Chapter 3
Alcohols, Phenols, Ethers, Thiols
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3.1 Organic Compounds with Oxygen Atoms
sp3
..
-O..
Alcohols and ethers (Chp 3)
..
or O=
..
sp2
Aldehydes and ketones (Chp 4),
amides (Chp 6)
BOTH KINDS OF OXYGEN ATOMS IN
Carbohydrates (Chp 7), carboxylic acids and esters (Chp 5)
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3.2 Organic Compounds with Oxygen Atoms
Derived from water H-O-H
sp3
Alcohols -OH hydroxyl
CH3-OH
CH3CH2-OH
saturated
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Hydroxy groups have the same
molecular shape as water
H
O
O
H
CH3
?
?
H
Bond angle = ?
Molecular shape = ?
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3.3 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
1-propanol
OH
CH3CHCH3
CH3
2-propanol
OH
CH3CHCH2CH2CHCH3
5-methyl-2-hexanol
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Name and locate any other
substituents present
CH3
OH
CH3CHCH2CH2CHCH3
5-methyl-2-hexanol
In cyclic alcohols the –OH is attached to
carbon 1
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In cyclic alcohols the –OH is
attached to carbon 1
OH
2-methylcyclohexanol
Naming alcohols that contain C=C and rings …
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Alcohols with more than one hydroxyl
antifreeze
HO-CH2-CH2-OH
1,2-ethanediol (ethylene glycol)
OH
glycerol HO-CH2-CH-CH2OH
glycerin
1,2,3-propanetriol
IUPAC name?
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3.4 Isomerism in alcohols
CH3
OH
CH3CHCH2CH2CHCH3
CH3
5-methyl-2-hexanol
OH
CH3CHCH2CHCH2CH3
5-methyl-3-hexanol
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1. Constitutional isomerism
O
OH
2. Skeletal isomerism
OH
OH
OH
3. Positional isomerism
4. Stereoisomerism
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OH
OH
OH
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Learning Check
Name the following alcohols:
A.
OH
CH3CHCHCH2CH3
CH3
OH
B.
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Solution
Name the following alcohols:
A.
OH
3-methyl-2-pentanol
CH3CHCHCH2CH3
CH3
OH
B.
cyclobutanol
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3.5 Common alcohols
CH3OH
CH3CH2OH
methanol
ethanol
OH
Isopropyl
Alcohol
CH3CHCH3
rubbing alcohol
antiseptic
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3.5 Common alcohols (cont.)
ethylene glycol
HO-CH2-CH2-OH
(antifreeze)
OH
glycerol
HO-CH2-CH-CH2OH
propylene glycol
(in soap, cosmetics)
HO-CH2-CH2-CH3
OH
(drug formulations, cosmetics)
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