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Contain one or more hydroxyl groups, —OH Named from parent hydrocarbon; suffix changed to -ol and number designates carbon to which hydroxyl is attached.
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LecturePLUS Timberlake 1
1.5Alcohols and
Ethers
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.
LecturePLUS Timberlake 4
Compounds with Oxygen Atoms
Alcohols -OH hydroxyl CH3-OH
CH3CH2-OH
Phenols
Ethers -O- CH3-O-CH3
OHOH
LecturePLUS Timberlake 5
Learning Check Al1
Classify each as an alcohol (1), phenol (2), or an ether (3):
A. _____ CH3CH2-O-CH3 C. _____ CH3CH2OH
B. _____
OH
CH3
LecturePLUS Timberlake 6
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__
OH
CH3
LecturePLUS Timberlake 7
Naming AlcoholsA 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 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
LecturePLUS Timberlake 9
Some Typical Alcohols OH “rubbing alcohol” CH3CHCH3
2-propanol (isopropyl alcohol)
antifreeze HO-CH2-CH2-OH1,2-ethanediol (ethylene glycol)
OH
glycerol HO-CH2-CH-CH2OH
Anti-
freez
e
LecturePLUS Timberlake 10
Learning Check Al 2
Name the following alcohols:A. OH
CH3CHCHCH2CH3
CH3
OHB.
LecturePLUS Timberlake 11
Solution Al 2
Name the following alcohols:A. OH 3-methyl-2-pentanol
CH3CHCHCH2CH3
CH3
OHB. cyclobutanol
LecturePLUS Timberlake 12
Phenols
IUPAC name for benzene with a hydroxyl group
Many are used as antiseptics and disinfectants
OH
Phenol
LecturePLUS Timberlake 13
Phenols in Medicine
OH
OH
OH OH
OHCH2CH2CH2CH2CH2CH3
Resorcinol 4-Hexylresorcinal(antiseptic) (antiseptic)
Phenol
LecturePLUS Timberlake 14
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 formCH3-O-CH3 methoxy methane
Methanol reacts with ethanol to form
CH3-O-CH2CH3 methoxy ethane
Ethers
• Tend to be quite unreactive.• Therefore, they are good polar
solvents.
LecturePLUS Timberlake 16
Ethers as Anesthetics
Anesthetics inhibit pain signals to the brainCH3CH2-O-CH2CH3 used for over a century
(Morton, 1846)Causes nausea and is highly flammable1960s 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 17
MTBE2-Methoxy-2-methyl propane (methy tert-butyl ether)
CH3
CH3-O-C-CH3
CH3
Second in production or organic chemicals Additive to improve gasoline performanceUse in question with discovery of contaminated
water supplies
