Authors

Judelene I. Adriano

Mieraflor C. Estrella

Josephine R. Mariano

Rose Ann Zabala

 In Partial Fulfillment of the Requirements

for the Degree Master of Arts in Education,

Major in Chemistry

Authors

Judelene I. Adriano

Mieraflor C. Estrella

Josephine R. Mariano

Rose Ann Zabala

Reviewed by

Eleonor R. Basilio

ORGANIC CHEMISTRY MODULE FOR JUNIOR HIGH SCHOOL by CHEMISTRY STUDENTS is

licensed under a Creative Commons Attribution 4.0 International License.
 TABLE OF CONTENTS

TOPIC PAGE

I. Introduction to Chemistry ……………………………… 1 - 12

II. Alkanes ………………………………………………… 12 - 27

III. Alkenes …………………………………………………. 28-40

IV. Alkynes …………………………………………………. 41-48

V. Alkyl Halides ……………………………………………. 49-68

VI. Alcohols …………………………………………………. 69-82

VII. Esters …………………………………………………….. 83-99

VIII. Carboxylic acid …………………………………………..100 - 118

IX. Ethers ……………………………………………………. 119-134

X. Aromatic Compounds ……………………………………. 135-155

XI. Aromatic compounds

 PREFACE

Every chemistry teacher desires to make the study of chemistry easy and fun. Thus, we
decide to come up with an instructional module that intends to convey the subject for all to
understand and appreciate. The aim of this module is to link the observations that are familiar to
students with the concept of chemistry. We believe that the student’s daily experiences serve as
springboard for them to learn more and understand better the world of atoms.

The module provides many examples to guide both the teacher and the student in
understanding and working with organic chemistry ideas. It also provides chapter-end exercises to
help the students master the subject. Throughout, the module target to demonstrate that organic
chemistry is not the difficult subject that is often mistaken to be. Rather, the message which the
module puts across is that organic chemistry is well within every student’s capability to understand
and enjoy, especially if he/she forms the habit of doing the exercises designed for them.

We hope that the students will find this module as their tool in exploring the complicated,
yet interesting world of chemistry.

The Authors
 ACKNOWLEDGEMENT

We, the authors, would like to express our sincerest gratitude to everyone who made the
completion of this module possible. Their guidance, which came in various forms, has been
valuable towards the accomplishment of this project.

Thank you to our families and friends who extended their understanding during our
"module-writing moments." Those times when we could not go out and spend time with each and
every one of you were the moments we were busy planning and writing this module.

To our professor, Ms. Eleonor Basilio, thank you. The knowledge you imparted upon us is
on every page of this module. This module is a reflection of how your sincere guidance and
constant reminders motivated us to accomplish every task.

To each and every member of this group, whose battle cry has always been "One for all,
all for one," thank you. We made the seemingly insurmountable task of writing a module in
Organic Chemistry possible. We can now call ourselves "authors."

And to God Almighty, thank you for giving us wisdom and courage from beginning to end,
and for blessing us with the right people to carry on this task. Truly, with You, all things are
possible.

May this module, which is a product of our hard work, be beneficial to both the learners
and the teachers.
 The study of carbon-containing molecules, also referred to as organic compounds, is
known as organic chemistry. It is possible to separate and purify organic substances from both
plants and animals. Additionally, a lab can be used to prepare them.

After going through this module, you are expected to

a. Describe the various compounds that carbon can make,

b. Distinguish between organic and inorganic substances,
c. Create organic compound structural formulae,
d. Determine the various categories of hydrocarbons,
e. Identify organic chemicals, and
f. Describe the uses and applications of carbon in daily life.

PRETEST

DIRECTION: Encircle the letter of the correct answer.

1. Which of the following compounds is not organic?

a. CH4
b. C2H2
c. CO
d. CCl4

2. What are the Aliphatic Hydrocarbons?

a. Open chained carbon-hydrogen organic compounds
b. Open chained carbon hydrogen organic compounds

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 c. Closed chained carbon hydrogen organic compounds
d. Closed chained carbon hydrogen and some other elements organic compounds

3. Which type of formulas represents only combination ratio of the constituent atoms?
a. Structural Formula
b. Molecular Formula
c. Empirical Formula
d. Condense Formula

4. 4. Is this hydrocarbon saturated or unsaturated?

a. saturated
b. unsaturated

5. Organic compounds made only of the elements carbon and hydrogen are called...
a. Hydrocarbons
b. Carbohydrates
c. Carbohydrogens
d. Hydrocarbonates

6. At which pipe: M or N are hydrocarbons with lower boiling points collected?

a. M
b. N

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7. Name this alkane
a. Methane
b. Propane
c. Ethane
d. Butane

8. The following compounds have a molecular formula of

a. CnH2n+2
b. C6H14
c. CH4
d. CH3CH2CH2CH2CH2CH3

9. Give the IUPAC name for this compound

a. 3-methyl-4-ethylhexane
b. 3-methyl-4-ethylheptane
c. 3-ethyl-4-methylhexane
d. 3-ethyl-4-methylheptane

10. What is the IUPAC name of the figure below?

Answer:

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THE CARBON ATOM

The periodic table of element with the symbol C and atomic number 6 is carbon. Only about
0.027 percent of the earth's crust is made up of carbon, hence it is not widely distributed there.
Although carbon can exist in elemental forms, the majority of it is found in mixed forms. It can be
found in carbonates, coal and other fossil fuels, as well as in biological things.

The three crystalline forms of carbon are fullerenes, graphite, and diamond. A soft, black,
slick substance with a metallic shine and electrical conductivity is called graphite.

Diamond is a transparent, extremely hard solid with a Mohs hardness of 10 and a covalent
network made up of four carbon atoms. Diamond has a density of 3.55 g/cm3 whereas graphite
only has a density of 2.25 g/cm3. The primary purposes of industrial diamond production are as
cutting, grinding, and polishing tools.

The molecular forms of carbon are called fullerenes. These molecules are found in the forms
of C-60, which resembles soccer balls and C-70, also known as buckminsterfullerene or buckyball
(examples are nanotubes).

Carbon can also be found in amorphous forms in carbon black, charcoal, and coke. When
hydrocarbons, like methane, burn in an oxygen-deficient environment, carbon black is created.
Black inks contain carbon black as a pigment; significant quantities are also used to make tires for
automobiles.

When the wood is burned to a high temperature without any air, charcoal is created. Coconut
shells are roasted, ground, and treated with superheated steam to create activated charcoal in the
Philippines. It is used in filters to get rid of water pollutants that are colored or have a foul taste
and unwanted scents from the air.

When coal is burned vigorously without the presence of air, coke, an impure form of carbon,
is created. It works well as a reducing agent in metallurgical operations.

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 Carbon nanofoam is a recently discovered novel allotrope of carbon. It is a spongy solid that
is remarkably light and has an odd magnetic attraction.

The first person to recognize that carbon is tetravalent—that it can create four covalent bonds
with other elements, particularly H, O, and N—as well as with other carbon atoms—was Scottish
chemist August Kekule von Stradonitz (1831–1892). The ability of carbon atoms to form
extremely powerful covalent bonds is their most distinguishing characteristic. Numerous and
various compounds can be formed from carbon.

Numerous additional elements can form stable bonds with carbon atoms (H, F, Cl, Br, I, O,
N, S, P, etc.). A few hydrogens are present in the majority of organic molecules, and occasionally
oxygen, nitrogen, sulfur, phosphorus, etc. Carbon atoms are capable of forming a variety of
intricate structures, including rings, long chains, branched chains, chiral compounds (compounds
with a specific "handedness"), complicated 3D geometries, etc. Carbon atoms can produce a huge
range of compounds due to the variation in bonding and complexity. Compared to around 600,000
inorganic compounds, there are more than 16,000,000 known organic compounds.

Complex organic substances, such vitamins, carbohydrates, lipids, proteins, enzymes, ATP,
DNA, and RNA, can carry out a variety of beneficial biological functions that are investigated in
biochemistry. Carbohydrates, proteins, lipids, and other complex organic components are found in
the foods we eat. Most medicines, whether they originate from a chemical plant or a green plant,
are organic compounds. Most fuels are organic molecules (wood, coal, natural gas, gasoline,
kerosene, diesel fuel, oil, and other petroleum-based products). Additionally valuable in
technology are complex organic molecules (paints, plastics, rubber, textiles, etc.).

1.1 ORGANIC AND INORGANIC COMPOUNDS

Most of the carbon-containing compounds that are involved in the chemical reactions that
support life processes in living creatures are very big molecules with hundreds or even thousands
of carbon atoms. The human race uses additional organic substances for a variety of useful
purposes. These materials include textiles made of cotton and synthetic fibers, common fuels like

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wood and petroleum, paint and varnish additives, synthetic and antibiotic medications, rubber,
plastic, and insecticides, as well as materials used to make protective coatings like paint and
varnish.

Hydrogen, oxygen, nitrogen, and other elements can also be found in organic molecules in
addition to carbon.

Inorganic compounds include substances like hydrochloric acid (HCl), lye (NaOH), lime
(CaO), and table salt (NaCl). However, there are also substances that contain carbon that fall under
the category of inorganic substances. Some of these are carbon monoxide (CO), carbon dioxide
(CO2), substances containing cyanide (CN-), carbonate (CO3 2-), and carbides such as SiC. They
are regarded as being inorganic because they have characteristics that are comparable to those of
inorganic compounds.

Inorganic Compounds Organic Compounds

1. High melting and boiling points 1. Low melting and boiling points
2. Generally soluble in water and rarely 2. Generally soluble in non-polar solvents
soluble in nonpolar solvents. and most are not soluble in water.
3. Conduct electric current (electrolyte) 3. Do not conduct electric current (
nonelectrolyte)
4. Generally nonflammable and 4. Usually flammable and combustible.
noncombustible
5. Presence of ionic bond. 5. Presence of covalent bond.

1.2 THE STRUCTURAL FEATURES OF ORNANIC COMPOUNDS

Since carbon has unique chemical properties that are not present or significant in the chemistry
of other elements in the periodic table, organic chemistry is a distinct field of science.

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 The combining ability of carbon can be understood by considering its electronic configuration.
At the ground state, the following is the electronic configuration of carbon:
C 1s2 2s2 2p1x 2p1y

In the excited state, one of the paired electrons in the 2s orbital in the valence shell can be
elevated to the p orbital, as follows:
C 1s2 2s1 2p1x 2p1y2p1z

However, the configuration above cannot explain the presence of four equivalent single bonds
to carbon and thus it has been proposed that the orbitals in the valence shell are mixed to form a
hybrid orbital which has the features of one s-orbital combined with three p orbitals, as follows:
C 1s2 (2p3)1 (2p3)1 (2p3) (2p3)1

The mixing of atomic orbitals of carbon explains the observed tetrahedral geometry of carbon
compounds.

One very special feature of carbon is its ability to form covalent bonds with other carbon atoms
in continuous chains of unlimited length, as illustrated below:

Other elements such as silicon and nitrogen can form bonds between their atoms which can
also exist in a continuous structure, but the length of the chain is severely limited. One example of
an organic compound containing a continuous carbon chain of several thousand carbon atoms is
polyethylene, a material used in the manufacture of plastics to form

Another interesting feature of carbon is its ability to form covalent bonds with a number of
elements. For example, carbon can bond with oxygen, nitrogen, or a halogen such as chlorine.

carbon-oxygen bond carbon-nitrogen bond

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 This ability of carbon to form covalent bonds with a number of elements accounts for a
wide diversity of organic compounds.

Lastly, another important feature of carbon is its ability to form multiple bonds with itself
or with selected elements such as oxygen, sulfur, and nitrogen. Thus, two carbon atoms may be
linked by a single, double or triple bond. Carbon may bond to oxygen through a single or a double
bond. With nitrogen, carbon can form single, double or even triple bonds. No other element has
the ability to form a variety of multiple bonds. This is why carbon can form a variety of multiple
bonds. This is why carbon can form many organic compounds.
A. Carbon-carbon double bond e.g., ethylene
B. Carbon-carbon triple bond e.g., acetylene

The electronic configuration of a doubly bonded carbon atom consists of the combination in
the valence shell one s-orbital and two p orbitals, resulting in the hybrid orbital (sp2), with one p
orbital remaining combined, as follows:
1s2 (2p2)1 (2p3)1 (2p2) (2p2)12p1

The three hybrid orbitals form the three bonds (with one C and two H atoms); the unhybridized
2p1 orbital forms the other bond between the two carbon atoms resulting in a triple bond, C C.

The electronic configuration of the triply bonded carbon atom consists of the combination in
the valence shell of one s-orbital and one p orbital, resulting in the hybrid orbital (sp) with the
remaining two p orbitals uncombined, as follows:
1s2 (2p)1 (2p)1 2p1 2p1

The two hybrid orbitals form the two bonds (with one C and one H atom); the two
unhybridized 2p1 orbitals form the two other bonds between the two carbon atoms resulting in a
triple bond, C C.

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1.3 HYDROCARBONS

Since there are countless carbon-based chemicals, it is practical to group them into categories
based on structural similarity. The functional groups, a particular configuration of atoms, are what
connects the organic molecules to one another.

The class of organic substances known as hydrocarbons, which only include carbon and
hydrogen, is the most basic and frequently found. Based on the kind of connection that exists
between the carbon atoms, hydrocarbons are categorized as saturated or unsaturated. Saturated
hydrocarbons are those in which all carbon atoms are connected by a single bond, while
unsaturated hydrocarbons are those in which at least a carbon-carbon double or triple bond is
present.

Aliphatic hydrocarbons and aromatic hydrocarbons are additional subcategories of

hydrocarbons. A hydrocarbon is categorized as being of the chain type if it is made up of carbon
links that are long, straight, or branched. The hydrocarbon is referred to as cyclic type when the
carbon bonds form a ring. Alkane, alkene, and alkynes are chain-type hydrocarbons, and aliphatic
hydrocarbons include their cyclic analogs. The structural unit known as benzene, a six-carbon ring

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with three alternate double bonds, or closely comparable rings like naphthalene, are found in the
aromatic hydrocarbons, on the other hand.

To create plastics, textiles, rubber, solvents, explosives, and other industrial chemicals,
hydrocarbons are used as fuel, lubricants, and raw materials

ACTIVITY 1: Organic vs Inorganic

Procedure: Fill in the following table of organic and inorganic compounds and answer the
questions that follow.

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Questions:
1. What element is present in all organic compounds?

2. The majority of the light organic molecules (those with fewer than 10 carbon atoms) are used
for what?

3. Which seems more complex, inorganic or organic compounds, based on their formulas? To
support your position, provide some instances.

4. How do the chemical compositions of organic foods and organic fuels compare? Explain.

ACTIVITY 2: Fractional Distillation

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After going through this module, you are expected to

a. Define alkanes,
b. Write and name alkanes, and
c. Explain how alkanes are used or applied in everyday life.

The hydrocarbons known as alkanes only have single bonds and are also known as
paraffins (low affinity). With a general formula of CnH2n+2, where n denotes the number of carbon
atoms, they are categorized as saturated hydrocarbons (with all carbon atoms linked by single
bonds). This means that the chemical formula for an alkane with two carbon atoms is C 2H6, and
the simplest ratio of the atoms in the alkane with one carbon atom is CH4 (empirical formula).
Methane, also known as CH4, is the most basic alkane and is a key ingredient in natural gas, which
is a common source of home heating in colder climates.

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 Alkanes are saturated hydrocarbons (the maximum number of hydrogen atoms are
contained in each carbon atom). Alkanes only have single carbon-carbon bonds. Standard
equation: CnH2n+2 (no rings). Alkanes are a good source of energy since they burn easily (e.g.,
gasoline). Alkanes serve as the starting point for the synthesis of a variety of other, more
complicated compounds (plastics, etc.).
Natural gas's primary component, methane, or CH4, is created by bacteria when organisms
decompose in the absence of oxygen. It accounts for around 85% of natural gas (marsh gas, cow
flatulence). It burns cleanly, making it useful for cooking. - odorless; ethanethiol is added to make
natural gas leaks noticeable. Ethane, or CH3CH3 (C2H6), makes up just about 10% of natural gas.
Propane, or CH3CH2CH3 (C3H8), is a fuel used in industry, as well as for cooking and heating
homes.
Butane, CH3CH2CH2CH3 (C4H10), is an unbranched (normal) alkane and is used in
cigarette lighters. The alkane C4H10, which has a three-carbon chain with a one-carbon group
attached in the center, is another example of a branched alkane. - The other isomer must have a
separate name: CH3CH(CH3)CH3 [or CH3CH(CH3)2 is designated as isobutane] (or 2-
methylpropane). Isobutane and butane are structurally equivalent.
Structural formulas are important because physical and chemical properties of compounds
are always related to their structure. One important point to consider in the structure of organic
compounds is that the structures are not flat like when they are written on paper, but they also have
a three-dimensional feature which defines the relationships of the bonds and atoms in the
molecules.

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 VALUING

Oil refineries use fractional distillation, a

method that divides crude oil into several
hydrocarbon compounds that are more valuable
based on their respective molecular weights in a
distillation tower. Since it performs the initial
rough separation of the various fuels, this is the
first step in the processing of crude oil and is
regarded as the principal separation process.
Fractions are the various parts that are dispersed
during this procedure. Gasoline, diesel,
kerosene, and bitumen are among the fractions
that are separated out. Many beneficial items
may be produced from crude oil tanks to
fractional distillation, but using those beneficial
products has a huge impact on the environment!

