LecturePLUS Timberlake1 Alcohols, Phenols, Ethers, Aldehydes, and Ketones Alcohols, Phenols, and Thiols Ethers Reactions of Alcohols

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

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. _____

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__

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 )

LecturePLUS Timberlake6 Ethanol CH 3 CH 2 OH Acts as a depressant Kills or disables more people than any other drug mg/dL ethanol metabolized by a social drinkers in one hour 30 mg/dL ethanol metabolized by an alcoholic in one hour.

LecturePLUS Timberlake7 Alcohol in Some Products % EthanolProduct 50%Whiskey, rum, brandy 40%Flavoring extracts 15-25%Listerine 12%Wine, Cepacol 3-9%Beer

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

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

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

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

LecturePLUS Timberlake12 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. CH 3 -O-CH 3 methoxymethane CH 3 -O-CH 2 CH 3 methoxyethane

LecturePLUS Timberlake13 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

LecturePLUS Timberlake14 MTBE Methyl tert-butyl ether CH 3 CH 3 -O-C-CH 3 CH 3 Second in production of organic chemicals Additive to improve gasoline performance Use in question with discovery of contaminated water supplies

LecturePLUS Timberlake15 Reactions of Alcohols Combustion CH 3 OH + 2O 2 CO 2 + 2H 2 O + Heat Dehydration H OH H +, heat H-C-C-H H-C=C-H + H 2 O H H alcohol alkene

LecturePLUS Timberlake16 Reactions of Alcohols With sodium 2Na + 2CH 3 CH 2 OH  H 2 + 2CH 3 CH 2 O - Na + Oxidation Primary CH 3 CH 2 CH 2 OH  CH 3 CH 2 CHO + 2H + + 2e - aldehyde CH 3 CH 2 CHO + H 2 O  CH 3 CH 2 COOH + 2H + + 2e - carboxylic acid

LecturePLUS Timberlake17 Reactions of Alcohols Oxidation Secondary CH 3 CHOHCH 3  CH 3 COCH 3 + 2H + + 2e - ketone Tertiary Does not oxidise