9

NOT

Science
Technology &
Advance
Engineering Chemistry
Quarter 4 - Module 2
Program

Marites Ellana-Pascual
Author
Science Technology and Engineering Program
Alternative Delivery Mode
Quarter 1 - Module 2: Nature of Organic Chemistry
First Edition, 2020

An Initiative of Cagayan National High School-Science Department

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The institution and the author do not represent nor claim ownership over
them.

Author: Marites E.Pascual

Science Department Head: Eduardo C. Dela Rosa

School Principal: Elpidio D. Mabasa

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Assistant Schools Division Superintendent: Marites L. Llanes,PhD

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Author: marites.pascual001@deped.gov.ph
 What I Need t o Know

Almost anything you see at home, in your school, in the grocery, shopping mall, gas
station and everywhere is made of organic compounds. Organic chemistry is the study of
carbon compounds. Carbon compounds characterize life. To understand life is to understand
organic chemistry which involves scientific study of the composition, structures, properties,
and preparation of carbon-based compounds, hydrocarbons, and their derivatives. This
module will provide you deeper understanding of the properties of carbon compounds.

After going through this module, you are expected to:

1. Compare and contrast organic from inorganic compounds.
2. Explain why a carbon atom is unique.
3. Write the structural formula of saturated and unsaturated hydrocarbons.
 What I Know

Directions: Choose the letter that corresponds to the correct answer.

1. Which of the following hydrocarbons that contain only single carbon-carbon bonds and
carbon-hydrogen bonds?
A. Aromatic B. Alicyclic C. Saturated D. Unsaturated
2. Which of the following is the basic element of all organic compounds?
A. Carbon B. Hydrogen C. Oxygen D. Nitrogen
3. In the study of hydrocarbons, which of the following is commonly used in writing the
formulas of a compound?
I. Molecular Formula II. Expanded Structural Formula III.Condensed Structural Formula
A. I only B. II only C. I and II D. II and III
4. Which of the following refers to the molecules that contain only carbon and hydrogen?
A. Amines B. Amides C. Hydroxyl D. Hydrocarbons
5. Which is TRUE about carbon atoms?
I. Carbon exhibits allotropism.
II. Carbon atom is unique in its ability to combine with other carbon.
III. Carbon is the sixteenth of the elements, which is abundance on the Earth’s crust.
A. I and II only B. II and III only C. I and III only D. I,II and III
6. Carbon is unique in its ability to bond with other carbon atoms? Which of the
following statement is incorrect about carbon atoms?
A. Carbon atoms form stable carbon compounds.
B. Carbon atom combines only with non-metals like O,N,S,P.
C. Carbon atoms from double or triple bonds with other carbon atoms.
D. Carbon atoms have unlimited capacity to bond with other carbon atoms.
7. Which condensed structural formula represents an unsaturated compound?
A. CH3CHCHCH3 B. CH3CH2CH3 C. CH3CH3 D. CH4
8. Given the formula representing a compound, which formula represents an isomer of this
compound?

H
|
H–C–H

H H
| |
H–C–C–C–H
| | |
HHH
A. H HH H B. HH HH
| | | | | | |
C=C–C–C–H H–C–C–C–C–H
| | | | | |
H H H HH HH

C. D. HH H
HH | | |
| | H–C–C–C–H
H–C≡C–C–C–C–H | |
| | H H
HH
H–C–H
|
H
9. Which of the following compound is saturated?
A. Butene B. Ethene C. Heptene D. Propyl
10. Butene is a highly flammable, colorless, easily liquefied gas that quickly vaporizes at
room temperature? Which of the following is the expanded structural formula of butene?

A. C. H HH H
H H H H
| | |
| | | |
C–C–C–C–H
H–C–C–C–C
| | | | | |
H H H H H H H

B. C. H H H H
H H | | | |
| | H–C–C–C–C–H
H–C–C–C–H | | | |
| | H H H H
H H

H–C–H
|
H
 Lesson 1 Nat ure of Or ganic Chemistry

Organic chemistry is a branch of chemistry that studies carbon-based compounds

known as organic compounds. Approximately 90% of the 12 million known chemical
compounds are organic compounds.