Fractional distillation is a relatively easy but effective method for separating crude oil's many
intricate components. The crude oil is first heated until it vaporizes and then delivered into the
base of a distillation tower. The resultant vapor then ascends through the vertical column. The
temperature falls as the gases ascend through the tower. Certain hydrocarbons start to condense
and flow off at various rates when the temperature drops. Hydrocarbon molecules with a
comparable number of carbon atoms are present in each fraction that condenses off at a particular
level. These boiling point "cuts" make it possible to separate out several hydrocarbons in a single
step. This cooling, along with the tower's height, makes it possible for the separation.

After this initial rough refinement, specific fuels may go through more refinement to get rid of
impurities or undesired elements, or to crack the fuel to raise its quality. The usable fractions that
are distilled from crude oil can be categorized in a number of different ways. One method is to

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divide fractions into light, moderate, and heavy categories. Towards higher temperatures, heavier
c omponents condense and are eliminated at the bottom of the column. The lighter fractions
can be removed at slightly higher levels because they can rise higher in the column before being
cooled to their condensing temperature. In addition, the fractions have the following
characteristics:

• Light distillate is one of the more important fractions, and its products have boiling
points around 70-200°C. Useful hydrocarbons in this range include gasoline, naphtha (a
chemical feedstock), kerosene, jet fuel, and paraffin. These products are highly volatile,
have small molecules, have low boiling points, flow easily, and ignite easily.

• Medium distillate are products that have boiling points of 200-350°C. Products in this
range include diesel fuel and gas oil - used in the manufacturing of town gas and for
commercial heating.
• Heavy distillate are the products with the lowest volatility and have boiling points
above 350°C. These fractions can be solid or semi-solid and may need to be heated in
order to flow. Fuel oil is produced in this fraction. These products have large
molecules, low volatility, flow poorly, and do not ignite easily.

2.1 ALKANES NOMENCLATURE

Straight-chain alkanes are named by combining a prefix which indicates the number of carbon
atoms in the chain, and a suffix indicating the functional group of the molecule.

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2.2 NAMING BRANCHED-CHAIN ALKANES

To name organic structures, chemists use the following systematic rules approved by the
International Union of Pure and Applied Chemistry (IUPAC).

Step 1. Count the number of carbon atoms in the longest continuous chain. Use the name of the
straight-chain alkane with that number of carbons as the name of the parent chain of the structure.

Step 2. Number each carbon in the parent chain. Locate the end carbon closest to a substituent
group. Label that carbon Position 1. This step gives all the substituent groups the lowest position
numbers possible.

Step 3. Name each alkyl group substituent. Place the name of the group before the name of the
parent chain.

Step 4. If the same alkyl group occurs more than once as a branch on the parent structure, use a
prefix (di-, tri-, tetra-, and so on) before its name to indicate how many times it appears. Then, use
the number of the carbon to which each is attached to indicate its position.

Step 5. When different alkyl groups are attached to the same parent structure, place their names in
alphabetical order. Do not consider the prefixes (di-, tri-, tetra-, and so on) when determining
alphabetical order.

Step 6. Write the entire name, using hyphens to separate numbers from words and commas to
separate numbers. Do not add between the substituent name and the name of the parent chain.

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ACTIVITY: Naming Alkanes

Given IUPAC name

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2.3 CYCLO-ALKANES

The ability of carbon atoms to build structures is one of the factors that contributes
to the wide variety of organic molecules. Cyclic hydrocarbons are organic compounds that have
a hydrocarbon ring in them. The prefix cyclo- is added to the hydrocarbon name to denote the
presence of a ring structure. Cycloalkanes are cycle hydrocarbons that only have one single bond,
for this reason.

Cycloalkanes can have rings with three, four, five, six, or even more carbon atoms.
Cyclohexane is the name of the six-carbon cycloalkane. Petroleum-derived cyclohexane is used to
create paint and varnish removers as well as to extract essential oils for perfume. Because a valence
electron from each of the two carbon atoms is now forming a carbon-carbon bond rather than a
carbon-hydrogen link, cyclohexane (C6H12) has two less hydrogen atoms than straight-chain
hexane (C6H14).

Names for substituted cycloalkanes. Cycloalkanes, like other alkanes, can have
substituted groups. The same IUPAC guidelines used for straight-chain alkanes, with a few
variations, are used to designate substituted cycloalkanes. With cycloalkanes, the ring is always
regarded as the parent chain, so there is no need to locate the longest chain. The carbon attached
to the substituent group is where the numbering begins because cyclic structures don't have

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endings. When there are two or more substituents, the carbons are numbered so that the lowest set
of numbers is available for the substituents. There is no need for a number if the ring is only tied
to one group.

ACTIVITY: Naming Cyclo-alkanes

Given Structure

1,3-dimethylcyclohexane

2-ethyl-3-methylcyclopentane

1-bromo-2-methylcyclohexane

1-bromo-2-iodocyclopentane

1-fluoro-4-methylcycloheptane

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2.4 PROPERTIES OF ALKANES

Some important physical properties of alkanes are:

1. Alkanes are colorless and odorless.
2. They possess weak Van Der Waals forces of attraction.
3. Alkanes having 1-4 carbon atoms are gases, then from 5-17 carbon atoms they are liquid
and alkanes having 18 or more carbon atoms are solid at 298K.
4. Structure of alkanes: In alkanes all the carbon atoms are sp³ hybridized which means that
they form four sigma bonds with either carbon or hydrogen atoms. Their general formula
Is CₙH2n+2. The bond angle between them is 109.5° and they exhibit tetrahedral geometry.
5. Melting and boiling point
Shorter chain alkanes have low melting and boiling points but as the number of carbon
atoms in the chain increases melting and boiling points rise.
Boiling Point: it increases with the increasing molecular weight as the Van Der Waals
force increases with the increasing molecular weight. Straight chain alkanes have a higher
boiling point than their structural isomers.
Melting Point: It also increases with increasing molecular weight because it is difficult to
break the intermolecular forces of attraction between higher alkanes as they are generally
solids. Even-numbered alkanes have a better packing in the solid phase than the odd ones
as they form a well-organized structure which is difficult to break hence even-numbered
alkanes have a higher melting point than odd-numbered ones.
6. Solubility Alkanes are generally non-polar molecules because of the covalent bonds
between C-C and C-H and also because of the very small difference between
electronegativities of carbon and hydrogen. We know that polar molecules are soluble in
polar solvents and nonpolar molecules are soluble in non-polar solvents generally so this
implies alkanes are insoluble in water or hydrophobic in nature. When a non-polar alkane
is added to a polar solvent the water molecules are attracted to each other and alkane
molecules are attracted to each other but water and alkane molecules do not attract each
other. In organic solvents, they are soluble because the energy required to overcome
existing Van Der Waals forces and to generate new Van Der Waals forces is quite
comparable.

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 7. Alkanes have a lower density than water, they float on water. Density increases with an
increase in molecular mass.
8. Apart from weak Van Der Waals forces, London forces, Dispersion forces, weak
intermolecular forces act between the molecules of alkanes.

Chemical Properties of Alkanes

Some important chemical properties of alkanes are given below.
1. Combustion of alkanes
In excess of oxygen O2, alkanes readily undergo combustion producing carbon dioxide gas,
water and energy in the form of heat and light.
Alkane + Oxygen → Carbon Dioxide gas + Water + Energy
C4 H10 (g) + 6½O2 (g) → 4CO2 (g) + 5H2O(l) + 2874 KJ mol-1

The above reaction is the combustion reaction of butane. With the increasing molar mass of
straight-chain alkane the energy released increases. Also, with the increasing carbon chain length
the combustion energy increases. In the absence of sufficient oxygen, alkanes try to undergo
incomplete combustion. Incomplete combustion produces water and carbon monoxide or carbon.

2. Halogenation
Alkanes are less reactive. Without ultraviolet light, they do not react with halogens. With UV
light halogenated alkane is produced. It is a substitution reaction in which one or more hydrogen
atoms are substituted by halogen atoms.
CH3 -CH2 -CH3 + Br2 → CH3 -CH2-CHBr + HBr
Here propane is reacting with bromine. The general substitution reaction equation can be given as
R-H +X2 → R-X + H-X
where R is a carbon chain and X is a halogen.

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 VALUING

The characteristics of alkanes make them very valuable. Among the applications are:

1.When liquefied at low temperatures, propane and butane are utilized as propellants or aerosol
sprays in propane gas burners.

2.For an internal combustion engine, pentane to octane fuels is ideal.

3.High viscosity nonane and hexadecane are used as aviation fuel and diesel.

4.Paraffin wax candles, anti-corrosive compounds, and lubricating oils all contain up to C-35
alkanes. Smaller alkanes are created by cracking higher alkanes, which are subsequently used.

SUMMARY

The chemistry of carbon-based substances is known as organic chemistry, while the

chemistry of the other elements is known as inorganic chemistry. Because carbon atoms may create
stable covalent bonds with both other carbon atoms and atoms of other elements, tens of millions
of organic molecules are possible. Only hydrogen and carbon atoms are present in hydrocarbons.

Alkanes, also known as saturated hydrocarbons, are hydrocarbons where each carbon atom
is connected to four other atoms. The typical formula for them is C nH2n+2. Each alkane in a series
differs from the following one by one CH2 unit. A homologous series is any group of compounds
where adjacent members differ from one another by a specific amount.

Alkanes can have straight or branched carbon atom chains. Isomers are distinct substances
with the same molecular formula but a different structural formula. The three smallest alkanes do
not have isomeric forms; starting with C4H10, all other alkanes do.

A structural formula shows all the carbon and hydrogen atoms and how they are attached
to one another. A condensed structural formula shows the hydrogen atoms right next to the

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carbon atoms to which they are attached. A line-angle formula is a formula in which carbon atoms
are implied at the corners and ends of lines. Each carbon atom is understood to be attached to
enough hydrogen atoms to give each carbon atom four bonds.

Cycloalkanes are saturated hydrocarbons whose molecules are closed rings rather than
straight or branched chains. Rings restrict rotation, so if there are two non-hydrogen substituents
on different carbons of a cyclohexane, two cis-trans isomers (or geometric isomers) can exist.

Any hydrocarbon containing either a double or triple bond is an unsaturated

hydrocarbon. Alkenes have a carbon-to-carbon double bond. The general formula for alkenes
with one double bond is CnH2n. Double bonds cannot rotate so if there is one non-hydrogen
substituent on each of the double-bonded carbons, two cis-trans isomers can exist. Alkynes have
a carbon-to-carbon triple bond. The general formula for alkynes is CnH2n − 2.

The physical properties of hydrocarbons reflect the fact that the molecules are nonpolar.
Hydrocarbons are insoluble in water and less dense than water. Size and presence of polar
functional groups can affect the water solubility, melting point, and boiling point of organic
compounds. The IUPAC System of Nomenclature provides rules for naming organic
compounds. An alkyl group is a unit formed by removing one hydrogen atom from an alkane.

A functional group is any atom or atom group that confers characteristic properties to a
family of compounds. Alkanes are generally unreactive toward laboratory acids, bases, oxidizing
agents, and reducing agents; they do burn in oxygen (undergo combustion reactions). Alkenes
and alkynes are more reactive, susceptible to addition by halogens or water, for
example. Carboxyl functional groups are weak acids and amine functional groups are weak
bases.

POST TEST

DIRECTION: Encircle the letter of the correct answer.

1.. At which pipe: M or N are hydrocarbons with lower boiling points collected?

24 | P a g e
 A. M
B. N

3. What is the IUPAC name of the figure below?

a. 3-methyl-4-ethylhexane
b. 3-methyl-4-ethylheptane
c. 3-ethyl-4-methylhexane
d. 3-ethyl-4-methylheptane

3. What is the IUPAC name of the figure below?

4.. Which of the following compounds is not organic?

a. CH4
b. C2H2
c. CO
d. CCl4

5. What are the Aliphatic Hydrocarbons?

a. Open chained carbon-hydrogen organic compounds
b. Open chained carbon hydrogen organic compounds

25 | P a g e
 c. Closed chained carbon hydrogen organic compounds
d. Closed chained carbon hydrogen and some other elements organic compounds

6. Which type of formulas represents only combination ratio of the constituent atoms?
a. Structural Formula
b. Molecular Formula
c. Empirical Formula
d. Condense Formula

7. Is this hydrocarbon saturated or unsaturated?

a. saturated
b. unsaturated

8. Name this alkane

a. Methane
b. Propane
c. Ethane
d. Butane

9. The following compounds have a molecular formula of

a. CnH2n+2

26 | P a g e
b. C6H14
c. CH4
d. CH3CH2CH2CH2CH2CH3

10. Organic compounds made only of the elements carbon and hydrogen are called...
a. Hydrocarbons
b. Carbohydrates
c. Carbohydrogens
d. Hydrocarbonates

27 | P a g e
LEARNING OUTCOME
After going through this module, you are expected to

1. name the structures of alkenes;

2. describe the physical and chemical properties of alkenes; and
3. appreciate the existence of alkene compounds in the surrounding.

PRETEST

Direction: Read the statements carefully and encircle the letter of the best answer.

1. Which of the following statements is NOT true about alkenes?

a. Alkenes have pi bonds joining the carbon atoms together.
b. Both alkanes and alkenes have similar physical properties.
c. Alkenes are less reactive than alkanes.
d. The reaction of polymerization occurs with alkenes.

2. In Alkenes the Carbon atoms are connected by a ___________.

a. Single bond
b. Double bond
c. Triple bond
d. Not connected

3. Which among the following alkenes show the condensed formula for 4-chlorobut-1-ene?
a. CH2Cl-CH2=CH-CH2
b. CH2Cl-CH2-CH-CH2

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 c. CH2Cl=CH2-CH=CH2
d. CH2Cl-CH2-CH=CH2

4. Which among the following is not belong to the alkenes?

a. Butene
b. Ethene
c. Methene
d. Propene

5. Which among the following alkenes are found in coffee?

a. Butadiene
b. 1,2-butadiene
c. 1,3-butadiene
d. 2-butadiene

6. Considered the simplest alkene with colorless and flammable gas having a sweet taste
and odor?
a. Butene c. Methene
b. Ethene d. Propene

For items 7-10: Name the following structure/formula

a. 5-Chloro-3-heptene c. cis-2-butene e. trans-2-butene
b. octa-2,4-diene d. 1-methylcyclobutene

7.

8.

9. CH3CH=CHCH=CHCH2CH2CH3

10.

29 | P a g e
 REVIEW

In your previous lesson, you have learned about the organic compounds and alkanes,
the properties and characteristics of an alkane and its naming. Can you still remember your lesson
about it? Let us have some practice exercises to refresh your mind. Answer the following activities.

A. Complete the table below

MOLECULAR SKELETAL
COMPOUND NAME
FORMULA STRUCTURE

1. Nonane

2.

3. 1,4-dimethylcyclohexane

4.
C5H12

5.

B. True or False: Read each item carefully. Write TRUE if the statement is correct and FALSE if
it is not.

________________1. In alkanes, each carbon atom is bonded to 2 or more atoms.

________________2. Hydrocarbons that contain a double bond are classified as alkenes.

________________3. Single bonds, such as those in alkanes, are also called pi bonds.

30 | P a g e
________________4. Alkanes are more reactive than alkenes and alkynes.

________________5. Hydrogen, oxygen, nitrogen, and other elements can also be found in

organic molecules in addition to carbon.

ALKENES
Alkenes are unsaturated hydrocarbons with double or triple carbon-carbon bonds that
allow them to add hydrogen atoms. They are highly reactive. Alkenes, also known as olefins,
have the general formula CnH2n, where n = 1, 2, 3. . . They serve as the foundation for many
well-known plastics (polyethylene, vinyl plastics, acrylics) and other important synthetic
materials (e.g., alcohols, antifreeze, and detergents).

Ethylene, also known as ethene, is a colorless, flammable gas with a sweet taste and odor.
Its natural sources include both natural gas and petroleum. Ethene has the chemical formula
C2H4, which means that both carbon atoms double bond with a sigma bond and a pi bond
H2C=CH2.

ALKENE NOMENCLATURE

We indicate the positions of the carbon-carbon double bonds when naming alkenes.
Compounds with C = C bonds have names that end in -ene. The number of carbon atoms in the
longest chain/root chain with the end nearest a double bond carbon atom determines the name of
the parent compound, as it does for alkanes. If the double bond is in the chain's center, the
nearest substituent rule is used to determine where the numbering begins. If the compound
contains more than one double bond, it is named with a diene, triene, or equivalent prefix
indicating the number of double bonds, and each double bond is assigned a locator number.
Consider the following examples:

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Naming Straight Chain

1-Pentene 2-Pentene

For straight chain alkenes, it is the same basic rules as the nomenclature of alkanes apply
except the -ane suffix is changed to -ene. Start numbering from the end of the parent chain which
gives the lowest possible number to the double bond. The name “pentene” means that there are
five carbon atoms in the longest chain.

Cis-2-butene Trans-2-butene
https://chem.libretexts.org/@api/deki/files/27306/cis%252C_trans.j
pg?revision=1

In the condensed structural formula of CH3CH=CHCH3, we could simply name it as 2-

butene since the double is in the 2nd carbon, but there are two ways of naming this compound based
on the cis-trans isomerism. Cis-trans (geometric) isomerism exists when there is restricted rotation
in a molecule and there are two nonidentical groups on each doubly bonded carbon atom.

