GENERAL CHEMISTRY 1 - GRADE 12 (STEM) Self-Instructional Packets (SIPACKs)

LESSON 4: FUNCTIONAL GROUPS

Look at the following medicine structures. These are all examples of compounds with functional
groups that are being used in the field of medicine.

Q4. What is/are the use of aspirin?

Q5. What is/are the use of adrenaline?

The Chemical Basis for Life

Carbon is the most important element to living things because it can form many kinds of bonds
and form essential compounds. Carbon is the fourth most abundant element in the universe and
is the building block of life on earth. On earth, carbon circulates through the land, ocean, and
atmosphere, creating what is known as the Carbon Cycle. This global carbon cycle can be divided
further into two separate cycles: the geological carbon cycles takes place over millions of years,
whereas the biological or physical carbon cycle takes place from days to thousands of years. In a
nonliving environment, carbon can exist as carbon dioxide (CO2), carbonate rocks, coal,
petroleum, natural gas, and dead organic matter. Plants and algae convert carbon dioxide to
organic matter through the process of photosynthesis, the energy of light.

Carbon is Important to Life

In its metabolism of food and respiration, an animal consumes glucose (C6H12O6), which
combines with oxygen (O2) to produce carbon dioxide (CO2), water (H2O), and energy, which is
given off as heat. The animal has no need for the carbon dioxide and releases it into the
atmosphere. A plant, on the other hand, uses the opposite reaction of an animal through
photosynthesis. It intakes carbon dioxide, water, and energy from sunlight to make its own glucose
and oxygen gas. The glucose is used for chemical energy, which the plant metabolizes in a similar
way to an animal. The plant then emits the remaining oxygen into the environment.
Cells are made of many complex molecules called macromolecules, which include proteins,
nucleic acids (RNA and DNA), carbohydrates, and lipids. The macromolecules are a subset of
organic molecules (any carbon-containing liquid, solid, or gas) that are especially important for
life. The fundamental component for all of these macromolecules is carbon. The carbon atom has
unique properties that allow it to form covalent bonds to as many as four different atoms, making
this versatile element ideal to serve as the basic structural component, or “backbone,” of the
macromolecules.

Structure of Carbon
Individual carbon atoms have an incomplete outermost electron shell. With an atomic number
of 6 (six electrons and six protons), the first two electrons fill the inner shell, leaving four in the
second shell. Therefore, carbon atoms can form four covalent bonds with other atoms to satisfy
the octet rule. The methane molecule provides an example: it has the chemical formula CH4. Each
of its four hydrogen atoms forms a single covalent bond with the carbon atom by sharing a pair of
electrons. This results in a filled outermost shell.

GC1: Lesson 4 / Second Quarter / First Semester / COLumba 1

Q6. Draw the Lewis symbol of carbon.
Q7. How many valence electrons does it have?
Q8. What would be the maximum number of bonds that it can form with other atoms?

Organic Compounds
Scientists of the 18th and early 19th centuries studied compounds obtained from plants and
animals and labeled them organic because they were isolated from “organized” (living) systems.
Compounds isolated from nonliving systems, such as rocks and ores, the atmosphere, and the
oceans, were labeled inorganic. For many years, scientists thought organic compounds could be
made by only living organisms because they possessed a vital force found only in living systems.
The vital force theory began to decline in 1828, when the German chemist Friedrich Wöhler
synthesized urea from inorganic starting materials. He reacted silver cyanate (AgOCN) and
ammonium chloride (NH4Cl), expecting to get ammonium cyanate (NH4OCN). What he expected
is described by the following equation.
AgOCN + NH4Cl → AgCl + NH4OCN
Instead, he found the product to be urea (NH2CONH2), a well-known organic material readily
isolated from urine. This result led to a series of experiments in which a wide variety of organic
compounds were made from inorganic starting materials. The vital force theory gradually went
away as chemists learned that they could make many organic compounds in the laboratory.
Today organic chemistry is the study of the chemistry of the carbon compounds, and inorganic
chemistry is the study of the chemistry of all other elements. It may seem strange that we divide
chemistry into two branches—one that considers compounds of only one element and one that
covers the 100-plus remaining elements. However, this division seems more reasonable when we
consider that of tens of millions of compounds that have been characterized, the overwhelming
majority are carbon compounds.
Hydrocarbons
The simplest organic compounds are those composed of only two elements: carbon and
hydrogen. These compounds are called hydrocarbons. Hydrocarbons themselves are separated
into two types: aliphatic hydrocarbons and aromatic hydrocarbons. Aliphatic hydrocarbons are
hydrocarbons based on chains of C atoms. There are three types of aliphatic
hydrocarbons. Alkanes are aliphatic hydrocarbons with only single covalent bonds. Alkenes are
hydrocarbons that contain at least one C–C double bond, and Alkynes are hydrocarbons that
contain a C–C triple bond. Occasionally, we find an aliphatic hydrocarbon with a ring of C atoms;
these hydrocarbons are called cycloalkanes (or cycloalkenes or cycloalkynes).

