Alcohols, Phenols, and Ethers

Hydroxy groups the OH functional group.

Alcohol has an OH group attached to an aliphatic
carbon. General formula R-OH.
Phenol has an OH group on a benzene ring.
Ether a compound that has the functional group

Seager & Slabaugh, 2004

Naming Alcohols
Step 1: Name the longest chain to which the OH group is
attached. Use the alkane name of the chain, drop the e
ending, and replace it with ol.
Step 2: Number the longest chain to give the lowest
number to the carbon with the OH.
Step 3: Locate the OH position.
Example:
OH
|
CH3CH2CH2CHCH2CH3
6
5
4
3
2
1
3-hexanol

Naming Alcohols, cont.

Step 4: Locate and name any other groups attached to
the longest chain.
Step 5: Combine the name and location of other groups,
the location of the OH, and the longest chain into the final
name.
Example:

CH3 OH CH3
|
|
|
CH3CH2CH2CHCHCH3
6
5
4
3
2
1
2,4-dimethyl-3-hexanol

Seager & Slabaugh, 2004

Classification of Alcohols

Physical Properties of Alcohols

The OH group is polar and capable of hydrogen bonding.
This makes low molecular weight alcohols highly soluble in
water.
Hydrogen bonding in a water-methanol solution:

Physical Properties of Alcohols, cont.

Larger alkanes have greater hydrophobic regions and are
less soluble or insoluble in water.
Water interacts only with the OH group of
1-heptanol:

Physical Properties of Alcohols, cont.

The OH group can hydrogen bond between alcohol
molecules leading to relatively high boiling points.
Hydrogen bonding in pure ethanol:

Alcohol Reactions
The removal of water (dehydration) from an alcohol is an
elimination reaction and produces an alkene.

Alcohol Reactions, cont.

Under slightly different conditions, a dehydration reaction
can occur between two alcohol molecules to produce an
ether.

Alcohol Reactions, cont.

Oxidation the removal of hydrogen atoms.

Alcohol oxidations with an oxidizing (O) agent:
Primary alcohols aldehyde carboxylic acid.
Secondary alcohols ketone.
Tertiary alcohols no reaction.

Seager & Slabaugh, 2004

Alcohol Reactions, cont.

Primary alcohol oxidation

Secondary alcohol oxidation

Important Alcohols
Methanol (wood alcohol) CH3OH.
Production:

Useful as a solvent and industrial starting material.

Highly toxic, causes blindness and/or death.

Seager & Slabaugh, 2004

Important Alcohols, cont.

Ethanol (ethyl alcohol, grain alcohol) CH3CH2OH.
Produced commercially from ethylene and through
biological (yeast) fermentation of carbohydrates. Useful as
a solvent, industrial starting material, fuel (gasohol), and
found in alcoholic beverages. Moderately toxic.

Seager & Slabaugh, 2004

Important Alcohols, cont.

2-propanol (isopropyl alcohol) is the main component of
rubbing alcohol.
1,2,3-propanetriol (glycerol) is used as a food moistening
agent (nontoxic) and for its soothing qualities (soaps).

Seager & Slabaugh, 2004

Important Alcohols, cont.

Antifreezes
1,2-ethanediol (ethylene glycol).

1,2-propanediol (propylene glycol).

Phenols
Phenol behaves as a weak acid in water

And can react with bases to form salt.

Uses of Phenols:
In a dilute solution, phenol is a disinfectant.
Phenol derivatives used as disinfectants
0-phenylphenol
2-benzyl-4-chlorophenol
Phenol derivatives used as antioxidants in food
BHA (butylated hydroxy anisole)
BHT (butylated hydroxy toluene)

Ethers
Naming ethers the O-R group is called an alkoxy group.
The yl ending of the smaller R group is replaced by oxy.

Cyclic Ethers
Heterocyclic rings contain atoms other than carbon in the
ring.

Properties of Ethers
Much less polar than alcohols.
More soluble in water than alkanes, but less soluble than
alcohols.
Low boiling and melting points because of the inability to
hydrogen bond between molecules.

 Hydrogen bonding of dimethyl ether: (a) with water and (b)

no hydrogen bonding in the pure state:

Ether Reactions
Like alkanes, ethers are inert and do not react with most
reagents.
Also like alkanes, they are highly flammable.

Thiols: the SH (sulfhydryl) group

Most distinguishing characteristic is their strong and
offensive odor.
Ethanethiol added to natural gas.
1-propanethiol odor in garlic and onions.
Trans-2-butene-1-thiol odor associated with skunks.

Thiol Reactions
Oxidation forms disulfide (-S-S-) linkages which are
important structural features of some proteins.

Seager & Slabaugh, 2004

Thiol Reactions, cont.

Oxidation reactions can be reversed with a reducing agent
(H).

Thiol Reactions, cont.

Reacts with heavy metals (Pb2+, Hg2+) to form insoluble
compounds, with adverse biological results.

Polyfunctional Compounds
Compounds with two or more functional groups.
Functional groups determine chemical properties of
compounds.
Example:

Seager & Slabaugh, 2004