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Naming with Substituents

(a)

2-ethyl-1-hexene or 2-ethylhex-1-ene
(b)
https://chem.libretexts.org/@api/deki/files/372625/Rule_2.svg?
revision=1&size=bestfit&width=607&height=12 4-ethyl-2-methyl-3-hexene or 4-ethyl-methylhex-3-ene

https://chem.libretexts.org/@api/deki/files/381
103/nomenclature_example_-_4-ethyl-2-methyl-
3-hexene.svg?revision=1

Identify the longest chain that gives the lowest possible number to the double bond and
adds substituent and its position to the alkene as prefixes which is ethyl for example a, ethyl, and
methyl for example b. Remember substituents are written in alphabetical order.

Naming Cycloalkenes and Aromatic Hydrocarbons

Cycloalkenes don't have chain ends, hence the double bond is presumed to have the
numbers C1 and C2, and its location number is not necessary for the name. The direction of
numbering is determined by which will assign the lowest number to the substituent nearest to the
double bond. It could be essential to specify the location numbers of the double bonds in the name
if there are several double bonds present.

1,3-Cyclohexadiene or
cyclobutene 3-Methylcyclopentene Cyclohexa-1,3-diene 1,3-dimethylcyclohexene

33 | P a g e
 Aromatic hydrocarbons have 6-membered ring structures with alternating double bonds
that refer to a benzene ring or have benzene-like properties (but not necessarily a strong aroma).
Take a look at the examples below.

https://chem.libretexts.org/Bookshelves/Introductory_Chemistry/The_Basics_of_GOB_Chemistry_(Ball_et_al.)/13%3
A_Unsaturated_and_Aromatic_Hydrocarbons/13.08%3A_Structure_and_Nomenclature_of_Aromatic_Compounds

PROPERTIES AND REACTIONS OF ALKENES

Table 1. Physical Properties of Some Selected Alkenes

https://wou.edu/chemistry/files/2017/01/table_8.1.png

34 | P a g e
 Alkenes have the same physical properties as alkanes. The table above shows that, like
alkanes, the boiling points of straight-chain alkenes increase with increasing molar mass. The
boiling points of molecules with the same number of carbon atoms and the same general shape
usually differ only slightly, just as we would expect for substances with molar masses that differ
by only two hydrogen atoms. The alkenes, like other hydrocarbons, are insoluble in water but
soluble in organic solvents..

Chemical Properties of Alkenes

Alkenes are more reactive than alkanes due to the presence of a double bond. The σ- bond
is strong but the π- bond is weak. The typical reactions of alkenes involve the addition ofan
electrophile across the double bonds proceeding through the ionic mechanism. However, addition
reactions proceed through free-radical mechanism. Ozonolysis and polymerization are some of the
characteristic reactions of alkene

Reaction of Alkenes

Because of the presence of a double bond, alkenes are more reactive than alkanes.
Although the sigma bond is strong, the pi bond is weak. The typical alkene reaction involves the
addition of an electrophile across the double bonds via the ionic mechanism. However, addition
reactions take place via the free-radical mechanism.:

Addition reactions, in which one molecule adds to another to form a single product, are
common in unsaturated hydrocarbons such as alkenes. An example of an addition reaction is
hydrogenation. Other C=C bond addition reactions include

35 | P a g e
 where X represents a halogen (Cl, Br, or I). The addition of a hydrogen halide to an
unsymmetrical alkene such as propene is more complicated because two products are possible

Vladimir Markovnikov proposed a generalization in 1871 that allows us to predict the

outcome of such an addition reaction. This generalization, known as Markovnikov's rule, states
that when unsymmetrical (polar) reagents are added to alkenes, the positive portion of the
reagent (usually hydrogen) adds to the carbon atom with the most hydrogen atoms. In the preceding
example, only 2-bromopropane is formed. This phenomenon was observed in all unsymmetrical
reagent-alkene reactions.

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USES OF ALKENES

1. Alkenes have a wide range of industrial applications. They are used in the synthesis of alcohols,
plastics, liquors, detergents, and fuels.
2. In the polymer industry, ethene is the most important organic feedstock. PVC, Sarans, and
polyethylene are a few examples. These polymers are used to make floor tiles, shoe soles, synthetic
fibers, raincoats, pipes, and other products. See the table below for some examples of polymer
applications.

Table 2: Some uses of Polymers

https://wou.edu/chemistry/files/2017/01/table-of-polymers.png

3. Natural alkenes include 1-octene, which is found in lemon oil, and octadecene (C18H36), which
is found in fish liver. Polyenes (three or more double bonds) and dienes (two double bonds)
are also common. Coffee contains butadiene (CH2=CHCH=CH2). Lycopene and carotenes are
isomeric polyenes (C40H56) that give watermelons, tomatoes, carrots, and other fruits and
vegetables attractive red, orange, and yellow colors. Carotene is a source of vitamin A, which
is required for good vision. Without alkenes, the world would be a much less colorful place.

37 | P a g e
 ACTIVITY 1: NAMING OF ALKENES

Direction: Complete the table.

MOLECULAR SKELETAL
COMPOUND NAME
FORMULA STRUCTURE

1. Cyclohexene

2. trans-1,2-dibromoethene

3.

4.
C7H14

5.

ACTIVITY 2

Direction: Write your answer in the space provided.

1. Briefly describe the physical properties of alkenes. How do these properties compare to those
of the alkanes?
___________________________________________________________________________
___________________________________________________________________________
______________________________________________________

38 | P a g e
 2. Arrange the following alkenes in order of increasing boiling point:
____________, ___________, ______________, ___________

3. Briefly identify the important distinctions between a saturated hydrocarbon and an unsaturated
hydrocarbon.
___________________________________________________________________________
___________________________________________________________________________
______________________________________________________

SUMMARY

• An unsaturated hydrocarbon is any hydrocarbon with a double or triple bond.

• Alkenes are hydrocarbons with a double carbon bond.
• Alkenes have a double bond from carbon to carbon. CnH2n is the general formula for alkenes
with one double bond. Straight-chain, branched-chain, and cyclic alkenes are all possible.
Simple alkenes frequently have common names, but all alkenes can be named using the
International Union of Pure and Applied Chemistry system and end in -ene.
• Alkenes have similar physical properties to alkanes in that their boiling points increase with
increasing molar mass and they are insoluble in water but soluble in organic solvents.

VALUING

Alkenes are used in numerous manufacturing processes. They are used as raw materials
in the production of alcohols, plastics, lacquers, detergents, and fuels. Ethene, propene, and
1,3-butadiene are the three most important alkenes in the chemical industry.

Some alkenes, such as alpha-pinene and limonene, smell nice (and aren't too toxic), so
they're used to flavor candles and cleaning products. Alkenes include vitamin A (including
beta-carotene) and lycopene, an antioxidant found in tomatoes.

39 | P a g e
 Polymers are used widely, which pollutes the environment and clogs up landfills. Because consumer
products contain a variety of polymers, recycling requires classifying the polymers into different sub-types,
labeling them with codes and symbols, and recycling each sub-type separately.

POST TEST

Direction: Read the statements carefully and encircle the letter of the best answer.

1. In alkenes as number of C atoms ____________, melting point and boiling point also __________.
a. decreases; decreases
b. decreases; increases
c. increases; decreases
d. increases; increases

2. Name this compound C3H6

a. Ethane
b. Ethene
c. Propane
d. Propene

3. Lycopene and carotenes are isomeric polyenes with a chemical formula of ____________.
a. C37H50
b. C38H52
c. C39H54
d. C40H56

4. Which of the following shows the structure of ethene?

a. c.

b. d.

5. Which are the following are all alkenes?

40 | P a g e
 a. methane, ethane, propane
b. methane, ethene, propene
c. methene, ethene, propene
d. ethene, propene, butene

6. Alkenes are ____________ than alkanes due to the presence of a _____________.

a. Less reactive; single bond
b. Less reactive; double bond
c. More reactive; single bond
d. More reactive; double bond

7. In 2-butene, If the methyl groups are on the same side of the double bond, we call it ___alternating
a. delta- 2-butene
b. cis-2-butene
c. sigma-2-butene
d. trans-2-butene

For items 8-10: Name the following structure/formula

a. benzene c. cyclohexene
b. 5-Ethyl-2,4-heptadiene d. 5,5-dimethyl-2,4-heptadiene

8.

9.

10.

41 | P a g e
LEARNING OUTCOME
At the end of this lesson, you are expected to:
4. name the structure of alkynes;
5. differentiate the alkynes from alkenes and alkanes by structure and properties; and
6. appreciate the existence of alkenes in daily life.

PRETEST

Direction: Read the statements carefully and encircle the letter of the best answer.
1. Alkenes are less reactive than alkynes.
a. True
b. False

2. Select the incorrect statement regarding terminal alkynes.

a. Methylacetylene is an example of terminal alkynes
b. Terminal alkynes are more acidic when compared with alkenes
c. Terminal alkynes are not as acidic as alkanes
d. These have a replaceable acidic hydrogen atom

3. Acetylene is extremely sensitive to shock and highly explosive in its liquid state.
a. True
b. False

4. Alkynes are all colorless and odorless except acetylene which has a garlic odor.
a. True
b. False

5. It is composed of two carbon atoms joined by three triple bonds known as the acetylenic bond, which
allows each carbon to form a bond with a single hydrogen atom.

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 a. Ethene
b. Ethyne
c. Propene
d. Propyne

6. What is the general formula of the alkynes?

a. CnH2n+1
b. CnH2n+2
c. CnH2n-1
d. CnH2n-2

7. Which of the following could contain a triple bond?

a. C4H10
b. C4H8
c. C4H6
d. C4H12

8. What is the name of this compound?

a. Methyne
b. Ethyne
c. Ethene
d. Butyne

9. Acetylene, an unsaturated hydrocarbon, can be hydrogenated to yield ethylene

a. False
b. True

10. Alkynes, like other hydrocarbons, are frequently hydrophobic.

a. True
b. False

43 | P a g e
 REVIEW

In your previous lesson, you have learned about the alkenes and its properties and basic
reactions. Can you still remember your lesson about it? Let us have some practice exercise to refresh your
mind. Write the term which fits the description below inside the box.

1. ____________ and ______________are isomeric polyenes (C40H56) that

give attractive red, orange, and yellow colors to watermelons, tomatoes,
carrots, and other fruits and vegetables.
2. states that when unsymmetrical (polar) reagents are added to alkenes, the
positive portion of the reagent (usually hydrogen) adds to the carbon atom
with the most hydrogen atoms.
3. Unsaturated hydrocarbons like alkenes are commonly undergo
______________ reactions, in which one molecule adds to another to
form a single product.
4. It refers to the thermal decomposition of a large hydrocarbon into smaller
molecules.
5. The boiling points of _______________ alkenes increase with increasing
molar mass, just as with alkanes

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 ALKYNES

In organic chemistry, an alkyne with a general formula of CnH2n-2, is an unsaturated

hydrocarbon with at least one triple bond between carbon atoms. Alkynes, like other hydrocarbons, are
frequently hydrophobic. People are more familiar with ethyne, also known as acetylene. The most basic of
the alkynes is composed of two carbon atoms joined by three triple bonds known as the acetylenic bond,
which allows each carbon to form a bond with a single hydrogen atom.

In both physical and chemical properties, alkynes are like alkenes. Many of the typical addition
reactions of alkenes, for example, occur in alkynes. The names of alkynes in the International Union of Pure
and Applied Chemistry (IUPAC) are like those of alkenes, with the exception that the family ending is -yne
rather than -ene. Ethyne is the IUPAC name for acetylene.

ALKYNES NOMENCLATURE
Names of compounds containing C C bonds end with -yne. Again, the name of the parent
compound is determined by the number of carbon atoms in the longest chain. As in the case of alkenes, the
names of alkynes indicate the position of the carbon-carbon triple bond

a. b. c.

For
example in letter c, the double bond and the substituent (near) is in the C1 in which it gives lower number
than the triple bond in C4 where the substituent methyl group is too far.

PROPERTIES AND REACTIONS OF ALKYNES

The first three members are gases, next eight are liquids and the higher alkynes are solids. They
are all colorless and odorless except acetylene which has a garlic odor. They are, however, water-insoluble
but soluble in benzene and acetone. Another property of an alkyne is that if it is burned, the resulting flame
is a sooty flame.

Let's compare alkynes' acidity and boiling point to those of other hydrocarbons, alkenes
(hydrocarbons with double bonds) and alkanes (hydrocarbons that are only made of single bonds). In
general, alkynes (terminal alkynes) are more acidic than alkenes and alkanes, and their boiling points are
slightly higher than those of alkenes and alkanes.
45 | P a g e
 The simplest alkyne is ethyne, better known as acetylene (C 2H2). Acetylene is a colorless gas
(b.p. 284°C) prepared by the reaction between calcium carbide and water:

Acetylene has numerous industrial applications. This reaction can occur with explosive
violence due to its high heat of combustion in the presence of a suitable catalyst or when the gas is kept
under pressure. To be transported safely, the gas must be dissolved in a moderately pressured organic
solvent such as acetone. Acetylene is extremely sensitive to shock and highly explosive in its liquid state.

Acetylene, an unsaturated hydrocarbon, can be hydrogenated to yield ethylene:

USES OF ALKYNES
Acetylene is used in oxy acetylene torch used for welding and cutting metals. It is used for the
manufacture of PVC, polyvinyl acetate, polyvinyl ether, orlon and neoprene rubbers. In addition, it is for
making organic compounds like ethanol, ethanoic acid, acrylic acid, etc.

46 | P a g e
 ACTIVITY 1: NAMING OF ALKYNES

A. Direction: Draw the skeletal structure for each compound in the space provided.

1. Acetylene

2. 3-methyl-1-hexyne

3. 3-octyne

4. CH3CH2CH2C≡CH

5. CH3CH2CH2C≡CCH3

47 | P a g e
 ACTIVITY 2: THINK DEEPLY

Direction: Read answer each question briefly.

1. Briefly identify the important differences between an alkene and an alkyne. How are they similar?
_______________________________________________________________________________
_______________________________________________________________________________
__________________________________________________________
2. Do alkynes show cis-trans isomerism? Explain
_______________________________________________________________________________
_______________________________________________________________________________
__________________________________________________________
3. Do alkynes are soluble in water? Why or why not?
_______________________________________________________________________________
_______________________________________________________________________________
__________________________________________________________

VALUING

Many alkynes are toxic to humans when used in pharmaceuticals. Certain alkynes known as
ene-diynes, on the other hand, contain a potent and effective anti-tumor compound. Calicheamicin is one
such tumor-fighting agent..

SUMMARY

• Alkynes, with the general formula CnH2n-2, are unsaturated hydrocarbons with a triple carbon-
carbon bond that consists of two pi-bonds and one sigma bond.
• To name the alkynes, look at the location of the triple bond that gives the lower number (assigned)
and follow the same procedure as for alkenes, but instead of adding "ene," add "yne."
• Alkynes are commonly found in gaseous form and can be odorless and colorless, but they are highly
reactive with a high acidity, melting point, and boiling point.

48 | P a g e
 • Alkynes are used in the production of polymers and their precursors. However, like ethyne, it is used
in the preparation of many organic solvents capable of dissolving other unsaturated compounds.The
alkynes are more acidic than alkenes and alkanes, and their boiling points are slightly higher than
those of alkenes and alkanes.

POST TEST

Direction: Draw a Lewis or Skeletal structure and give the Iupac Name

CONDENSED FORMULA SKELETAL STRUCTURE IUPAC NAME

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 As of October 27, 2021, the size of the hole in our ozone layer is 24.8 million square kilometers,
roughly the size of North America. While the news sounds alarming, the ozone hole has actually been
closing since it was first detected during the early 1980s. This is all because of the Montreal Protocol, which
initiated the phasing-out of the use of ozone-depleting substances such as chlorofluorocarbons, or CFCs.

CFCs are halogenated hydrocarbons that have various industrial uses. This, along with other alkyl halides,
will be discussed in this chapter.

LEARNING OUTCOMES

At the end of this chapter, you should be able to:

a. describe an alkyl halide in terms of properties, uses, and classification;

b. develop values that will make you a good steward of creation;
c. write the condensed structural formulas and names of alkyl halides.

PRETEST

Multiple Choices Read and analyze each question. Write the letter of the correct answer.

_____1. What are alkane-derived compounds where one or more of its hydrogen atoms are replaced by
halogen atoms?

A. alkyl alkane B. alkyl halide C. haloalkane D. halohalide

_____2. Which of the following is an alkyl halide?

A. CH3 – CH2 – CH2 – Br C. CH3 – CH2 – CH2 – CH2 – CH2 - OH

B. CH3 – CH2 – CH2 – CH3 D. CH3 – CH2 – CO – CH2 – CH3

50 | P a g e
_____3. According to the number of halogens, what kind of alkyl halide is CH3Cl?

A. monohaloalkane C. trihaloalkane

B. dihalolkane D. tetrahaloalkane

_____4. According to the number of halogens, what kind of alkyl halide is CHI 3?

A. monohaloalkane C. trihaloalkane

B. dihalolkane D. tetrahaloalkane

_____5. According to the position of the halogen in the carbon chain, what kind of alkyl halide is CH 3Cl?

A. primary B. secondary C. tertiary D. quaternary

_____6. To which carbon atom is the halogen bonded to in this compound:

CH3 – CH2 – CH – CH3

I
Cl

A. carbon 1 B. carbon 2 C. carbon 3 D. carbon 4

_____7. What is the parent chain of this compound?

CH3 CH3 Cl
I I I
CH3 – CH – CH – CH – CH2 – CH2 – Br

A. pentane B. heptane C. hexane D. heptane

_____8. What is the name of the compound in question number 8?

A. 1,1,2-dimethyl-3-chloro-5-bromopentane C. 1-bromo-3-chloro-4,5,5-trimethylpentane

B. 1-bromo-3-chloro-4,5-dimethylhexane D. 6-bromo-4-chloro-2,3-dimethylhexane

51 | P a g e
_____9. Which among the following has the highest density?