GC1: Lesson 4 / Second Quarter / First Semester / COLumba 2

 Aromatic hydrocarbons have a special six-carbon ring called a benzene ring. Electrons in
the benzene ring have special energetic properties that give benzene physical and chemical
properties that are markedly different from alkanes. Originally, the term aromatic was used to
describe this class of compounds because they were particularly fragrant. However, in modern
chemistry the term aromatic denotes the presence of a six-membered ring that imparts different
and unique properties to a molecule.

(EXPLAIN)
F. Developing mastery
Let’s Study This! Read the notes below:

Functional Groups
Functional groups refer to specific atoms bonded in a certain arrangement that give a
compound certain physical and chemical properties.

The Role of Functional Groups

In organic chemistry, a functional group is a specific group of atoms or bonds within a
compound that is responsible for the characteristic chemical reactions of that compound. The
same functional group will behave in a similar fashion, by undergoing similar reactions,
regardless of the compound of which it is a part. Functional groups also play an important part
in organic compound nomenclature; combining the names of the functional groups with the
names of the parent alkanes provides a way to distinguish compounds.
The atoms of a functional group are linked together and to the rest of the compound by
covalent bonds. The first carbon atom that attaches to the functional group is referred to as the
alpha carbon; the second, the beta carbon; the third, the gamma carbon, etc. Similarly, a
functional group can be referred to as primary, secondary, or tertiary, depending on if it is
attached to one, two, or three carbon atoms.

GC1: Lesson 4 / Second Quarter / First Semester / COLumba 3

Functional Groups and Reactivity
Functional groups play a significant role in directing and controlling organic reactions. Alkyl
chains are often nonreactive, and the direction of site-specific reactions is difficult; unsaturated
alkyl chains with the presence of functional groups allow for higher reactivity and specificity.
Often, compounds are functionalized with specific groups for a specific chemical reaction.
Functionalization refers to the addition of functional groups to a compound by chemical
synthesis. Through routine synthesis methods, any kind of organic compound can be attached
to the surface. In materials science, functionalization is employed to achieve desired surface
properties; functional groups can also be used to covalently link functional molecules to the
surfaces of chemical devices.
In organic chemistry, the most common functional groups are carbonyls (C=O), alcohols (-
OH), carboxylic acids (CO2H), esters (CO2R), and amines (NH2). It is important to be able to
recognize the functional groups and the physical and chemical properties that they afford
compounds.

Alcohols
Alcohols are organic compounds in which the hydroxyl functional group (-OH) is bound to a
carbon atom. Alcohols are an important class of molecules with many scientific, medical, and
industrial uses.

Structure of alcohol
Structure and Physical Properties of Alcohols
The structure of an alcohol is like that of water, as it has a bent shape. This geometrical
arrangement reflects the effect of electron repulsion and the increasing steric bulk of the
substituents on the central oxygen atom. Like water, alcohols are polar, containing an
unsymmetrical distribution of charge between the oxygen and hydrogen atoms. The high
electronegativity of the oxygen compared to carbon leads to the shortening and strengthening
of the -OH bond. The presence of the -OH groups allows for hydrogen bonding with other -OH
groups, hydrogen atoms, and other molecules. Since alcohols can hydrogen bond, their boiling
points are higher than those of their parent molecules.

Application of alcohol (Ethanol)

Ethers
Ethers are a class of organic compounds characterized by an oxygen atom connected to
two alkyl or aryl groups. Ethers are a class of organic compounds that contain an ether group.
An ether group is an oxygen atom connected to two alkyl or aryl groups. They follow the general
formula R-O-R’. The C-O-C linkage is characterized by bond angles of 104.5 degrees, with the

GC1: Lesson 4 / Second Quarter / First Semester / COLumba 4

C-O distances being about 140 pm. The oxygen of the ether is more electronegative than the
carbons. Thus, the alpha hydrogens are more acidic than in regular hydrocarbon chains.

