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

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

3. Burning Benzene – Smokey flameBurning Benzene http://www.youtube.com/watch?v=XhRHk4 zLR8A

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

5. Phenol, C 6 H 5 OH, (carbolic acid )

6. Phenol, C 6 H 5 OH 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 CO 2 Only esterifies with acid chloride (i.e. not with a carbox. Acid, RCOOH) …RING MUCH MORE REACTIVE THAN 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. Phenol with Br 2 (aq) c.f. benzene!

9. http://upload.wikimedia.org/wikipedia/commons/5/5c/EAS-ortho-para-meta.png Phenol with cold dil HNO 3 c.f. benzene!

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

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

12. Other Reactions (N.O.S.) - Demonstrate increased reactivity of the 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 amines ethylamine 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. Making paracetamol #1 http://www.ch.ic.ac.uk/rzepa/mim/drugs/html/paracet_text.htm (good short notes on overdose problem)http://www.ch.ic.ac.uk/rzepa/mim/drugs/html/paracet_text.htm para-acetylaminophenol

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

19. Reduction of Nitrobenzene to phenylamime (aniline)

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

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

22. coloursMethyl Orange The colours of Methyl Orange Other Azocompounds (salters chem) < A diazo dye

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

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

26. ? = addition polymer repeating unit of sodium poly(acrylate) Product name : SAP-Super Absorbent Polymer Chemical name : Sodium polyacrylate Monomer Molecular formula : C 3 H 4 O 2 monomer Many COOH (or COONa) groups allow for widespread large amount of interaction with water molecules

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

28. Video

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

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

31. Condensation polymers TeryleneTerylene is used to make fishing nets clothes (quick-dry, non-iron) cassette and video tapes

32. Condensation polymers: There are two main types of condensation polymer made from carboxylic acid derivatives: polyesters and polyamides. Terylene 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.

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

34. Kevlar Poly(N-substituted amide)

35. Kevlar again.

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

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

39. 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). light blue The three amino acids in the light blue box are basic ("amine" group in the side chain).

40. Amino acids – Ninhydrin rxn and test

41. 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.

42. Amino acids – analysis with ninhydrin chromatography

43. Protein synthesis (biological) Video (real time) Video 2

44. Salters Organic Toolbox Salters Organic Reactions.mht