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Chapter 13 Alcohols, Phenols, Thiols, and Ethers
Learning Objectives:
1. Provide both IUPAC and common names for alcohols, phenols, ethers and thiols.
2. Recognize the physical properties of alcohols, phenols, ethers and thiols.
3. Write the dehydration equations of alcohols and predict the major product when
applicable.
4. Recognize the oxidation and reduction of alcohols and predict the products from
oxidation of primary and secondary alcohols.
5. Recognize the oxidation and reduction of thiols.
Sections:
13.1 Alcohols, Phenols and Thiols
13.2 Ethers
13.3. Physical properties of Alcohols, Phenols and Ethers
13.4 Reactions of Alcohol and Thiols
Recommended additional problems
13.39, 13.41, 13.49, 13.53, 13.55, 13.57
13.1 Alcohols, Phenols and Thiols
A. Classification
Alcohols: molecules with OH group (hydroxyl group)
Alkyl alcohol Aryl alcohol
For alkyl alcohols (ROH)
Primary (1°) alcohol
Secondary (2°) alcohol
Tertiary (3°) aleohol
Example
HO
OH
S
o
OH
Thiols (mercapto-): molecules with SH group (sulfhydry! group)
13.2. Ethers
Ethers: molecules contain oxygen aiom that is single-bonded to two alkyl or aryl
groups.
So
NUON
A. Nomenclature of ether
Common name
NN
TUPAC name (use of alkoxy as substituent)
Alkyl group Alkoxy group
OH
NN a
~~ OCH CHs
B. Structural isomers of alcohols and ethers
C. Cyclic ethers
13.3. Physical properties of Alcohols, Phenols and Ethers
Know the effect of hydrogen bond
A. Boiling points
B. Solubility in water
13.4 Reactions of Alcohol and Thiols
A. Combustion
B. Dehydration of alcohols
1 H2804
AY |_|
—c-6— _ + HO
tot —C=C—
H OH
Examples:
OH Ht
heat
—_————_—_—_>
OH .
heat
a
Saytzeff’s rule: