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derivatives of water (H2O) in which one of the hydrogen atoms has been replaced by an alkyl group,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.Alcohol molecules are organic molecules that contain an -OH group.
This -OH group makes the molecule reactive, so it is called a functional group.

Alcohol functional groups are

found in biological molecules such as sugars, amino acids, and vitamins. Alcohol functional groups are
also found in molecules that are used every day. You can find ethanol in drinks like wine, beer, vodka,
whiskey, gin, and rum, among many others. Ever had to check the antifreeze levels in your car? It
contains ethylene glycol, another alcohol.

Structure of ethylene glycol

Nomenclature

The alcohol functional group hydroxyl is an -OH group. When naming alcohols, the -e is removed from
the hydrocarbon name and an -ol suffix is added. A number in front of the hydrocarbon name tells the
location of the alcohol group.

For example, in 1-butanol, there are four carbon atoms, so the parent hydrocarbon name is butane. The
-e is dropped from butane and -ol is added, resulting in butanol. The 1 indicates the alcohol group is on
the first carbon.
1-butanol

The carbon chain should be numbered so that the alcohol has the lowest number. When naming the
molecule 1-butanol, you can either name it as 4-butanol or 1-butanol, depending on which side of the
molecule you begin to count. Since 1 is a smaller number than 4, 1-butanol is correct. If there are two
alcohol groups on a molecule the suffix is changed to -diol.

Alcohol Molecule Classification

Molecules can be classified based on the number of alcohol groups.

monohydric -one alcohol group on the molecule

dihydric - two alcohol groups on the molecule

polyhydric - more than 2 alcohol groups on the molecul

Solubility

The number of alcohol groups that a molecule has will affect its solubility. As the number of alcohol
groups increase on the molecule with the same number of carbons, the solubility in water increases. For
example, 1,4- butandiol is more soluble in water than
1-butanol.

1-butanol (above) is less soluble than 1,4-butandiol, because it has fewer alcohol groups
butanol

Another way to think about this is that as the number of carbon atoms increase in an alcohol, the
solubility in water decreases. So, 1-octanol with eight carbons per alcohol group is less soluble in water
than 1-butanol with four carbons per alcohol group.

Classification of Alcohols

Some of the properties of alcohols depend on the number of carbon atoms attached to the specific
carbon atom that is attached to the OH group. Alcohols can be grouped into three classes on this basis.

A primary (1°) alcohol is one in which the carbon atom with the OH group is attached to one other
carbon atom. Its general formula is RCH2OH.

A secondary (2°) alcohol is one in which the carbon atom with the OH group is attached to two other
carbon atom. Its general formula is R2CHOH

A tertiary (3°) alcohol is one in which the carbon atom (in red) with the OH group is attached to three
other carbon atoms (in blue). Its general formula is R3COH.
Alcohol Functional Group Classification

Alcohols can also be classified based on the carbon to which they are attached.

primary - the alcohol is attached to a carbon with two hydrogens

secondary - the alcohol is attached to a carbon with one hydrogen

tertiary - the alcohol is attached to a carbon atom with no hydrogens

Examples of primary, secondary, and tertiary alcohols

classification of alcohols

Physical properties of alcohols)

IUPAC name. common name. formula

methanol. methyl alcohol. CH3OH

ethanol. ethyl alcohol. CH3CH2OH

1-propanol. n-propyl alcohol. CH3CH2CH2OH

2-propanol. isopropyl alcohol. (CH3)2CHOH

Physical Properties of Alcohols

The physical properties of alcohol can be explained by the following points –

i. Alcohols are colourless.

ii. They generally give a sweet smell except for glycerol and a few lower alcohols.

iii. They are flammable and produce a blue flame.

iv. They don’t produce any smoke while burning.

v. They are generally liquid at room temperature. Although glycerol is a viscous liquid.

vi. Boiling Point of Alcohol - They generally have higher boiling points if we compare them with other
hydrocarbons. For example, ethanol shows a boiling point of 78.29 ℃ while he Hixane shows a boiling
point of 69℃. This is because of the presence of intermolecular hydrogen bonding between hydroxyl
groups of alcohols. The boiling point of alcohol increases with an increasing number of carbon atoms in
organic alcoholic compounds.

vii. Alcohols work as suitable solvents for many organic compounds as organic compounds are insoluble
in water.

viii. Alcohols are acidic in nature. They react with metals such as sodium, potassium etc. It is due to the
polarity of the bond between a hydrogen atom and the oxygen atom of the hydroxyl group. Primary
alcohols are more acidic than secondary and tertiary alcohols.

ix. Due to the polar -OH bond in alcohols, they are more soluble in water than other simple
hydrocarbons. For example, methanol and ethanol are miscible in water.

