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Alcohols, Phenols, Ethers & Thiols
Chapter 13 – Test Objectives
Topics

Make sure you have read the entire chapter including 13.3 Medically Important
Alcohols.

Make sure you review the concepts of the labs we performed: Formation of an Alkene
and Evaporation and Intermolecular Attractions.

You should be able to explain the structure and properties of alcohols, phenols, ethers,
and thiols.

You should be able to explain the uses of alcohols, phenols, ethers, and thiols.

You should know how to name and draw the structures for the following classes of
compounds: alcohols, ethers (both IUPAC and common ways), phenols (see ch. 12), and
thiols.
Reactions
1. Hydration of alkenes to form alcohols
R
R
R
H
+
R
O
H+
R
H
R
OH
H
R
R
** Markovnikov’s Rule applies!**
2. Hydrogenation of aldehydes
Aldehydes form primary alcohols, ketones form secondary alcohols.
3. Dehydration of alcohols
H
H
C
C
H
OH
H
H+, heat
R
R
H
C
H
CH2 +
O
H
**Zaitsev’s rule applies!**
4. Oxidation reactions:
Oxidation of primary alcohol
OH
O
[O]
R
C
H
C
H
R
H
(aldehyde)
Oxidation of secondary alcohol
OH
O
[O]
R
C
R
C
H
R
R (ketone)
Oxidation of tertiary alcohol
OH
[O]
R
C
No Reaction
R
R
5. Dehydration synthesis of ether
R
OH +
R'
OH
H
H+
R
O
R'
+
O
H
Practice Problems
Name the following compounds. Classify the alcohols as primary, secondary, or tertiary.
OH
1.
CH3CHCH2CHCH3
SH
2.
OH
SH
CH3CHCH2CHCH3
H3C
OH
3.
CH3
OH
CH2CH3
4.
5. CH3CH2CH2OCH2CH3
OH
6.
H3C
7
O
8.
9.
Draw the following molecules. Classify the alcohols.
1. 2-methyl-2-butanol
2. 3-methyl-1,3,4-pentanetriol
3. 2,4,6-trinitrophenol
4. m-butylphenol
5. 3-ethoxyhexane
6. butyl methyl ether
7. 1,3,5-hexanetrithiol
8. 1-chloro-1,2-butanedithiol
Write a complete equation for each of the following reactions using structural formulas. Name
the reactants and products when possible. If more than one product is formed, please indicate
the major and minor product.
1. Oxidation of cyclopentanol
2. Hydration of 2-pentene
3. Dehydration of 1-pentanol
4. Oxidation of 1-butanol
5. Oxidation of 2-methyl-2-butanol
6. Synthesis of methoxybutane
7. Hydrogenation of
O
CH3CH2CHCH2CH3
8. Hydration of 3-methyl-1-butene
9. Dehydration of 4-chloro-2-pentanol
10. Hydrogenation of CH3CH2CH2CH=O
11. Dehydration of 2 molecules of ethanol.