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Understanding Aromatic Hydrocarbons and Alcohols in Organic Chemistry II

This presentation covers the fundamental concepts of aromatic hydrocarbons and alcohols, focusing on their structure, reactivity, and naming conventions. Aromatic hydrocarbons, such as benzene and its derivatives, display unique stability due to resonance and substitution reactions. The section on alcohols introduces the classification of primary, secondary, and tertiary alcohols, along with key reactions like esterification and oxidation. By the end of this presentation, students will grasp the importance of these compounds in organic chemistry applications.

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Understanding Aromatic Hydrocarbons and Alcohols in Organic Chemistry II

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

  2. Aromatic Hydrocarbons • Contain double or triple bonds, but do not show the same reactivity as other unsaturated hydrocarbons • Benzene: C6H6 • Used mainly as solvents • Substitution rather than Additionis favoured This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

  3. Resonance Structure:Rearrange the bonding electrons 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 Delocalised orbital clouds 6 p-orbitals This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

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

  5. Reactions of Aromatic Hydrocarbons 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 meta-Dinitrobenzene para-Dinitrobenzene This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

  6. Alcohols • –OH group (hydroxyl group) • Replace -e with -ol • CH3OH, 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 (1o) Secondary Alcohol (2o) Tertiary Alcohol (3o) This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

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

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

  9. Ethers • –O- group (ether group) • CH3OCH3, 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 This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

  10. Aldehydes and Ketones • Both contain a carbonyl group (C=O) Aldehyde Ketone 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

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

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

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

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

  15. Ester • 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 This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

  16. R2OH R+ Ester H2O Acid R2NH base Amide Reactions of Esters Substitution Reduction of esters Hydrolisis of esters (basic) Carboxylate ester Sodium hydroxide Sodium Carboxylate Alcohol This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

  17. Amines • 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 Primary amine (1o) Secondary amine (2o) Tertiary amine (3o) Ammonia This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

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

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

  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

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