Prepared by: MARY JANE T.

DELA CRUZ
E-mail Address: maryjane.delacruz@clsu2.edu.ph

Central Luzon State University

Science City of Muñoz 3120
Nueva Ecija, Philippines

Instructional Module for the Course

Organic Chemistry Lecture

Module 8

Lesson 8. Identification of
Alcohols and Phenols

Overview

Module 8 aims to introduce the different classifications of alcohols and

to learn the uses, properties and nomenclature of Alcohols and phenols.
o Lesson 8.1 – Introduction to Alcohols and phenols o Lesson 8.2
– Classifications of Alcohols
o Lesson 8.3 – Sources, uses and physical properties of Alcohols
and phenols
o Lesson 8.4 – Nomenclature of Alcohols and phenols

I. Objectives

On successful completion of the module, students should be able to;

1. classify alcohols as primary, secondary, and tertiary alcohols;

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 2. learn the sources, uses and physical properties of alcohols and phenols;
and

3. name different compounds of alcohols and phenols

II. Learning Activities

Lesson 8.1 – Introduction to Alcohols and Phenols

Specific groups of atoms in an organic molecule can determine its physical and
chemical properties. These groups are referred to as functional groups. Organic
compounds which contain the functional group-OH, the hydroxyl group, are
called alcohols.

Alcohols are important commercially and include use as solvents, drugs, and
disinfectants. The most widely used alcohols are methanol or methyl alcohol,
CH3OH, ethanol or ethyl alcohol, CH3CH2OH, and 2-propanol or isopropyl
alcohol, (CH3)2CHOH. Methyl alcohol is found in automotive products such as
antifreeze and "dry gas." Ethyl alcohol is used as a solvent for drugs and
chemicals, but is more popularly known for its effects as an alcoholic beverage.
Isopropyl alcohol, also known as "rubbing alcohol," is an antiseptic.

Alcohols may be classified as either primary, secondary, or tertiary.

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Note that the classification depends on the number of carbon- containing
groups, R (alkyl or aromatic), attached to the carbon bearing the hydroxyl
group. Examples of each type are as follows:

Phenols bear a close resemblance to alcohols structurally since the hydroxyl

group is present. However, since the -OH group is bonded directly to a carbon

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that is part of an aromatic ring, the chemistry is the different from that of
alcohols.

Phenol

In this laboratory exercise, you will examine physical and chemical

properties of representative alcohols and phenols. You will be able to
compare the differences in chemical behavior between these compounds.

Solubility of alcohols in water

Hydrogen bonding occurs between molecules in which a hydrogen atom is

attached to a strongly electronegative element: fluorine, oxygen or
nitrogen. In the case of alcohols, hydrogen bonds occur between the
partially-positive hydrogen atoms and lone pairs on oxygen atoms of other
molecules.

The hydrogen atoms are slightly positive because the bonding electrons are
pulled toward the very electronegative oxygen atoms. In alkanes, the only
intermolecular forces are van der Waals dispersion forces. Hydrogen bonds
are much stronger than these; therefore, more energy is required to
separate alcohol molecules than to separate alkane molecules. This is the
main reason for higher boiling points in alcohols.

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 Since the hydroxyl group is present in alcohols and phenols, these
compounds are polar. The polarity of the hydroxyl group, coupled with its
ability to form hydrogen bonds, enables alcohols and phenols to mix with
water. Since these compounds also contain non-polar portions, they show
additional solubility in many organic solvents, such as dichloromethane and
diethyl ether.

Small alcohols are completely soluble in water; mixing the two in any proportion
generates a homogenous solution. However, solubility
decreases as the length of the hydrocarbon chain in the alcohol increases.
At four carbon atoms and beyond, the decrease in solubility is noticeable; a
two-layered substance may appear in a test tube when the two are mixed.

Consider ethanol as a typical small alcohol. In both pure water and pure ethanol
the main intermolecular attractions are hydrogen bonds.

As the length of the alcohol increases, this situation becomes more

pronounced, and thus the solubility decreases

Boiling points of alcohols

Hydrogen bonding is not the only intermolecular force alcohols experience.

They also experience van der Waals dispersion forces and dipole-dipole
interactions. The hydrogen bonding and dipole-dipole interactions are
similar for all alcohols, but dispersion forces increase as the size of the
alcohols increase. These attractions become stronger as the molecules
lengthen and contain more electrons. This increases the sizes of the
temporary dipoles formed. This is why the boiling points increase as the
number of carbon atoms in the chains increases. It takes more energy to
overcome the dispersion forces; thus, the boiling points rise.

