Lecture materials for the Introductory Chemistry course for Forensic Scientists, University of Lincoln, UK. See http://forensicchemistry.lincoln.ac.uk/ for more details.

1. This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Organic Chemistry II University of Lincoln presentation

3. Resonance Structure: Rearrange the bonding electrons This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Delocalisation, Resonance: Stabilise molecules, so make them less reactive Three sp2 hybrid orbitals arrange themselves as far apart as possible -which is at 120° on a plane. The remaining p orbital is at right angles to them. Each carbon atom uses the sp2 hybrids to form σ-bonds with two other carbons and one hydrogen atom. Delocalised or Conjugated System: π-bonding electrons can move within the molecule 6 p-orbitals Delocalised orbital clouds

4. Naming Aromatic Hydrocarbons This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Flurobenzene Toluene Ethylbenzene 2,4,6-Trinitrotoluene (TNT) Aniline 1,2-Dichlorobenzene Phenol 1,3-Dichlorobenzene 1,4-Dichlorobenzene o -Xylene m -Bromostyrene Benzoic acid -ortho -para -meta

7. Naming Alcohols This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Polyhydroxy alcohols are alcohols that possess more than one hydroxyl group methanol ethanol propanol 2-propanol or propan-2-ol or isopropyl alcohol 2-ethyl-1-butanol or 2-ethyl-butan-1-ol 1,2-Ethanediol (ethylene glycol) 1,2-propanediol (propylene glycol) 1,2,3-propanetriol (glycerol)

8. Reactions of Alcohols This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License ■ Reaction with acids to produce Esters ■ Redox reaction (Reduction and oxidation) Ethanol Acetic Acid (ethanoic acid) Ethyl acetate Acetaldehyde Alcohol Dehydrogenase Acetic Acid

11. Reactions of Aldehydes and ketones This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Synthesis: produced by oxidation of alcohol Reduction of carbonyl group to produce alcohols Primary Alcohol Oxidation Reduction Secondary Alcohol Oxidation Reduction Tertiary Alcohol Cannot be oxidised

12. Oxidation of carbonyl group This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Oxidation Strong Oxidation Reduction Reduction Carboxylic acid

14. Reactions of Carboxilic acids This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License ■ Esterification reactions ■ Reduction to aldehydes Acetic Acid (ethanoic acid) Ethyl acetate

16. Reactions of Esters This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Substitution Reduction of esters Hydrolisis of esters (basic) Carboxylate ester Sodium hydroxide Sodium Carboxylate Alcohol Ester Acid Amide R 2 OH R + H 2 O R 2 NH base

18. Amines This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License 1,4-butanediamine Putrescine (found in decaying meat) (1 o ) Amphetamine (dangerous stimulant) (1 o ) Piperidine Triethylamine (3 o ) Isopropylamine (1 o ) 1,5-pentanediamine Cadaverine (found in the putrefaction of cadavers

19. Reactions of Amines This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Alkylation Oxidation reduction Phenylamine