LecturePLUS Timberlake1 1.5 Alcohols and Ethers

Alcohols

Contain one or more hydroxyl groups, —OH Named from parent hydrocarbon; suffix changed to -ol and number designates carbon to which hydroxyl is attached.

LecturePLUS Timberlake4 Compounds with Oxygen Atoms Alcohols-OH hydroxyl CH 3 -OH CH 3 CH 2 -OH Phenols Ethers -O- CH 3 -O-CH 3

LecturePLUS Timberlake5 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 Timberlake6 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 Timberlake7 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 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 Phenols IUPAC name for benzene with a hydroxyl group Many are used as antiseptics and disinfectants

LecturePLUS Timberlake13 Phenols in Medicine

LecturePLUS Timberlake14 Ethers Contain an -O- between two carbon groups Formed by a condensation reaction of 2 alcohols to remove a molecule of water Methanol reacts with methanol to form CH 3 -O-CH 3 methoxy methane Methanol reacts with ethanol to form CH 3 -O-CH 2 CH 3 methoxy ethane

Ethers Tend to be quite unreactive. Therefore, they are good polar solvents.

LecturePLUS Timberlake16 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

LecturePLUS Timberlake17 MTBE 2-Methoxy-2-methyl propane (methy 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