Physical Properties of Alcohol

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Katrina Jade A.

Pajo
BS Physics II

PHYSICAL PROPERTIES OF ALCOHOL


Most of the common alcohols are colourless liquids at room temperature. Methyl
alcohol, ethyl alcohol, and isopropyl alcohol are free-flowing liquids with fruity odours. The
higher alcohols—those containing 4 to 10 carbon atoms—are 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.

1. Boiling Point of Alcohols


Alcohols generally have higher boiling points in comparison to other hydrocarbons having
equal molecular masses. This is due to the presence of intermolecular hydrogen bonding
between hydroxyl groups of alcohol molecules.

This graph shows the comparison of boiling points of methane with methanol, ethane with
ethanol, propane with propanol, and butane with butanol.
From the graph we can see that the boiling point of an alcohol is always much higher than the
boiling point of the corresponding alkane with the same hydrocarbon chain. The boiling point of
alcohols also increase as the length of hydrocarbon chain increases.
The reason why alcohols have a higher boiling point than alkanes is because the
intermolecular forces of alcohols are hydrogen bonds, unlike alkanes with van der Waals forces
as their intermolecular forces.

In general, the boiling point of alcohols increases with an increase in the number of carbon
atoms in the aliphatic carbon chain. On the other hand, the boiling point decreases with an
increase in branching in aliphatic carbon chains the Van der Waals forces decreases with a
decrease in surface area. Thus primary alcohols have a higher boiling point.
The factors affecting the boiling/melting points of
alcohols are not only hydrogen bonds, but also van der
Waals dispersion forces and dipole-dipole interactions.
The hydrogen bonds and dipole-dipole interactions will
remain relatively the same throughout the series of alcohols.
The van der Waals dispersion forces increase as the length
of hydrocarbon chain increases. This is due to the increase
in number of electrons in the molecules, which in turns
increases the strength and size of the temporarily induced
dipole-dipole attraction. Hence, more energy is required to
overcome the intermolecular forces, resulting in the increase
in boiling/melting points.

2. Solubility of Alcohols
Alcohols are soluble in water. The solubility of alcohol in water is governed by the
hydroxyl group present. The hydroxyl group in alcohol is involved in the formation of
intermolecular hydrogen bonding. Thus, hydrogen bonds are formed between water and alcohol
molecules which make alcohol soluble in water.

However, the alkyl group attached to the hydroxyl group is hydrophobic in nature. Thus, the
solubility of alcohol decreases with the increase in the size of the alkyl group.

With four carbon in the hydrocarbon chain and higher, the decrease in solubility becomes
visible as the mixture forms two immiscible layers of liquid. The reason why the solubility
decreases as the length of hydrocarbon chain increases is because it is requires more energy to
overcome the hydrogen bonds between the alcohol molecules as the molecules are more tightly
packed together as the size and mass increases.

In the image on the left, the partially negative oxygen atom


in the ethanol molecule forms a hydrogen bond with the
partially positive hydrogen atom in the water molecule.

3. The Acidity of Alcohols


Alcohols react with active metals such as sodium,
potassium etc. to form the corresponding alkoxide. These
reactions of alcohols indicate their acidic nature. The acidic
nature of alcohol is due to the polarity of –OH bond. The acidity of alcohols decreases when an
electron-donating group is attached to the hydroxyl group as it increases the electron density on
the oxygen atom. Thus, primary alcohols are generally more acidic than secondary and tertiary
alcohols. Due to the presence of unshared electrons on the oxygen atom, alcohols act as
Bronsted bases too.

4. Viscosity
Viscosity is the property of a fluid that resists the force tending to cause the fluid to flow.
The viscosity of alcohols increase as the size of the molecules increases. This is because the
strength of the intermolecular forces increases, holding the molecules more firmly in place.
5. Polarity
Amide > Acid > Alcohol > Ketone ~ Aldehyde > Amine > Ester > Ether > Alkane
Amide is the most polar while alkane is the least. Alcohol is ranked third in terms of
polarity due to its hydrogen bonding capabilities and presence of one oxygen atom in an alcohol
molecule. Carboxylic acids are more polar than alcohols because there are two oxygen atoms
present in a carboxylic acid molecule.
6. Flammability
The flammability of alcohols decrease as the size and mass of the molecules increases.
Combustion breaks the covalent bonds of the molecules, so as the size and mass of the
molecules increases, there are more covalent bonds to break in order to burn that alcohol. Hence,
more energy is required to break the bonds, therefore the flammability of alcohols decrease as
size and mass of molecules increases.