A. CH3Br B. CH3I C. CCl3F D. CCl3CF3

_____10. What does the Montreal Protocol do?

A. It monitors industries that release effluents to bodies of water.

B. It phases out the production of substances that cause water pollution.

C. It phases out the production of substances that cause ozone depletion.

D. It regulates the production of haloalkanes of different industries.

REVIEW
A. Name the following alkynes:

1.

Br

CH ≡ C – CH2 – C – CH3

Cl

2.

F CH3 Br

I I I

CH3 – CH – C – C ≡ C – CH2 – CH2 – CH – CH3

CH3

B. Write the condensed structural formula of:

52 | P a g e
 3 – methyl – 1 – pentyne

ALKYL HALIDES
What Is an Alkyl Halide?

An alkyl halide, also known as haloalkane or halogenoalkane, is an organic compound that contains
one or more halogens. It is formed when one or more hydrogen atoms of an aliphatic hydrocarbon is replaced
by one or more halogen atoms — fluorine, chlorine, bromine, or iodine. It has a general formula of:

R–X

where:

R – an alkyl group or a substituted alkyl group

X – the halogen

Let us have the reaction methane, CH4, and chlorine as an example. When methane and chlorine is
exposed to ultraviolet light, a substitution reaction happens and the alkyl halide chloromethane is formed.

uv light

CH4 + Cl2 CH3Cl + HCl

chloromethane

*Note that eventually, all hydrogen atoms of methane will be replaced by chlorine atoms.

Here are other examples of alkyl halides:

a. CH3 - CH2 - Br

b. CH3 – CH – CH3

53 | P a g e
 Cl

c. CH3 – CH – CH2 - Br
CH3

What are the Physical Properties of Alkyl Halides?

This table summarizes the physical properties of alkyl halides:

Physical Properties of Alkyl Halides

State - Lower members (like methyl chloride and ethyl bromide) – gases
- Higher members:
up to C18 – liquids
C19 and up - solids
Odor - Has a pleasant sweet odor in its pure state
- Higher members are odorless
Color - Colorless in its pure state
- Compounds of bromine and chlorine develop color when exposed to
light
Boiling Point - Considerably higher when compared to their corresponding alkanes
Solubility - Insoluble in water but soluble in organic solvents
Density - It increases as the number of carbons and halogens increases

What are the Uses of Alkyl Halides?

Here are some of the common alkyl halides and their uses:

Name of Compound Chemical Formula Uses

CFCs or chlorofluorocarbons

CFC-11 or Freon-11 CCl3F - refrigerant (for chillers),

(trichlorofluoromethane) solvent, foam-blowing agent

CFC-12 or Freon-12 CCl2F2 - refrigerant (air-conditioners

(dichlorodifluoromethane) for automobiles and trucks),
propellant for aerosol sprays

54 | P a g e
 CFC-113 CCl3CF3 - solvent, cosmetics
(1,1,2-trichloro-1,2,2-trifluoroethane)

CBrF3 - fire extinguisher

Halon 1301
(bromotrifluoromethane)

Halothane - general inhalation anesthetic

(2-bromo-2-chloro-1,1,1- C2HBrClF3
trifluoroethane)

DDT C14H9Cl5 - last-resort insecticide

or dichlorodiphenyltrichloroethane
(1,1,1-trichloro-2,2-bis(p-
chlorophenyl)ethane)

Chlordane C10H6Cl8
(octachlorohexahydromethanoindene) - insecticide

How Is an Alkyl Halide Classified?

An alkyl halide may be classified according to the number of halogen atoms present, and its
position in the chain of carbon atoms.

A. Number of Halogen Atoms

1. Monohaloalkane – This is an alkyl halide with one halogen.

Example:

CH3 – CH2 – Br

2. Dihaloalkane - This is an alkyl halide with two halogens.

Example:

Br – CH2 – CH2 – Br

55 | P a g e
 3. Trihaloalkane

Example:

Br – CH2 – CH2 – CH – CH2 – CH2 – Cl

Cl

QUICK CHECK A:
Classify the following alkyl halides according to the number of halogens present:

1. CH3 – CH2 – CH – CH2 – CH2 – Br ____________________

Cl

2. CH3 – CH2 – CH2 – CH – CH3 ____________________

3. CH3 – CH2 – CH2 – C – CH2 - CH2 – Br ____________________

B. Position of the Halogen Atom in the Chain of Carbon Atoms

1. Primary Alkyl Halide – In a primary alkyl halide (1⁰), the carbon where the halogen is bonded
is attached to one alkyl group. It can be represented as:

R – CH2 – X

Let us consider the following examples:

a.

CH3 – CH2 – Br

56 | P a g e
In this example, the underlined carbon where the halogen -Br is bonded to, is only attached to one
alkyl group, CH3. Thus, this is classified as a primary alkyl halide.

b.

CH3 – CH2 – CH2 – CH2 – CH2 - Br

5 4 3 2 1

This is a pentane with a halogen, -Br, bonded to carbon 1. Looking closely, carbon 1 is only attached
to carbon 2. Still, this is an example of a primary alkyl halide.

2. Secondary alkyl halide – In a secondary alkyl halide (2⁰), the carbon where the halogen is bonded
is directly attached to two alkyl groups. These two alkyl groups may be the same or not. It can be
represented as:

R – CH – R

Let us consider the following examples:

a.

CH3 – CH – CH3

Br

In this example, the carbon where the halogen -Br is bonded to is attached to two similar alkyl
groups, -CH3 and -CH3.

b.

CH3 – CH – CH2CH3

Cl

The second example shows an secondary alkyl halide whose carbon is attached to two different alkyl
groups, -CH3 (methyl) and -CH2CH3 (ethyl).

57 | P a g e
 c. Tertiary alkyl halide - In a tertiary alkyl halide (3⁰), the carbon where the halogen is bonded is
directly attached to three alkyl groups, which may be the same or different. It can be represented as:

R–C–R

Let us consider the following examples:

a.

CH3

CH3 – C – CH3

Cl
In this example, the carbon where the halogen -Cl is bonded to is attached to three similar alkyl
groups, -CH3.

b.

CH3

CH3 – C – CH2CH3

I
The carbon where the halogen –I is bonded to in the second example is attached to two methyl
groups and one ethyl. Hence, this is an example of a tertiary alkyl halide.

QUICK CHECK B:
Classify the following alkyl halides according to the position of the underlined halogen atoms:

1. CH3 – CH2 – CH – CH2 – CH2 – Br ____________________

Cl

58 | P a g e
 F

2. CH3 – CH2 – CH2 – CH – CH3 ____________________

CH2CH3

3. CH3 – CH2 – CH2 – C – CH2 - CH2Br ____________________

How are Alkyl Halides Named?

Like any organic compound, alkyl halides may be named in two ways: common names and IUPAC
names.

A. Common Names

The common name of an alkyl halide is closely related to its alkane name. This method is only
applicable to alkyl halides with simple alkyl groups.

The following steps will tell you how to give common names to some alkyl halides:

Step 1. Identify and name the alkyl group where the halogen is bonded to.

Step 2. Identify and name the halogen but change its ending to –ide.

Let us study the following examples:

a. CH3 – Br

The alkyl group here is methyl (-CH3) and the halogen is bromine (-Br). Therefore, the
common name of this alkyl halide is:

Methyl bromide

59 | P a g e
b. CH3 – CH2 – F

The alkyl group is ethyl (-CH2 – CH3) and the halogen is fluorine (-F). Therefore, the
common name of this alkyl halide is:

Ethyl fluoride

B. IUPAC Names

For alkyl groups with a large number of carbon atoms and multiple alkyl groups, the IUPAC method
for naming compounds is employed.

Let us consider this example:

CH3

CH3 – CH – CH2 – CH2 – CH – CH2 – CH3

Br

The following steps will tell you how to name an alkyl halide using the IUPAC method:

Step 1. Identify and name the parent chain by identifying the longest carbon chain.

CH3

CH3 – CH – CH2 – CH2 – CH – CH2 – CH3

Br
parent chain = heptane

Step 2. Number the carbon in the parent chain by starting at the terminal carbon where the
substituent is nearest.

CH3

60 | P a g e
 CH3 – CH – CH2 – CH2 – CH – CH2 – CH3
7 6 5 4 3 2 1

Br
If we start numbering with the carbon on the right, the first substituent is on carbon number 3.

CH3

CH3 – CH – CH2 – CH2 – CH – CH2 – CH3

1 2 3 4 5 6 7

Br

If we start numbering with the carbon on the left, the first substituent is on carbon number 2.
Hence, this is the correct number of carbon in the parent chain.

Step 3. Identify each substituent’s location based on the carbon where it is bonded. Remember to
use a comma to separate numbers, and a hyphen to separate a number and a name or prefix. In
naming the halogens, only their prefixes are used:

fluoro- = fluorine

bromo- = bromine

chloro- = chlorine

iodo- = iodine

CH3

CH3 – CH – CH2 – CH2 – CH – CH2 – CH3

1 2 3 4 5 6 7

Br

substituents:

2-methyl

5-bromo

Step 4. Write all the substituents alphabetically followed by the name of the parent chain.

61 | P a g e
 CH3

CH3 – CH – CH2 – CH2 – CH – CH2 – CH3

1 2 3 4 5 6 7

Br
The name of this compound is:

5-bromo-2-methylheptane

Let us study this example:

Cl

CH3 – C – CH2 – CH2 – CH –CH2 - Br

Cl CH3

Step 1: The parent chain of this compound is:

Cl

CH3 – C – CH2 – CH2 – CH –CH2 - Br

Cl CH3
Step 2: The numbering of carbon in the parent chain is:

Cl

CH3 – C – CH2 – CH2 – CH –CH2 - Br

6 5 4 3 2 1

Cl CH3
Step 3: The substituents are:

5,5-dichloro

62 | P a g e
 2-methyl

1-bromo

Step 4: The name of this compound is:

1-bromo-5,5-dichloro-2-methylhexane

QUICK CHECK C:
Give the common name and IUPAC name of this compound:

CH3 – CH – CH3

common name: __________________

IUPAC name: ____________________

Give the IUPAC name of this compound:

CH3 Br

CH3 – C – CH – CH – CH2 –CH3

Cl CH2CH3

IUPAC name: ____________________

63 | P a g e
 EXPERIMENT

Reactivity of Alkyl Halides

In this experiment, you will test the reactivity of alkyl halides by observing the rate at which silver
halide precipitates are formed. The order of reactivity of alkyl halides is as follows:

tertiary > secondary > primary.

E. Objectives

At the end of this activity, you should be able to:

- examine the reactivity of alkyl halides;

- determine the precipitate formed;

- develop analytical and critical thinking.

F. Materials

1 drop of each of the following

1 – bromobutane

1 – bromo – 2 – methylpropane

G. – bromo – 2 – methylpropane

benzene bromide

bromobenzene

10 Ml 0.1M silver nitrate in 95% ethanol

10 Ml 1M nitric acid solution

steam bath set up

5 test tubes with stopper

6 droppers

pen and masking tape (for labelling)

64 | P a g e
C. Procedure

1. Place 2 Ml of 0.1 M solution of silver nitrate in 95% ethanol in each of the 5 test tubes.

2. Add 1 drop of each of the alkyl halide in each test tube. Label each test tube accordingly.

3. Put the stopper on and shake each test tube. Take note of your observations.

4. If no reaction is observed within five minutes, use a steam bath to warm the mixture. Take note of your
observations. Keep in mind the color of the following precipitates:

Silver chloride – white

Silver bromide – pale yellow

Silver iodide – yellow

H. To the test tube that formed a precipitate, add 3-4 drops of nitric acid solution. Take
note of your observations. Keep in mind that if the precipitate remains even after
adding nitric acid solution, the compound is a silver halide.

D. Guide Questions

1. Data and Observations:

ALKYL HALIDE + AgNO3 OBSERVATIONS

1 – bromobutane
1 – bromo – 2 – methylpropane
2 – bromo – 2 – methylpropane
benzene bromide
bromobenzene

I. Which mixture/s produced precipitate? Describe the precipitate forme

.
J. Which mixture’s precipitate remained even after adding of nitric acid solution? How will
you identify the compound?

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 K. Which among the alkyl halides is the most reactive?

______________________________________________________________________________

E. Conclusion

______________________________________________________________________________

______________________________________________________________________________

SUMMARY

An alkyl halide:

• Has a general formula of R – X.

• Is an organic compound that contains one or more halogens: fluorine, chlorine, bromine and
iodine
• May be called in its common name or its IUPAC.
• May be classified according to the number of halogens present: monohaloalkane,
dihaloalkane or trihaloalkane.
• May also be classified according to the position of the halogen atom in the carbon chain:
primary alkyl halide, secondary alkyl halide or tertiary alkyl halide.
• Has many industrial uses, such as refrigerant, propellant, solvent, and as a fire extinguisher.

VALUING

Read the article Ozone layer 'rescued' from CFC damage by Victoria Gill written last February 11, 2021,
that can be found at the web address below then answer the questions that follow:

https://www.bbc.com/news/science-environment-56014092

1. What is the ozone layer, and what does it do?

66 | P a g e
 ________________________________________________________________________

_______________________________________________________________________

2. A study in 2018 showed that the level of CFCs in the atmosphere was not decreasing as
expected. What caused the delay?

________________________________________________________________________

_______________________________________________________________________

3. Has the Montreal Protocol been successful in decreasing the levels of ozone-depleting
substances in the atmosphere? Explain.

________________________________________________________________________

_______________________________________________________________________

_______________________________________________________________________

4. How can the Philippines participate in the goal of the Montreal Protocol?

________________________________________________________________________

_______________________________________________________________________

POST TEST

Multiple Choices Read and analyze each question. Write the letter of the correct answer.

_____1. What are alkane-derived compounds where one or more of its hydrogen atoms are replaced by
halogen atoms?

A. alkyl alkane B. alkyl halide C. haloalkane D. halohalide

_____2. Which of the following is an alkyl halide?

A. CH3 – CH2 – CH2 – Br C. CH3 – CH2 – CH2 – CH2 – CH2 - OH

B. CH3 – CH2 – CH2 – CH3 D. CH3 – CH2 – CO – CH2 – CH3

67 | P a g e
_____3. According to the number of halogens, what kind of alkyl halide is CH3Cl?

A. monohaloalkane C. trihaloalkane

B. dihalolkane D. tetrahaloalkane

_____4. According to the number of halogens, what kind of alkyl halide is CHI 3?

A. monohaloalkane C. trihaloalkane

B. dihalolkane D. tetrahaloalkane

_____5. According to the position of the halogen in the carbon chain, what kind of alkyl halide is is
CH3Cl?

A. primary B. secondary C. tertiary D. quaternary

_____6. To which carbon atom is the halogen bonded to in this compound:

CH3 – CH2 – CH – CH3

I
Cl

A. carbon 1 B. carbon 2 C. carbon 3 D. carbon 4

_____7. What is the parent chain of this compound?

CH3 CH3 Cl
I I I
CH3 – CH – CH – CH – CH2 – CH2 – Br

A. pentane B. heptane C. hexane D. heptane

_____8. What is the name of the compound in question number 8?

68 | P a g e
 A. 1,1,2-dimethyl-3-chloro5-bromopentane C. 1-bromo-3-chloro-4,5,5-trimethylpentane

B. 1-bromo-3-chloro-4,5-dimethylhexane D. 6-bromo-4-chloro-2,3-dimethylhexane

_____9. Which among the following has the highest density?

A. CH3Br B. CH3I C. CCl3F D. CCl3CF3

_____10. What does the Montreal Protocol do?

A. It monitors industries that release effluents to bodies of water.

B. It phases out the production of substances that cause water pollution.

C. It phases out the production of substances that cause ozone depletion.

D. It regulates the production of haloalkanes of different industries.

69 | P a g e
 Of all the organic compounds, alcohols might be the most widely-known. With the onset of the
COVID pandemic, many people started using alcohol. Aside from being used as a disinfectant and
antiseptic, another common household product with alcohol are the alcoholic drinks such as beer, wine, and
whiskey.

You will learn more about alcohols as you study this lesson.

I. LEARNING OUTCOMES

At the end of this chapter, you should be able to:

- describe an alcohol in terms of properties, uses and classification;

- develop values that will make you a good steward of creation;

- write the condensed structural formulas and names of alcohols;

PRETEST

True or False. Write TRUE if the statement is correct and FALSE if it not.

__________1. Ethyl alcohol is soluble in water.

__________2. An alcohol is an organic compound characterized by the presence of hydroxide ion.

__________3. Methanol is the alcohol present in alcoholic drinks.

__________4. Ethanol is a primary alcohol.

__________5. In naming alcohols using the IUPAC system, the numbering starts at the end where the
hydroxyl group is nearest.

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Multiple Choices Read and analyze each question. Write the letter of the correct answer.

_____6. Which pair is NOT correct (alcohol and classification)?

A. 3 – pentanol ; tertiary alcohol

B. 2 – methyl – 2 – propanol ; tertiary alcohol

C. 1 – hexanol ; primary alcohol

D. 2 – hexanol ; secondary alcohol

_____7. Which among the following is a secondary alcohol?

A. CH3 - CH2 – OH C. CH3 – CHOH - CH3

B. CH3 – OH D. OH – CH2 – CH2 – CH2 – CH3

_____8. The general formula for alcohol is __________.

A. R – COOH C. R - OH

B. R – NH2 D. R – COOH

_____9. What is the IUPAC name of this alcohol?

Cl Br OH
I I I
CH3 – CH – CH – CH2 – CH2 – CH – CH3

A. 3 – bromo – 2 – chloro – 6 – heptanol

B. 2 – chloro – 3 – bromo – 6 – heptanol

C. 5 – bromo – 6 – chloro – 2 – heptanol

D. 6 – chloro – 5 – bromo – 2 – heptanol

71 | P a g e
_____10. Which among the following statements is NOT true about alcohols?