What ’s In

Organic Compounds versus Inorganic Compounds

The element carbon is found in all organic compounds. Organic compounds primarily
contain carbon, but they also contain hydrogen, nitrogen, oxygen, and sulfur as common and
significant components. Organic chemistry is a branch of chemistry that studies about
carbon compounds except for oxides, cyanates, carbonates, carbides, and hydrogen
carbonates.

Some compounds may contain carbon but are considered inorganic as their properties
resemble more of those of inorganic compounds. Among these compounds are carbon
monoxide (CO), cyanide (CN-), cyanate (CNO-), carbon dioxide (CO2), carbonic acid
(H2CO3) and carbonate (CO32-).
The basic distinction is that organic compounds are produced by living things while
inorganic compounds are produced by non-living natural processes or by human intervention
in the laboratory. For better understanding, the differences between organic and inorganic
compounds are summarizes below:

Table 1: Properties of Organic and Inorganic Compounds

Organic Compounds Inorganic Compounds

1.Always contain carbon 1. Contain metals and other elements
2. Characterized by carbon-hydrogen bonds2. Do not contain carbon-hydrogen
bonds
3. Low melting point and boiling point 3. High melting point and boiling point
4. Do not conduct electric current 4. Conduct electric current
5. Generally flammable 6. Generally inflammable
7. Most are not soluble in water but are 7. Generally soluble in water and rarely
generally soluble in non-polar solvents soluble in non-polar solvents
8. Covalent bonding 8. Ionic bonding
9. Unable to make salts 9. It can make salts
10. It contains long, complex chains of 10. Do not contain have long, complex
molecules chains of molecules
The Carbon Compounds

Carbon is very special because it can form so many compounds. Carbon is the central
atom of organic compounds because it has the ability to bind or link to itself in many
times. Carbons present in an organic compound bind strongly to each other, they
can have single bond, double bond and triple bond (the strongest among the three) in
the carbon backbones. It has a strong bonds with other carbon atoms to form chains and
rings. In some carbon compounds, these bonds are branched, and not in ring formation. Such
property is called catenation.

Catenation permits carbon atoms to bond with other carbon atoms and form over
millions of natural and synthetic carbon compounds. Another reasons for its uniqueness is it
can form strong covalent bonds with other elements particularly hydrogen, oxygen, nitrogen,
sulfur and the halogens. Organic compounds consisting only of carbon and hydrogen are
called hydrocarbons.

What ’s New

Hydrocarbons

A hydrocarbon is an organic chemical compound composed exclusively of hydrogen

and carbon atoms. They are known as the simplest organic compounds. Hydrocarbons are
naturally-occurring compounds and form the basis of crude oil, natural gas, coal, and other
important energy sources.Hydrocarbons can be classified according to their structure which
can be aliphatic or aromatic as shown below:

HYDROCARBONS

Contain benzene rings

Aliphatic (open chains) Aromatic

(rings)
Do not contain benzene rings
e.g.
benzene(C6H6)

Saturated Unsaturated

Alkanes
(Single bond)
Alkenes Alkynes
CnH2n + 2
(Double bond) (Triple bond)
e.g. ethane
CnH2n CnH2n -2
(C2H6)
e.g. ethene e.g.
(C2H4) ethyne(C2H2)
Isomerism
Carbon compounds form so many different bonds and bonding patterns, thus
producing different configurations. There are three ways in which we can represent the
bonding of carbon atoms. It can be through the molecular formula, expanded structural
formula,and condensed structural formula. In the study of hydrocarbons, chemists commonly
used the expanded structural formula,and condensed structural formula instead of molecular
formula because you need to know the structure or arrangement of atoms and bonds in a
molecule. The example below distinguishes the molecular formula from structural formula.

