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Alcohols, Phenols, Ethers, Aldehydes, and Ketones

Alcohols, Phenols, Ethers, Aldehydes, and Ketones. Alcohols, Phenols, and Thiols Ethers Reactions of Alcohols. 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 Al1.

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Alcohols, Phenols, Ethers, Aldehydes, and Ketones

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  1. Alcohols, Phenols, Ethers, Aldehydes, and Ketones Alcohols, Phenols, and Thiols Ethers Reactions of Alcohols LecturePLUS Timberlake

  2. Compounds with Oxygen Atoms Alcohols -OH hydroxyl CH3-OH CH3CH2-OH Phenols Ethers -O- CH3-O-CH3 LecturePLUS Timberlake

  3. Learning Check Al1 Classify each as an alcohol (1), phenol (2), or an ether (3): A. _____ CH3CH2-O-CH3C. _____ CH3CH2OH B. _____ LecturePLUS Timberlake

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

  5. 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) LecturePLUS Timberlake

  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. LecturePLUS Timberlake

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

  8. More Names of Alcohols • IUPAC names for longer chains number the chain from the end nearest the -OH group. CH3CH2CH2OH 1-propanol OH CH3CHCH32-propanol CH3 OH CH3CHCH2CH2CHCH35-methyl-2-hexanol LecturePLUS Timberlake

  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 LecturePLUS Timberlake

  10. Learning Check Al 2 Name the following alcohols: A. OH CH3CHCHCH2CH3 CH3 OH B. LecturePLUS Timberlake

  11. Solution Al 2 Name the following alcohols: A. OH 3-methyl-2-pentanol CH3CHCHCH2CH3 CH3 OH B. cyclobutanol LecturePLUS Timberlake

  12. Ethers • Contain an -O- between two carbon groups • Simple ethers named using the longest carbon chain as the stem and the shorter chain given the name alkoxy. CH3-O-CH3 methoxymethane CH3-O-CH2CH3 methoxyethane LecturePLUS Timberlake

  13. Ethers as Anesthetics • Anesthetics inhibit pain signals to the brain • CH3CH2-O-CH2CH3 used for over a century (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 LecturePLUS Timberlake

  14. 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 LecturePLUS Timberlake

  15. 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 LecturePLUS Timberlake

  16. Reactions of Alcohols With sodium 2Na + 2CH3CH2OH  H2 + 2CH3CH2O-Na+ Oxidation Primary CH3CH2CH2OH  CH3CH2CHO + 2H+ + 2e- aldehyde CH3CH2CHO + H2O  CH3CH2COOH + 2H+ + 2e- carboxylic acid LecturePLUS Timberlake

  17. Reactions of Alcohols Oxidation Secondary CH3CHOHCH3 CH3COCH3 + 2H+ + 2e- ketone Tertiary Does not oxidise LecturePLUS Timberlake

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