Chemical Properties of Alcohols

The chemical properties of alcohol can be explained by the following points –

i. Oxidation Reaction of Alcohol – Alcohols produce aldehydes and ketones on oxidation. The reaction is
given below –

C₂H₅OH + 2O 🡪 CH₃COOH + H₂O

Ethanol Methanoic acid

ii.Combustion of Alcohol – On heating ethanol gives carbon dioxide and water and burns with a blue
flame. The reaction is given below –

C₂H₅OH + 3O₂ 🡪 2CO₂ + 3H₂O

iii. Dehydration of Alcohol – Alcohol can be dehydrated in an acidic medium. The removal of water
molecules from a compound is called dehydration. Upon dehydration of alcohol alkenes are produced.
The reaction is given below –

C2H5OH (conc. H₂SO₄,▵)→C₂H₄ + H₂O

iv.The reaction of Alcohol With Metal – Due to its acidic nature alcohol reacts with metal and forms
alkoxide. For example, when ethanol reacts with sodium forms sodium ethoxide and hydrogen gas. The
reaction is given below –

2C₂H₅OH + 2Na →2C₂H₅ONa + H₂

v. Formation of Halides From Alcohols – Alcohol reacts with HCl and forms alkyl halides by removal of
hydroxyl groups. The reaction is given below

ROH + HCl (Zn) 🡪 R-Cl + H₂

vi.Esterification – Alcohol reacts with a carboxylic acid in presence of a catalyst and forms ester. It is
called Fischer esterification. The reaction is given below –

C₂H₅OH + C₂H₃COOH →C₄H₈O₂ + H₂O

Application of Alcohol

There is a long history of alcohol for myriad uses. For instance, mono-alcohols are the most important
alcohols that are used in industries. Some of the applications of alcohol are as follows:-

i. For formaldehyde and fuel additive production, methanol is mainly used.

ii. For alcoholic beverages, fuel additives, solvent production, ethanol is mainly used.

iii. 1-propanol, 1-butanol, and isobutyl alcohol are used as a solvent and precursors to solvents.

iv. C6–C11 alcohols are used for plasticizers in polyvinylchloride and many more.

v. fatty alcohol (C12–C18) are utilized as precursors to detergents.

Reactions of alcohols

Uses of the first four alcohols

Methanol is used as a chemical feedstock. It is toxic, so it is deliberately added to industrial ethanol

(methylated spirits) to prevent people from drinking it.

Ethanol is the alcohol present in alcoholic drinks. It is also used as a fuel and a solvent.

Propanol and butanol are also used as solvents and fuels.

Combustion

The alcohols undergo complete combustion to form carbon dioxide and water. For example, ethanol is
used as a fuel:

ethanol + oxygen → carbon dioxide + water

C2H5OH + 3O2 → 2CO2 + 3H2O

When less oxygen is present, incomplete combustion will occur, producing water and either carbon
monoxide or carbon.
Reactions with sodium

If a small piece of sodium is dropped into ethanol, bubbles of hydrogen gas are produced and the liquid
contains sodium ethoxide. The reaction is:

sodium + ethanol → sodium ethoxide + hydrogen

2Na + 2C2H5OH → 2C2H5ONa + H2

Methanol, propanol and butanol undergo similar reactions.

Solubility in water

When the alcohols with the shortest hydrocarbon chains, eg methanol, ethanol or propanol, are added
to water, they mix easily to produce a solution. However, the solubility decreases as the length of the
alcohol molecule gets longer, so butanol is less soluble than propanol. It may not mix easily, and two
distinct layers might be left in the container.

Oxidation of alcohols

The alcohols can also be oxidised without combustion to produce carboxylic acids. For example, ethanol
can be oxidised to ethanoic acid using an oxidising agents.

ethanol + oxidising agent → ethanoic acid + water

CH3CH2OH + 2[O] → CH3COOH + H2O

It is easier to understand what happens if ethanol is shown as CH3CH2OH in the balanced equation:

Each of the two oxygen atoms provided by the oxidising agent are shown as [O]. Notice that the left-
hand side of the ethanol molecule is unchanged. The reaction involves the -OH group on the right-hand
side.