A. Alcohols have –OH group.

B. Ethyl alcohol has higher boiling point than ethane.

C. Alcohols are generally liquids at room temperature.

D. Methanol is used as synthetic food flavoring.

REVIEW

True or False. Write TRUE if the statement is correct and FALSE if it not.

__________1. Alkyl halides are soluble in organic solvents.

__________2. 1-bromobutane is a primary alkyl halide.

__________3. CFCs are ozone-enriching substances.

__________4. Halon-1301 is a pesticide.

__________5. 1-bromobutane has a higher boiling point than butane.

ALCOHOLS
What is an Alcohol?

An alcohol is an organic compound characterized by the presence of the functional group hydroxyl
(-OH) attached to a carbon of the hydrocarbon chain. It can be represented as:

R – OH

where:

R – alkyl or aryl group

-OH – hydroxyl group

Note that the hydroxyl group is comprised of an oxygen atom bonded to a hydrogen atom.
Oxygen’s higher electronegativity results to oxygen being partially negative and to hydrogen being

72 | P a g e
partially positive. The unequal sharing of electrons enhances the overall polarity of alcohols, which
explains why some alcohols are miscible in water.

Look at the example:

CH4 CH3 – OH
methane methanol or methyl alcohol

One of the hydrogen atoms of the alkane methane, CH4, is substituted by the hydroxyl group, -OH.
The alcohol is called methanol, CH3OH, a toxic, colorless and flammable liquid commonly used as a
solvent and alternative source of fuel.

Here are other examples of alcohols:

CH3 – CH2 – OH
ethanol or ethyl alcohol

CH3 – CH – OH
I
CH3
isopropyl alcohol

What are the Physical Properties of an Alcohol?

This table summarizes the physical properties of an alcohol:

Physical Properties of an Alcohol

State - Most are liquids at room temperature
Odor - Faint alcoholic odor
Color - Most are colorless
Boiling Point Higher boiling point than corresponding alkane
Solubility - Soluble in water
- Alcohols with long carbon chain are less soluble in water
Polarity - Polar

73 | P a g e
What are the Uses of Alcohols?

Name of Compound Chemical Formula Uses

-industrial feedstock (formaldehyde,
Methanol CH3OH ethanoic acid)
- fuel or petrol additive
- solvent (inks, adhesives, resins and dyes
- antifreeze
- the ‘alcohol’ in alcoholic drinks
Ethanol C2H5OH - fuel or petrol additive
- solvent (cosmetics, detergents, inks)
- antiseptic
Propanol C3H7OH - solvent (ink, cosmetics)
- industrial feedstock (used in the
Butanol C4H9OH manufacture of butyl ethanoate, a synthetic
fruit flavoring)
- fuel (biofuel, produced from fermentation
of sugar and carbohydrates)
- solvent (inks, adhesives, resins and dyes

How is an Alcohol Classified?

An alcohol is classified according to the number of alkyl groups attached to the carbon where the
hydroxyl group is directly bonded to.

1. Primary Alcohol – In a primary alcohol (1⁰), the carbon where the hydroxyl group is bonded is
attached to one alkyl group. The general formula for primary alcohol is:

R – CH2 – OH

Study this example:

CH3 – CH2 – OH

The hydroxyl group is bonded to the underlined carbon. Looking closely, this carbon is only
attached to one alkyl group, the –CH3.

Let us have another example:

CH3 – CH2 – CH2 – OH

74 | P a g e
 3 2 1

In this example, the hydroxyl group is bonded to carbon 1. Carbon 1 is attached to carbon 2, which
makes this example a primary alcohol.

2. Secondary Alcohol - In a secondary alcohol (2⁰), the carbon where the hydroxyl group is bonded
is attached to two alkyl groups. The general formula for secondary alcohol is:

R2 – CH – OH or R – CH – R

OH

Here are some examples of secondary alcohols:

a.
OH
I
CH3 – CH2 – CH – CH3

b.

CH3 – CH2 – CH – CH2 – CH3

I
OH

These are secondary alcohols since the carbon where each of the hydroxyl group is bonded is
attached to two other alkyl groups.

3. Tertiary Alcohol - In a tertiary alcohol (3⁰), the carbon where the hydroxyl group is bonded is
attached to three alkyl groups. The general formula for tertiary alcohol is:

R3 – C – OH or R – C - OH

75 | P a g e
 Study the following examples of tertiary alcohols:

a.
CH3

CH3 – CH2 - C – OH

CH3

b.
CH3

CH3 – CH2 – C – CH2 – CH3

OH

How are Alcohols Named?

The names of alcohols are derived from the hydrocarbons from which they are derived. Just like
alkyl halides, alcohols may be named by their common names or the IUPAC System.

A. Common Names

To give the common name of an alcohol, the name of its alkyl group is simply combined with the
word alcohol.

Look at the following examples:

a.
CH3 - OH
methyl alcohol

b.

76 | P a g e
 CH3 – CH2 – OH
ethyl alcohol

c.
OH
I
CH3 – CH – CH3
isopropyl alcohol

B. IUPAC Names

Another system is used for alcohols with complex alkyl groups. Look at the example given below.
Aside from the hydroxyl group, the compound also contains methyl as a substituent.

CH3
I
CH3 – CH – CH2 – CH2 - OH

The IUPAC system of naming alcohol uses the location of the hydroxyl group, the name of the
parent alkane and the suffix –ol.

Here are the steps to be followed in naming an alcohol:

Step 1. Identify and name the parent chain by identifying the longest carbon chain.

CH3
I
CH3 – CH – CH2 – CH2 - OH

parent chain = butane

Step 2. Number the carbon in the parent chain by starting at the terminal carbon where the
hydroxyl group is nearest.

77 | P a g e
 CH3
I
CH3 – CH – CH2 – CH2 - OH
4 3 2 1

Step 3. Identify each substituent’s location based on the carbon where it is bonded. Remember to
use a comma to separate numbers, and a hyphen to separate a number and a name or prefix.

CH3
I
CH3 – CH – CH2 – CH2 - OH

hydroxyl group – carbon 1

methyl – carbon 3

Step 4. Write all the substituents alphabetically followed by the name of the parent chain, which
ends in –ol.

CH3
I
CH3 – CH – CH2 – CH2 - OH

The name of this compound is:

3-methyl-1-butanol

Note: You may refer to the following for alcohols with multiple hydroxyl groups:

propanediol – 2 hydroxyl groups

propanetriol – 3 hydroxyl groups

QUICK CHECK A:

78 | P a g e
 Give the IUPAC name of each of the following alcohols:
1.
Cl OH CH3
I I I
CH2 – CH2 – CH – CH – CH2 – CH3

2. OH
I
CH3 – C – CH2 – CH3
I
OH

EXPERIMENT

Determining Alcohol Classification

In this experiment, you are going to distinguish primary and secondary alcohols from tertiary
alcohol. Chromic acid will oxidize primary alcohol first and then the secondary alcohol. The tertiary alcohol
will not react with chromic acid. The primary and secondary alcohols have oxidized when its color changes
to blue green.

A. Objectives

At the end of this experiment, you should be able to:

- distinguish primary and secondary alcohols from tertiary alcohols;

- differentiate among primary, secondary and tertiary alcohols;

- develop analytical and critical thinking.

B. Materials
79 | P a g e
 2 mL ethyl alcohol

2 mL isopropyl alcohol

2 mL tert-butyl alcohol

6 mL acetone

6 mL Chromic Test Acid Reagent

3 test tubes

dropper

marker and masking tape (labelling)

C. Procedure

1. Label each test tube as follows: ethyl alcohol, isopropyl alcohol and tert-butyl alcohol.

2. Put 3-4 drops of the alcohol in each test tube, respectively.

3. Add 2 mL of acetone to each test tube. Make sure that the substances fall into the test tube and not on
the sides of the test tube.

4. Add 2 drops of Chromic Acid Test Reagent to each test tube. Take note of your observations.

D. Guide Questions

1. Data and Observations

ALCOHOLS OBSERVATIONS
ethyl alcohol
isopropyl alcohol
tert-butyl alcohol

2. What happened to each alcohol after adding the chromic acid test reagent?

________________________________________________________________________

________________________________________________________________________

3. Based on the result of the experiment, which alcohol/s is/are primary and secondary and which is/are
tertiary?
80 | P a g e
 ________________________________________________________________________

________________________________________________________________________

4. How were you able to classify the alcohols?

_______________________________________________________________________

________________________________________________________________________

E. Conclusion

________________________________________________________________________

________________________________________________________________________

SUMMARY

An alcohol:

• Has a general formula of R – OH.

• Is an organic compound characterized by the presence of hydroxyl (-OH).
• May be called by its common name or its IUPAC.
• May be classified as primary alcohol, secondary alcohol or tertiary alcohol.
• Has many industrial uses, such as antiseptic, fuel, solvent, and industrial feedstock.

VALUING

Alcohol abuse is one of the most common substance abuse in the world. It is considered an alcohol use
disorder when it is already causing distress and harm to the person. In your opinion, why do some people
drink too much? What will you do to avoid alcohol abuse?

81 | P a g e
_____________________________________________________________________________________
_____________________________________________________________________________________
_____________________________________________________________________________________
_____________________________________________________________________________________

POST TEST

True or False. Write TRUE if the statement is correct and FALSE if it not.

__________1. Ethyl alcohol is soluble in water.

__________2. An alcohol is an organic compound characterized by the presence of hydroxide ion.

__________3. Methanol is the alcohol present in alcoholic drinks.

__________4. Ethanol is a primary alcohol.

__________5. In naming alcohols using the IUPAC system, the numbering starts at the end where the
hydroxyl group is nearest.

Multiple Choices Read and analyze each question. Write the letter of the correct answer.

_____6. Which pair is NOT correct (alcohol and classification)?

A. 3 – pentanol ; tertiary alcohol

B. 2 – methyl – 2 – propanol ; tertiary alcohol

C. 1 – hexanol ; primary alcohol

D. 2 – hexanol ; secondary alcohol

_____7. Which among the following is a secondary alcohol?

A. CH3 - CH2 – OH C. CH3 – CHOH - CH3

B. CH3 – OH D. OH – CH2 – CH2 – CH2 – CH3

_____8. The general formula for alcohol is __________.

A. R – COOH C. R - OH
82 | P a g e
 B. R – NH2 D. R – COOH

_____9. What is the IUPAC name of this alcohol?

Cl Br OH
I I I
CH3 – CH – CH – CH2 – CH2 – CH – CH3

A. 3 – bromo – 2 – chloro – 6 – heptanol

B. 2 – chloro – 3 – bromo – 6 – heptanol

C. 5 – bromo – 6 – chloro – 2 – heptanol

D. 6 – chloro – 5 – bromo – 2 – heptanol

_____10. Which among the following statements is NOT true about alcohols?

A. Alcohols have –OH group.

B. Ethyl alcohol has higher boiling point than ethane.

C. Alcohols are generally liquids at room temperature.

D. Methanol is used as synthetic food flavoring.

83 | P a g e
 Are you familiar with ethers? Maybe you have used it in your daily life, but you didn’t
know it was ether. In this module, we will discuss the details about ethers, especially how it is
named, their properties, structure, and their reactions. Are you ready to learn? If you say so,
then I warmly welcome you to the world of ethers.

Learning Outcomes:

After completing this module, you will be able to:

1. Draw the structure of ethers

2. Name the ethers in common and IUPAC names

3. Analyze the different methods used in the preparation of ethers

4. Understand the reaction of ethers

PRETEST

Directions: Choose the letter of the correct answer. Write your answers on a separate sheet of
paper.

1. Which of the following molecules is an ether?

A. CH3-O-CH3 C. R-C-OH

B. R-C-OR’ D. R-OH

2. What are some of the chemical properties of ethers?

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 A. Colorless and sweet-smelling C. Low boiling point

B. Liquid at room temperature D. All of the answers are correct

3. Which two molecules react in a Williamson ether synthesis?

A. Alkoxide ion and alkyl halide C. Ether and oxygen

B. Alkoxide ion and alcohol D. Alkyl halide and ether

4. Ethers are not very reactive, but can participate in:

A. Cleavage by HI and HBr C. Chlorination reactions

B. Oxidation reactions D. All of these answers are correct

5. What is the IUPAC name of the compound (CH3-CH2-O-CH3)?

A. methoxy methane C. ethoxy methane

B. methoxy ethane d. ethoxy ethane

6. Ethers are:

A. Neutral
B. Basic
C. Acidic

7. Among the following, the compound with functional group -O- is

A. Acetone C. Acetic acid

B. Methyl alcohol D. Ethyl methyl ether

8. Ethers are polar in nature.

A. True B. False

9. The boiling point of methoxy methane is higher than that of ethanol.

A. True B. False

10. Ether is less soluble in water than alcohol.

A. True B. False

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 REVIEW

In our previous module, we learned that the hydroxyl group (-OH) is found in the alcohol
and phenol functional groups. (Note: That differs from hydroxide (OH-), which is an ionic
compound). Kindly name some common alcohols and provide their structural formula. Use the
space provided below.

ETHERS

What are ethers?

Ethers are a class of compounds that contain oxygen between two alkyl groups. They
have the formula R-O-R’, with R’s being the alkyl groups or aryl (benzene ring) groups.

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 Nomenclature of Ethers

IUPAC names

The ether functional group does not have a characteristic IUPAC nomenclature suffix, so it is
necessary to designate the smaller alkyl group.

Steps in naming ethers in IUPAC name:

Step 1: Start with the longest carbon chain. The parent name will be based on the longest
carbon chain.

Step 2: Since we have methane on the longer carbon chain, the shorter carbon chain attached
to the oxygen will be an alkoxy compound which will give us the “methoxy”.

Step 3: We will now combine the names that we found from the compound. Alkoxy group
name will be the first followed by the parent name. Therefore, the name for this compound is
methoxy methane.

Let us have some examples in giving IUPAC names for our ethers.

Step 1: Identify the longest carbon chain in order for us to get the parent name.

Step 2: Our longest chain is ethane. And then, the substituent that is attached to oxygen will be
an alkoxy group and its name will be methoxy.

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Step 3: We can now combine the names for each group. Remember that the alkoxy group is
always written first before the parent name. Therefore, the name of this compound is methoxy
ethane.

Let us name another compound in the second example.

Again, we just need to follow the three steps that were given.

Step 1: Find the longest carbon chain for our parent name.

Step 2: Since we have 4 carbon chains, we will name it as butane. There are also 2 carbon chains
attached to the oxygen which will be named as ethoxy.

Step 3: We can now combine the names that we have given. Since the alkoxy group is attached
to the second carbon chain, we will now put a number before the alkoxy group. Therefore, the
name of this compound is 2-ethoxy butane.

Let us have our third example.

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Step 1: Find the longest carbon chain.

Step 2: We have a 6 carbon chain on the left ring and since the compound is a ring, it will be
named as cyclohexane. We also have 5 carbon chain on the right side that is attached to
oxygen giving us the name cyclopentoxy.

Step 3: We can now combine the following names. Again, the alkoxy group will be written
first before the parent name. Therefore, the name of this compound is
cyclopentoxycyclohexane.

I hope you’ve learned something in giving IUPAC names for ether. Let us have some
exercise before we proceed to the common name.

ACTIVITY 1: NAMING ETHERS

Direction: Give the following IUPAC name for each compound. Follow the steps given in
naming the organic compounds.

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1. 2.

3. 4.

5.

Since you already know how to give IUPAC name to ethers, let’s now proceed to common
names of ethers.

Common Names

The common names of ethers are derived by naming the alkyl groups bonded to the oxygen and
then listing them in alphabetical order followed by the word “ether”. Under the current system,
the alkyl groups should be named in alphabetical order, but many people still use the old system,
which named the groups in order of increasing complexity.

Let us use the previous example. These are the steps in giving a common name to ethers:

Step 1: Identify the groups attached to the oxygen. As you can see, we have two methyls on

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each side of the oxygen.

Step 2: Since it is composed of two methyl groups, we can write it as “dimethyl”.

Step 3: “Ether” will be the parent name for the common names. So in our example, we can
write it as dimethyl ether.

Let’s have our second example.

Step 1: Again, identify the names of each group attached to the oxygen. Our next example is
composed of the methyl group and ethyl group.

Step 2: Write the names of the groups in alphabetical order so in this case, we have ethyl
methyl.

Step 3: Write the “ether” on the last part as our parent name. So, the name of this compound is
ethyl methyl ether.

For our last example, let’s have this compound.

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 What do you think is the correct common name for this compound?

Answer: Ethyl isopropyl ether

Properties of Ether

▪ The bond angle in ethers is very similar to that found in water and alcohol.

o The larger the -R group, the larger the bond angle

▪ Recall alcohols have relatively high boiling points, because of H bonding.

▪ Ethers can act only as H-Bond acceptors.

▪ However, ethers cannot H-bond among themselves.

▪ Since ethers cannot H-

bong among themselves, their boiling points are much lower than alcohols of comparable size.

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▪ The larger the ether, the higher the boiling point

▪ Ethers are common solvents used for organic reactions:

▪ Since ethers have relatively low boiling points (easily removed by evaporation), they are
unreactive.