Structure of ether

Properties of Ethers
Ethers are rather nonpolar due to the presence of an alkyl group on either side of the central
oxygen. The presence of the bulky alkyl groups that are adjacent to it means that the oxygen
atom is largely unable to participate in hydrogen bonding. Ethers, therefore, have lower boiling
points compared to alcohols of similar molecular weight. However, as the alkyl chain of the
ethers becomes longer, the difference in boiling points becomes smaller. Ethers are more polar
than alkenes, but not as polar as esters, alcohols, or amides of comparable structures.

Aldehydes and Ketones

Aldehydes and ketones are classes of organic compounds that contain a carbonyl (C=O)
group.
Ketones
When a carbonyl functional group is placed within a molecule, it is known as a ketone.
Ketones are organic compounds with the structure RC(=O)R’, where R and R’ can be a variety
of carbon-containing substituents. IUPAC nomenclature rules dictate that ketone molecules are
named by changing the suffix of the parent carbon molecule to “-one.”

Structure of ketone
Structure of Ketone
Due to the carbonyl group, ketones are polar and can interact with other compounds through
hydrogen bonding; this hydrogen bond capability makes ketones more soluble in water than
related methylene compounds. As a result, ketones are often more volatile than alcohols and
carboxylic acids of comparable molecular weights. Ketones have alpha -hydrogens which
participate in keto-enol tautomerism. In the presence of a strong base, enolate formation and
subsequent deprotonation of the enolate will occur.

GC1: Lesson 4 / Second Quarter / First Semester / COLumba 5

Aldehyde
An aldehyde is an organic compound that contains a carbonyl group with the central carbon
bonded to a hydrogen and R group (R-CHO). Aldehydes differ from ketones in that the carbonyl
is placed at the end of the carbon skeleton rather than between two carbon atoms of the
backbone. Aldehydes are named by dropping the suffix of the parent molecule, and adding the
suffix “-al.”

Structure of aldehyde

Carboxylic Acids
Carboxylic acids are organic acids that contain a carbon atom that participates in both a
hydroxyl and a carbonyl functional group. A carboxyl group (COOH) is a functional group
consisting of a carbonyl group (C=O) with a hydroxyl group (O-H) attached to the same carbon
atom. Carboxyl groups have the formula -C(=O)OH, usually written as -COOH or CO2H.
Carboxylic acids are a class of molecules which are characterized by the presence of one
carboxyl group. Generally, in IUPAC nomenclature, carboxylic acids have an “-oic acid ” suffix,
although “-ic acid” is the suffix most commonly used.

GC1: Lesson 4 / Second Quarter / First Semester / COLumba 6

 Structure of carboxylic acid

Carboxylic acids are used in the production of polymers, pharmaceuticals, solvents, and
food additives. As such, they are often produced industrially on a large scale. Carboxylic acids
are generally produced from oxidation of aldehydes and hydrocarbons, and base catalyzed
dehydrogenation of alcohols.

Esters
Esters are functional groups produced from the condensation of an alcohol with a carboxylic
acid, and are named based on these components. Esters are an important functional group in
organic chemistry, and they are generally written RCOOR’ or RCO2R’. As usual, R and R’ are
both alkyl groups or groups initiating with carbon. Esters are derivative of carboxylic acids
where the hydroxyl (OH) group has been replaced by an alkoxy (O-R) group.

Structure of ester

GC1: Lesson 4 / Second Quarter / First Semester / COLumba 7

 Amines
Amines are compounds characterized by the presence of a nitrogen atom, a lone pair of
electrons, and three substituents. The amine functional group contains a basic nitrogen atom
with a lone pair of electrons. As such, the group is derivative of ammonia, in which one or more
hydrogen atoms have been replaced by a carbon-containing substituent. Compounds with the
nitrogen group attached to a carbonyl within the structure are referred to as amides, and they
have the structure R-CO-NR’R”. Amine groups bonded to an aromatic (conjugated cyclic)
structure are known as aromatic amines.

Structure of amine

Amines are ubiquitous in biology. Many important molecules are amine-based, such as
neurotransmitters and amino acids. Their applications in the world include being starting
material for dyes and models for drug design. They are also used for gas treatment, such as
removing CO2 from combustion gases.

(ELABORATE)
G. Finding practical applications of concepts and skills in daily living
Answer the following on your answer sheet.
Complete the table by drawing the structure of the functional group on the second column and
write one application of this functional group on the third column.

