9

NOT

Science
Technology &
Advance
Engineering Chemistry
Quarter 4 - Module 3
Program

Marites Ellana-Pascual
Author
Science Technology and Engineering Program
Alternative Delivery Mode
Quarter 1 - Module 3: Hydrocarbon Derivatives
First Edition, 2020

An Initiative of Cagayan National High School-Science Department

Borrowed materials included in this module are owned by their respective

copyright holders. Every effort has been exerted to locate and seek
permission to use these materials from their respective copyright owners.
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

EPS-Science: Myrna Q. Adduru, PhD

Assistant Schools Division Superintendent: Marites L. Llanes,PhD

Schools Division Superintendent: Reynante Z. Caliguiran, PhD

Printed in the Philippines by:

Department of Education –SDO Tuguegarao City, Cagayan National High School

Office Address: Bagay Road, San Gabriel, Tuguegarao City, 3500
Telephone Nos: (078) 844-1232; (078) 844-7768
E-mail Addressess: Institution: cnhs.tuguegarao@deped.gov.ph
Author: marites.pascual001@deped.gov.ph
 What I Need t o Know

This module was designed and written with you in mind. It is here to help you
understand naming of hydrocarbon derivatives and its importance. The scope of this module
permits it to be used in many different learning situations. The language used recognizes the
diverse vocabulary level of students. The order in which you read them can be changed to
correspond with the textbook you are now using.

This module contains;

Lesson 1- Hydrocarbon Derivatives
Lesson 2- Uses/Importance of Hydrocarbons

After going through this module, you are expected to:

1. Determine the functional groups and write the structural formula of hydrocarbon
derivtaives.
2. Name hydrocarbon derivatives and identify their uses or importance
 What I Know

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

1. Which of the following are classified based on the functional group they contain?
A. organic compounds C. Hydrocarbon
B. Organic compounds D. Hydrocarbon derivatives
2. Which of the following organic compound DOES NOT have the carbonyl group?
A. Aldehyde B. Carboxylic acids C. Ethers D. Ketones
3. Which functional group undergoes the greatest boiling point increase?
A. Amino B. Carboxylic C. Carboxyl D. Hydroxyl
4. The tart of citrus is due to citric acid. The vinegar used in adobo is acetic acid. Both acids
are examples of what name of functional group?
A. Amino B. Carbonyl C. Carboxyl D. Hydroxyl
5. Which of the following is an example of an alcohol/
A. C6H6 C. CH3–O– CH3
B.
CH3–C–CH3
D. C2H5 – OH
||
O

O
6. The group is called
–C

H
A. Aldehyde group B. Carbonyl group C. Hydroxyl group D. Ketones
7. Which of the following is the chemical formula of methyl ethanoate?
A. C2H5–COO–CH3 C.CH3–COO–C2H5
B. CH3–COO–CH3 D. C2H5–COO–C2H5
8. Which of the following is responsible fro the smell or fragrance of fruits and flowers?
A. Amides B. Amines C. Ethers D. Esters
For items 9-10, refer to the general formulas of organic compounds below:
O
I. R–O III. ||
R R
H

O
II. IV. O
||
||
R H
R OH

9. Which general formula represents an aldehyde?

A. I B. II C. III D. IV
10. Which general formula represents ketones?
A. I B. II C. III D. IV
 Lesson 1 Hydrocarbon Derivat ives

Hydrocarbon derivatives are all around us. They fill our cabinet in the form of
aspirin, cosmetics, throat lozenges, hair spray and cologne. Hydrocarbon derivatives contain
at least one element other than hydrogen or carbon, such as oxygen, nitrogen or one of the
halogen atoms (elements in column 7A).
Most of the time, the atoms present in a hydrocarbon derivative are attached as part of
a distinct group. These groups are known as functional groups because they affect how the
compound behaves. These functional groups confer distinctive chemical and physical
properties of a compound as well.

What ’s In

Hydrocarbon derivatives are classified based on the functional group that they
contain. A functional group is an atom or group of atoms that defines the reactivity of an
organic molecule.They are formed through a base molecule and an R (hydrocarbon ) group.
Table 1 gives you the major classes of organic compounds according to their functional
groups.