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 Preparation of Ethers

Williamson Ether Synthesis

▪ The Williamson ether synthesis is a viable approach for many asymmetrical ethers.

▪ Since the 2nd step is SN2 substitution, it only works well with unhindered alkyl halides

Dehydration of Alcohols

▪ The preparation of ethers by dehydration of alcohol is a nucleophilic substitution

reaction. The alcohol involved in the reaction plays two roles: one alcohol molecule
acts as a substrate while the other acts as a nucleophile. It can follow either an SN1
or SN2 mechanisms

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Let us try to solve this example using the Williamson Ether Synthesis What will be
the product of this compound?

Answer:

How did we come up with that answer?

The first step is deprotonation by a base. OH will act as a base and going to remove
the H.

The second step is alkylation by means of SN2 process. Br is more electronegative

than C that is why Br is partially negative, and C is partially positive. The oxygen
with the negative charge will attack the carbon kicking out the leaving group.

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So, the result will be an ether which is methoxy cyclohexane.

ACTIVITY 2

Directions: Show the mechanism for this Williamson Ether Synthesis.

1.

2.

Common Reactions of Ethers

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 The most common reaction of ethers is Acidic cleavage of ethers (SN2). When
ethers are treated with strong acid in the presence of nucleophile, they can be cleaved
to give alcohols and alkyl halides. If the ether is a primary carbon this may occur
through SN2 pathway.

Common acids for this purpose are HI and other hydrogen halides, as well as
H2SO4 in the presence of H2O. In the case where the ether being cleaved is secondary
and has a stereocenter, there will be an inversion of configuration.

These are the examples:

The third example could also be written “H3O+”. Note that excess HI will
convert primary alcohols to alkyl halides via SN2, but not phenol (C6H5OH) since
sp2 hybridized carbons do not undergo SN1 or SN2 reactions.

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Mechanism:

Notes: In cases where the ether being cleaved is secondary and has a stereocenter,
there will be an inversion of configuration.

Example 2: Opening of tetrahydrofuran (THF) with aqueous acid.

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 SUMMARY

Two alkyl or aryl groups are linked to a central oxygen atom in ethers.
Ethers can result from the condensation of alcohols. Ethers are colorless, pleasant-
smelling liquids at room temperature. Compared to alcohols, ethers are less dense,
less soluble in water, and have lower boiling temperatures. They are useful as
solvents for fats, oils, waxes, fragrances, resins, dyes, gums, and hydrocarbons
because they are relatively unreactive. Certain ether vapors are utilized as soil
insecticides, miticides, and fumigants.

Ethers are also important in medicine and pharmacology, especially for use as
anesthetics. For example, ethyl ether, simply known as ether, was first used as a
surgical anesthetic in 1842. Codeine, a potent pain-relieving drug, is the methyl ether
of morphine. Because ether is highly flammable, it has largely been replaced by less-
flammable anesthetics, including nitrous oxide and halothane.

POST TEST

I. Naming Ethers

1. 2.

3. 4.

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 5.

II. Reactions of Ether

1. Two of the ethers shown below were cleaved by HI (via an SN2

pathway). Which one would be faster? Provide structures of products
and explain which reaction is slow and why.

2. Draw the products of ether cleavage with excess HBR. Will the product of
cleavage using H2SO4 in H2O (here written as H3O+) be the same?

3. Give the product and mechanism of this reaction

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 Do you like eating street foods? Filipinos are a fan of fish balls, kikiam, barbecue,
and grilled isaw. The famous street food dip in the Philippines is vinegar. The odor of the
vinegar is caused by the presence of acetic acid, a carboxylic acid, in the vinegar.

This module will help you in widening your knowledge about Carboxylic acids,
especially how it is named, their properties, preparations, and their reactions. Also, you’ll
appreciate their existence once you’re done with this topic.

Learning Outcomes:

1. Identify what is a carboxylic acid;

2. Name the carboxylic acid using the IUPAC format;

3. Describe the different properties of carboxylic acid; and

4. Describe the reactions of Carboxylic Acids.

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 PRETEST

Directions: Choose the letter of the correct answer. Write your answers on a separate sheet
of paper.

1. Give the name for the below structure based on IUPAC nomenclature.

A. 2-methyl-4-butanoic acid B. 2-methyl-4-pentanoic acid

C. 3-methylbutanoic acid D. 3-methylpentanoic acid

2. Which of the following acids is the most soluble in water?

A. Acetic acid B. Benzoic acid

C. Stearic acid D. Caprylic acid

3. The products of the reaction of carboxylic acid and alcohol would be. A.Ketone and water
B. Amide and water

C. Acid chloride and water D. Ester and water

4. Carboxylic acids react with metals to form?

A. Metal Carboxylate and Hydrogen B. Metal Carboxylate and Water

C. Metal Carboxylate, Water and Carbon Dioxide

5. 2-butanol heated with acidified KMnO4 solution produced__________.

A. butanone B. butene C. butanoic acid D. butane

6. When benzyl alcohol is oxidized with KMnO4, the product obtained is which of the
following compound?

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A. Benzaldehyde B. Benzoic acid

C. CO2 and H2O D. Benzophenone

7. What is the proper name for this molecule?

A. 2,5-dimethylhexane B. 2,5-methylhexanoic acid

C. 2,5-dimethylhexanoic acid D. 2,5-dimethylhexan-6-oic acid

8. Is the carboxyl carbon always carbon number 1?

A. YES B. NO

9. 2-methyl-1-propanol heated with acidified K2Cr2O7 solution produced_______.

A. alkene B. carboxylic acid

C. alcohol D. ketone

10. Which compound has the highest boiling point?

A. Butane B. Dimethyl ether

C. Propan-1-ol D. Acetic acid

11. Which of the following could result from this reaction as one of the products?

A.

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B.

C.

D.

12. Which compound has the highest boiling point?

A. Propane B. Propanone

C. Propanoic acid D. Propan-1-ol

8. What is the correct IUPAC name for formic acid?

A.Ethanoic acid B. Methanoic acid

C. Acetic acid D. Valeric acid

13.Which of the following carboxylic acid readily dissolves in water?

A.Decanoic Acid B. Ethanoic Acid

C. Heptanoic Acid D. Benzoic Acid

14.Which of these carboxylic acids has the highest boiling point?

A. Methanoic acid B. Butanoic acid

C. Decanoic acid D. Hexanoic acid

15. 2-butanol heated with acidified KMnO4 solution produced__________.

A. butanone B. butene C. butanoic acid D. butane

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 REVIEW

Answer the following questions about Ether.

1. What is the chemical formula of ether?

2. Are ethers water soluble?
3. Alcohol has a higher boiling point than ethers of comparable molecular masses. Why?

CARBOXYLIC ACID

The carboxyl functional group that characterizes the carboxylic acids is composed of
two functional groups, a hydroxyl group bonded to a carbonyl group. It is frequently
written in condensed form as -COOH or -CO2.

Nomenclature of Carboxylic Acids

Just like aldehydes, the carboxyl group must be located at the end of a carbon chain.
The carboxyl carbon is referred to as carbon #1 in the IUPAC nomenclature scheme, and
other substituents are placed and labeled correspondingly. "-oic acid" is the typical IUPAC
suffix for a carboxyl group.

RULES IN NAMING CARBOXYLIC ACID

• The longest carbon chain with a -COOH group must be identified if the parent
chain is noncyclic, and the suffix must be changed from "ane" to "oic acid"
dropping the “e”.

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 • When substituents are present on the parent chain, the substituents are
numbered based on the position of the COOH group and placed in
alphabetical order.

Naming Carboxylic Acids on a Ring

When the -COOH group is on a ring, the ring is named, and “carboxylic acid” is added
after the name. See the example below.

If substituents are also present, the numbering begins at the carbon linked to the

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COOH group and moves in a manner that minimizes the numbering of the
substituents:

Physical Properties of Carboxylic Acids

• The melting and boiling points of a homologous group of carboxylic acids

with one to ten carbon atoms are shown in the table below. As the boiling
points increased with size in a regular manner, the melting points did not rise.

• Exhibits strong hydrogen bonding between molecules. Therefore, carboxylic

acids have high boiling points compared to other functional groups.

• Because dipole forces become less significant and dispersion forces become
more significant, solubility decreases as the length of the carbon chain
increases.

• Carboxylic acid molecules are polar due to the presence of two electronegative
oxygen atoms.

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 • Generally, have a strong sour smell.

Preparation of Carboxylic Acids

Acetic acid, one of the most prevalent carboxylic acids, is used in a wide variety of
products, from vinegar to the synthesis of organic compounds, such as polyvinyl
acetate used in paints and adhesives:

Here are some of the methods for preparing carboxylic acids in the laboratory:

Oxidation of Alcohols and Aldehydes

One method is to use powerful oxidizing agents like chromic acid (Jone's
oxidation), potassium permanganate (KMnO4), or sodium hypochlorite (NaClO -
bleach) to oxidize primary alcohols and aldehydes:

Primary
and secondary alkyl benzenes can be benzylic oxidized to produce benzoic acid. Most
potent oxidizing agents, as demonstrated above, would be effective for this
transformation:

Keep in mind that several chemicals, like pyridinium chlorochromate (PCC),

pyridinium dichromate (PDC), the Swern oxidation, and the Dess-Martin oxidation,
permit the selective oxidation of primary alcohols to aldehydes. The Oxidation of
alcohols covers the mechanistic details and selectivity of each oxidizing agen

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Carboxylic Acids from Nitriles

It is also possible to create carboxylic acids from alcohols and ketones converting
them into cyanohydrins, which are then hydrolyzed to create hydroxy acids:

Of course, nitrile groups can also be converted to carboxylic acids in other

compounds besides cyanohydrins. If there are no other functional groups on the molecule
that make it acid or base labile, any nitrile can be hydrolyzed into carboxylic acids by an
acid or base:

Grignard
Reaction with CO2

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 Additionally, carboxylic acids can be made by carbonating alkyl and aryl
magnesium halides:

Oxidative Cleavage

The oxidative cleavage of alkenes and alkynes by KMnO4 or ozone is another

technique for making carboxylic acids:

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 Reactions of Carboxylic Acids

1. Acid-Base Reaction

• Carboxylic acids are weak acids with pKa values ~ 4-5.

• The carboxylate ion is a resonance-stabilized carbanion.

• The water-soluble carboxylate ion is created when carboxylic acids combine with a dilute
aqueous sodium hydroxide solution.

Example:

2. Esterification

• An ester and water are produced when alcohol and carboxylic acid combine.
• The reaction is an equilibrium
• A catalyst, usually H+, is required

Example:

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TRIVIA about Carboxylic Acid

✓ Aspirin is a carboxylic acid medication.

✓ Ibuprofen, a non-aspirin pain killer is also a carboxylic acid.

✓ Vinegar has a sour flavor because of carboxylic acid

ACTIVITY 1

Directions:

1. Below is an illustration of a compound's line formula:

How many carbon atoms make up the root chain?

How many alkyl substituents are on this chain?

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 Give the IUPAC name of the compound.

2. Below is an illustration of a compound's line formula:

How many carbon atoms make up the root chain?

Give the IUPAC name of the compound.

ACTIVITY 2

Laboratory Preparation of Acetic Acid

Preparation of acetic acid (Ethanoic acid):

As we mentioned earlier, acetic acid is one of the most important carboxylic

acids which is used as a food preservative. It can be made in a lab by oxidizing ethanol
with potassium permanganate. It can also be obtained by passing the vapors of ethanol
through copper oxide as described in this experiment.

Objective: To make acetic acid in a lab setting by oxidizing ethanol

Materials: Goggles, test tubes, test tube rack, quick fit apparatus, 250 mL beaker,

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pipettes, Bunsen burner, stand, clamp, tripod, wire gauze, digital balance, blue litmus
paper, broken porcelain pieces.

Chemicals: Sodium dichromate, 1 M sulphuric acid, Ethanol, 0.5 M sodium carbonate

solution

Procedure:

1. Set up the Quick- fit apparatus for refluxing as shown in the figure below.

2. Put about 10 mL of 1 M sulphuric acid into the 250 mL round-bottom flask.

3. Ass 2-3 g pf sodium dichromate (Na2Cr2O7) and a few pieces of broken porcelain.
The flask's contents should be stirred until the solution is finished (warm if necessary).
4. Under a running faucet, cool the mixture.
5. Drop 1 mL of ethanol into the flask
6. Distil 2-3 mL of the liquid after 20 minutes of boiling with reflux.
7. Compare the product's (distilled liquid) scent to that of ethanol.
8. Mix a small amount of solid sodium carbonate with a few drops of the distilled
liquid.

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 9. Drop a small amount of the distilled liquid onto moistened blue litmus paper.

Observation and Analysis:

1. What happened to the flask's solution's color?

2. What part does sodium dichromate play in the above reaction? Is it oxidized or
reduced?

3. Write the chemical reaction for this reaction.

4. What do you conclude from this experiment?

SUMMARY

An organic substance with a carboxyl group is referred to as a carboxylic acid. A

carboxyl group is a functional group that contains a carbon-oxygen double bond and an -OH
group also attached to the same carbon, but it has characteristic properties of its own. Many
carboxylic acids are colorless liquids with disagreeable odors and exhibit strong hydrogen
bonding between molecules. Therefore, in comparison to other compounds of similar mass,
they have high boiling points. Carboxylic acids occur widely in nature, whether in the
laboratory or in the body, the oxidation of aldehydes or primary alcohols forms carboxylic
acids. Carboxylic acids are very important, industrially. Making soap, detergents, and
shampoos is one of the most significant industrial uses for long-chain carboxylic acid.
Additionally, carboxylic acids are also important in the production of greases, crayons, and
plastics

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 VALUING

Some organic salts are added to food goods as preservatives. They stop spoiling by
limiting the development of fungus and bacteria. For instance, sodium sorbate and potassium
sorbate are added to soft drinks, wine, and fruit juices; sodium propionate is added to
processed cheese and bread goods; and sodium benzoate is added to syrups, jellies, pickles,
and cider. The next time you go grocery shopping, it is better to check for them on ingredient
labels.

POST TEST

Direction: Choose the letter of the correct answer. Write your answers on a separate sheet
of paper.

1. The products of the reaction of carboxylic acid and alcohol would be.
A. Ketone and water B. Amide and water

C. Acid chloride and water D. Ester and water

2. Which of the following acids is the most soluble in water?

A. Acetic acid B. Benzoic acid

C. Stearic acid D. Caprylic acid

3. Give the name for the below structure based on IUPAC nomenclature.

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 A. 2-methyl-4-butanoic acid B. 2-methyl-4-pentanoic acid
C. 3-methylbutanoic acid D. 3-methylpentanoic acid

4. When benzyl alcohol is oxidized with KMnO4, the product obtained is which of the
following compound?

A. Benzaldehyde B. Benzoic acid

C. CO2 and H2O D. Benzophenone

5. Carboxylic acids react with metals to form?

A. Metal Carboxylate and Hydrogen B. Metal Carboxylate and Water

C. Metal Carboxylate, Water and Carbon Dioxide

6. What is the proper name for this molecule?

A. 2,5-dimethylhexane B. 2,5-methylhexanoic acid

C. 2,5-dimethylhexanoic acid D. 2,5-dimethylhexan-6-oic acid

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7. Is the carboxyl carbon always carbon number 1?

A.YES B. NO

8. What is the correct IUPAC name for formic acid?

A. Ethanoic acid B. Methanoic acid C. Acetic acid

D. Valeric acid

9. 2-butanol heated with acidified KMnO4 solution produced__________.

A. butanone B. butene C. butanoic acid
D. butane

10. 2-methyl-1-propanol heated with acidified K2Cr2O7 solution produced_______.

A. alkene B. carboxylic acid C. alcohol
D. ketone

11. Which compound has the highest boiling point?

A. Butane B. Dimethyl ether C. Propan-1-ol D.

Acetic acid

12. Which of the following might be obtained as one of the products in this reaction?

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A.

B.

C.

D.

13. Which compound has the highest boiling point?

A. Propane B. Propanone C. Propanoic acid D. Propan-1-

ol 14. Which of these carboxylic acids has the highest boiling point?
A. Methanoic acid B. Butanoic acid C. Decanoic acid D.
Hexanoic acid 15. Which of the following carboxylic acid readily dissolves in
water? A. Decanoic Acid B. Ethanoic Acid
C. Heptanoic Acid D. Benzoic Acid

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 Have you checked the latest skin care products that went viral on famous social media
platforms? Well, for sure before you decide whether you are going to purchase these products or
not, you have probably searched first for reliable online reviews on the internet. One particular
ingredient that enhances the quality of these wide selections of personal care products is the esters.
And based on statistics, there is a rising demand for esters in the personal care market today.

In this module, you will explore the functional group esters, their properties, reactions,
examples, and uses in daily life.

At the end of the lesson, you are expected to:

1. determine the functional group and illustrate the general structure of an ester;
2. write the name of esters;
3. describe the properties of esters;
4. analyze the preparation and reactions involving esters; and
5. recognize the importance of esters by citing applications in everyday life.

PRETEST

1. Based on the given structures, which is an ester?

a. c.

c. d.

