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Compounds with Oxygen Atoms

Compounds with Oxygen Atoms. Alcohols -OH hydroxyl CH 3 - OH CH 3 CH 2 - OH Phenols Ethers -O- CH 3 -O- CH 3. Learning Check. Classify each as an alcohol (1), phenol (2), or an ether (3):

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Compounds with Oxygen Atoms

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  1. Compounds with Oxygen Atoms Alcohols -OH hydroxyl CH3-OH CH3CH2-OH Phenols Ethers -O- CH3-O-CH3

  2. Learning Check Classify each as an alcohol (1), phenol (2), or an ether (3): A. _____ CH3CH2-O-CH3C. _____ CH3CH2OH B. _____

  3. Solution Classify each as an alcohol (1), phenol (2), or an ether (3): A. __3__ CH3CH2-O-CH3C. __1__ CH3CH2OH B. _ 2__

  4. Naming Alcohols • A carbon compound that contain -OH (hydroxyl) group • In IUPAC name, the -e in alkane name is replaced with -ol. CH4 methane CH3OH methanol (methyl alcohol) CH3CH3 ethane CH3CH2OH ethanol (ethyl alcohol)

  5. Alcohols • How is the -OH group different from the hydroxide ion? -OH group forms covalent bond with the carbon Hydroxide ion forms ionic bond with a metal

  6. Ethanol CH3CH2OH • Acts as a depressant • Kills or disables more people than any other drug • 12-15 mg/dL ethanol metabolized by a social drinkers in one hour • 30 mg/dL ethanol metabolized by an alcoholic in one hour.

  7. Alcohol in Some Products % Ethanol Product 50% Whiskey, rum, brandy 40% Flavoring extracts 15-25% Listerine, Nyquil, Scope 12% Wine, Dristan, Cepacol 3-9% Beer, Lavoris

  8. More Names of Alcohols • IUPAC names for longer chains number the chain from the end nearest the -OH group. CH3CH2CH2OH1-propanol OH CH3CHCH32-propanol CH3 OH CH3CHCH2CH2CHCH35-methyl-2-hexanol

  9. Some Typical Alcohols OH “rubbing alcohol” CH3CHCH3 2-propanol (isopropyl alcohol) antifreeze HO-CH2-CH2-OH 1,2-ethanediol (ethylene glycol) OH glycerol HO-CH2-CH-CH2OH Anti-freeze

  10. Classification of Alcohols Primary (1º) Secondary (2º ) Tertiary (3º) H CH3CH3 CH3-C-OH CH3-C-OH CH3-C-OH H H CH3 1 C 2 C 3 C attached attached attached to C-OH to C-OH to C-OH

  11. Learning Check Classify the following as 1º, 2º, or 3º alcohols: OH A. CH3CH2CH2OH B. CH3-CH-CH2CH3 C. D. OH CH3-C-CH2CH3 CH3

  12. Solution Classify the following as 1º, 2º, or 3º alcohols: OH A. CH3CH2CH2OH 1º B. CH3-CH-CH2CH3 2º C. 2º D. OH 3º CH3-C-CH2CH3 CH3

  13. Properties of Alcohols • Ethyl alcohol (ethanol) used in the intoxicating beverages; an important industrial solvent • Many aliphatic alcohols used in laboratories, clinics, and industry • Isopropyl alcohol (2-propanol) is rubbing alcohol; used as antiseptic, and a base for perfume, creams, lotions, and other cosmetics

  14. Properties of Alcohols • Glycerol (1,2,3-propanetriol) - used as a moistening agent in cosmetics, foods, and drugs; also a component of fats and oils

  15. Learning Check Name the following alcohols: A. OH CH3CHCHCH2CH3 CH3 OH B.

  16. Solution Name the following alcohols: A. OH 3-methyl-2-pentanol CH3CHCHCH2CH3 CH3 OH B. cyclobutanol

  17. Properties of Alcohols • Much like water, alcohols are capable of hydrogen bonding between molecules • this means they will boil at a higher temp. than alkanes and halocarbons with a comparable number of atoms

  18. Properties of Alcohols • Alcohols of up to 4 carbons are soluble in water in all proportions; more than 4 carbons are usually less soluble, because…?