IUPAC Nomenclature for Alcohols

The following procedure should be followed in giving alcohol IUPAC substitutive names.

1. Select the longest continuous chain to which the hydroxyl group is directly attached. Change the
name of the alkane corresponding to the chain by dropping the final -e and adding the suffix -ol.

2. Number the longest continuous carbon chain so as to give the carbon atom bearing the hydroxyl
group the lower number. Indicate the position of the hydroxyl group by using this number as a locant.

3. Indicate the position of another substituent as a prefix by using the numbers corresponding to their
positions along the carbon chain as locants.

The following example shows how the rules are applied.

IUPAC Nomenclature for Alcohols

Types of Nomenclature in Alcohols

There are three systems of naming alcohols

Common or trivial system

Carbinol system and

IUPAC system

Formula Parent Hyrocabon Common name IUPAC name

CH3-OH Methane Methyl alcohol Methanol

CH3-CH2-OH Ethane Ethyl alcohol Ethanol

CH3-CH(OH)-CH3 Propane Isopropyl alcohol 2-Propanol

(CH3)3-CH-OH 2-Methyl propane Tert-butyl alcohol 2-methyl-2-

propanol

Uses of Alcohols

1. Alcoholic Drinks.

2. Industrial methylated spirits.

3. Use of ethanol as a fuel.

4. Ethanol as a solvent.

5. Methanol as a fuel.

6. Methanol as an industrial feedstock.

Uses of Alcohols

There are several uses of alcohols. Some are listed below.

1. Alcohols are consumed as beverages where the alcohols specifically consist of 30–40 per cent of
ethanol by volume.

2. These are used as an anti-freezing agent with a mix of a solution containing ethylene glycol dissolved
in water.

3. Alcohol ethanol is used as an antiseptic agent.

4. Some alcohols are used as fuels in the internal combustion engines like the methanol.

5. In the field of medicine, a few of them are used as preservatives for the specimens in laboratories.

6. Ethanol is used in spirits, as fuel, and as a solvent.

7. Methanol is also used as fuel and in the manufacture of other organic compounds like methanal
(formaldehyde), ethanoic acid, and methyl esters.

Nomenclature of Diols

In an earlier article, we discussed the nomenclature of alcohols and mentioned that the presence of a
hydroxyl is identified by changing the parent suffix from “e” to “ol”:

Now, compounds
with two hydroxy
groups are called diols in
the IUPAC nomenclature. So, to name a diol, the suffix -diol is added to the name of the parent chain
alkane, and the positions of these hydroxyl groups are indicated with numbers just like for any
functional group we have seen before.

For example,

Notice that unlike in regular alcohols, an “e” appears in between the parent and the suffix “diol”.
Simple diols are also commonly named as glycols which is also accepted by the IUPAC system.

Having two hydroxyl groups

brings some change to the physical properties of diols due to the additional hydrogen bonding. For
example, diols are used in as antifreeze to cool down internal combustion engines of automobiles. And
in order to qualify for this application they need to have a significantly lower freezing point and higher
boiling point than water. The combination of ethylene glycol (f.p. = -12.9 °C) and propylene glycol (f.p. =
-59 °C) is most commonly used in antifreeze solutions.

Reactions of Alcohols

1. Oxidation
Primary and secondary alcohols are readily oxidized. We saw earlier how methanol and ethanol are
oxidized by liver enzymes to form aldehydes. Because a variety of oxidizing agents can bring about
oxidation,

126.comwe can indicate an oxidizing agent without specifying a particular one by writing an equation
with the symbol [O] above the arrow. For example, we write the oxidation of ethanol—a primary alcohol
—to form acetaldehyde—an aldehyde—as follows:

Formula of ethanol reacting to form acetaldehyde with an O in a bracket above the right pointing arrow.
Alcohol oxidation is important in living organisms. Enzyme-controlled oxidation reactions provide the
energy cells need to do useful work. One step in the metabolism of carbohydrates involves the oxidation
of the secondary alcohol group in isocitric acid to a ketone group: