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

2. This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Contain double or triple bonds, but do not show the same reactivity as other unsaturated hydrocarbons Benzene: C 6 H 6 Used mainly as solvents Substitution rather than Addition is favoured Aromatic Hydrocarbons

3. 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 Resonance Structure: Rearrange the bonding electrons 6 p-orbitals Delocalised orbital clouds

4. This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License FlurobenzeneTolueneEthylbenzene 2,4,6-Trinitrotoluene (TNT) Aniline 1,2-DichlorobenzenePhenol1,3-Dichlorobenzene 1,4-Dichlorobenzeneo-Xylenem-Bromostyrene Benzoic acid -ortho -para -meta Naming Aromatic Hydrocarbons

5. This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Substitution Aromatic Substitution reaction – Aromatic compound loses a hydrogen atom and another atom or group takes its place. It is possible for substitution to occur in more than one place on the ring. otha-Dinitrobenzenepara-Dinitrobenzenemeta-Dinitrobenzene Reactions of Aromatic Hydrocarbons

6. This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License –OH group (hydroxyl group) Replace -e with -ol CH 3 OH, methanol, simplest alcohols are classified as primary (1°), secondary (2°), or tertiary (3°) depending on the number of carbon atoms bonded to the carbon bearing the - OH group Primary Alcohol (1 o ) Secondary Alcohol (2 o ) Tertiary Alcohol (3 o ) Alcohols

7. 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 methanolethanolpropanol 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) Naming Alcohols

8. 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 Reactions of Alcohols

9. This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License –O- group (ether group) CH 3 OCH 3, dimethyl ether simplest Soluble in water- H-bonding to water - Polar Flammable – Ether can cause flash fires Low Reactivity – Make Good Reaction Solvents Naming: alkyl groups in alphabetical order followed by ether Ethers

10. Naming Aldehydes Change -e ending to –al ethane ethanal (acetaldehyde) Ketones Change -e ending to –one propanepropanone (acetone) This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Both contain a carbonyl group (C=O) Aldehyde Ketone Aldehydes and Ketones

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

13. This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Contains C=O and –OH group on same carbon Change -e to -oic acid Acetic acid: acid in vinegar Simplest: methanoic acid (formic acid) Methanoic acidEthanoic acidPropanoic acid Carboxilic acids

14. 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 Reactions of Carboxilic acids

15. This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Derived from carboxylic acids and alcohols Tend to be fragrant –Methyl butyrateapple –Ethyl butyratepineapple An ester name has two parts - the part that comes from the acid (propanoate) and the part that shows the alkyl group (methyl). Example: Methyl propanoate Ester

16. 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) Ester Acid Amide R 2 OH R+R+ H2OH2O R 2 NH base Carboxylate ester Sodium hydroxide Sodium Carboxylate Alcohol Reactions of Esters

17. This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Derived from ammonia by substituting H for alkyl groups. It is an alkali We have primary, secondary or tertiary amines depending on the number of H substituted Amines Ammonia Primary amine (1 o ) Secondary amine (2 o ) Tertiary amine (3 o )

18. 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 Amines

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

20. This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Acknowledgements JISC HEA Centre for Educational Research and Development School of natural and applied sciences School of Journalism SirenFM http://tango.freedesktop.org