Chapter 14 and GHW#4
Questions
Introduction Alcohols, Phenols, and
Ethers:
1. Bonding Characteristics of Oxygen Atoms
in Organic Compounds
Structural Characteristics of Alcohols
1. Identify the Alcohols, Phenols, and Ethers from the
following and give their common and/or IUPAC names.
1. Identify the Alcohols, Phenols, and Ethers from the
following and give their common and/or IUPAC names.
2. Circle the constitutional isomers of 1-
hexanol among following alcohols.
3. Classify each of the following as
1', 2', or 3' alcohols.
a)
d)
b)
c)
Chemical Reactions of Alcohols
1) Combustion: Alcohol are very flammable and the combustion
products are carbon dioxide and water.
2) Substitution Reactions: OH group is replaced by a another
group such as halogen.
a) Elimination Reactions:
Intramolecular dehydration : Water is removed from a alcohol
molecule and a alkene is produced. ( H2SO4 at 180)
Intermolecular dehydration : Water is removed from two alcohol
molecules and an ether is produced. ( H2SO4 at 140) Williamson Ether
synthesis.
4a. Complete the following reactions of alcohol.
a) Dehydration:
4b) What is Zaitsev Rule?
Zaitsev’s rule (or the opposite of
Markovnikov’s rule)
Dehydration of an alcohol can result in more than
one alkene product, because hydrogen loss can occur
from either of the neighboring carbon atoms.
Hydrogen is removed from the carbon with lowest
hydrogen atoms ( poor get poorer)
5) Complete the following reactions of
alcohol oxidation:
6) Draw condensed formula of each of the
following:
a. 3-Hexanol
b. 1,2,3-Pentanetriol
c. 2-Methyl-2-pentanol
d. Cyclohexanol
e. 3,4-dimethyl-3-heptanol
6) Draw the alkene products of the
dehydration of the following alcohols:
a. 3-Hexanol
b. 1,2,3-Pentanetriol
c. 2-Methyl-2-pentanol
d. Cyclohexanol
e. 3,4-Dimethyl-3-heptanol
7) Draw the alkene products of the dehydration
of the following alcohols:
a)2-Pentanol:
b)3-Methyl-1-pentanol:
c) 2-Butanol:
d)4-Chloro-2-pentanol:
e)1-Propanol:
8) Give the oxidation products of the following
alcohols. If no reaction occurs, write N.R.