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2. Which of the following mineral acids is used as a catalyst for the esterification of alcohol
and carboxylic acid?
a. nitric acid c. sulfuric acid
b. phosphoric acid d. sulfurous acid

3. What is the characteristic smell of esters?

a. rotten egg smell c. roasted coffee smell
b. fruity smell d. alcoholic smell

4. What is the name of the ester given below?

a. ethyl butanoate c. butyl acetate

b. ethyl pentanoate d. butyl ethanoate

5. Which of the following products will be produced as a result of the hydrolysis of esters in
a basic medium?
a. aldehyde and alcohol c. alcohol and sodium carboxylate
b. ether and alcohol d. sodium carboxylate

6. Which of the following is NOT a common use of esters?

a. fuel for power stations c. plastic bottles
b. flavorings d. medical drugs

7. What is the name of the ester given below?

a. phenyl propanoate c. propyl benzoate

b. benzyl methanoate d. phenyl benzoate

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8. In order to form an ester, which of the following molecules must react together?
a. carboxylic acid and alcohol c. carboxylic acid and alkene
b. ketone and alcohol d. ether and alkane

9. Which of the following statements correctly describes the use of esters as emollients in
personal care products?
a. improves the texture of skin
b. allow liquids to mix and remain in suspension
c. dissolve ingredients so they can mix together
d. enhance the consistency and viscosity of skin care products

10. What is the correct order (lowest to highest) of solubility in water of the following esters?
i. ethyl ethanoate
ii. ethyl methanoate
iii. ethyl propanoate
iv. ethyl butanoate
a. ii–i–iii–iv c. i-ii-iii-iv
b. iv-iii-i-ii d. iv-i-ii-iii

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 ESTERS
What is an ester?

An ester is an organic compound that is a derivative of a carboxylic acid in which the

hydrogen atom of the hydroxyl group has been replaced with an alkyl group. The general formula
for ester is shown below, which involves a carbonyl –C=O, bonding to a side chain, R, and an
alkoxy group, -OR. The side chains, R, are carbon-based groups like alkyls and aryls while the
alkoxy group is basically an alkyl group bonding to an oxygen atom.

Naming Esters

Esters are named on the basis of the alcohol and the carboxylic acid from which they are
prepared. The following steps with corresponding examples must be followed in naming esters.

Step 1: Find the location of the ester, COO, functional group.

Step 2: Name the alkyl group that has replaced the H of the carboxyl group.

= methyl

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Step 3: Identify the name of the alkanoic acid chain and change its ending from “oic acid” to
“oate”.

2 carbon atoms in the alkanoic acid chain = acetic acid (ethanoic acid)

acetic acid → acetate ethanoic acid → ethanoate

Step 4: Put together the name of the ester by writing the name of the alkyl group first followed
by the modified name of the acid. (Note: Do not forget to leave a space between these
two words.)

methyl acetate (preferred IUPAC name)

(methyl ethanoate is systematic but not preferred)

Step 5: Other substituents that are attached on either side of the ester must be named in the same
way as they are on regular alkane chains. See to it that the name of the substituent is
correctly placed on the part of the name that corresponds to the side of the ester that it is
on.

3-bromopentyl 2-chlorobutanoate

Step 6: Name esters attached to a ring by writing the name of the alkyl group at the beginning
followed by the combined name of the ring and carboxylate.

methyl cyclohexanecarboxylate

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Properties of Esters

The presence of the carbonyl group (C=O) and the length of the hydrocarbon chain (R and
R’) affect the physical and chemical properties of esters. Although the carbonyl group gives some
polarity to esters, the surrounding hydrocarbon chain is non-polar and as a result esters are only
slightly soluble in water. In general, the solubility of esters in water decreases as their mass
increases. Moreover, the carbon and hydrogen chain also influences the physical state of esters;
fewer carbon atoms are liquid at room temperature while longer carbon chains are solid.
Additionally, esters have low melting and boiling points due to the absence of the polar hydroxyl
group. In terms of appearance and odor, esters are colorless and have a strong, fruity smell.

Preparation of Esters

Esters are made through the reaction called esterification, wherein a carboxylic acid and
an alcohol are heated in the presence of a strong acid catalyst.

It is important to note that esterification is not the only process that can produce esters.
They can also be prepared from alcohols and phenols using acyl chlorides (acid chlorides) and
acid anhydrides.

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 ACTIVITY 1: WHAT’S THAT SMELL

I. Objectives:
1. Produce a variety of esters.
2. Describe the reactions that occur in the formation of esters.

II. Materials:
organic alcohols in dropper bottles (see the table below for suggestions)
organic acids in dropper bottles (see the table below for suggestions)
sulfuric acid H2SO4 (18 M)
sodium carbonate, Na2CO3
test tube holder
test tubes
Bunsen burner

III. Procedures:
1. In a test tube, add 15 drops of Ethanol to 20 drops of glacial acetic acid.
2. Add one drop of concentrated sulfuric acid
3. Mix the reactants by gently tapping the test tube
4. Gently heat the bottom of the test tube for several minutes
a. Keeping the test tube on a slight angle helps control vapor loss.
b. If solution starts to boil, remove from heat
5. Carefully smell by wafting. Dilute with water if the smell is still too strong.
6. See the chart for more combinations. Use 0.5g of solid acids such as salicylic acid.

IV. Data and Observations:

ACID ALCOHOL ODOR

acetic acid ethanol

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 acetic acid 1-butanol

acetic acid 2-butanol

acetic acid 1-pentanol

acetic acid isoamyl alcohol

benzoic acid ethanol

salicylic acid methanol

anthranilic acid methanol

butanoic acid ethanol

V. Guide Questions:
1. Write the chemical reactions for each of the esters produced in the above procedures?
________________________________________________________________________
________________________________________________________________________
______________________________________
________________________________________________________________________
___________________
2. What is the function of concentrated sulfuric acid in the preparation of esters?
________________________________________________________________________
________________________________________________________________________
______________________________________
________________________________________________________________________
___________________

VI. Conclusion:
______________________________________________________________________________
______________________________________________________________________________

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______________________________________________________________________________
____________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
________________________________________

Hydrolysis of Esters

The acidic hydrolysis of esters is the opposite of esterification. This happens when esters
are heated with a large excess of water containing a strong-acid catalyst, but just like esterification,
the reaction is reversible and does not go to completion.

In the given specific example below, butyl acetate reacts with water in order to produce
acetic acid and 1-butanol. This reaction is reversible and does not reach completion.

During the basic hydrolysis, a base (NaOH or KOH) is used to hydrolyze an ester. This
reaction results in the formation of a carboxylate salt and an alcohol. The process called
saponification is utilized in the preparation of soap via alkaline hydrolysis of fats and oils. In a
saponification reaction, the base is part of the reactant and not just a catalyst. This type of reaction
goes into completion.

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 In the given specific example below, ethyl acetate reacts with sodium hydroxide in order
to produce sodium acetate and ethanol.

ACTIVITY 2: MAKE YOUR OWN SOAP

I. Objectives:
1. Produce soap using organic materials
2. Explain the chemical reaction involved in the production of soap.
II. Materials:

distilled water beaker filter paper

castor oil test tube funnel
sodium hydroxide stirring rod iron stand
sodium chloride pipette iron ring
ethanol aspirator spatula

III. Procedures:

1. Measure 2 mL of castor oil and transfer it in a 100 mL beaker.

2. Measure 5 mL of ethanol and add to the beaker containing castor oil.

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 3. Measure 10 mL of 5.0 M of NaOH and to the beaker containing castor oil and
ethanol.
4. Add 100 mL of hot water to a large beaker.
5. Gently place the 100 mL beaker containing the castor oil and NaOH inside the
larger beaker. Stir the mixture for at least 5 minutes.
6. Measure 10 mL of saturated solution of NaCl and add it to the beaker containing
the castor oil and NaOH. Stir the mixture.
7. Cool the mixture by placing it in a larger beaker with iced water. Stir the mixture
occasionally for 15 minutes.
8. Filter off the precipitate.
9. In a test tube combine a small amount of soap and distilled water. Test the soap by
shaking the test tube, observe if it forms lather.

IV. Data and Observations:

COLOR SMELL TEXTURE

soap

V. Guide Questions:
1. Write the chemical reaction involved in soap making and explain.

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 __________________________________________________________________
__________________________________________________________________
__________________________________________________________________
_________________________________________________________
2. Do you think different fats or oils will produce the same type of soap in terms of
color, smell, and texture?
__________________________________________________________________
__________________________________________________________________
__________________________________________________________________
_________________________________________________________

VI. Conclusion:
________________________________________________________________________
________________________________________________________________________
________________________________________________________________________
________________________________________________________________________
________________________________________________________________________
________________________________________________________________________
_______________________

Uses of Esters

Esters fall under the category of oleochemicals, which means that they are naturally derived
chemicals rather than synthetic. They are characterized as having a sweet and fruity smell
especially those with low molecular weight and because of that esters are extensively used in the
food industry as flavoring. In recent years, there is an increasing demand for esters in the
manufacture of perfume and personal care products wherein esters can function as emollient,
solvent, thickening agent, surfactant, and fragrance. Esters are also used in the production of
polymers and certain medicines.

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 SUMMARY

● An ester is a compound that is derived from carboxylic acid in which at least one –OH
hydroxyl group is replaced by an –O- alkyl group.

● In general, esters have a sweet fruity smell that is why they are used in flavors, perfumes
and cosmetics. Esters are also used as solvents, plasticizers, flame retardants, polymers,
and in the production of some medical drugs.

● Due to their structure, esters have low solubility in water with increasing mass, low melting
and boiling points.

● Name esters as derivatives of carboxylic acids by replacing the –ic acid ending with –ate.
The beginning part of an ester’s name specifies the substituent that replaces the hydrogen
of the corresponding carboxylic acid.

● Esters are made through the reaction called esterification, wherein a carboxylic acid and
an alcohol are heated in the presence of a strong acid catalyst.

● Hydrolysis is the most important reaction of esters. Acidic hydrolysis of an ester gives a
carboxylic acid and an alcohol while basic hydrolysis of an ester gives a carboxylate salt
and an alcohol.

VALUING

To understand life is to understand organic chemistry. One of the important functional

groups are the esters and we cannot deny that the varieties of materials that we are enjoying right
now are examples of this type of compound, from the food that we eat, beverages that we drink,
and personal care products that we consume.

There are things in this life that we seem to not recognize and give importance to. We tend
to neglect them because we think that they have nothing to do with our lives or that they can easily
be replenished. However, once they are gone, that is the time that we realize their presence and

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relevance to our daily lives. So, let us learn to appreciate everything and most importantly every
person that comes along with us, because in one way or another, they could affect and influence
our lives.

POST TEST

1. Which of the following products will be produced as a result of the hydrolysis of esters in
an acidic medium?
a. alcohol and ether c. alcohol and sodium carboxylate
b. alcohol and carboxylic acid d. sodium carboxylate

2. Which of the following terms describes the alkaline hydrolysis of esters?

a. hydrolysis reaction c. neutralization reaction
b. esterification reaction d. saponification reaction

3. Which of the following properties are attributed to esters with low molecular weight?
a. toxicity c. flammability
b. fragrance d. color

4. Which of the following structures represents an ester?

a. c.

b. d.

5. Which of the following reactants will result in the formation of the given ester below?

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 a. 2-methyl-1-propanol and propanoic acid
b. 4-methyl-3-pentanol and pentanoic acid
c. d. 3-methyl-1-butanol and heptanoic acid
d. 1-butanol and propanoic acid

6. Which of the following formulas represent the correct combination of alcohol and
carboxylic acid that will lead to the formation of the given ester below?

a. CH3-(CH2)14-OH and CH3-(CH2)9-COOH

b. CH3-(CH2)14-COOH and CH3-(CH2)9-OH
c. CH3-CH2-COOH and CH3-CH2-OH
d. CH3-COOH and CH3-CH2-OH

7. What is the name of the ester ?

a. cyclobutyl butanoate c. cyclic butanoate

b. butyl cyclobutanoate d. cyclobutanoate

8. What is the name of the ester ?

a. 2-methylbutyl-2-methylbutanoate c. 3-methylbutyl-3-methylbutanoate
b. 2-methylbutyl-3-methylbutanoate d. 3-methylbutyl-2-methylbutanoate

9. What is the name of the ester ?

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 a. benzyl methanoate c. ethyl benzoate
b. phenyl propanoate d. propyl benzoate

10. Which of the following is not a use of esters?

a. flavoring c. paint additive
b. solvent d. thickening agent

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 When something is described as aromatic, the first thing that will come into our minds is
that it is fragrant or something that gives off a pleasant smell like freshly brewed coffee and newly
baked bread. But in the world of organic chemistry, the term aromatic goes beyond odor, in fact
some aromatic compounds do not smell anything at all.

In this module, you will find out the properties of aromatic compounds, their structure,
nomenclature, reactions, and important applications in daily life.

At the end of the lesson, you are expected to:

1. describe the properties of aromatic compounds;

2. draw the structure of aromatic compounds;
3. write the name of aromatic compounds;
4. explain the reactions involving aromatic compounds; and
5. recognize the importance of understanding aromatic compounds by practicing ways on
how to handle and store such compounds.

PRETEST

1. Which of the following is NOT an aromatic compound?

a. c.

b. d.

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 2. When 1-bromopropane and benzene undergo Friedel-Crafts alkylation, which of the
following would NOT be a product?
a. c.

b. d. none of the above

3. Which of the following is the correct structure for 2-bromonitrobenzene?

a. c.

b. d.

4. What is the name of the aromatic compound shown below?

a. o-chlorobenzaldehyde c. p-chlorobenzoate
b. m-chlorobenzoic acid d. m-chlorosalicylic acid

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5. Which of the following statements about the reaction of benzene with Cl 2 in the presence
of AlCl3 is false?
a. AlCl3 acts as a catalyst.
b. Chlorobenzene is formed.
c. The mechanism is electrophilic addition.
d. The mechanism goes via an intermediate cation.

6. In the nitration of an aromatic ring, which of the following is an important reactive

electrophile?
a. NO2+ c. NO+
b. N2+ d. N2O+

7. Which of the following statements is true about the IUPAC system of naming aromatic
compounds?
a. Substituents of aromatic compounds are named in reverse alphabetical order.
b. Substituents of aromatic compounds are named using prefixes ortho, meta and para.
c. Substituents of aromatic compounds are named using their original names, like
toluene.
d. Substituents of aromatic compounds are named with numbers indicating their
positions in the ring.

8. What is the name of the given aromatic compound?

a. 1-bromo-6-chloro-3,5-dimethylbenzene
b. 1-bromo-2-chloro-3,5-dimethylbenzene
c. 1-chloro-6-bromo-2,4-dimethylbenzene

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 d. 1-chloro-2-bromo-4,6-dimethylbenzene

9. Which of the following aromatic compounds is predominantly used as fumigant insecticide

by directly changing from solid state to vapor phase?
a. benzene c. aniline
b. toluene d. naphthalene

10. Which of the following statements is NOT true about aromatic compounds?
a. Aromatic compounds exhibit planarity.
b. Aromatic compounds follow Huckel’s Rule.
c. Aromatic compounds have characteristic odors.
d. Aromatic compounds are made of rings consisting of alternating double bonds.

AROMATIC COMPOUNDS

How do you know if a compound is aromatic?

Aromatic compounds are cyclic compounds that contain alternating single and double
bonds in their ring structure. The general structure of aromatic compounds is presented below,
which shows at least one planar carbon ring and have alternating single and double bonds in the
carbon ring. The best and well-known examples of this type of compounds are benzene and
toluene.

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 Aromatic compounds are categorized into two: benzenoids (contains benzene ring) and
non-benzenoids (does not contain benzene ring). A hydrocarbon is considered aromatic if it
follows the Huckel’s Rule, which states that for a ring to be aromatic it should possess the
following properties;(1) planarity, (2) complete delocalization of the π electrons in the ring, and
(3) presence of (4n + 2) π electrons in the ring where n is an integer. The following structures are
examples of aromatic compounds, following Huckel's rule.

ACTIVITY 1: DISTILLING AROMATIC COMPOUNDS

I. Objectives:
1. Isolate compounds that are made up of familiar fragrances and natural flavors.
2. Perform the process of distillation.

II. Materials:
condenser boiling chips or rocks
beaker (250 mL) crushed ice
beaker (100 mL) salt
graduated cylinder (10 mL) stirring rod
ring stand pipet
mortar and pestle assorted spices
heater stirrer hot water

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III. Procedures:
1. Fill a 250 mL beaker with crushed ice.
2. Fill a 100 mL beaker ¼ with the sample spices. If your spice is powdered, just add it in but
if it is not, use the mortar and pestle to crush it into small pieces.
3. Add about 30 mL of hot water into the beaker containing the spice. Place a boiling chip or
rock into the beaker and stir the mixture for 30 seconds.
4. Place the beaker on the heater stirrer.
5. See to it that the temperature sensor opening on the condenser is closed with a stopper. Fill
the top of the condenser with crushed ice and add salt all over.

6. As shown in the above image, suspend the condenser over the beaker using a ring stand.
7. Heat the spice-water mixture until it boils.
8. Observe how the spice mixture boils and how the steam rises out of the beaker and is
condensed on the underside of the condenser. The condensed steam is called the distillate.
9. Continue distilling the mixture until the chamber has collected 10 mL of distillate. In order
to check the volume of the distillate collected, carefully lift the top half of the condenser
that contains ice. Look for the 10 mL line on the inside ring at the bottom half of the
condenser. To keep the mixture distilling properly, do the following measures:

● If the water level in the sample mixture drops to half of its original level, place 15
mL of hot water.

● If the ice in the condenser melts, remove the melted water with a pipet and add
more crushed ice. Add salt all over the ice as before.

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 10. Once the distillation is complete, waft the collected distillate. Describe and record the
odor.

IV. Data and Observations:

Encircle the functional group present on the structural formulas of each spice. Identify the
name(s) of the functional group(s) circled on each molecule.