Table 1. Functional Groups

Functional Compound Structure Example Formula Example Name Naming
Group Name Suffix/Prefix
Hydroxyl Alcohols R–OH CH3–OH methanol -ol
Ethers R–O–R C2H5–O–C2H5 diethyl ether ether
Carbonyl Aldehyde O O acetaldehyde -al
|| ||
R–C–H CH3–C–H
Ketones O O acetone -one
|| ||
R–C–R CH3–C–CH3
Carboxyl Carboxylic O O acetic acid -ic
acids || || -oic
R–C–OH CH3–C–OH
Esters O O Ethyl ethanoate -oate
|| || or ethyl acetate
R–C–OR CH3–C–O–CH2CH3
Amino Amines R–NH2 CH3–NH2 methylamine -amine
Amides O O acetamide -amide
|| ||
R–C–NH2 CH3–C–NH2
 What ’s New

Hydroxyl Group
Alcohol
Alcohols are used widely in chemical reactions and as solvents. Alcohols have a
general formula of R–OH, where R represents an organic group, such as an alkyl, and –OH
is the functional group called hydroxyl. The four most common alcohols with their structures
are shown in table 2.
Table 2. Structure of Common Alcohols
Common Name of Alcohols R–OH
Methyl Alcohol H
|
H–C–OH
|
H
Isopropyl Alcohol H H H
| | |
H–C–C–C–H
| | |
H OH H
Ethy Alcohol H H
| |
H–C–C––OH
| |
H H
Propyl Alcohol H H H
| | |
H–C–C–C–OH
| | |
H H H

Naming Alcohols

1. Select the longest continuous carbon chain, containing the hydroxyl group, and derive
the parent name by replacing the -e ending with -ol.
2. Number the carbon chain, beginning at the end nearest to the hydroxyl group.
3. Number the substituents and write the name, listing substituents alphabetically.
4. Molecules that have more than one-OH groups are called diols, triols, and so on.
Examples
OH
|
1. CH3–CH2–CH–CH2–CH2–CH3 3-Hexanol

OH CH3
| |
2. CH3–CH2–CH–CH2–CH–CH3 5-Methyl-3-hexanol

3.
OH OH
2, 3-Butanediol
| |
CH3–CH–CH–CH3

Uses Of Alcohols

Alcohol is an organic compound commonly used a reagents, solvents, and fuels.

Methanol, ethanol, propanol are the most common alcohols. Methanol ( CH3OH)can be used
as a gasoline, additive and fuel. It is obtained form the distillation of wood and therefore
called as the wood alcohol.Ethanol ( C2H5OH) is a product of the fermentation of sugar. The
fermentation of ethanol is responsible for the production of beer, wine, and other beverages.
It is also responsible fro the ring of bread dough. Isopropyl alcohol or 2-propanol is sued in
sponge baths to reduce high fever. It removes heat from the body through rapid
evaporation.Throat lozenges contain menthol, which is an alcohol. It causes the mucous
membranes to increase their secretions, which soothe the respiratory tract.

Ethers

Ethers are compound in which two alkyl groups are bonded to one oxygen atom. They
are usually represented as R-O-R, where R and R are a hydrogen group, and O is oxygen.
Ethers usually forms an explosive peroxide which it needs with moisture and ethyl alcohol.

Naming Ethers

Ethers are named by first naming the alkyl group attached to oxygen atom in
alphabetical order with space between the names, followed by the word ether. The prefix -di
is used if both alkyl groups are the same.

Examples

a. CH3–O–CH3 dimethyl ether

b. CH–CH2–O–CH3 ethylmethyl ether
c. CH–CH2–O–CH2–CH3 diethyl ether
Uses of Ethers

Ethers are generally less dense, less soluble in water and have lower boiling points
than alcohol. They are useful as solvents for fats, oils, waxes, perfumes, resins,dyes and
gums. Diethyl ether is used as anesthetic for surgical procedures while dimethyl ether is used
as refrigerant and an aerosol spray propellant.

What is It

Carbonyl Group

Aldehydes

When an oxygen atom is double bonded to the carbon atom at O the

end of the chain, an aldehyde is formed. The general formula for ||
aldehyde is C
R H
The term aldehyde comes from the word “alcohol
dehydrogenated”.Aldehyde derive their names from the dehydration
of alcohols.

