Senior High School

General Chemistry 1
Module 12
Structural Isomerism and Simple

AIRs - LM
LU_General Chemistry1_Module12
Reactions of Organic Compounds
STEM - GENERAL CHEMISTRY 1
Quarter 2 - Module 12: Structural Isomerism and Simple Reactions of Organic Compounds
Second Edition, 2021

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 Senior High School

General Chemistry 1
Module 12
Structural Isomerism and Simple
Reactions of Organic Compounds
Introductory Message
This Self-Learning Module (SLM) is prepared so that you, our dear
learners, can continue your studies and learn while at home. Activities,
questions, directions, exercises, and discussions are carefully stated for you
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Thank you.
 Target
Organic compounds can arrange themselves differently in nature but bringing
the same number of molecules. In this case, we call these molecules ISOMERS,
because they have the same molecular formula, but have different arrangements of
their atoms. This is phenomenon is caused by either the rotation of the molecule
as a whole or rotation of particular bonds. Organic compounds also undergo
chemical reactions with other molecules. They say, “You are what you eat.”
Literally and chemically explaining, the molecules are incorporated into our bodies
through the food we eat. Organic compounds make up our cells and body are
classified into four classes namely: carbohydrates, lipids, proteins and nucleic
acids.
In the past lessons, you learned how special the carbon atom. How it bonds
with hydrogen and other atoms which makes up an organic compound. Thus, you
learned what an organic compound is and described the different functional
groups. You already learned how to name basic organic compounds such as
alkanes, alkenes and alkynes.
This learning material will provide you with information and activities that will
help you understand organic compounds specifically on structural isomerism and
some simple reactions of these compounds.

Most Essential Learning Competencies

After going through this module, you are expected to:
A. describe structural isomerism; give examples (STEM_GC11OCIIg-j-89);
and
B. describe some simple reactions of organic compounds: combustion of
organic fuels, addition, condensation, and saponification of fats
(STEM_GC11OCIIg-j-90).

Learning Objectives
At the end of the module, you are expected to:
A. identify where structural isomerism takes place; and
B. identify the number of isomers of given compounds.

Jumpstart

Jump in. Do the activity to get a better grasp of the

concept. Don’t forget to give your best shot in
answering the questions.

Activity 1: Pretest
Direction: Write the CAPITAL letter of the correct answer on a separate paper.

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1. In what type of compounds does structural isomerism happen?
A. inorganic B. liquid C. organic D. solid
2. What is the other name for structural isomer?
A. constitutional B. institutional C. instructional D. structural
3. How many isomers does a propane have
A. 0 B. 1 C. 2 D. 3
4. Which of the following alkanes have an isomer?
A. butane B. ethane C. methane D. propane
5. How many isomers does butane have?
A. 1 B. 2 C. 3 D. 4
6. Isomers can be in different forms either in chain or branch. What type of
structural isomerism is this?
A. chain B. organic
B. positional D. quaternary
7. Aside from a new substance is formed, what is the end product of
condensation?
A. CO B. CO2 C. H2O D. H2O2
8. Which of the following is NOT an isomer of C3H6O?
A. alcohol B. aldehyde C. ketone D. propanal
9. Which of the following organic reactions is considered MOST common?
A. addition B. combustion
B. condensation D. saponification
10. Aside from carbon dioxide, what is the other end product of combustion?
A. HCl B. H2O C. HBr D. HI
11. When double or triple bond is broken and a new compound is attached to the
hydrocarbon chain, what type of organic reaction is produced?
A. Addition B. condensation
C. combustion D. saponofocation
12. What is the product of addition of a new compound to an alkyne?
A. alcohol B. alkane C. alkene D. alkyne
13. Which of the following is a process is esters through saponification reaction?
A. addition B. hydrolysis C. oxidation D. reduction
14. Which of the following is a product of saponification?
A. carboxylate ion B. carboxylic acid
C. oxygen D. water
15. From what Latin word does saponification come from?
A. sap B. sapo C. soap D. sopa

Discover
Structural isomer is also known as a constitutional isomer, in which two or
more organic compounds have the same molecular formula but have different
structures. One example is the isomer of butane, C 4H10, having the same chemical
formula, but have different orientation and named differently because they differ in
the location of methyl group. Therefore, they are named as butane and 2-methyl
propane respectively.

