LecturePLUS Timberlake 1.4 Alcohols and Ethers LecturePLUS Timberlake

Alcohols

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.

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

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

LecturePLUS Timberlake 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__ LecturePLUS Timberlake

LecturePLUS Timberlake 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

LecturePLUS Timberlake More Names of Alcohols IUPAC names for longer chains number the chain from the end nearest the -OH group. CH3CH2CH2OH propan-1-ol OH CH3CHCH3 propan-2-ol CH3 OH CH3CHCH2CH2CHCH3 5-methylhexan-2-ol LecturePLUS Timberlake

LecturePLUS Timberlake Some Typical Alcohols OH “rubbing alcohol” CH3CHCH3 propan-2-ol (isopropyl alcohol) antifreeze HO-CH2-CH2-OH ethane-1,2-diol (ethylene glycol) glycerol HO-CH2-CH-CH2OH propan-1,2,3-triol Anti-freeze LecturePLUS Timberlake

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

LecturePLUS Timberlake Solution Al 2 Name the following alcohols: A. OH 3-methylpentan-2-ol CH3CHCHCH2CH3 CH3 OH B. Cyclobutan-1-ol LecturePLUS Timberlake

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

LecturePLUS Timberlake Phenols in Medicine LecturePLUS Timberlake

LecturePLUS Timberlake 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 CH3-O-CH3 methoxy methane Methanol reacts with ethanol to form CH3-O-CH2CH3 methoxy ethane LecturePLUS Timberlake

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

LecturePLUS Timberlake 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 LecturePLUS Timberlake

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