Chapter 12 Organic Compounds

with Oxygen and Sulfur

12.2
Properties of Alcohols, Ethers,
and Thiols

Copyright 2005 by Pearson Education, Inc.

Publishing as Benjamin Cummings

1
Boiling Points of Alcohols

Alcohols
contain polar OH
groups.
form hydrogen bonds
with other alcohol
molecules.
have higher boiling
points than alkanes and
ethers of similar mass.

Copyright 2005 by Pearson Education, Inc.

Publishing as Benjamin Cummings

2
Boiling Points of Ethers

Ethers
do not have a polar
group.
have an O atom,
but there is no H
attached.
cannot form
hydrogen bonds
between ether
molecules.
Copyright 2005 by Pearson Education, Inc.
Publishing as Benjamin Cummings

3
Solubility of Alcohols and Ethers in
Water
Alcohols and ethers
are more soluble in water than alkanes because the
oxygen atom can hydrogen bond with water.
with 1-4 C atoms are soluble, but not with 5 or more
C atoms.

4
Comparing Solubility and Boiling
Points
Molar Boiling Soluble
Compound Mass Point (C) in Water?
Alkane CH3CH2CH3 44 -42 No

Ether CH3OCH3 46 -23 Yes

Alcohol CH3CH2OH 46 78 Yes

5
Reactivity of Alkanes vs. Alcohols

Hydrocarbon + O2 carbon dioxide + water + heat energy

D

Ex. CH4 + 2O2 CO2 + 2H2O Heat released is 802 kJ/mol

D of methane

Effect of partially oxidizing a hydrocarbon, lets look at the

combustion reaction of CH3OH (methanol), in which 1 H has
been replaced by an OH group.

2CH3OH + 3O2 2CO2 + 4H2O Heat released is 640 kJ/mol

D of methanol
(1.5 moles of O2 required to with 1 mole of CH3OH!)
6
These reactions illustrates two important principles.

1st, the more reduced a molecule, the more energy is

released during oxidation on a molar basis.
Methane is fully reduced and gives off more energy during
combustion than methanol.

2nd, the number of oxygen molecules required to react

with a fuel molecule can give an estimate of how much
energy is available.

More highly reduced molecules require more oxygen during

combustion and produces more energy.

7
Reduction of
hydrocarbons vs. their oxidation

OH

CH3OH
Partially Oxidized

8
Solubility of Phenol

Phenol
is soluble in water.
has a hydroxyl group that ionizes slightly (weak acid).
is corrosive and irritating to skin.

OH O-

+ H2O + H3O+