P.l alcohols and phenols

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P.l alcohols and phenols

  1. 1. Alcohols and Phenols
  2. 2. ALCOHOL a compound that contains an -OH (hydroxyl) group bonded to a tetrahedral carbon. Methanol (CH3OH): simplest alcohol
  3. 3. CHEMICAL PROPERTIES  An alcohol is made up of a chain of carbons and hydrogen, where an –OH molecule attaches to where a Hydrogen molecule is supposed to be attached to a Carbon.  The position of the OH group has little effect on the chemical properties except in their response to mild oxidizing agents.
  4. 4. USES OF ALCOHOLS  Disinfectants  Solvents  Liquor  High efficiency fuels  Used to synthesize other organic compounds Fungicides Cosmetics Used to make vinegar Used in the manufacturing of plastics
  5. 5. USES (CONTINUED)  Methanol- Solvent for fats, oils, and resins. Manufacture of dyes, antifreeze, and plastics.  Ethanol- Solvent for paints, glues, pharmaceuticals, and explosives.  Cyclohexanol-Intermediate in making chemicals used in nylon manufacture.
  6. 6. DANGEROUS PROPERTIES  Very combustible  Poisonous to an extent  Addiction  Bodily damage caused by exposure
  7. 7. Alcohol products Product % of Ethyl Alcohol BEER 3.5-9 WINE 12 BRANDY 40-45 WHISKEY 45-55 RUM 45
  8. 8. Ethanol  Toxic to humans  Acute poisoning kills several hundred a year (drinking contests)  Long term poisioning  Most serious drug problem in US  40 times more addicts than heroin
  9. 9. Isopropyl Alcohol  Rubbing alcohol  Rapid evaporation  Antiseptic  More toxic than ethanol, but induces vomitting  Used for the manufacture of acetone
  10. 10. PHYSICAL PROPERTIES  Boiling point increases as MW increases.  Solubility in water decreases as MW (due to increase in C-H) increases.  Alcohols are semi-polar molecules  C-O and O-H bonds: polar covalent  C-H bonds: non-polar covalent
  11. 11. Phenol  The antiseptic property of phenol was discovered in 1865 by Joseph Lister, a physician in Scotland.  Listerine, named after him, contains phenol as the active ingredient.  Today, over two million tons of phenol are made each year in the US alone.  Phenol is used for resins, glue to make plywood, plastics, and pharmaceuticals. OH
  12. 12. Phenols Ar-OH 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.
  13. 13. Experimental Result 1 ml water + Solubility pH Methanol Miscible Basic Ethanol Miscible Basic Propanol Miscible Basic N-butyl Immiscible Basic N-amyl Immiscible Basic Phenol Immiscible Acidic
  14. 14. CHEMICAL PROPERTIES  Reaction with Lucas Reagent  Lucas reagent: ZnCl2 in HCl  Positive result: formation of turbidity or two layers  General equation: R - OH R - Cl + H2O ZnCl2,HCl
  15. 15. Experimental Result most reactive more reactive least reactive Reactivity turbidity 3o-butyl alcohol turbidity 2o-butyl alcohol turbidity n-butyl alcohol Product/s formed Visible (+) Result Compound Ethanol (Ethyl alcohol) 1-Propanol (Propyl alcohol) 2-Propanol (Isopropyl alcohol) 1-Butanol (Butyl alcohol) OH OH OH OH 2-Butanol (sec-Butyl alcohol) 2-Methyl-1-propanol (Isobutyl alcohol) 2-Methyl-2-propanol (tert-Butyl alcohol) OH Cyclohexanol (Cyclohexyl alcohol) OH OH OH 1-Propanol (Propyl alcohol) 2-Propanol (Isopropyl alcohol) OH OH 2-Butanol (sec-Butyl alcohol) 2-Methyl-1-propanol (Isobutyl alcohol) yl-2-propanol OH Cyclohexanol OH OH OH Ethanol yl alcohol) 1-Propanol (Propyl alcohol) 2-Propanol (Isopropyl alcohol) -Butanol tyl alcohol) OH OH OH OH 2-Butanol (sec-Butyl alcohol) 2-Methyl-1-propanol (Isobutyl alcohol) 