  19. Properties of Alcohols • Denatured alcohol- means it has been made poisonous by the addition of other chemicals, often methyl alcohol (methanol, or wood alcohol). As little as 10 mL of methanol has been known to cause permanent blindness, and 30 ml has resulted in death!!!

  20. Reactions of Alcohols Combustion CH3OH + 2O2 CO2 + 2H2O + Heat Dehydration H OH H+, heat H-C-C-H H-C=C-H + H2O H H H H alcohol alkene

  21. Oxidation • Is a gain of oxygen (O) or • A loss of hydrogen (H)

  22. Oxidationof Alcohols 1°alcohols are oxidized to aldehydes and 2° alcohols are oxidized to ketones Alcohols 1° 2° aldehydesketones

  23. Oxidation of Alcohols [O] Primary alcohol aldehyde OH O [O]  CH3-C-H CH3-C-H H Ethanol Ethanal (ethyl alcohol) (acetaldehyde)

  24. Oxidation of Alcohols [O] Secondary alcohol ketone OH O [O]  CH3-C-CH3 CH3-C-CH3 2-Propanol 2-propanone (isopropyl alcohol) (dimethyl ketone, “acetone”)

  25. Oxidation of Alcohols [O] Tertiary alcohols no reaction OH [O] CH3-C-CH3 no product CH3 no H on the C-OH to oxidize 2-Methyl-2-propanol

  26. Oxidation of Ethanol in the Body • Enzymes in the liver oxidize ethanol • Aldehyde product impairs coordination • Blood alcohol over 0.4% can be fatal. O O [O]  [O]  CH3CH2OH CH3CH CH3COH 2CO2 + H2O ethyl alcohol acetaldehyde acetic acid

  27. Learning Check Select the product for the oxidation of CH3CH2CH2OH: O  1) CH3CH=CH2 2) CO2 + H2O3) CH3CH2CH

  28. Solution Select the product for the oxidation of CH3CH2CH2OH: O  [O] 3) CH3CH2CH

  29. Reduction • Is a loss of oxygen (O) or • gain of hydrogen (H)

  30. Reduction Aldehydes are reduced to 1° alcohols and ketones are reduced to 2° alcohols Alcohols 1° 2° aldehydes ketones

  31. Phenols • IUPAC name for benzene with a hydroxyl group • Many are used as antiseptics and disinfectants

  32. Phenols in Medicine

  33. Ethers • Contain an -O- between two carbon groups • Simple ethers named from -yl names of the attached groups and adding ether. CH3-O-CH3 dimethyl ether CH3-O-CH2CH3 ethyl methyl ether

  34. Ethers as Anesthetics • Anesthetics inhibit pain signals to the brain • CH3CH2-O-CH2CH3 used for over a century; commonly called just ether (Morton, 1846) • Causes nausea and is highly flammable • 1960s developed nonflammable anesthetics Cl F F Cl F H H-C-C-O-C-H H-C-C-O-C-H F F F H F H Ethane(enflurane) Penthrane

  35. MTBE • Methyl tert-butyl ether CH3 CH3-O-C-CH3 CH3 • Second in production of organic chemicals • Additive to improve gasoline performance • Use in question with discovery of contaminated water supplies

  36. Learning Check Write the structure of the following: A. 3-pentanol B. Dimethyl ether C. 3-methylcyclobutanol

  37. Solution Write the structure of the following: OH | A. 3-pentanol CH3CH2CHCH2CH3 B. Dimethyl ether CH3-O-CH3 C. 3-methylcyclobutanol

  38. Thiols • Contain the functional group -SH • Named by adding thiol to the name of the longest carbon chain • Number the -SH group in longer chains CH3-SH methanethiol CH3-CH2SH ethanethiol SH CH3-CH-CH3 2-propanethiol

  39. Thiols • Many thiols have disagreeable odors • Used to detect gas leak • Found in onions, oysters, garlic and oysters Onions CH3CH2CH2-SH 1-propanethiol Garlic CH2=CHCH2-SH 2-propene-1-thiol Skunk spray CH3 trans-2-butene-1-thiol CH = CH CH2SH

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