ALCOHOL

Alcohol, any of a class of organic compounds

characterized by one or more hydroxyl (OH)
groups attached to a carbon atom of an alkyl
group (hydrocarbon chain). Alcohols may be
considered as organic derivatives of water

(H2O) in which one of the hydrogen atoms has

been replaced by an alkyl group, typically
represented by R in organic structures. For
example, in ethanol (or ethyl alcohol) the alkyl
group is the ethyl group, CH2CH3.

Alcohols are among the most common organic

compounds. They are used as sweeteners and in
making perfumes, are valuable intermediates in
the synthesis of other compounds, and are
among the most abundantly produced organic
chemicals in industry. Perhaps the two bestknown alcohols are ethanol and methanol (or
methyl alcohol). Ethanol is used in toiletries,
pharmaceuticals, and fuels, and it is used to
sterilize hospital instruments. It is, moreover,
the alcohol in alcoholic beverages. The
anesthetic ether is also made from ethanol.
Methanol is used as a solvent, as a raw material

for the manufacture of formaldehyde and

special resins, in special fuels, in antifreeze, and
for cleaning metals.

One way of classifying alcohols is based on

which carbon atom is bonded to the hydroxyl
group. If this carbon is primary (1, bonded to
only one other carbon atom), the compound is a
primary alcohol. A secondary alcohol has the
hydroxyl group on a secondary (2) carbon
atom, which is bonded to two other carbon
atoms. Similarly, a tertiary alcohol has the

hydroxyl group on a tertiary (3) carbon atom,

which is bonded to three other carbons.
Alcohols are referred to as allylic or benzylic if
the hydroxyl group is bonded to an allylic
carbon atom (adjacent to a C=C double bond)
or a benzylic carbon atom (next to a benzene
ring), respectively.

Alcohols may be classified as primary,

secondary, or tertiary, according to which
carbon of the alkyl group is bonded to the
hydroxyl group. Most alcohols are colourless
liquids or solids at room temperature. Alcohols
of low molecular weight are highly soluble in
water; with increasing molecular weight, they
become less soluble in water, and their boiling
points, vapour pressures, densities, and
viscosities increase.

NOMENCLATURE
As with other types of organic compounds,
alcohols are named by both formal and
common systems. The most generally
applicable system is that adopted at a meeting
of the International Union of Pure and Applied
Chemistry (IUPAC) in Paris in 1957. Using the
IUPAC system, the name for an alcohol uses
the -ol suffix with the name of the parent
alkane, together with a number to give the
location of the hydroxyl group. The rules are
summarized in a three-step procedure:

1. Name the longest carbon chain that

contains the carbon atom bearing the
OH group. Drop the final -e from the
alkane name, and add the suffix -ol.
2. Number the longest carbon chain
starting at the end nearest the OH
group, and use the appropriate number,
if necessary, to indicate the position of
the OH group.
3. Name the substituents, and give their
numbers as for an alkane or alkene.

The first example below has a longest chain of

six carbon atoms, so the root name is hexanol.
The OH group is on the third carbon atom,
which is indicated by the name 3-hexanol.
There is a methyl group on carbon 3 and a
chlorine atom on carbon 2. The complete
IUPAC name is 2-chloro-3-methyl-3-hexanol.

The prefix cyclo- is used for alcohols with

cyclic alkyl groups. The hydroxyl group is
assumed to be on carbon 1, and the ring is
numbered in the direction to give the lowest
possible numbers to the other substituents, as
in, for example, 2,2-dimethylcyclopentanol.

PHYSICAL
PROPERTIES OF ALCOHOLS
Most of the common alcohols are colourless
liquids at room temperature. Methyl alcohol,
ethyl alcohol, and isopropyl alcohol are freeflowing liquids with fruity odours. The higher
alcoholsthose containing 4 to 10 carbon

atomsare somewhat viscous, or oily, and they

have heavier fruity odours. Some of the highly
branched alcohols and many alcohols
containing more than 12 carbon atoms are
solids at room temperature

The oxygen atom of the strongly polarized

OH bond of an alcohol pulls electron density
away from the hydrogen atom. This polarized
hydrogen, which bears a partial positive charge,
can form a hydrogen bond with a pair of
nonbonding electrons on another oxygen atom.
Hydrogen bonds, with a strength of about 5

kilocalories (21 kilojoules) per mole, are much

weaker than normal covalent bonds, with bond
energies of about 70 to 110 kilocalories per
mole. (The amount of energy per mole that is
required to break a given bond is called its bond
energy.)

Water and alcohols have similar properties

because water molecules contain hydroxyl
groups that can form hydrogen bonds with
other water molecules and with alcohol
molecules, and likewise alcohol molecules can
form hydrogen bonds with other alcohol
molecules as well as with water. Because
alcohols form hydrogen bonds with water, they
tend to be relatively soluble in water. The
hydroxyl group is referred to as a hydrophilic
(water-loving) group, because it forms
hydrogen bonds with water and enhances the

solubility of an alcohol in water. Methanol,

ethanol, n-propyl alcohol, isopropyl alcohol,
and t-butyl alcohol are all miscible with water.
Alcohols with higher molecular weights tend to
be less water-soluble, because the hydrocarbon
part of the molecule, which is hydrophobic
(water-hating), is larger with increased
molecular weight. Because they are strongly
polar, alcohols are better solvents than
hydrocarbons for ionic compounds and other
polar substances.

The mixture of carbon monoxide and hydrogen

needed to make methanol can be generated by
the partial burning of coal in the presence of

water. By carefully regulating the amount of

water added, the correct ratio of carbon
monoxide to hydrogen can be obtained.

Methanol has excellent properties as a polar

organic solvent and is widely used as an
industrial solvent. It is more toxic than ethanol,
however, and may cause blindness or death if
large amounts are inhaled or ingested.
Methanol has a high octane rating and a low
emission of pollutantscharacteristics that
make it a valuable fuel for automobile engines.
From the late 1960s until 2006, the cars at the
Indianapolis 500, the automobile race held
annually at the Indianapolis Motor Speedway,
were powered by methanol-burning engines.
Methanol was once under consideration as a

commercial motor fuel because it is cheaper

than ethanol and can be made from natural gas
and coal resources. However, increasing
interest in ethanol-based fuels and difficulties
involving the solvent properties of methanol,
which cause problems with fuel systems
especially in fuel-injected carshave resulted
in diminished commercial interest in methanol
fuels. Methanol tends to dissolve the plastic and
rubber components employed in modern fuel
systems, and different materials must be used
that can survive exposure to methanol over long
periods of time without dissolving or cracking.