Organic Chemistry: Classification of Organic Compounds
- 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. Aromatic Hydrocarbons 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
- 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
- 5. Reactions of Aromatic Hydrocarbons 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 -Dinitrobenzene para -Dinitrobenzene meta -Dinitrobenzene
- 6. Alcohols 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 )
- 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
- 9. Ethers 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
- 10. Aldehydes and Ketones Naming Aldehydes Change -e ending to –al ethane ethanal (acetaldehyde) Ketones Change -e ending to –one propane propanone (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
- 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
- 13. Carboxilic acids 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 acid Ethanoic acid Propanoic 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
- 15. Ester 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 butyrate apple Ethyl butyrate pineapple 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
- 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
- 17. Amines 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 Ammonia Primary amine (1 o ) Secondary amine (2 o ) Tertiary amine (3 o )
- 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
- 20. Acknowledgements JISC HEA Centre for Educational Research and Development School of natural and applied sciences School of Journalism SirenFM http:// tango.freedesktop.org This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License