Science: Organic Compounds and Functional Groups
Science: Organic Compounds and Functional Groups
Science: Organic Compounds and Functional Groups
LESSON 9.2
Organic Compounds and Functional Groups
Table of Contents
Introduction 1
Learning Competency 2
Learning Objectives 2
Warm-Up 2
Learn about It 4
Properties of Organic Compounds 5
Classi cation of Organic Compounds 6
Common Functional Groups and Their Uses 9
Alkanes 10
Straight-chain and Branched-chain Alkanes 12
Some Examples of Alkanes 13
Alkenes 14
Some Examples of Alkenes 15
Alkynes 16
Some Examples of Alkynes 17
Aromatic Hydrocarbons 18
Some Examples of Aromatic Hydrocarbons 19
Alcohols 21
Aldehydes 22
Ketones 24
Carboxylic Acids 25
Esters 27
Ethers 28
Amines 30
Key Points 31
Photo Credits 35
Bibliography 36
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Lesson 9.2
Organic Compounds
and Functional Groups
Large quantities of organic compounds are present in natural gas and petroleum products.
Introduction
Daily living would be impossible without the presence of organic compounds. Moreover,
since there are millions of varieties of organic compounds, it would be challenging to study
these compounds without classifying them. However, are all carbon-containing
compounds considered organic compounds?
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Learning Competency
At the end of this lesson, the given DepEd learning competency should be met
by the students:
● Recognize the general classes and uses of organic compounds
(S9MT-IIh-18).
Learning Objectives
In this lesson, you should be able to do the following:
● Differentiate organic from inorganic compounds.
● Recognize general properties of organic compounds.
● Recognize the general classes of organic compounds.
Warm-Up
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straight-chain made
major component of
octane up of eight carbon
gasoline
atoms
has a hydroxide
major component of
isopropyl alcohol group at a middle
rubbing alcohol
carbon
also known as
formalin, used for one carbon atom
formaldehyde embalming or doubly bonded to an
preserving biological oxygen atom
samples
used as a food
preservative and has a hydroxide
flavoring agent, group (OH–) and a
lactic acid
produced by carboxylic acid group
fermentation of (COOH)
sugar from yogurt
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From the Lewis structures, look at similarities and differences. Group the molecules based
on similar structures. How many groups did you get?
Learn about It
Organic compounds contain carbon and other elements. However, not all carbon-containing
compounds are considered organic compounds. For example, in its carbonate ion (CO3-2)
form, carbon bonds ionically with metals such as calcium and forms an inorganic compound
calcium carbonate (CaCO3). Provided below is the list of all inorganic compounds with
carbon in it.
carbon monoxide CO
carbides C4-
carbonates CO32-
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cyanides CN-
The volatility and viscosity of organic compounds may also differ depending on the
functional groups attached to them. Volatility refers to the ability of a compound to
become vapor, while viscosity refers to the ability of a liquid to resist flowing. The size of
the molecule extremely affects these two properties, as molecules in short chains tend to be
very volatile and less viscous, while molecules in long chains like to be in liquid form and are
very viscous.
Fig. 1. Perfume and honey show the volatility and viscosity of organic compounds.
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Essential Question
What is a functional group?
A functional group is an atom (or a group of atoms) that is mainly responsible for a
molecule's characteristic behavior and properties. Thus, compounds belonging to the same
functional group share common properties. Table 9.2 shows some of the common families
of organic compounds and their corresponding functional groups.
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Organic compounds belonging to the same family have the same functional group. They
have similar properties, and there is a gradual change in their physical properties as more
carbon atoms are added to their chain.
Example
Organic
Functional Group
Compound
Name Structure Use
ethylene helps in
alkenes
(ethene) ripening fruits
acetylene
alkynes used in torches
(ethyne)
dissolves
ketones acetone adhesives and
paints
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preservative
aldehydes formaldehyde used in
embalming
solvent for
ethers diethyl ether
waxes and oils
carboxylic
lactic acid found in yogurt
acid
gives
ester ethyl acetate pineapple’s
scent
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used in oil
amine ethylamine
refining
softener for
amide formamide
fibers
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classifications: alkanes, alkenes, and alkynes. These three differ in the types of bonds
present in them.