Spice Aromatic Name Structural Formula Functional Group(s) Characteristic Odor

& Formula

Eugenol
Allspice
C10H12O2

Cinnamaldehyde

Cinnamon C9H8O

Vanillin
Vanilla
C8H8O3

Caraway Carvone

C10H14O

Anethole
Anise
C10H12O

Cuminaldehyde
Cumin
C10H12O

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 Myristicin
Nutmeg
C11H12O3

Turmerone
Tumeric
C15H20O

V. Guide Questions:
1. How are aromatic compounds isolated through distillation?
________________________________________________________________________
________________________________________________________________________
________________________________________________________________________
_________________________________________________________
2. What is the purpose of adding boiling chips? What do you think will happen if the
aromatic compounds are subjected to a very high temperature?
________________________________________________________________________
________________________________________________________________________
________________________________________________________________________
_________________________________________________________
3. What similarities have you observed in all these molecules? What implication can you
make about many aromatic compounds based on these similarities?
________________________________________________________________________
________________________________________________________________________
________________________________________________________________________
_________________________________________________________

VI. Conclusion:
________________________________________________________________________
________________________________________________________________________
________________________________________________________________________
________________________________________________________________________

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Properties of Aromatic Compounds

Generally, aromatic compounds are nonpolar and are insoluble in water. Moreover these
compounds are mostly unreactive and are utilized as solvents for different other nonpolar
compounds. The ratio of carbon-hydrogen is high which results in a sooty yellow flame when
burned.

Nomenclature of Aromatic Compounds

1. Monosubstituted Benzenes
A substituted benzene is formed by replacing one or more hydrogen atoms of
benzene by another atom or group of atoms. Name these benzenes by adding the name of
the substituent group as a prefix to the word benzene. Note that the name is written as one
word and the position of the substituent is not important because all the positions are
equivalent in a monosubstituted benzene.

chlorobenzene ethylbenzene nitrobenzene

Some monosubstituted benzenes have special names and these are used as parent names
for other substituted compounds, so they must be learned.

toluene phenol benzoic acid

benzaldehyde aniline

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 2. Disubstituted Benzenes
When two substituent groups replace two hydrogen atoms in a benzene molecule,
three different isomeric compounds are possible. In naming this type of compounds, the
prefixes ortho-, meta-, and para- ( abbreviated o-, m-, and p-) are used. Ortho indicates 1,
2 disubstitution, meta designates 1, 3 disubstitution, and para represents 1, 4 disubstitution.

o-dichlorobenzene m-dichlorobenzene p-dichlorobenzene

(1,2-dichlorobenzene) (1,3-dichlorobenzene) (1,4-dichlorobenzene)

When the two substituents are not the same and neither is part of a compound with a special
name, the names of the two substituents are given in alphabetical order, followed by the word
benzene.

o-bromochlorobenzene p-ethylnitrobenzene

The disubstituted compound is named as a derivative of the parent compound when one
of the substituents corresponds to a monosubstituted benzene that has a special name,

o-nitrophenol p-bromoaniline

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 The dimethylbenzenes have the special name xylene.

o-xylene m-xylene p-xylene

3. Polysubstituted Benzenes
When there are more than two substituents on a benzene ring, the carbon atoms in
the rings are numbered starting at one of the substituted groups. Numbering may be either
clockwise or counterclockwise but must be done in the direction that gives the least
possible numbers to the substituted groups. When the compound is named as a derivative
of one of the special compounds, the substituent of the parent compound is considered to
be on carbon 1 of the ring.

1,2,4-tribromobenzene 5-bromo-2-chlorophenol

4. Polycyclic Aromatic Compounds

Polycyclic aromatic compounds or fused aromatic ring systems consist of two or
more rings in which two carbon atoms are common to two rings. Three of the most
commonly known examples in this category are naphthalene (C 10H8), anthracene (C14H10),
and phenanthrene (C14H10). One hydrogen is attached to each carbon atom except at the
carbons that are common to two rings.

naphthalene anthracene phenanthrene

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Chemical Reactions of Benzene and Alkylbenzenes

Generally, the reagents that react with the aromatic ring of benzene and its derivatives are
called electrophiles. The general formula ArH can be used to represent an arene, where Ar stands
for an aryl group, while the electrophilic portion of the reagent replaces one of the hydrogens on
the ring.
Ar – H + E+ → Ar - E

This reaction is called electrophilic aromatic substitution wherein an electrophile attacks

an aromatic ring and substitutes for one of its hydrogens.

1. Halogenation of Benzene
Chlorine reacts with benzene in the presence of FeCl 3 as a catalyst to give n-
chlorobenzene.
FeCl3
C6H6 + Cl2 C6H5Cl + HCl

2. Nitration of Benzene
Heating benzene with a mixture of concentrated nitric acid and sulfuric acid results
in the formation of nitrobenzene. In this reaction, a nitro group (-NO2) replaces a hydrogen
atom of benzene.
H2SO4 500C
C6H6 + HO - NO2 C6H5NO2 + H2O

3. Sulfonation of Benzene
Benzene is treated with hot concentrated sulfuric acid and forms benzenesulfonic
acid. A sulfonic acid group (-SO3H) replaces one of the ring hydrogens.

C6H6 + HO – SO3H C6H5SO3H + H2O

4. Friedel-Crafts Alkylation of Benzene

Alkyl halides react with benzene in the presence of AlCl 3 to produce alkylbenzenes.
AlCl3
C6H6 + CH3CH2Br C6H5CH2CH3 + HBr

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 5. Friedel-Crafts Acylation of Benzene
In the presence of AlCl3, an analogous reaction occurs between acyl halides and
benzene to form acylbenzenes.

AlCl3
C6H6 + CH3COCl C6H5COCH3 + HCl

6. Oxidation of Alkylbenzenes
An alkyl side chain on a benzene ring is oxidized on being heated with a mixture
of aqueous Na2Cr2O7 and H2SO4. The alkyl groups, regardless of their chain length, are
converted to carboxyl groups, thus, the product is benzoic acid or a substituted derivative
of benzoic acid. The other carbon atoms of the side chain are converted to CO 2.

7. Halogenation of Alkylbenzenes
The side-chain halogenation of toluene can produce the mono-, di-, and tri- halo
compound consecutively.

An alkylbenzene with a side chain more complex than methyl may offer more than
one position for attack and so we must consider the likelihood of obtaining a mixture of isomers.

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Experimental evidence shows, however, that abstraction of benzylic hydrogens (hydrogen atoms
attached to carbon joined directly to an aromatic ring) is greatly preferred.

ACTIVITY 2: REACTIONS OF ALIPHATIC AND

AROMATIC HYDROCARBONS

I. Objectives:
1. Compare the reaction of aliphatic and aromatic hydrocarbons.

II. Materials:

III. Procedures:
Part A
1. Prepare 6 dry, clean test tubes. Label them A to F.
2. Add 1 mL of cyclohexane in test tube A and B, 1mL of cyclohexene in test tube C
and D, and 1mL toluene in test tube E and F.
3. Wrap test tube A, C and E with black sugar paper and add 4 to 5 drops of
Bromine in each test tube.
4. Keep test tubes A, C, E in a dark place while test tubes B, D, F in sunlight.
Record your observations.

Part B
1. Prepare 3 dry, clean test tubes. Label them G, H, and I
2. Place 1mL cyclohexane, cyclohexene, and toluene in each test tube.
3. Add 5 drops of alkaline KMnO4. Record your observations.

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IV. Data and Observations:
Bromine test
TEST

HYDROCARBONS Baeyer’s Test

Under sunlight In the dark

Cyclohexane

Cyclohexene

toluene

V. Guide Questions:
1. Write the chemical reactions involved in each part and explain.
__________________________________________________________________
__________________________________________________________________
__________________________________________________________________
_________________________________________________________
2. How do aliphatic compounds differ from aromatic compounds based on the
results of the experiment?
__________________________________________________________________
__________________________________________________________________
__________________________________________________________________
_________________________________________________________

VI. Conclusion:
________________________________________________________________________
________________________________________________________________________
________________________________________________________________________
_______________________________________________________________________

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Uses of Aromatic Compounds

Aromatic hydrocarbons are good non-polar solvent for other molecules. Moreover,
aromatic compounds can be used as additives in lacquers, paints, gasoline and other solutions.
Some of the most common examples of aromatic compounds are listed below.

● Benzene is a colorless and highly-flammable liquid used as a constituent in motor fuels. It

is widely used as a solvent for oils, fats, resins, waxes, paints, rubber, and plastics. It is also
utilized in the extraction of oils from seeds and nuts and as a chemical intermediate.
Benzene is used in the production of explosives, detergents, pharmaceuticals, and
dyestuffs. Acute exposure to benzene may cause dizziness, drowsiness, headaches,
irritation of the eyes, skin, and respiratory tract, and unconsciousness at high levels.
Chronic inhalation exposure of benzene can cause various disorders in the blood, including
reduced count of red blood cells and aplastic anemia.

● Toluene is generally used as a mixture added to gasoline. It is also used as solvent in paints,
adhesives, inks, synthetic fragrances, and cleaning agents. Toluene is used in the
production of polymers used to make plastic soda bottles, nylon, polyurethanes, cosmetic
nail products, dyes, pharmaceuticals, and organic chemicals. Acute exposure to elevated
levels of toluene may lead to central nervous system dysfunction and narcosis. On the other
hand, chronic inhalation of toluene causes irritation of the upper respiratory tract and eyes,
sore throat, headache and dizziness.

● Xylene is a colorless, combustible liquid with a sweet odor. It is used for various industrial
purposes; as solvent in the production of chemicals, agricultural sprays, coatings and
adhesives, paints, inks, gums, rubbers, resins and lacquers; as an ingredient in aviation fuel
and gasoline; and as feedstock in manufacturing different polymers. Exposure to low levels
of xylene may cause irritation of the eyes, nose, skin and throat. It can also cause dizziness,
headaches, loss of muscle coordination, confusion, and even death at high doses.

● Aniline is a clear to slightly yellowish liquid with a musty fishy odor. It is primarily used
as a chemical intermediate for the production of polymer, rubber, dye, and agricultural
industries. It is also used as a solvent and antiknock compound for gasoline. Acute and
chronic exposure to aniline may cause upper respiratory tract irritation and congestion.

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● Phenol appears colorless to white solid when pure and has a characteristic odor that is
sickeningly sweet and tarry. Phenol is predominantly used in the manufacture of phenolic
resins, nylon, and other synthetic fibers. It is also used as a disinfectant and antiseptic, and
in medicinal preparations such as sore throat lozenges and mouthwash. Short term exposure
to phenol may cause irritation to the eyes, nose, throat, skin, and nervous system. On the
other hand, severe exposure can cause liver and/or kidney damage, tremor, convulsions,
twitching, and skin burns.

● Naphthalene is a white, crystalline, volatile solid with a strong mothball odor. It is mainly
used in the production of dyes, resins, fuels and plastics. Naphthalene is also used as a
fumigant insecticide that works by changing directly from a solid state into a toxic vapor.
Short-term exposure to naphthalene may cause irritation to the eyes, nose, throat and skin,
headache, fatigue, confusion, tremor, nausea and vomiting. High and repeated exposure
may lead to cataract, damage to liver and kidneys, and anemia.

SUMMARY

● Aromatic compounds are cyclic compounds that contain alternating single and double
bonds in their ring structure.

● Generally, aromatic compounds are nonpolar and are insoluble in water.

● Aromatic compounds are named depending on whether the benzene ring is

monosubstituted, disubstituted or polysubstituted.

● The reagents that react with the aromatic ring of benzene and its derivatives are called
electrophiles.

● The chemical reactions of benzenes and alkylbenzenes include the following: halogenation,
nitration, sulfonation, Friedel-Crafts Alkylation, Friedel-Crafts Acylation, and oxidation.

● Aromatic hydrocarbons are good non-polar solvent for other molecules. Moreover,
aromatic compounds can be used as additives in lacquers, paints, gasoline and other
solutions.

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 VALUING

Numerous aromatic compounds, specifically benzene, toluene, and xylene, were once
commonly used as laboratory and industrial solvents. However, tests conducted have shown that
the use of such compounds must be limited because they can have potentially harmful effects to
the health of people who are exposed to them regularly. Health risks related to aromatic compounds
include liver problems, damage to the nervous system, and respiratory ailments. Understanding
the properties, reactions involving aromatic compounds is important in order to develop ways on
how people can be protected from the harmful effects of such compounds.

POST TEST

1. Why do aromatic compounds burn with sooty flame?

a. Because they resist reaction with oxygen in the air
b. Because they have a ring structure of carbon atoms
c. Because they have a relatively high percentage of carbon
d. Because they have a relatively high percentage of hydrogen

2. Which of the following statements correctly describes benzene?

a. π electrons are delocalized in the benzene ring
b. benzene has to types of C-C bonds
c. due to unsaturation benzene easily undergoes addition
d. in monosubstitution of benzene, 3 isomeric forms are formed

3. Acute exposure to elevated levels of ________ may lead to central nervous system
dysfunction and narcosis.
a. benzene c. toluene
b. xylene d. phenol

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 4. The bromination of benzene, an aromatic compound,
a. occurs in the absence of a catalyst
b. occurs by substitution rather than addition
c. occurs by addition rather than substitution
d. occurs more rapidly than bromination of a nonaromatic compound

5. What is the name of the aromatic compound found below?

a. o-bromotoluene c. p-bromotoluene
b. m-bromotoluene d. tribromotoluene

6. What is the name of the aromatic compound ?

a. 1,3-dichloro benzaldehyde
b. 1,3-dichlorophenol
c. 2,4-dichloro benzoic acid
d. 2,4-dichlorophenol

7. Which of the following sets of reagents would most likely bring about the given reaction
below?

a. Br2 in CCl4 c. NaBr with H2SO4

b. Br2 with FeBr3 d. Br2 with UV light

8. What will be the product of the halogenation of the given reactant below?

154 | P a g e
 a. c.

b. d.

9. What is the name of this aromatic compound ?

a. 3,6-dimethyl-1-ethylbenzene
b. 1-ethyl-3,6-dimethylbenzene
c. 2,5-dimethyl-1-ethylbenzene
d. 1-ethyl-2,5-dimethylbenzene

10. Which of the following structures has the special name phenanthrene?
a. c.

b. d.

155 | P a g e
Pre-test Post test
1. C 1. A
2. A 2. C
3. C 3. 1-cloro-3-floro-5-methylcyclohexane
4. A 4. C
5.A 5. A
6.A 6. C
7.B 7. A
8.B 8. B
9.C 9. B
10.1-cloro-3-floro-5-methylcyclohexane 10. A
Activity: Organic vs Inorganic
Substance Organic or Inorganic Use
Octane Organic Fuel
Starch Organic Textile and food
Steel Inorganic Construction
Butane Organic Fuel
Baking Soda Inorganic Food preparation
Olive Oil Organic Food preparation
Methane Organic Fuel
Vaseline Organic Lubricant
Neon Inorganic
Sodium Inorganic
Lactose Organic Food preparation
Ethyl alcohol Organic Disinfectant
Steroid Organic Lubricant
Hydrogen Peroxide Inorganic Disinfectant
Propane Organic Fuel
Glycerin Organic Lubricant
Fructose Organic Food preparation
Aluminum Inorganic Construction
Ammonia Inorganic Fertilizer
Wax Organic Lubricant
Sodium Chloride Inorganic Food preparation
Isopropyl alcohol Organic Disinfectant
Sand Inorganic Construction
Sucrose Organic Food preparation
Water Inorganic Solvent
Canola oil Organic Food preparation
Cellulose Organic Food preparation
Drano Inorganic Paper industry
Glucose Organic Food preparation
INTRODUCTION TO ORGANIC CHEMISTRY ANSWER KEY
Questions:
1.C
2. fuel
3. organic = many more elements, some with same formula
4. Former tested foods contain C, H. and O; fuels only C and H
Activity: Fractional Distillation
Activity: Naming Alkanes
1. 2,3,3-trimethylhexane
2. 2,3-dimethyl-4-propylheptane
3. 3-ethyl-4-methylhexane
4. 4,4-diethyl-2,3-dimethylheptane
5. 2,2,4-trimethylpentane
Activity: Cyclo-alkanes
ANSWER KEY ALKENES
ANSWER KEY ALKYNES
 ANSWER KEY ALKYL HALIDES

Pretest/Posttest

1. C

2. A

3. A

4. C

5. A

6. B

7. C

8. B

9. D

10. C
Quick Check A

1. dihaloalkane 2. monohaloalkane 3. trihaloalkane

Quick Check B

1. primary 2. secondary 3. Tertiary

Quick Check C

1. common name: isopropyl iodide IUPAC name: 2-iodopropane

2. IUPAC name: 3-bromo-2-chloro-4-ethyl-2-methylhexane

ANSWER KEY ALCOHOLS

Pretest/Posttest

1. True 9. C

2. False 10. D

3. False

4. True

5. True

6. A

7. C

8. C
Quick Check A

1. 1-chloro-4-methyl-3-hexanol

2. 2,2-butanediol

ANSWER KEY ESTERS

Pre-test Post-test

1. C 1. B

2. C 2. D

3. B 3. B

4. B 4. C

5. C 5. A

6. A 6. B

7. C 7. A

8. A 8. B

9. A 9. D

10. A 10. C
ANSWER KEY AROMATIC COMPOUNDS

Pre-Test Post-Test

1. C 1. C

2. D 2. A

3. A 3. C

4. B 4. B

5. C 5. A

6. A 6. D

7. B 7. B

8. B 8. A

9. D 9. D

10. D 10. C
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