Molecular Formula
C4H10

Expanded Structural Formula

CH3–CH2–CH2 –CH3 Condensed Structural Formula

There are compounds have the same molecular formula but different arrangement of
atoms. Chemical compounds that have identical chemical formula but differ in properties and
the arrangement of atoms in the molecule are called isomers. Therefore, the compounds that
exhibit isomerism are known as isomers. One type of of isomerism is characterized by
compounds called structural isomers. An example of isomer is given in the figure below:

Butane (C4H10) Iso-Butane/2-Methylpropane (C4H10)

CH3–CH2–CH2–CH3 CH3–(CH2)2–CH3

Butane have the same molecular formula (C4H10) but their structures are arranged differently.
 What is It

Aliphatic Hydrocarbons
Aliphatic hydrocarbons are compounds containing hydrogen and carbon joined
together in straight chains, ranched chains, or nonromatic rings. They do not contain benzene
ring. Aliphatic hydrocabons are classified as saturated or unsaturated based on the type of
bond between two carbon atoms. When all the carbon atoms are linked by single bonds, the
compound is classified as saturated. However, when the carbon to carbon link is either to
double or triple bond, the compound is classified as unsaturated.

Saturated Hydrocarbons: Alkanes

The alkanes family, also called the paraffins and saturated hydrocarbons, are the most
fundamental class of organic compounds. Alkanes are hydrocarbons in which the carbon
atoms are held together by single bonds. They a general chemical formula CnH2n+2. Alkanes
contain the maximum number of hydrogen atoms that can bond with all the carbons present.
The simplest alkane has the formula CH4 (methane), which means has one carbon atom
(n=1). Below is the list of IUPAC names of the first ten (10 straight-chained alkanes.

Table 1.IUPAC Names for Simple Alkanes

Number of Prefix Name Molecular Condensed Structural Formula

Carbon Formula
atoms
1 Meth Methane CH4 CH4
2 Eth Ethane C2H6 CH3–CH3
3 Prop Propane C3H8 CH–CH2–CH3
4 But Butane C4H10 CH3–CH2–CH2–CH3
5 Pent Pentane C5H12 CH3–CH2–CH2–CH2–CH3
6 Hex Hexane C6H14 CH3–CH2–CH2–CH2–CH2–CH3
7 Hept Heptane C7H16 CH3–CH2–CH2–CH2–CH2–CH2–CH3
8 Oct Octane C8H18 CH3–CH2–CH2–CH2–CH2–CH2–CH2–CH3
9 Non Nonane C9H20 CH3–CH2–CH2–CH2–CH2–CH2–CH2–CH2–CH3
10 Dec Decane C10H22 CH3–CH2–CH2–CH2–CH2–CH2–CH2–CH2–CH2–CH3

Note that the names in Table 1 have common feature-they end in the suffix -ane. This
consistent suffix is an important feature of the IUPAC System; any organic compound ending
in -ane is an alkane. The molecular formula shows the number of atoms of carbon and
hydrogen. Condensed structural formula shows the sequential arrangement of how each
carbon atom is bonded to another.
Unsaturated Hydrocarbons: Alkenes and Alkynes

Alkanes and Alkynes are unsaturated hydrocarbons. This means that they have at least
one carbon-carbon double bond or triple bond. Alkenes are also known as olefins. Alkenes
contain at least one carbon-carbon double bond. Open chains alkenes have the general
formula CnH2n, where n equals the number of carbon atoms. Alkynes are also generally
known as acetylenes from the first compound series. Alkynes contain at least carbon-carbon
triple bond. Open-chain alkynes have the general formula C nH2n-2, where n equals the
number of carbon atoms. Below is the IUPAC Names of some selected alkenes and alkynes-
with their names and structures.