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 Photo credits from: chem.libretexts.org. Two isomers of butane, C 4H10

The carbon atom can form a vast number of compounds. This makes
organic compounds abundant in nature. Another reason for the great number of
organic compounds is the existence of two or more different organic compounds
having the same chemical formula. This is known as isomerism.
Isomers are compounds with the same molecular formula but with
different structural formula. The molecular formula gives the actual number of
atoms in an organic molecule, while the structural formula tells how the atoms are
bonded to each other. A compound can have one molecular formula but with
different structural formulas.
Isomers have three common types.
Molecules arrange differently in nature; they have varied arrangement of
atoms in space but have the same molecular formula. These molecules are called
isomers. It does not include rearrangement of the molecule due to rotation of the
molecule as a whole, or rotation of particular bonds, like the example below. They
are both butane, not isomers.

Photo credits from: chem.libretexts.org. Two isomers of butane, C 4H10

As long as it is a long straight chain of this molecule, there are endless

possible ways that this molecule could twist itself. Every single bonds of carbon-
carbon bond have a complete free rotation, that is why if this is rearranged into
different orientation just by rotating single bonds, there is no difference, it is still
the same molecule, butane in our example.
Types of Structural Isomerism Chain Isomerism

These isomers arise because of the possibility of branching in carbon chains.

For example, there are two isomers of butane, C4H10. In one of them, the carbon
atoms lie in a “straight chain” whereas in the other the chain is branched.
Isomers in this category is caused by branching of carbon from the chain.
From the illustration below, butane has forms as a chain and as a branched
molecule. The names of various forms of structural isomerism probably don’t
matter that much, but being aware of different possibilities when drawing isomers
is a must.

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 Photo credits from: chem.libretexts.org. Two isomers of butane, C 4H10

Be careful in drawing structural isomers in chain isomerism, because bending

the straight chain molecule does not result to an isomer. This is called “false”
isomer for it was only a twisted version of the original.

Photo credits from: chem.libretexts.org.

Example: Chain Isomers in Pentane

Pentane, C5H12, has three chain isomers. If you think you can find any
others, they are simply twisted versions of the ones below.

Photo credits from: chem.libretexts.org.

1. Position Isomerism
In position isomerism, what makes this an isomer is the movement of
important groups like halogens, hydroxides but the carbon skeleton remains
unchanged.
In example for C3H7Br, Bromine is the important group here that is why
it will rearrange itself to create an isomer.

Photo credits from: chem.libretexts.org.

In this example, there are two structural isomers with the molecule C 3H7Br
in which the bromine atom is located at the end of the chain and the other is
attached in the middle. In order to do that, from the straight chain, you have to

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break the bromine off at the end and re-attach it to the middle carbon. That
removes one hydrogen atom and be attached to the terminal carbon.

Example: C4H9OH

Photo credits from: chem.libretexts.org.

Using the chain isomerism, we can have the possibility of having an isomer of
2, which are butan-1-ol and butan-2-ol. However, other forms are possible when
position isomerism are used, namely, 2-methylpropan-1-ol and 2-methylpropan-2-
ol. As long as it is possible to make different isomers, chain isomerism and position
isomerism is the mostly used to find different structural isomers. There is no
restriction to used only chain isomerism or position isomerism only, but it could be
a mixture of the two.

Photo credits from: chem.libretexts.org.

Structural isomerism is also possible for organic compounds having benzene

rings. In this case position isomerism is only possible. In example C 7H7Cl,
producing 4 different isomers.

Photo credits from: chem.libretexts.org.

2. Functional Group Isomerism

Structural isomerism in this type contains functional groups that belong
to different families or what we called homologous series.

Example:
A molecule which having a formula of C3H6O can be an aldehyde or a
ketone. An aldehyde (RCHO), is formed when an organic compound is
connected to a carbon double bonded to an oxygen and to a hydrogen.

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 And a ketone (RCOR), carbon double bonded to oxygen is connected in
between to an alkyl group.