Aside from hydrogen and carbon atoms, organic compounds can also contain other
elements. Other classes of organic compounds include oxygen and nitrogen atoms.
Oxygen-containing organic compounds are also classified based on their bond with carbon
atoms.
Alkanes
Alkanes are a group of hydrocarbon compounds that contain carbon-carbon single (C-C)
bonds and carbon-hydrogen (C-H) bonds only. Alkanes have a general formula of CnH2n+2
where n is the number of carbon atoms (n = 1, 2, 3, …). Their names end in –ane. Since
alkanes are the only hydrocarbons that contain purely single bonds throughout their
structures, they are classified as saturated hydrocarbons.
Alkanes are insoluble in water but soluble in organic solvents such as toluene and
chloroform. They are also less dense than water. The physical state of alkanes at room
temperature varies depending on the number of carbon atoms. Those with one to four
carbon atoms are gases, five to seventeen carbon atoms are generally liquid, while those
beyond seventeen are solids.
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Fig. 4. Hexane, an alkane made up of six hydrocarbons, usually exists in liquid form
and is usually used in liquid-liquid extraction procedures.
Generally, alkanes have low melting and boiling points. As more carbon atoms are added to
the alkane chain, there is an increase in melting and boiling points, viscosity, and
flammability decrease.
Alkanes are also known to be generally unreactive. These compounds consist only of single
carbon-carbon bonds and carbon-hydrogen bonds, which are strong and hard to break.
However, they are known to react with oxygen in a process known as combustion. A
hydrocarbon reacts with gaseous oxygen molecules during combustion to form gaseous
carbon dioxide and liquid water. For example, propane, a three-carbon alkane with the
formula C3H8, reacts with five molecules of oxygen gas and forms three molecules of CO2
and four molecules of water, as shown below.
This reaction produces a tremendous amount of heat, which can be used to power up
electrical devices and heat industrial and residential houses. This unique property of
hydrocarbons makes them excellent petroleum products.
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On the other hand, branched-chain alkanes are composed of a parent chain and
substituents. The parent chain is defined as the longest straight-chain alkane present in the
hydrocarbon structure. Substituents are alkyl groups attached to one or more non-terminal
carbon atoms belonging to the parent chain. An example of a branched alkane is
isopropane, whose structure is given below.
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(a) (b)
Fig. 7. (a) Natural gas drilling station in Russia and (b) methane molecule
Another example of an alkane is propane (C3H8), which is used in barbeque and camp
stoves, and liquefied petroleum gas. It is also commonly called bottled gas. Aside from its
commercial use, propane is also used to power heating and refrigeration appliances.
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(a) (b)
Fig. 8. (a) Camp stove powered by bottled gas and (b) propane molecule
Butane (C4H10), like the other two alkanes mentioned above, is a colorless and flammable
gaseous compound. It immediately turns into liquid under 0oC and typical atmospheric
pressure and is mostly used in disposable lighters and LPG.
(a) (b)
Alkenes
Alkenes are hydrocarbon compounds that contain carbon-carbon double (C=C) bond. They
are also known as olefins. They have a general formula of CnH2n, where n is the number of
carbon atoms (n = 2, 3, 4, …). The number of hydrogen atoms is twice the number of carbon
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atoms. Their names end in –ene. Because of the presence of a carbon-carbon double bond,
alkenes are considered unsaturated hydrocarbons.
Just like alkanes, alkenes are generally insoluble and less dense in water. The physical state
of alkenes at room temperature varies depending on the number of carbon atoms. Those
with two to four carbon atoms are gases, five to sixteen carbon atoms are generally liquid,
while those beyond sixteen are solids. The alkenes' boiling point and melting point increase
as more carbon atoms are added to their chain.