Table 2. Some Representatives of Alkenes with their Names and Structures

IUPAC Name Molecular Formula Condensed Structural Formula
ethene C2H4 CH2=CH2
propene C3H6 CH2=CHCH3
1-butene C4H8 CH2=CHCH2CH3
1-pentene C5H10 CH2=CH(CH2)2CH3
1-hexene C6H12 CH2=CH(CH2)3CH3
1-heptene C7H14 CH2=CH(CH2)4CH3
1-octene C8H16 CH2=CH(CH2)5CH3

Table 2, shows the names of alkenes which are based on the names of the alkanes with the
same number of carbon atoms, but the ending -ane is replaced with -ene. This group of
unsaturated hydrocarbons is characterized by a double bond between two carbon atoms.

Table 3. Some IUPAC Names of Alkynes

IUPAC Name Molecular Formula Condensed Structural Formula
Ethyne C2H2 CH≡CH
Propyne C3H4 CH ≡C–CH3
1-Butyne C4H6 CH≡C–CH2–CH3
1-Pentyne C5H8 CH≡C–CH2–CH2–CH3
1-Hexyne C6H10 CH≡C–CH2–CH2–CH2–CH3
1-Heptyne C7H12 CH≡C–CH2–CH2–CH2–CH2–CH3
1-Octyne C8H14 CH≡C–CH2–CH2–CH2–CH2–CH2–CH3
1-Nonyne C9H16 CH≡C–CH2–CH2–CH2–CH2–CH2–CH2–CH3
1-Decyne C10H18 CH≡C–CH2–CH2–CH2–CH2–CH2–CH2–CH2–CH3

Table 3 shows the alkyne group of unsaturated hydrocarbons, which is characterized by a

triple bond between two carbon atoms and the rest are single bonds. The names of the
alkynes are based on the names of alkanes with the same number of carbon atoms, but the
ending -ane is replaced with -yne.
 What ’s More

Naming Alkanes, Alkenes and Alkynes

The system of naming compounds is referred to as nomenclature.With millions of
organic compounds, it became necessary to develop a system of nomenclature. The
International Union of Pure and Applied Chemistry (IUPAC) system is used for naming
organic compounds. The rule of this system are as follows:
1. Select the longest continuous carbon chain in the molecule. Refer to the hydrocarbon name
in table 4.This becomes the base name.
Molecular Condensed Structural Formula Name Alkyl
Formula (CnH2n+1)
CH4 CH4 Methane Methyl
C2H6 CH3–CH3 Ethane Ethyl
C3H8 CH–CH2–CH3 Propane Propyl
C4H10 CH3–CH2–CH2–CH3 Butane Butyl
C5H12 CH3–CH2–CH2–CH2–CH3 Pentane Pentyl
C6H14 CH3–CH2–CH2–CH2–CH2–CH3 Hexane Hexyl
C7H16 CH3–CH2–CH2–CH2–CH2–CH2–CH3 Heptane Heptyl
C8H18 CH3–CH2–CH2–CH2–CH2–CH2–CH2–CH3 Octane Octyl
C9H20 CH3–CH2–CH2–CH2–CH2–CH2–CH2–CH2–CH3 Nonane Nonyl
C10H22 CH3–CH2–CH2–CH2–CH2–CH2–CH2–CH2–CH2– Decane Decyl
CH3
2. Add the following endings to the base name.
-ane-alkane
-ene-alkene
-yne-alkyne

Thus, the IUPAC names of the following hydrocarbons are

A. CH3–CH2–CH2–CH3 ( Butane)
B. CH2=CH2 (Ethene)
C. CH≡CH (Ethyne)
3. In naming alkenes and alkynes, number the chain beginning at the end that is closer to the
double or triple bond. To indicate the position of the multiple bond, use a prefix number
before the alkene or alkyne name.
For example
5 4 3 2 1
CH3–CH2–CH=CH–CH3
2-Pentene
3-

In compounds containing two double bonds, the ending -diene is used.

 1 2 3 4 5 6
CH3–CH=C=CH–CH2–CH3
2, 3 Hexadiene

4. In branched hydrocrabons, consider the branch as a substituent group and name it by

changing -ane to -yl (alkyl).