USES OF ALCOHOL
Methanol
Methanol (methyl alcohol) was originally produced by heating wood chips in the absence of
air. Some of the carbohydrates in the wood are broken down to form methanol, and the methanol
vapour is then condensed. This process led to the name wood alcohol as another common name
for methanol. Methanol is synthesized commercially by a catalytic reaction of carbon
monoxide (CO) with hydrogen gas (H2) under high temperature and pressure.

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 pollutants—characteristics 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 cars—have 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.

Ethanol
Ethanol (ethyl alcohol) has been produced since prehistoric times, mostly through
the fermentation of fruit juices. The fermented juice could be stored in a sealed container, and
this primitive wine remained safe to drink throughout the winter. Many different sources can
provide the sugars and starches that are broken down to simpler compounds during
fermentation.
Ethanol is called grain alcohol because it is often made from grains, such
as corn (maize), wheat, rye, and barley. The grain is first boiled in water to produce the mash,
which is incubated with malt (sprouted barley) to yield the wort. Malt provides
an enzyme (diastase) that converts starches in the grain to the sugar maltose. The wort is
incubated with brewer’s yeast, which secretes the enzyme maltase to convert maltose
to glucose and the enzyme zymase to convert glucose to ethanol. Two of the six carbon atoms in
glucose are oxidized to carbon dioxide (CO2); this oxidation provides energy to the yeast cells.

Fermentation yields a solution that is only about 12–15 percent alcohol because higher
concentrations are toxic to the yeast cells. This solution can be distilled, however, to raise the
ethanol content to as high as 95 percent.
Fermentation is a relatively expensive method of making ethanol. Industrial ethanol is more
commonly synthesized by the high-temperature catalytic addition of water to ethylene (C2H4).

Ethanol is an excellent motor fuel with a high octane rating and low emissions; however, it
should be used in a fuel system designed to withstand the alcohol’s tendency to dissolve plastic
parts. Solutions of 10 percent ethanol in gasoline (gasohol) can be used in most cars without any
adjustments. Today, ethanol fuels are typically made from natural products, such
as corn or sugar.
Isopropyl alcohol

Isopropyl alcohol (2-propanol) is made by indirect hydration of propylene (CH2CHCH3).


Isopropyl alcohol is commonly used as an industrial solvent and as a rubbing alcohol applied to
the skin. Although isopropyl alcohol is more toxic than ethanol, it has less of a drying effect on
the skin, and it is not regulated and taxed by the U.S. government as is ethanol.

Ethylene glycol
The name ethylene glycol refers literally to “the glycol made from ethylene.” Its systematic
name is ethane-1,2-diol. Ethylene glycol is commonly used as automotive antifreeze and as an
ingredient in hydraulic fluids, printing inks, and paint solvents. It is also used as a reagent in
making polyesters, explosives, alkyd resins, and synthetic waxes.

Glycerol
Glycerol (also called glycerine) is a sweet syrupy substance with three alcohol hydroxyl
groups. Its systematic name is propane-1,2,3-triol. Glycerol was first obtained as a by-product of
soap manufacture, through the saponification (hydrolysis in base) of fats. About 25 kg (60
pounds) of glycerol is obtained with each ton of soap. It can also be obtained by fermentation
from molasses and sugar. During World War II, large quantities of glycerol were needed for the
production of glyceryl trinitrate (nitroglycerin); this need was met by synthetic glycerol made
from propylene, CH2=CH―CH3.

A large amount of glycerol is still used for making nitroglycerin, which is the primary
explosive in dynamite and blasting gelatin. Nitroglycerin is also used as a coronary vasodilator
(a drug that relaxes and expands blood vessels) for symptomatic relief of chest pain caused by
poor circulation to the heart. Glycerol is also used as a solvent, moisturizing agent, plasticizer,
antifreeze, and water-soluble lubricant. It is found in a wide variety of products, including foods,
soaps, cosmetics, printing inks, hydraulic fluids, and pharmaceuticals.
References:
https://sites.google.com/site/chemistryolp/properties-of-alcohols

https://www.toppr.com/guides/chemistry/alcohols-phenols-and-ethers/physical-properties-of-alc
ohols-phenols-and-ethers/

https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Map%3A_Organic_Chemistry_(W
ade)/13%3A_Structure_and_Synthesis_of_Alcohols/13.03%3A_Physical_Properties_of_Alcoho
ls
https://www.britannica.com/science/alcohol/Physical-properties-of-alcohols

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