They are also highly flammable and very reactive. Their reactivity is brought by the presence
of the carbon-carbon double bond. Alkenes are way more reactive than alkanes. They
decolorize strongly colored reagents such as potassium permanganate (KMnO4) and liquid
bromine (Br2).
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finding ways to inhibit this alkene as high concentrations of synthesized leukotriene can
cause constriction of the lungs, which ultimately results in asthma.
Fig. 11. Leukotriene C causes smooth muscles to constrict. When asthmatic people take in
allergens like pollens, their leukotriene level increases, thus resulting in constriction of the
lungs.
One of the most popular biomolecules which contain an alkene group is β-carotene
(C40H56). This molecule, which is abundant in yellowish vegetables, serves as a precursor to
the synthesis of vitamin A. When vitamin A undergoes an enzymatic reaction, a series of
reactions follows in the retina, enabling our eyes to sense vision in bright, dim, and colored
light.
Alkynes
Alkynes are a group of hydrocarbon compounds containing carbon-carbon triple (C≡C)
bond. They have a general formula of CnH2n–2 where n is the number of carbon atoms (n = 2,
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3, 4, …). Their names end in –yne. The presence of a carbon-carbon triple bond in an alkene
makes it an unsaturated hydrocarbon.
Alkynes are insoluble in water and are slightly soluble in some organic solvents. Like alkanes
and alkenes, alkynes' physical states at room temperature vary depending on the number of
carbon atoms. Those with two to four carbon atoms are gases, five to seventeen carbon
atoms are generally liquid, while those beyond seventeen are solids. They also show an
increase in boiling point and melting point as the number of its carbon atoms increases.
Most are less dense than water, and some are explosives. Some are used in pharmacy,
manufacturing plastics, and artificial ripening of fruits.
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One unique compound which contains alkyne is ichthyotherol (C14H14O2). Poison dart frogs
naturally secrete this compound. Local tribes in the Amazon smudge this poison to their
arrows; victims who were targeted by these arrows experience convulsions due to the
poison.
Aromatic Hydrocarbons
Aromatic hydrocarbons are classified as unsaturated cyclic hydrocarbons. They are also
called arenes. It has the benzene ring as its functional group. A benzene is a six-carbon ring
compound having three alternating double bonds. It contains a hybrid bonding which
results from the alternate single and double bonds. The bond strength is half-way between
a single and double carbon-carbon bond.
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All three double bonds found in the ring can actually move around; this movement of
electrons in benzene is called resonance. This makes the benzene ring structure highly
stable and unreactive.
The name of aromatic hydrocarbons usually ends with -benzene. The simplest aromatic
hydrocarbon is benzene (C6H6).
Aromatic hydrocarbons are known for their aromatic or fragrant smell. Primary sources of
aromatic compounds include petroleum and coal tar. Fragrant oils also contain aromatic
hydrocarbons.
Aromatic compounds are insoluble in water. They are used as solvents in organic reactions.
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Fig. 19. Quinine has been used for a long time as a muscle relief to leg cramps.
Alcohols
ー
Alcohols contain carbon, hydrogen, and oxygen. They have the hydroxyl ( OH) functional
group.
At room temperature and pressure, alcohols exist as volatile liquids, though they still have
higher boiling points than typical hydrocarbons as (1) they can form hydrogen bonds,
and (2) they have higher polarizability due to the rich electrons of oxygen. They are also
soluble in water as long as the molecule has less than five carbon atoms.
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Fig. 21. Ethanol is used as the main ingredient in alcoholic drinks and as solvent in
perfumes.
It is also widely used as a solvent for organic chemicals because it dissolves many insoluble
substances in water. Since it is volatile, it is used in paints, deodorants, perfumes, and
cologne.
Alcohols also undergo combustion reactions. Therefore, they can be used to fuel cars. Some
race cars run on methanol. Methanol is considered a clean fuel. It is less volatile than
petrol. It is also less likely to explode in case of an accident.