For alkanes, number the chain starting at the end that is closer to the branch.

For example
CH3
|
CH3–CH–CH2–CH2–CH2–CH3
1 2 3 4 5 6
2-methylhexane

If identical substituent are present, use the prefixes di, tri, tetra, penta and so on, then
indicate the numbers. Separate the numbers with a comma. If different substituents are
present, arrange them alphabetically.

For Examples
C2H5
CH3 CH3 7 6 5 4| 3 2 1
| | CH3–CH2–CH–CH–CH2–CH–CH3
CH3–CH2–CH–CH2–CH–CH3 | |
6 5 4 3 2 1 CH3 CH3
2,4-dimethylhexane 4-ehtyl-2,5-dimethylheptane

For branched alkenes and alkynes, follow rule 3 in numbering the carbon chains. Thus,

5 4 3 2 1 C2H5
CH3–CH–CH=CH–CH3 1 2 3 4 5| 6
| CH≡C–CH–CH–CH–CH3
CH3 | |
4-methyl-2-pentene CH3 CH3

4-ethyl-3,4-dimethyl-1-hexyne

What I Have Learned

Directions: Compare and contrast organic and inorganic compounds based on the given
material .Write your answer on the space provided for you.
 ORGANIC
INORGANIC

_______________________ SIMILIRATIES ________________________

_______________________ ________________________
_______________________ ________________________ ________________________
_______________________ ________________________ ________________________
_______________________ ________________________ ________________________
_______________________ ________________________ ________________________
_______________________ ________________________
________________________
_______________________ ________________________
_______________________ ________________________ ________________________
_______________________ ________________________ ________________________
_______________________ ________________________ ________________________
_______________________ ________________________ ________________________
__________________ _____
________________________
________________________
________________________
 What Can I Do

A. On Molecular, Condensed and Expanded Structural Formulas

1. Write the molecular formula for each of the following:

a. CH3– CH2–CH2–CH2–CH2–Cl
b. CH3–CH2)5–OH
c. CH3–CH–CH–CH3
| |
CH3 CH3
2. Write the condensed structural formula for each of the following:
a. b.
H H H H H H H
| | | | | | |
H–C–C–C–H H–C–C–C–C–N–H
| | | | | | | |
H HH HH HH H

c.

H H–C–H H H–C–H H
| | | | |
H–C C C C C–H
| | | | |
H H H–C–H H H

3.Write the expanded structural formula for each of the following:

a. CH3–CHBr–CH2–SH
b. C4H10S
c. C5H12

B. On Naming Alkanes, Alkenes and Alkynes

1. Give the IUPAC name for each of the following hydrocarbons:

a. CH3–CH=C–CH2–CH3
b. CH3–C≡C–CH3
|
CH3
c. d. CH3
CH2=CH–CH=CH–CH2–CH3 |
CH3–CH–CH2–CH–CH–CH3
e. | |
e. C2H5 CH3
CH3–C≡C–CH–CH–CH3
| |
CH3 C2H5
 Assessment

Directions. Draw the structures for each of the following compounds.

1. 2-methyl-2-pentene
2. 6-methyl-3-heptyne
3. 2,4,4-trimethyl-2-octene
4. 1,3-hexadiene
5. 2-ethyl-4-,5-dimethyl-1,3-heptadiene

Addit ional Act ivit ies

1. Make gumdrop and toothpick models for each of the following compounds. Use a wad of
cotton to represent Π -bond. (Research for their chemical formulas and structures)
A. Acetylene
B. ethylene
 Answer Key

What I Can Do
What I Know A. On Naming Alkanes, Alkenes and Alkynes
1. C 1. Give the IUPAC name for each of the
2. A following hydrocarbons:
3. D
4. D a.3-methyl-2-pentene
5. D b.3-2-butyne
6. B c.1, 3-Hexadiene
7. A d.4-ethyl-2,3-dimethylhexane
8. B e.5-ethyl-4methyl-2-hexyne
9. A
10. D