Notice that:

• The boiling point of an alcohol is always significantly higher than that of the
analogous alkane.
• The boiling points of the alcohols increase as the number of carbon atoms
increases.

The patterns in boiling point reflect the patterns in intermolecular attractions.

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 Acidity of Phenol.

Phenol is also called carbolic acid. Phenol is an acid and will react with base;
thus phenols readily dissolve in base solutions. In contrast, alcohols are
(weakly acidic) not acidic. Phenol gives red color with litmus paper. The
dissociation of phenol in water is represented as follows:

CLASSIFICATIONS OF ALCOHOLS

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A. According to the number of Hydroxyl group

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B. According to the location of -OH group

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 USES OF SOME IMPORTANT ALCOHOLS

1. METHANOL (methyl alcohol;

wood alcohol; CH3OH)
• the lowest molecular weight alcohol
• Wood alcohol because it can be obtained by
heating wood in the absence of air, a process called
destructive distillation.
• Widely use as a solvent and industrial starting material
• Highly toxic, if taken internally causes blindness and/or
death

2. ETHANOL (ethyl alcohol; grain alcohol; CH3 CH2OH)

• Grain alcohol because starch from grain when

hydrolyzed to sugars and fermented by enzymes,
produces ethanol and CO2
• Useful as a solvent in tinctures, essences and
extracts
• It evaporates rapidly and consequently reduces body temperature
• Used in the manufacture of ether, chloroform, ethylene, iodoform, and
many other preparations
• Found in alcoholic beverages (4-50%); and 50%-70% solution is used
as germicides
• Prolonged overuse of ethanol can lead to liver damage

Beer 3-6% alcohol

Most wines 12-15% alcohol
Whiskey, gin 40-50% distilled liquors

PROOF SPIRIT= the alcoholic content of liquors

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 4. GLYCEROL (1,2,3-Propanetriol ; CH2OH-CHOH-CH2OH)

It is used in the preparation of toothpastes to

keep them moist and in the manufacture of lotions,
in the manufacture of dynamite and other explosives.
It is used as a food moistening agent
(nontoxic) , as lubricants and for its soothing
qualities (soaps)

When nitroglycerin is mixed with a solid material such as

= a solution of alcohol in water containing half of
its volume of absolute alcohol
Example: 80 proof means 40% alcohol

3. ISOPROPYLALCOHOL(2-Propanol;
CH3CHOHCH3)

• It is the main component of rubbing alcohol.

• A 70% solution is used for its antibacterial properties

nitrocellulose (which is made by treating cotton or wood pulp with nitric

acid), the product is dynamite.

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 5. ETHYLENE GLYCOL (CH2OH-CH2OH; 1,2-ethanediol)
It is used as an antifreeze in the radiators of automobiles

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 6. PHENOLS

It behaves as a weak acid in water. Phenol can react with

bases to form salt.
In a dilute solution (about 2-5%) phenol, is used as a
disinfectant.
Phenol derivatives are used as antioxidants in food
It is also used in the manufacture of drugs, dyes, explosives,
nylons and plastics.

III. REFERENCES

https://slideplayer.com/slide/8733823/
https://www.google.com/search?q=monohydric+alcohol+structure&tbm=isch&hl=en&sa
=X&ved=2ahUKEwj3lMmEosfsAhXDeN4KHVQdDQYQrNwCKAB6BQgBENAB&biw=1221&
bih=568#imgrc=jnNE_jWAjL1ysM

https://www.google.com/search?q=monohydric+alcohol+structure&tbm=isch&hl=en&sa
=
X&ved=2ahUKEwj3lMmEosfsAhXDeN4KHVQdDQYQrNwCKAB6BQgBENAB&biw=1221&
bih=568#imgrc=anjU6ax-VxtE9M&imgdii=5wojUWSE7ZlMRM

https://www.google.com/search?q=monohydric+alcohol+structure&tbm=isch&hl=en&sa
=
X&ved=2ahUKEwj3lMmEosfsAhXDeN4KHVQdDQYQrNwCKAB6BQgBENAB&biw=1221&
bih=568#imgrc=quMX2a2xmNKJWM&imgdii=anjU6ax-VxtE9M

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