Another common example is illustrated by the molecular formula. Another

example is a molecule having a formula C3H6O2;
A carboxylic acid (RCOOH) is formed when an alkyl group is connected to
COOH; and,

An ester (RCOOR) is formed when a carbon atom double bonded to oxygen

and single bonded to another oxygen (COO) and connected in between two alkyl
groups.

Lastly, structural isomerism does not only occur in alkanes, but also in
other organic compounds just like we have proved from the examples above.

Simple reactions of Organic Compounds

Organic compounds are compounds that contains hydrocarbons. These

compounds undergo chemical reactions forming new chemicals that are used in
various fields like in medicine, transportation, food and drugs and the like. Some
of these simple reactions includes combustion, addition, condensation and
saponification of fats.
1. Combustion Reaction
The most common reaction of organic compounds and is also known as
burning. This is an exothermic process wherein oxygen reacts with a hydrocarbon.
The end-product of a complete combustion of a hydrocarbon such as methane
always produces carbon dioxide and water. An incomplete combustion will result
in a carbon monoxide.

CH4 + 2 O2 CO2 + 2 H2O

Combustion of Methane
Example: Combustion of Ethane, C2H6
Step 1- Write the reaction:
C2H6 + O2 CO2 + H2O

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 Step 2- Balance the reaction:
*If this happens that when balancing, you will end up writing a fraction,
multiply the whole reaction by 2.
(C2H6 + 72O2 2 CO2 + 3 H2O) x 2

Final Balanced Equation: 2 C2H6 + 7 O2 4 CO2 + 6 H2O

Example: Combustion of Butane, C4H10

Step 1- Write the reaction:
C4H10 + O2 CO2 + H2O
Step 2- Balance the reaction:
13
(C4H10 + 2 O2 4 CO2 + 5 H2O) x 2

2 C4H10 + 13 O2 8 CO2 + 10 H2O

Example: Combustion of Ethanol, C2H5OH

Step 1- Write the reaction:
C2H5OH + O2 CO2 + H2O
Step 2- Balance the reaction:
C2H5OH + 3 O2 2 CO2 + 3 H2O

2. Addition Reaction
Addition reaction takes place to a hydrocarbon with multiple bonds (those who
have double and triple bonds) and components A and B are added to the bonds
being broken. Take note of the double/triple bond breaks because it is where
added molecules will be attached.
Example: Addition of HCl to Ethylene (ethene, C2H4)

H2C=CH2 + HCl CH3CH2Cl

Photo credits from: quora.com, chem.nlm.nih.gov, toppr.com

Example: Addition of HI to Ethyne, C2H2

Photo credits from: guidechem.com, reddit.com, melfellah.angelfire.com

3. Condensation Reaction
Condensation reaction is a reaction between two molecules forming single
molecule and a release water molecule as a product. Biological process such as
production of protein, Amino acids combine during condensation reaction. An

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amino acid has an amine functional group on one end and a carboxylic acid
function on the other end, and these two ends will have covalent bonds during a
condensation reaction.

Photo credits from: chem.libretexts.org

4. Saponification Reaction
Saponification reaction happens through hydrolysis reaction of an ester. This
process takes place because of hydrolysis of long-chain esters called fatty acids
esters to produce soap molecules, which are the salts of fatty acids.

Example: Saponification of sodium stearate, C17H35COO−Na+

Soap molecule is sodium stearate is created from the hydrolysis of ethyl stearate.

Photo credits from: chem.libretexts.org

Saponification came from the Latin word “sapo” which means “soap”, and is
made from hydrolysis of fats. Because of basic conditions, a carboxylate ion rather
a carboxylic acid is produced and an alcohol, represented by the general formula of
saponification below.

Photo credits from: chem.libretexts.org

Explore

Accomplish the activities below. This would help you

strengthen your skills and basic concepts you have
learned in this lesson.

Enrichment Activity 1: What are my forms?

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Directions: Illustrate the different structural isomers of the following molecules.
Use another sheet of paper for your answers.
1. C6H14

2. C5H11Cl

3. C7H7I
containing
benzene
ring

4. C4H8O

5. C4H8O2
Enrichment Activity 1.2: How many rings do you want?
Direction: Draw as many
benzene ring ( structural isomers as you can for C 8H10 containing

). Use another sheet of paper for your answers.