Naming Aldehydes

1. Locate the longest carbon chain attached to the C =O group, determining its alkane name,
and replacing -e in the parent alkane with the suffix -al.
2. The carbon in the C=O group is always numbered as carbon 1 in the aldehydes.
3. If another chain in the molecule contains more carbon atoms, the name of the compound is
always based on the longest carbon chain attached to the C =O group.
Examples O
O ||
a. b. CH3–CH2–CH2–CH–CH2–C–H
||
H–C–H
Methanal
Hexanal

c. O
||
CH3–CH2–CH2–CH2–CH–C–H 2-ethylhexanal
|
CH3–CH2
Uses of Aldehydes

Some aldehydes are used as food flavoring agents. The primary taste in natural
almond, cinnamon and vanilla flavors are produced by aldehyde compounds. Aldehydes also
have industrial uses such as solvents, perfumes or as intermediates in the manufacture of
plastics, dyes and pharmaceuticals. The methanal or formaldehyde is used as a solvent,
embalming agent, and preserving agent for biological specimens. Retinal, which is combined
with a protein (opsin) in the retina of the eye to form rhodopsin is the main compound
involved in the process of vision-which is also an aldehydes.

Ketones

A ketone is a functional group characterized by a carbonyl group (O=C), in which the

carbon atom is covalently bonded to an oxygen atom. It is represented by the formula RCOR,
where the two R’s are alkyl groups. Ketone differ from aldehydes in that the carbonyl is
placed between two carbons rather than at the end of a carbon skeleton.

Naming Ketones

1. The IUPAC name is derived from the parent alkane, but the -e is replaced with -one (so
propane becomes propanone and heptane becomes heptanone).
2. To determine the alkene root name, the longest chain containing the C =O unit is located
and the C=O is assigned the lowest possible number.
Examples
O O
a. b.
|| ||
CH3–C–CH3 CH3–CH2–CH2–CH2–C–CH2–CH3

Propanone or acetone 3-Heptanone

Uses of Ketones

Ketones are fairly flammable and require careful handling. Ketones are often used in
perfumes and paints to stabilize the other ingredients so that they do not degrade as quickly
over time. Acetone (propanone), the simplest ketone is a useful solvent found in paint
remover, nail polish and nail polish remover. Methylethyl ketone (2-Butanone), is use as a
solvent in the production of plastics and textile, lacques and coatings, varnishes and paint
removers. Diethyl ketone (3-pentanone) is sometimes used as solvent, but its major uses are
in medicine and organic synthesis.
Carboxyl Group

Carboxylic Acids

A carboxylic acid is organic acid in which carbon is bonded to an oxygen atom by

double bond, forming a crabonyl group (C=O) and to a hydroxyl group (-OH) by a single
bond. It has a general formula of O
||
R–C–OH

Carboxylic acids are widespread in nature, often combined with other functional groups, but
they sometimes exist in the “free” state, where they have a strong, rather unpleasant odor.

Naming Carboxylic Acids

1. Select the longest carbon containing the carbonyl group.

2. The -e ending of the parent alkane name is replaced by the suffix -oic acid.
3. The carbonyl carbon is always numbered 1 but the number is not included in the name.
4. Number additional substituent groups, groups attached to the main carbon, according to the
carbon they branch from. List all substituent in alphabetical order as prefixes prior to the
carboxylic acid name.

Examples

O
a. ||
CH3–CH2–CH2–CH2–C–OH Pentanoic acid

b.
CH3 O
3-methylpentanoic acid
| ||
CH3–CH2–CH–CH2–C–OH
5 4 3 2 1

Uses of Carboxylic Acids

Most carboxylic acids are weak acids that lower the pH of a solution only slightly.
Carboxylic acids are used in the production of polymers, pharmaceuticals, solvents,and food
additives.The tart of citrus is due to citric acid. The vinegar in adobo is acetic acid. The
painful sting of an ant or a bee is due to formic acid or methanoic acid. Applying a base, such
as baking soda, helps neutralize the acid, it prevent from swelling and reduce pain. Oxalic
acid having two carbonyl groups is used as a cleansing agents.