2-Methyl-2-propanol (tert-Butyl alcohol) OH Cyclohexanol (Cyclohexyl alcohol) OH OH OH Ethanol (Ethyl alcohol) (Pr 1-Butanol (Butyl alcohol) OH OH (sec- 2-Methyl-2-prop (tert-Butyl alco OH Ethanol (Ethyl alcohol) 1-Propanol (Propyl alcohol) (Iso 1-Butanol (Butyl alcohol) OH OH OH 2-Butanol (sec-Butyl alcohol) 2-Me (Iso 2-Methyl-2-propanol (tert-Butyl alcohol) O Cyclohexan (Cyclohexyl al OH OH Ethanol (Ethyl alcohol) 1-Propanol (Propyl alcoh 1-Butanol (Butyl alcohol) OH OH OH 2-Butanol (sec-Butyl alco 2-Methyl-2-propanol (tert-Butyl alcohol) (Cy OH OH 2-chloro-2-methylpropane 2-chlorobutane I-chlorobutane
  16. 16. Lucas Test  Alcohols: 2 layers formed, 2nd layer turbidity  Phenol: 1st layer turbidity
  17. 17. Lucas Test  Used to classify low molecular weight alcohols  no visible reaction at room temperature and cloudy only on heating: primary  solution turns cloudy in 3–5 minutes: secondary  solution turns cloudy immediately, and/or phases separate: tertiary
  18. 18. Oxidation  Oxidation by KMnO4 (dehydrogenation)  Oxidizing agent: KMnO4  Positive result: Decolorization with brown precipitation
  19. 19. Oxidation  Primary  Produces an aldehyde  Then goes through further oxidation to produce a carboxylic acid  Secondary  Produces a ketone  Tertiary  No reaction  Can’t break the carbon-carbon bond  Phenol  Produces quinones
  20. 20. R - C - H + KM4 OH H heat R - C - OH2 + O R - C - R' R - C - R' OH O H [O] R - C - R' OH [O] R'' NO REAC
  21. 21. Experimental Result compound was not oxidized compound was oxidized compound was oxidized Interpretation none Negative result 3o-butyl alcohol decolorization with brown precipitation 2o-butyl alcohol decolorization with brown precipitation n-butyl alcohol Product Formed Visible (+) Result Compound Ethanol (Ethyl alcohol) 1-Propanol (Propyl alcohol) 2-Propanol (Isopropyl alcohol) 1-Butanol (Butyl alcohol) OH OH OH OH 2-Butanol (sec-Butyl alcohol) 2-Methyl-1-propanol (Isobutyl alcohol) 2-Methyl-2-propanol (tert-Butyl alcohol) OH Cyclohexanol (Cyclohexyl alcohol) OH OH OH 1-Propanol (Propyl alcohol) 2-Propanol (Isopropyl alcohol) OH OH 2-Butanol (sec-Butyl alcohol) 2-Methyl-1-propanol (Isobutyl alcohol) -propanol l alcohol) OH Cyclohexanol (Cyclohexyl alcohol) OH OH OH anol alcohol) 1-Propanol (Propyl alcohol) 2-Propanol (Isopropyl alcohol) tanol alcohol) OH OH OH OH 2-Butanol (sec-Butyl alcohol) 2-Methyl-1-propanol (Isobutyl alcohol) 2-Methyl-2-propanol (tert-Butyl alcohol) OH Cyclohexanol (Cyclohexyl alcohol) OH OH OH 3-MHexanal 4 H O 1 2 3 4 5 6 butanal O CH3CH O CH3COH Acetaldehyde Acetic acid Methyl ethyl ketone O butanone
  22. 22. Iron chloride test  Used to detect phenols  The formation of a red, blue, green, or purple coloration indicates the presence of phenols  The ferric chloride test can be used to detect metabolites in urine in case of congenital metabolic problems or genetic diseases
  23. 23. Results Sample Color Indication N-butyl Yellow Negative Phenol Blue Positive
  24. 24.  Esterification  Reactants: alcohol + carboxylic acid  Product formed: ESTER  Positive result: distinct fragrant odor  General equation: O O ιι ιι R-OH + R-C-OH  R-C-O-R + H2O Alcohol Carboxylic acid Ester CH3 C-OH O H-OCH2 CH3 H2 SO4 CH3 COCH2 CH3 O H2 O Ethanoicacid (Aceticacid) ++ Ethyl ethanoate (Ethyl acetate) Ethanol (Ethyl alcohol)
  25. 25. Experimental Result Mint odor Methanol Paste glue odor Phenol ProductOdorAcid ReactantCompound Methyl salicylate
  26. 26. END!!!

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