1.4
Alcohols and
Ethers
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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
OH
OH
Phenols
Ethers
-O-
CH3-O-CH3
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Learning Check Al1
Classify each as an alcohol (1), phenol (2), or
an ether (3):
A. _____ CH3CH2-O-CH3
C. _____ CH3CH2OH
OH
B. _____
CH3
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Solution Al 1
Classify each as an alcohol (1), phenol (2), or
an ether (3):
A. __3__ CH3CH2-O-CH3
C. __1__ CH3CH2OH
OH
B. _ 2__
CH3
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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
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(ethyl alcohol)
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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
CH3
propan-2-ol
OH
CH3CHCH2CH2CHCH3
5-methylhexan-2-ol
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Some Typical Alcohols
OH
“rubbing alcohol”
CH3CHCH3
propan-2-ol (isopropyl alcohol)
antifreeze HO-CH2-CH2-OH
ethane-1,2-diol (ethylene glycol)
OH
glycerol
HO-CH2-CH-CH2OH propan-1,2,3-triol
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Learning Check Al 2
Name the following alcohols:
A.
OH
CH3CHCHCH2CH3
CH3
OH
B.
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Solution Al 2
Name the following alcohols:
A.
OH
3-methylpentan-2-ol
CH3CHCHCH2CH3
CH3
OH
B.
Cyclobutan-1-ol
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Phenols
 IUPAC name for benzene with a hydroxyl
group
OH
 Many are used as antiseptics and
disinfectants
Phenol
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Phenols in Medicine
OH
OH
OH
OH
OH
CH2CH2CH2CH2CH2CH3
Phenol
Resorcinol
(antiseptic)
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4-Hexylresorcinal
(antiseptic)
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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
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Ethers
• Tend to be quite unreactive.
• Therefore, they are good polar
solvents.
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
F F
H-C-C-O-C-H
F
HF
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H
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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
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