Esters
Esters are made by reacting a carboxylic acid with an alcohol, producing ester and
water. This process of producing ester is called estrefication. Esters have the general formula
of O Where R is similar to organic acids, except that another-R group has
replaced the hydrogen atom.
||
R–C–OR
Esters occur widely in nature. They have generally pleasant odors and often responsible fro
the characteristics fragrances of fruits and flowers.

Table 3. Some Examples of Esters

Ester Source
Octyl acetate Oranges
Methyl butyrate Apples
Amyl acetate Bananas
Ethyl butyrate Pineapples
Benzyl butyrate Flowers
Methyl anthranilate Grapes

Naming Esters

1. Identify and name the alkyl group portion contributed by the alcohol part first (No number
is assigned to this alkyl chain).
2. Name the acid part as carboxylic acid, changing the suffix -oic to -oate.
O
||
R– C– O – R

Acid part Alcohol part

3. Leave a space between the alkyl group name and the name of the carboxylic acid
derivative.

a.
O
CH3–CH2–CH2–C Ethyl butanoate
O–C2H5

b. O
||
CH3–C–O–CH3 Methyl ethanoate
Uses of Esters

Esters are important not only in cosmetics and flavorings but in other applications as
well. Beeswax, a mixture of esters such as C25H51COO–C30H61 and carnauba wax, another
ester, are used in many automobile and furniture polishes. The esters aspirin and methyl
salicylate are used in medicine as analgesics and anti-inflammatory. Methyl salicylate, also
called oil of wintergreen, is the main ingredient in wintergreen flavor. Ethyl acetate is used as
a nail polish.

What ’s More

Amino

Amines
Amines contain nitrogen and have the general formula R–NH2, where R can either be
H or an alkyl group. Amines are responsible fro the odors that emanate from decomposing
garbage and dead bodies, and they are one of the main causes of body odor. However, amines
are essential to life itself.
Amines are subdivided into three distinct categories-primary, secondary, and tertiary
on the number of organic groups attached to the Nitrogen group.

For primary amines, one of the three hydrogen atoms in ammonia is replaced by an alkyl
group. R–NH2

Secondary amines have two alkyl substituents, bond to nitrogen together with one hydrogen.
R–NH
|
R

In tertiary amines, the three hydrogen atoms are replaced by three R-group
R–N–R
|
R
Naming Amines

1. Name the alkyl groups that are attached to the nitrogen atom of the amine. If there is more
than one different alkyl group, put them in alphabetical order. If there are two or more of
the same alkyl group, use the di or tri prefix.
2. Follow the alkyl group name with the suffix -amine, with no spaces.

Examples
a. CH3–NH2 Methylamine

b. Dimethylamine
CH3–NH
|
CH3

Uses of Amines

Amines are used in the synthesis of disinfectants, insecticides, and dyes.Most

neurotransmitters are amines. Examples are epinephrine, dopamine, and histamine.
Chlorpheniramine helps relieve allergic disorder due to cold, itchy skin, and insects bites.
Likewise, the chlorpromazine is used as tranquilizer that relieves anxiety, excitement, and
restlessness.

Amides

Amides contain a functional group consisting of a carbonyl group linked to a nitrogen atom.
It has the general formula
Where the –NH2 group is attached directly to the
O carbonyl group.As with amines, the nomenclature used
|| for an amide depends on the number of carbons attached
R–C–NH2 to the nitrogen.

A primary (10) amide has nitrogen attached to a single carbon; a secondary (20) amide has
the nitrogen attached to two carbons and a tertiary (30) amide has the nitrogen attached to
three carbons.

Primary Amide O Secondary Amide

R NH2 O
||
CH3
R NH2
Tertiary Amide
O
||
CH3
R NH2
|
CH3
Naming Amides

1. According to IUPAC rules, the -oic or -ic in an acid naming is replaced by amide.
2. If alkyl group is attached to the nitrogen atom then it is named as N-alkyl in front of the
name amide.