Aldehydes
Aldehydes have carbonyl plus a hydrogen atom as their functional group. A carbonyl group
consists of carbon and an oxygen atom connected by a double bond. The carbonyl group in
aldehydes is always found at the end of the carbon chain.
The general formula of aldehydes is RCHO. R can be a hydrogen atom or an alkyl group.
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Generally, the boiling point of aldehydes increases together with their molecular size.
Aldehydes with less than five carbon atoms are soluble in water. Solubility in water
decreases as more carbon atoms are added to the chain of an aldehyde.
Fig. 23. Biological specimens that need to be preserved are placed in formalin.
Aldehydes have high chemical reactivity. They can combine with other molecules to
produce several types of common plastics.
Other examples of aldehydes also include sugars and other natural and synthetic hormones
and compounds such as retinal. Retinal is a derivative of vitamin A, which is important in
vision.
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Ketones
Just like aldehydes, ketones also have carbonyl as their functional group. In fact, ketones
are derivatives of aldehydes. Compared to aldehydes with one R group attached to their
carbonyl group, ketones have two R groups linked in their carbon atom. Hence, the carbonyl
group in ketones is always found in the middle of a carbon chain.
The general formula of ketones is RCOR. R can represent an alkyl group or an aryl group.
Like alcohols and aldehydes, ketones get higher boiling points when their molecular size
increases. Small ketones (those with less than five carbon atoms) are soluble in water due to
the polarity brought by the oxygen atom. In general, ketones are less reactive than
aldehydes.
The most common ketone is acetone (IUPAC name: propanone). Acetone is primarily used
as a solvent for organic compounds such as plastics and synthetic fibers. It is also used as a
major component in nail polish removers and paint thinners.
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Carboxylic Acids
Carboxylic acids are a group of hydrocarbons that contain the carboxyl (-COOH) functional
group. They are produced by oxidizing primary alcohols or aldehydes using potassium
dichromate.
Carboxylic acids normally produce cyclic dimers after forming hydrogen bonds with each
other. Because of this, carboxylic acids generally have higher boiling points than alcohols.
For example, three-carbon alcohol, propanol, has a boiling point of 97 oC, while its carboxylic
acid counterpart, propanoic acid, has a boiling point of 141 oC.
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As the name suggests, carboxylic acids are also weak acids, making them soluble in water
(given the condition that the molecule is composed of less than five carbons). When a
carboxylic acid loses the hydrogen (attached to oxygen) and replaces it with a metal ion, the
whole molecule ultimately becomes soluble in water.
(a) (b)
Fig. 29. Structures of (a) pentanoic acid, which is insoluble in water and
(b) sodium pentanoate, which, on the other hand, is water-soluble
Vinegar is the common name of dilute ethanoic acid. The oxidation of ethanol produces
this. Vinegar is used as a condiment and as a preservative. It is also used as a household
cleaning agent.
Carboxylic acids can be found widely in nature. Amino acids, for example, is a kind of
carboxylic acid that contains both the amino group (-NH2) and the carboxyl group. Amino
acids are the basic building blocks of proteins.
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Esters
Esters are a group of organic compounds produced from an alcohol and a carboxylic acid
reaction. This process is called esterification.
Esters have the functional group -COO. They have the general formula R’COOR, in which R’
can represent hydrogen, an alkyl, or an aromatic hydrocarbon group, and R can be an alkyl
group or an aryl group.
Esters, being sweet-smelling compounds, are responsible for the scent of most fruits and
flowers. As they are derivatives of carboxylic acids, esters are still expected to have higher
boiling points compared to hydrocarbons. This group of compounds is also volatile in
nature. The properties of esters make them suitable in producing artificial food flavorings
and as solvents for cosmetics and perfumes. Esters also naturally occur as animal fats
and vegetable oils, substances used in soap making.
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(a) (b)
Fig. 34. (a) Roses contain citronellyl acetate, which give them their fragrant smell.
