Organic Chemistry: Classification of Organic Compounds

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

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Organic Chemistry: Classification of Organic Compounds

  1. 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. 2. Aromatic Hydrocarbons This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License <ul><li>Contain double or triple bonds, but do not show the same reactivity as other unsaturated hydrocarbons </li></ul><ul><li>Benzene: C 6 H 6 </li></ul><ul><li>Used mainly as solvents </li></ul><ul><li>Substitution rather than </li></ul><ul><li>Addition is favoured </li></ul>
  3. 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. 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. 5. Reactions of Aromatic Hydrocarbons This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Substitution <ul><li>Aromatic Substitution reaction – Aromatic compound loses a hydrogen atom and another atom or group takes its place. </li></ul><ul><li>It is possible for substitution to occur in more than one place on the ring. </li></ul>otha -Dinitrobenzene para -Dinitrobenzene meta -Dinitrobenzene
  6. 6. Alcohols This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License <ul><li>– OH group (hydroxyl group) </li></ul><ul><li>Replace - e with - ol </li></ul><ul><li>CH 3 OH, methanol, simplest </li></ul><ul><ul><li>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 </li></ul></ul>Primary Alcohol (1 o ) Secondary Alcohol (2 o ) Tertiary Alcohol (3 o )
  7. 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. 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. 9. Ethers This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License <ul><li>– O- group (ether group) </li></ul><ul><li>CH 3 OCH 3 , dimethyl ether simplest </li></ul><ul><li>Soluble in water- H-bonding to water - Polar </li></ul><ul><li>Flammable – Ether can cause flash fires </li></ul><ul><li>Low Reactivity – Make Good Reaction Solvents </li></ul><ul><li>Naming: alkyl groups in alphabetical order followed by ether </li></ul>
  10. 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 <ul><li>Both contain a carbonyl group (C=O) </li></ul><ul><li>Aldehyde Ketone </li></ul>
  11. 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. 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. 13. Carboxilic acids This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License <ul><li>Contains C=O and –OH group on same carbon </li></ul><ul><li>Change - e to - oic acid </li></ul><ul><li>Acetic acid: acid in vinegar </li></ul><ul><li>Simplest: methanoic acid </li></ul><ul><li>(formic acid) </li></ul>Methanoic acid Ethanoic acid Propanoic acid
  14. 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. 15. Ester This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License <ul><li>Derived from carboxylic acids and alcohols </li></ul><ul><li>Tend to be fragrant </li></ul><ul><ul><li>Methyl butyrate apple </li></ul></ul><ul><ul><li>Ethyl butyrate pineapple </li></ul></ul><ul><li>An ester name has two parts - the part that comes from the acid (propanoate) and the part that shows the alkyl group (methyl). </li></ul><ul><li>Example: Methyl propanoate </li></ul>
  16. 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. 17. Amines This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License <ul><li>Derived from ammonia by substituting H for alkyl groups. It is an alkali </li></ul><ul><li>We have primary, secondary or tertiary amines depending on the number of H substituted </li></ul>Ammonia Primary amine (1 o ) Secondary amine (2 o ) Tertiary amine (3 o )
  18. 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. 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. 20. Acknowledgements <ul><li>JISC </li></ul><ul><li>HEA </li></ul><ul><li>Centre for Educational Research and Development </li></ul><ul><li>School of natural and applied sciences </li></ul><ul><li>School of Journalism </li></ul><ul><li>SirenFM </li></ul><ul><li>http:// tango.freedesktop.org </li></ul>This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

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