Examples

a. O
|| Methanamide
H–C–NH2

O
||
b. CH3–CH2–CH2–C–NH2 Butanamide

c.
O H
|| | N-Methylethanamide
CH3–C–N–CH3

d. O H
|| |
CH3–CH2–C–N–CH2–CH3 N-Ethylpropanamide

Uses of Amides

Organic compounds present in nylon, silk, and wool contain hundreds of amide
groups.Acetaminophen, an important analgesic, and sulfa drugs are amide-containing
pharmaceutical agents. Some amides are used as plasticizers, chemicals that soften plastics.
 What I Have Learned

Directions. Name the following molecules using the IUPAC system.

CH3 O
1. CH3–CH–CH2–OH 5. | ||
| CH3–CH–CH2–C–CH–CH3
OH

2.
CH3–CH–CH2–CH2–CH2–OH
| O
6.
CH3 ||
3. CH3–C–CH2–CH–CH––CH2–CH3
CH3 O
| |
| ||
CH3 CH3
CH3–CH–CH2–CH2–C–H

4 .
O

CH3–CH–CH2–C
| H
CH3
 What Can I Do

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

Substance Formula Organic or Use

Inorganic
Baking Soda NaHCO3
Methane C H4
Ethyl alcohol C2 H5 OH
Hydrogen peroxide H2O2
Canola oil C18H30O2
Fructose (fruit) C6H12O6
Butane C4 H10
Steroid C27 H 46
Glycerin C3H8O3
Isopropyl alcohol C3H7OH
 Assessment

A. What are the names fro the following ethers?

1. CH3–CH2–O–CH2–CH2–CH3
2. CH3–O–CH2–CH3

B. Name the following carboxylic acids by the IUPAC System.

1. OH 2.
CH3
|
| O
C=O
CH3–CH2–C–CH2–C
|
| OH
CH3–CH–CH2–CH2–CH3
CH3

C. Give the IUPAC Name of the following esters.

1.
O
CH3–CH2–CH2–CH2–C
O
CH3

2.
O
CH3–CH2–CH2–CH2–C
O
C2H5

D. Write the condensed structural formulas for each of the following amines and amides.

1. Diethylamine
2. Trimethylamine
3. Ethyldimethylamine
4. Propanamide
5. N-ethyl-ethanamide .
 Addit ional Act ivit ies

1. Collect ten (10) labels of different products such as medicines, food additives, personal
hygiene products, perfumes, and other commonly used chemicals at home. Look at the
Ingredients of the product, then research which of the given ingredients are hydrocrabon
derivatives. Write in your chemistry notebook the name of each product, name of
hydrocarbon derivative ingredient, type of hydrocarbon derivative, structural formula,
use(s) of the hydrocarbon derivative, and harmful effect(s) of the derivative.
 CH3–C–N–CH2–CH3 CH3–CH2–C–NH2
|| | ||
O 5. O 4.
CH3 CH3
CH3–N–CH2–CH3
|
N
CH3 3.
|
CH3
2. 6. CH3–CH2–NH–CH2–CH3
D. .Condensed Structural Formulas: Amines and Amides
Assessment
Assessment
A. Ethers What I Know
What I Have Learned
1. ethyl propyl ether
1. 1,2-propanediol 1. D
2. Ethyl methyl ether 2. B/C
2. 4-methyl-1-pentanol
3. 4-methyl-pentanal 3. B
B. Carboxylic acids 4. B
4. 3-methylbutanal
1. 2-methylpentanoic acid 5. D
5. 5-methyl-3-hexanone
2. 3,3-dimethylpentanoic acid 6. A
6. 4,5-dimethyl-2-heptanone 7. B
C.Esters 8. D
1. Methyl pentanoate 9. B
2. Ethyl butanoate 10. C
Answer Key
References

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House Inc.

Mapa, Amelia P., Fidelino, Trinidad B. & Rabago, Lilia M.2001. Chemistry Textbook,
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Websites
https://chem.libretexts.org/Bookshelves/General_Chemistry/Map%3A_Chemistry__
The_Central_Science_(Brown_et_al.)/25%3A_Chemistry_of_Life%3A
Organic_and_Biological_Chemistry/25.04%3A_Unsaturated_Hydrocarbons.
Date Accessed: March 09, 2021.

https://www3.wayne.kyschools.us/userfiles/71/Classes/9741/32InorganicVsOrganic
AWorksheet.pdf. Date Accessed: March 15, 2021.