(b) In the process of soap making, naturally-containing esters like fats
or oils are boiled with sodium hydroxide to produce soap.
Ethers
An ether group is an oxygen atom bonded to two alkyl or aryl groups. Ethers have the
general formula ROR’. R and R’ can represent alkyl or aryl groups.
Ethers exist as liquids at room temperature. They have slightly higher boiling points than
alkanes and are generally colorless. Ethers are also highly flammable; they can react with
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molecular oxygen to produce peroxides (some can be explosive). On the other hand, they
are unreactive towards acids and bases, making them good solvents.
An example of ether is diethyl ether, which is commonly referred to as ether. This was the
first anesthetic used in surgeries. However, it was discovered to cause nausea and can be
flammable. Scientists have since used methyl propyl ether as an alternative to diethyl ether.
Aside from its medical use, ethers are also widely used in the cosmetics industry. Methyl
phenyl ether (or methoxybenzene) produced by insects and plants is often used as a
precursor to fragrances due to its sweet smell, while polyethylene glycol (PEG) is used as a
thickening and binding agent in toothpastes and moisturizers.
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Amines
Amines are derivatives of ammonia, NH3. In amines, one or more hydrogen atoms are
replaced by a hydrocarbon group. R can be a hydrogen atom or an alkyl group.
Like alcohols, amines also have a higher boiling point compared to alkanes. Some amines
have distinct odors, like smaller ones that smell like fish and diamines (e.g., cadaverine,
putrescine) that smell like decaying bodies.
Compared to alcohols and ethers, amines are considered a stronger base. They form salts
when they react with acids. The salts produced in their reaction are generally colorless and
odorless solids soluble in water.
Amines are involved in the production of amino acids. They also form the basic units of
many vitamins, such as vitamin B1. Vitamin B1 is one of the B-complex vitamins which help
the body convert food into fuel. They also help the body metabolize fats and proteins.
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Amines are widely used in the pharmaceutical industry. Medicines based on amines include
morphine and pethidine. These drugs are commonly used as painkillers.
Key Points
● Organic compounds consist of carbon and hydrogen atoms as their base elements,
have low melting and boiling points, and have high flammability.
● A functional group is an atom (or a group of atoms) that is mainly responsible for a
molecule's characteristic behavior and properties.
● The following are the classifications of organic compounds based on their functional
groups:
○ Alkanes are a group of saturated hydrocarbon compounds that contain
carbon-carbon single (C-C) bonds and carbon-hydrogen (C-H) bonds only and
have a general formula of CnH2n+2 where n is the number of carbon atoms (n =
1, 2, 3, …).
○ Alkenes are a group of unsaturated hydrocarbon compounds that contain a
carbon-carbon double (C=C) bond. Also known as olefins, they have a general
formula of CnH2n, where n is the number of carbon atoms (n = 2, 3, 4, …).
○ Alkynes are a group of unsaturated hydrocarbon compounds that contains
carbon-carbon triple (C≡C) bond. They have a general formula of CnH2n–2,
where n is the number of carbon atoms (n = 2, 3, 4, …).
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________ 5. Alkanes react with oxygen to form carbon dioxide and water.
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Structure Classification
1.
2.
3.
4.
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5.
6.
7.
8.
9.
10.
C. Research examples for each functional group listed. Draw its Lewis structure on the
second column. Then, provide its use in the third column.
ketones
alkyl halide
ester
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amine
alcohol
Photo Credits
Fig. 2. Crude Oil Distillation by Psarianos, Theresa knott is licensed under CC BY-SA 3.0 via
Wikimedia Commons.
Fig. 4. N-Hexane by Danny S.-001 by Danny S. is licensed under CC BY-SA 3.0 via Wikimedia
Commons.
Fig. 14. Three tubes of 'Oblivon' capsules, England, 1953-1967 Wellcome L0058216.jpg by
Science Museum, London is licensed under CC BY 4.0 via Wikimedia Commons.
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