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John E. McMurry
Chapter 8
Alcohols, Phenols, Ethers
and Their Sulfur Analogs
Naming Ethers
identify the two organic substituent's and adding the word ether
If other functional groups are present, the ether part is considered
an alkoxy substituent
O
H2C CH2
Epoxides (oxiranes)
Alkyl
groups
make an
alcohol a
weaker
acid
Phenol Acidity
Phenols (pKa ~10) are much more acidic than
alcohols (pKa ~ 16) because of resonance
stabilization of the phenoxide ion
3 > 2 > 1
Oxidation of Alcohols
Oxidation of Alcohols
Many oxidizing agents such as CrO3 and Na2Cr2O7
oxidize primary alcohols to carboxylic acids
The intermediate aldehyde usually cannot be isolated
Can be
accomplished by
inorganic
reagents, such as
KMnO4, CrO3,
and Na2Cr2O7 or
by more selective,
expensive
reagents
Oxidation of Alcohols
phenols