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Chapter 12 Alcohols, Phenols, Ethers, Aldehydes, and Ketones

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Chapter 12 Alcohols, Phenols, Ethers, Aldehydes, and Ketones

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    1. LecturePLUS Timberlake 1 Chapter 12 Alcohols, Phenols, Ethers, Aldehydes, and Ketones Alcohols, Phenols, and Thiols Ethers Reactions of Alcohols

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

    3. LecturePLUS Timberlake 3 Learning Check Al1 Classify each as an alcohol (1), phenol (2), or an ether (3): A. _____ CH3CH2-O-CH3 C. _____ CH3CH2OH B. _____

    4. LecturePLUS Timberlake 4 Solution Al 1 Classify each as an alcohol (1), phenol (2), or an ether (3): A. __3__ CH3CH2-O-CH3 C. __1__ CH3CH2OH B. _ 2__

    5. 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)

    6. 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.

    7. LecturePLUS Timberlake 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. 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 CH3CHCH3 2-propanol CH3 OH CH3CHCH2CH2CHCH3 5-methyl-2-hexanol

    9. 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

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

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

    12. LecturePLUS Timberlake 12 Phenols IUPAC name for benzene with a hydroxyl group Many are used as antiseptics and disinfectants

    13. LecturePLUS Timberlake 13 Phenols in Medicine

    14. LecturePLUS Timberlake 14 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

    15. LecturePLUS Timberlake 15 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

    16. LecturePLUS Timberlake 16 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

    17. LecturePLUS Timberlake 17 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

    18. LecturePLUS Timberlake 18 MTBE Methyl tert-butyl ether CH3 CH3-O-C-CH3 CH3 Second in production or organic chemicals Additive to improve gasoline performance Use in question with discovery of contaminated water supplies

    19. LecturePLUS Timberlake 19 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

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