Functional Group Structure of the Functional Application

Group

Alcohol

Ether

GC1: Lesson 4 / Second Quarter / First Semester / COLumba 8

 Ketone

Aldehyde

Ester

Carboxylic acid

Amine

H. Making generalizations and abstractions about the lesson

After studying this lesson, remember the following science concepts:
• All living things contain carbon in some form.
• Carbon is the primary component of macromolecules, including proteins, lipids, nucleic
acids, and carbohydrates.
• Carbon’s molecular structure allows it to bond in many ways and with many different
elements.
• The carbon cycle shows how carbon moves through the living and non-living parts of the
environment.
• Functional groups are collections of atoms that attach the carbon skeleton of an organic
molecule and confer specific properties.
• Each type of organic molecule has its own specific type of functional group.
• Functional groups in biological molecules play an important role in the formation of
molecules like DNA, proteins, carbohydrates, and lipids.
• Functional groups are often used to “functionalize” a compound, affording it different
physical and chemical properties than it would have in its original form.
• Functional groups will undergo the same type of reactions regardless of the compound of
which they are a part; however, the presence of certain functional groups within close
proximity can limit reactivity.
• Due to the presence of an -OH group, alcohols can hydrogen bond. This leads to higher
boiling points compared to their parent alkanes.
• Alcohols are polar in nature. This is attributed to the difference in electronegativity between
the carbon and the oxygen atoms.
• Ethers are a class of organic compounds characterized by an oxygen atom connected to
two alkyl or aryl groups.
• Ketones and aldehydes can undergo keto- enol tautomerism. This refers to the equilibrium
between the two possible tautomers. The interconversion of the two forms involves the
movement of a proton and the shifting of bonding electrons. This equilibrium affords the
compounds more reactivity.
• Ketones and aldehydes participate in a variety of reactions. They can undergo oxidation
reactions, in which they become oxidized to the corresponding carboxylic acids.
• Carboxylic acids are used as precursors to form other compounds such as esters,
aldehydes, and ketones.
• Carboxylic acids can exhibit hydrogen bonding with themselves, especially in non- polar
solvents; this leads to increased stabilization of the compounds and elevates their boiling
points.
• Esters are a functional group commonly encountered in organic chemistry. They are
characterized by a carbon bound to three other atoms: a single bond to a carbon, a double
bond to an oxygen, and a single bond to an oxygen. The singly bound oxygen is bound to
another carbon.

GC1: Lesson 4 / Second Quarter / First Semester / COLumba 9

I. Evaluating learning
Instruction(s): Read each statement carefully. Write A if both statements X and Y are correct.
Write B if the statement X is correct, and statement Y is incorrect. Write C if statement X is
incorrect, and statement Y is correct. Write D if both statements X and Y are incorrect.
______1. X. Ketone is present in small amount in blood and urine.
Y. Ethers are functional groups produced from the condensation of an alcohol with a
carboxylic acid.
______2. X. Carboxylic acid contain a carbon atom that participates in both a hydroxyl and a
carbonyl functional group
Y. Aldehydes differ from ketones in that the carbonyl is placed at the end of the
carbon skeleton rather than between two carbon atoms of the backbone.
______3. X. Amines are present in neurotransmitters and amino acids.
Y. Diethyl ether has a history of medicinal use as anesthetic agent.
______4. X. Ethyl butanoate, an ether, is used as artificial pineapple flavoring for candies and
juices.
Y. Beer and wine contains methyl alcohol.
______5. X. Citral, an aldehyde, can give off odor of oranges.
Y. Acetic acid is present in vinegar (responsible for its sour taste).
______6. X. Benzoic acid acid is used in acne creams and synthesis of aspirin.
Y. Aldehydes and ketones are classes of organic compounds that contain a carbonyl
(C=O) group.
______7. X. Ethers are a class of organic compounds characterized by an oxygen atom
connected to three alkyl or aryl groups.
Y. The structure of an alcohol is like that of water, as it has a bent shape.
______8. X. Functional groups refer to specific atoms bonded in a certain arrangement that give
a compound certain physical and chemical properties.
Y. Alkyl chains are often nonreactive.
______9. X. The atoms of a functional group are linked together and to the rest of the compound
by nonpolar covalent bonds.
Y. Aliphatic hydrocarbons have a special six-carbon ring called a benzene ring.
______10. X. Alkynes are hydrocarbons that contain at least one C=C bond.
Y. Hydrocarbons are compounds that contains Hydrogen and carbon.

II. Identify the name of the following functional groups.

1. 2. 3.

4. 5.

GC1: Lesson 4 / Second Quarter / First Semester / COLumba 10