proteins

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  1. 5.4.2 Organic nitrogen compounds: amines, amides, amino acids and proteins

  2. BenzeneReactionsummary http://en.labs.wikimedia.org/wiki/A-level_Chemistry/OCR_%28Salters%29/Reactions_of_arenes

  3. Burning Benzene – Smokey flame • http://www.youtube.com/watch?v=XhRHk4zLR8A

  4. Methoxybenzene and methylbenzene (toluene) • Also undergo E+ subn. Do so more readily than benzene.

  5. Phenol, C6H5OH, (carbolic acid )

  6. Phenol, C6H5OH • Early anesthetic (but burned the skin) • Poorly soluble (8.3 g dissolving in 100 mL ) • Does NOT behave like an aliphatic alcohol- is acidic, pKa = 10.0 (ethanol=15.9, ethanoic acid=4.75) • Although acidic, unlike –COOH, phenol NOT will react with carbonates and hydrogencarbonates to form CO2 • Only esterifies with acid chloride (i.e. not with a carbox. Acid, RCOOH) …RING MUCH MORE REACTIVETHAN BENZENE

  7. Solubility of phenol and phenoxide anion. Phenol in water (org solvent at bottom) > NaOH added > acidified http://www.sciencephoto.com/image/4210/530wm/A5000274-Phenol_reactions-SPL.jpg

  8. PhenolwithBr2(aq)c.f. benzene!

  9. PhenolwithcolddilHNO3c.f. benzene! • http://upload.wikimedia.org/wikipedia/commons/5/5c/EAS-ortho-para-meta.png

  10. E+ Subn in phenol • Many (Kekule)resonance structures http://chem-guide.blogspot.com/2010/04/electrophilic-substitution-of-phenol.html

  11. Rxns of benzene • http://clem.mscd.edu/~wiederm/oc2chp/oc2chpphenols/phenolrxnsummary.gif

  12. OtherReactions(N.O.S.)- Demonstrateincreasedreactivity ofthe ring

  13. Aspirin (synthesis #1) • http://www.ch.ic.ac.uk/rzepa/mim/drugs/html/aspirin_text.htm

  14. Aspirin (synthesis #2) • http://www.ch.ic.ac.uk/rzepa/mim/drugs/html/aspirin_text.htm

  15. Amines, amides and amino acids • Aliphatic amines, & aromatic aminesethylamine phenylamine a. give examples of: i. molecules that contain amine and amide functional groups ii. amino acids

  16. b. describe and carry out, where appropriate (using butylamine and phenylamine), reactions to investigate the typical behaviour of primary amines. This will be limited to: • i. characteristic smell • ii. miscibility with water as a result of hydrogen bonding and the alkaline nature of the resulting solution • iii. formation of salts • iv. complex ion formation with copper(II) ions • v. treatment with ethanoyl chloride and halogenoalkanes, eg making paracetamol

  17. para-acetylaminophenol Making paracetamol #1 • http://www.ch.ic.ac.uk/rzepa/mim/drugs/html/paracet_text.htm (good short notes on overdose problem)

  18. Making paracetamol #2 • http://en.wikipedia.org/wiki/Paracetamol

  19. Reduction of Nitrobenzene to phenylamime (aniline)

  20. Diazo formation • 1o, 2o and 3o aromatic based amines. Video 1o amine undergoing decomposition T>10oC

  21. Methyl orange via diazo coupling http://www.science.cmu.ac.th/educate/couresware_chem/203204/Arputtinan6.htm

  22. The colours of MethylOrange < A diazo dye • Other Azocompounds (salters chem)

  23. Polymers • Video of polymer – ‘bubblegum’ a.k.a. Plastics, rubber, food colouring, sucrose and dextrose – yum huh?

  24. Nylons… • Video 1 – intro to polymers • Video 2 – nylon – brave? no glasses guy • Video 3 – specific chemicals used nylon

  25. Product name : SAP-Super Absorbent Polymer • Chemical name : Sodium polyacrylate • Monomer Molecular formula : C3H4O2 Many COOH (or COONa) groups allow for widespread large amount of interaction with water molecules monomer ? = addition polymer repeating unit of sodium poly(acrylate)

  26. Super Absorbent Polymers for Diaper http://www.made-in-china.com

  27. Video

  28. Other water interacting polymers • Propeneamide Dissolving Plastics Poly(ethanol) Propeneamide • Webpage: DissolvingPolymers.mht ? = addition polymer repeating unit of poly(propeneamide)

  29. Dun WORi, POLYURETHANES ARE NOT ON THE SYLLABUS !!! Polyurethane formation (isocyanate with polyol) PU video http://ec.gc.ca/substances/nsb/images/Polyurethane_S1.gif

  30. Condensation polymers • Terylene is used to makefishing nets clothes (quick-dry, non-iron) cassette and video tapes

  31. Condensation polymers: There are two main types of condensationpolymer made from carboxylic acid derivatives: polyesters and polyamides. i) Polyesters: A well-known polyester, Terylene, is made by heatingethane-1,2-diol with dimethylbenzene-1,4-dicarboxylate (dimethyl terepthalate):The dimethlybenzene-1,4-dicarboxylate is obtained via the following reactionpathway:The manufacture of ethane-1,2-diol has already been described in section 26.4.2.

  32. Or simpler rxn (more edexcel friendly) not using the diester as previously, but the dicarbox acid…

  33. Kevlar Poly(N-substituted amide)

  34. Kevlar again.

  35. Synthesis of Kevlar Should be familiar with monomers and polymer requirements now. Poly(N-substituted) amide – similar to Nylon

  36. Amino acids. • Naturally occurring ones are L acids (laevorotatory) • Strecker synthesis give L and R (next slide)

  37. 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).

  38. Amino acids – Ninhydrin rxn and test

  39. 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.

  40. Amino acids – analysis with ninhydrin chromatography

  41. Protein synthesis (biological) • Video (real time) • Video 2

  42. Salters Organic Toolbox • Salters Organic Reactions.mht

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