1. LecturePLUS Timberlake1 Chapter Organic Chemistry: Alcohols, Phenols, Ethers, Aldehydes, and Ketones Alcohols, Phenols, and Thiols Ethers Reactions of Alcohols

2. LecturePLUS Timberlake2 Compounds with Oxygen Atoms Alcohols-OH hydroxyl CH 3 -OH CH 3 CH 2 -OH Phenols Ethers -O- CH 3 -O-CH 3

3. LecturePLUS Timberlake3 Learning Check Al1 Classify each as an alcohol (1), phenol (2), or an ether (3): A. _____ CH 3 CH 2 -O-CH 3 C. _____ CH 3 CH 2 OH B. _____

4. LecturePLUS Timberlake4 Solution Al 1 Classify each as an alcohol (1), phenol (2), or an ether (3): A. __3__ CH 3 CH 2 -O-CH 3 C. __1__ CH 3 CH 2 OH B. _ 2__

5. LecturePLUS Timberlake5 Naming Alcohols A carbon compound that contain -OH (hydroxyl) group In IUPAC name, the -e in alkane name is replaced with -ol. CH 4 methane CH 3 OH methanol (methyl alcohol) CH 3 CH 3 ethane CH 3 CH 2 OH ethanol (ethyl alcohol )

6. LecturePLUS Timberlake6 Ethanol CH 3 CH 2 OH 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 Timberlake7 Alcohol in Some Products % EthanolProduct 50%Whiskey, rum, brandy 40%Flavoring extracts 15-25%Listerine, Nyquil, Scope 12%Wine, Dristan, Cepacol 3-9%Beer, Lavoris

8. LecturePLUS Timberlake8 More Names of Alcohols IUPAC names for longer chains number the chain from the end nearest the -OH group. CH 3 CH 2 CH 2 OH1-propanol OH CH 3 CHCH 3 2-propanol CH 3 OH CH 3 CHCH 2 CH 2 CHCH 3 5-methyl-2-hexanol

9. LecturePLUS Timberlake9 Some Typical Alcohols OH “rubbing alcohol”CH 3 CHCH 3 2-propanol (isopropyl alcohol) antifreeze HO-CH 2 -CH 2 -OH 1,2-ethanediol (ethylene glycol) OH glycerolHO-CH 2 -CH-CH 2 OH Anti-freeze

10. LecturePLUS Timberlake10 Learning Check Al 2 Name the following alcohols: A. OH CH 3 CHCHCH 2 CH 3 CH 3 OH B.

11. LecturePLUS Timberlake11 Solution Al 2 Name the following alcohols: A. OH 3-methyl-2-pentanol CH 3 CHCHCH 2 CH 3 CH 3 OH B. cyclobutanol

12. LecturePLUS Timberlake12 Phenols IUPAC name for benzene with a hydroxyl group Many are used as antiseptics and disinfectants

13. LecturePLUS Timberlake13 Phenols in Medicine

14. LecturePLUS Timberlake14 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 CH 3 -SH methanethiol CH 3 -CH 2 SH ethanethiol SH CH 3 -CH-CH 3 2-propanethiol

15. LecturePLUS Timberlake15 Thiols Many thiols have disagreeable odors Used to detect gas leak Found in onions, oysters, garlic and oysters Onions CH 3 CH 2 CH 2 -SH 1-propanethiol Garlic CH 2 = CHCH 2 -SH 2-propene-1-thiol Skunk spray CH 3 trans-2-butene-1-thiol CH = CH CH 2 SH

16. LecturePLUS Timberlake16 Ethers Contain an -O- between two carbon groups Simple ethers named from -yl names of the attached groups and adding ether. CH 3 -O-CH 3 dimethyl ether (methoxymethane) CH 3 -O-CH 2 CH 3 ethyl methyl ether (methoxyethane)

17. LecturePLUS Timberlake17 Ethers as Anesthetics Anesthetics inhibit pain signals to the brain CH 3 CH 2 -O-CH 2 CH 3 used for over a century (Morton, 1846) Causes nausea and is highly flammable 1960s developed nonflammable anesthetics Cl F F Cl F HH-C-C-O-C-H F F F H F H Ethane(enflurane) Penthrane

18. LecturePLUS Timberlake18 MTBE Methyl tert-butyl ether CH 3 CH 3 -O-C-CH 3 CH 3 Second in production or organic chemicals Additive to improve gasoline performance Use in question with discovery of contaminated water supplies

19. LecturePLUS Timberlake19 Reactions of Alcohols Combustion CH 3 OH + 2O 2 CO 2 + 2H 2 O + Heat Dehydration (Alcohol to alkene, water produced)) H OH H +, heat H-C-C-H H-C=C-H + H 2 O H H alcohol alkene

20. LecturePLUS Timberlake20 Alcohol + Alcohol in the presence of a strong acid produces an ether. ROH + R 1 OH= ROR 1 + H 2 O Primary alcohol can be oxidized to an aldehyde and further oxidized to a carboxylic acid Secondary alcohol can be oxidized to a ketone Tertiary alcohol cannot be oxidized