ORGANIC
INORGANIC
• Always contain carbon SIMILIRATIES • Contain metals and other
•Characterized by carbon- elements
hydrogen bonds _______________________ • Do not contain carbon-
•Low melting point and _______________________ hydrogen bonds
boiling point • High melting point and
_______________________ boiling point
•Do not conduct electric
_______________________ • Conduct electric current
current
_______________________ •Generally inflammable
•Generally flammable • Generally soluble in water
•Most are not soluble in _______________________ and rarely soluble in non
water but are generally _______________________ polar solvents
soluble in non polar solvents • Ionic bonding
_______________________
•Covalent bonding • It can make salts
•Unable to make salts
_______________________ • Do not contain have long,
•It contains long, complex _______________________ complex chains of
chains of molecules _______________________ molecules
_______________________
 What I Can Do
A. On Molecular, Condensed and Expanded Structural Formulas
H H H H
3. Expanded Structural Formula | | | |
a. c. H–C–C–C–S–C
| | | |
H H H H
H Br H
H H H H H | | |
b. | | | | | H–C–C–C–S–H
H–C–C–C–C–C–H | | |
| | | | | HH H
H H H H H
What I Can Do What I Can Do
A. On Molecular, Condensed and A. On Molecular,
Expanded Structural Formulas Condensed and Expanded
Structural Formulas
1. Condensed Structural Formula
a.CH3–CH2–CH3
b.CH3–CH2–CH2–CH2–NH2
2. Molecular Formula
c.CH3–CH–CH–CH–CH3 a. C5H11Cl
| | | b. C6H14O
CH3 CH3 CH3 c. C6H14
Answer Key
 Answer Key

Assessment

3.
CH3–C=CH–CH2–CH3 CH3 CH3
1. | | |
CH3 CH3–C=CH2–C–CH2–CH2–CH2–CH3
CH3 |
2.
| CH3
CH3–CH2–C≡C–CH2–CH2–CH3

4. CH2=CH–CH=CH–CH2–CH3

5. CH2=C–CH=C–CH–CH2–CH3
| | |
C2H3 CH3 CH3
References:

Books

Mendoza, Estrella E. & REligioso, Teresita F.2001. You and The Natural World
Series,Science and Technology Chemistry.927 Quezon Avenue, Quezon
City.Phoenix Publishing House Inc.
Gebelein, Charles G.1996. Chemistry and Our World.Dubuque,IA, United States.Wm C.
Brown Publishers.
Pedregosa, Elma F.1998. Chemistry.27 Quezon Avenue, Quezon City.Phoenix Publishing
House Inc.

Mapa, Amelia P., Fidelino, Trinidad B. & Rabago, Lilia M.2001. Chemistry Textbook,
Science and Technology, Third Year.Metro Manila, Davao and Cebu.SD
Publications, Inc.

Abistado, Jonna M., Valdoz, Meliza P., Aquino, Marites D. & Bascara, Mary Anne T.2014.
Worktext In Science and Technology, Science Links.Smapaloc, Manila. Rex
Bookstore, Inc.

Allas, Ian Mark F., Espinosa, Allen A., Lorenzo, Aloysius D. & Navarette Jr., Bonifacio
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Abecilla, Nesjohn L., Badilla, Daisy B., Desalon, Roselyn M., Leonor, Jigger P., Olipane,
Rica Angela P & Pineda, Roldan P.2014. Conceptual Science and Beyond 9.
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Websites

https://www2.chemistry.msu.edu/faculty/reusch/virttxtjml/nomen1.htm.
Date Accessed: March 05, 2021,

https://guides.hostos.cuny.edu/che120. Date Accessed: March 05, 2021

https://wou.edu/chemistry/files/2017/01/CH105-Chapter-8-PDF-file.pdf.
Date Accessed: March 12, 2021.