Alkohol dan fenol

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Alkohol dan fenol

  1. 1. Lisa Andina, S. Farm., Apt.
  2. 2. Alcohols <ul><li>Classification </li></ul><ul><li>Primary: carbon with –OH is bonded to one other carbon. </li></ul><ul><li>Secondary: carbon with –OH is bonded to two other carbons. </li></ul><ul><li>Tertiary: carbon with –OH is bonded to three other carbons </li></ul><ul><li>Aromatic (phenol): -OH is bonded to a benzene ring </li></ul>
  3. 3. Classify these:
  4. 4. IUPAC Nomenclature <ul><li>Find the longest carbon chain containing the carbon with the -OH group. </li></ul><ul><li>Drop the -e from the alkane name, add -ol. </li></ul><ul><li>Number the chain, starting from the end closest to the -OH group. </li></ul><ul><li>Number and name all substituents. </li></ul>
  5. 5. Name this:
  6. 6. Hydroxy Substituent <ul><li>When -OH is part of a higher priority class of compound, it is named as hydroxy. </li></ul><ul><li>Example: </li></ul>4-hydroxybutanoic acid
  7. 7. Naming Diols <ul><li>Two numbers are needed to locate the two -OH groups. </li></ul><ul><li>Use -diol as suffix instead of -ol. </li></ul>
  8. 8. Physical Properties <ul><li>Unusually high boiling points due to hydrogen bonding between molecules. </li></ul><ul><li>Small alcohols are miscible in water, but solubility decreases as the size of the alkyl group increases </li></ul>
  9. 9. Boiling Points
  10. 10. Solubility decreases as the size of the alkyl group increases . =>
  11. 11. Acidity of Alcohols <ul><li>p K a range: 15.5-18.0 (water: 15.7) </li></ul><ul><li>Acidity decreases as alkyl group increases. </li></ul><ul><li>Halogens increase the acidity. </li></ul><ul><li>Phenol is 100 million times more acidic than cyclohexanol! </li></ul>
  12. 12. Pembuatan <ul><li>Reduction of Aldehydes/Ketones </li></ul><ul><ul><li>Hydrogenation </li></ul></ul>
  13. 13. <ul><ul><li>Hydride Reductions </li></ul></ul>
  14. 14. <ul><li>Reduction of Carboxylic Acids and Esters </li></ul><ul><ul><li>Lithium Aluminum Hydride Reduction </li></ul></ul>
  15. 15. <ul><li>Acid-Catalyzed Hydration of Alkenes </li></ul>
  16. 16. <ul><li>Hydration of Alkenes via Oxymercuration/Demercuration </li></ul>
  17. 17. <ul><li>Hydroboration-Oxidation of Alkenes </li></ul>
  18. 18. <ul><li>Grignard Additions to Aldehydes/Ketones </li></ul>
  19. 19. <ul><li>Grignard Additions to Esters </li></ul>
  20. 20. <ul><li>Typical Alcohol Reactions </li></ul><ul><li>Reaction with Active Metals </li></ul>
  21. 21. <ul><li>Hydrogen Halide Conversion of Alcohols to Alkyl Halides </li></ul>
  22. 22. <ul><li>Haloform Reaction </li></ul>
  23. 23. Phenols Ar-OH <ul><li>Phenols are compounds with an –OH group attached to an aromatic carbon. Although they share the same functional group with alcohols, where the –OH group is attached to an aliphatic carbon, the chemistry of phenols is very different from that of alcohols. </li></ul>
  24. 24. Nomenclature. <ul><li>Phenols are usually named as substituted phenols. The methylphenols are given the special name, cresols. Some other phenols are named as hydroxy compounds. </li></ul>
  25. 25. physical properties <ul><li>phenols are polar and can hydrogen bond </li></ul><ul><li>phenols are water insoluble </li></ul><ul><li>phenols are stronger acids than water and will dissolve in 5% NaOH </li></ul><ul><li>phenols are weaker acids than carbonic acid and do not dissolve in 5% NaHCO3 </li></ul>
  26. 26. phenols, syntheses: <ul><li>1. From diazonium salts </li></ul><ul><li>2. Alkali fusion of sulfonates </li></ul>
  27. 27. <ul><ul><ul><li>Hydrolysis of Chlorobenzene (Dow Process) </li></ul></ul></ul><ul><ul><ul><ul><li>Chlorobenzene is heated with sodium hydroxide under high pressure </li></ul></ul></ul></ul>
  28. 28. From Cumene Hydroperoxide <ul><li>Benzene and propene are the starting materials for a three-step sequence that produces phenol and acetone </li></ul><ul><li>Most industrially synthesized phenol is made by this method </li></ul>

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