Enrichment Activity 2. Let’s Turn up the Heat!
Direction: Write the combustion reactions of the following organic compounds. Use
another sheet of paper for your answers.

1. Kerosene, C12H26
2. Cyclopropanol, C3H6O
3. C4H9OH
4. C5H12
5. Isopropyl Alcohol

Enrichment Activity 2.1. What’s my Sum?

Direction: Write the product of the addition reaction. Use another sheet of paper
for your answers.

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1. Addition of HBr to H2C=CH2
2. Addition of Br2 to Ethyne
3. CH3CH=CHCH3 + Cl2
4. Cyclobutene + Br2

5.

+ I2

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 Deepen
Performance Task: Isomers in reality!
Direction: Provide a (1) concept map of how isomers are utilized in various fields in
life. Example: medicine, transportation, agriculture etc. You are advised
to use diagrams and illustrations for your output. (2) Make a concept
map in one of the organic reaction of compounds learned. The scoring
rubric on the next page will be used in assessing your output. Use a
separate sheet for your answers.
Scoring Rubric
Category 1 point 3 points 5 points
Organization of Provided 1 sentence Explained less Explained well
ideas only Provided evidences Provided enough
Did not show Provided less than 5 evidences
understanding in sentences but not Provided 5
the concept more than 1 sentences at least
Did not write any sentence Shows
additional real-life Shows slight understanding of
example understanding of the the concept Shows
concept correct additional
Show slightly real-life examples
correct additional
real-life examples
Clarity of Did not show any Shows minimal Shows symbols,
Illustration/ symbol, line or amount of symbol, lines and
Diagrams arrow that could lines and arrows arrows that
help explaining the Shows some helped
concept of pressure incorrect placement explain well the
of symbols, arrows or concept of
lines pressure
Shows unclear Correct use and
diagrams but have placement of
appropriate content symbols, arrows or
lines
Shows appropriate
diagram to show
content
Neatness Show corrections Shows minimal No erasures or
and erasures on amount of erasures corrections in the
the answers Shows Shows no space provided
alteration of alteration of
answers answer on the
space provided

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 Gauge
Direction: Write the CAPITAL letter of the correct answer on a separate paper.

1. What type of structural isomerism is categorized by having a straight chain

isomer or branched isomer?
A branched B. chain C. organic D. positional
2. When an important group changed its location on a chain of the molecule, what
type of isomerism is produced?
A. branched B. chain C. organic D. positional
3. How many isomers does C4H9OH have?
A. 1 B. 2 C. 3 D. 4
4. Which of the following does NOT have an isomer?
A. propane B. butane C. pentane D. hexane
5. How many hydrogen atoms are found in a benzene ring?
A. 5 B. 6 C. 7 D. 8
6. How many structural isomers can C7H7Cl have?
A. 4 B. 5 C. 6 D. 7
7. When structural isomerism happens in functional groups and produced a
RCOOH structure, what group is produced?
A. alcohol B. aldehyde C. ketone D. carboxylic acid
8. What type of isomer does C3H6O if it the molecule has a RCOR?
A. alcohol B. aldehyde C. ketone D. propanal
9. If combustion reaction with oxygen, what type of heat process is this?
A. conduction B. endothermic C. exothermic D.
radiation 10. Which of the following is a production of an incomplete
combustion?
A. CO B. CO2 C. H2O D. H2O2
11. What biological macromolecule is essentially produced in the condensation of
amino acids?
A. carbohydrates B. lipids
B. nucleic acids D. proteins
12. Aside from a new substance is formed, what is the end product of
condensation?
B. CO B. CO2 C. H2O D. H2O2
13. Which of the following is a product of saponification?
A. alcohol B. ester C. ether D. thiols
14. In saponification reaction, what compound is used in the hydrolysis of ester?
A. acid B. base C. ketone D. water
15. What happens to an organic molecule if its single bond carbon atoms rotated
or the whole chain rotated? It will _____.
A. produce an isomer B. not produce isomer
C. produce many isomer D. produce an inorganic molecule

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