Module

in Organic
Chemistry
Prepared By:
Fontanilla, Mylene Jade H.
Casanillo, Kimberly M.
Balicat, Jade Noel L.
Doctor Jr., Randy G.
Adao, Jan Joyal M.
Carmen, Roselyn M.
Balao, Carnhel H.
Balanon, Thea G.
Casilla, Elna J.
Pitlongay, Julianne Rebecca M.
Sanglay, Roxanne Danielle A.
Orfiano, Lourdes Dianne N.
Tayco, Hannah Pearl N.
Subido, Hazel Mae J.
Nonan, Chris Jan C.
Diaz, Camille M.
Libao, Jojo N.

Instructor
Ms. Joana L. Abando
 PS18/2

Preface

The twentieth century finds man enjoying the comforts and

convenience of modern life, thanks to the great scientific and
technological developments that have taken place in recent years.
This module in Organic Chemistry in an instructional material
designed to facilitate and enrich the teaching-learning process. It
boosts and fortifies the knowledge and skills both required and acquired
in the subject.
This module consists of the basic concepts, such as general
formula, structural formula, IUPAC Naming and Common Naming, Physical
and Chemical Properties and Applications under Organic Chemistry.
Students has the task and responsibility to go through contents of
this module, then perform and accomplish the exercises which is present
at the end of each topic.
For better understanding, a summary of the lesson is given and list
of references is provided at the end of this module.
The authors hope this module will be of great help to students as
they learn and discover Organic Chemistry.
The Authors
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Introduction
Organic chemistry describes the structures, properties,
preparation and reactions of vast array of molecules that we call organic
compounds. We frequently hear the term “organic” in everyday language
where it describes that are “natural”. This is probably a result of the
notion of early scientists that all organic compounds came from living
systems and possessed a “vital force”. However, chemists learned over
170 years ago that this is not the case. Organic compounds are major
components of living systems, but chemists can make many of them in the
laboratory from substances that have no direct connection with living
things. Chemically speaking, a pure sample of an organic compound such
as Vitamin C prepared in a laboratory is chemically identical to a pure
sample of Vitamin C isolated from natural sources such as an orange or
other citrus fruits. Your journey through organic chemistry will be
challenging because of the large amount of information that you will
need to learn and understand.
Organic Chemistry
-is the study of hydrocarbons
Hydrocarbons are carbons with hydrogen attached to it and/or
carbons connected to chains.
Development of Organic Chemistry
In 1685, Organic Chemistry started. Nicholas Lemery studied the
organic compounds that could be found in plants and animals. These are
fats and oil, that came from animals and plants respectively. In 1769,
Scheele isolated the composition of chemical substances from plants and
animals. In 18th century, Antoinne Lavoisier was named as the Father of
Modern Chemistry. He performed the Combustion Experiment, which is a
process used to characterize chemical properties. This experiment is the
reaction of organic substances to Oxygen and it always gives out a
product of Water and Carbon Dioxide. Finally, in 1828, Modern Organic
Chemistry came into the world.
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Chapter I: Alkanes

In this chapter, you will learn how alkanes look like as to their
structure whether it is long chained hydrocarbon or cyclic. You will
also learn the rules on how to name alkanes and its physical properties.
This chapter also discusses different reactions of alkanes as well as
common alkanes and their uses. You are also engaged to activities at the
end of the lesson and advised to learn by heart every bit of the lesson.
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Learning Objectives

At the end of this chapter, the learners should be able to:

 Learn the general structure of an Alkane.

 Identify the different physical and chemical properties.
 Explain the different rules in naming Alkanes.
 Name and draw the different structures of an Alkane.

I. ALKANES

Alkanes are hydrocarbons arranged in a tree structure in which all

carbon atoms are in single bonds. They are considered acyclic (not in
cycle) and saturated (having single bonds) in nature. Alkanes have the
general chemical formula of CnH2n+2. In an alkane, each carbon atom has
4 bonds (either C-C or C-H), and each hydrogen atom is joined to one of
the carbon atoms. The longest series of linked carbon atoms in a molecule
is known as its carbon skeleton or carbon backbone. The size of an alkane
is determined by the number of carbon atoms present on it. Methane (CH4)
is considered as the simplest alkane.
II. CYCLOALKANES

Cycloalkanes are often referred to as cyclic alkanes or

continuously branched alkanes. They contain one or more rings. The
general chemical formula for cycloalkanes is CnH2n. Cyclopropane is
considered as the simplest cycloalkane.
III. NAMING ALKANES AND CYCLOALKANES

The IUPAC Nomenclature System

It is a set of logical rules devised and used by organic chemists
to circumvent problems caused by arbitrary nomenclature.
IV. RULES IN NAMING ALKANES AND CYCLOALKANES:

ALKANES
Rule Number 1:
Identify the parent chain, longest carbon chain (backbone) in the
molecule. If there is more than one carbon chain of equal length, then
identify the chain that is more substituted.
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Examples:
1.) CH3-CH2-CH2-CH3 - Butane
2.) CH3-CH2-CH2-CH2-CH2-CH3 – Hexane

Rule Number 2:
Number the carbon atoms in the longest chain (parent chain)
starting at the end nearest a substituent group.
Examples:
1. CH3-CH2-CH2-CH2-CH3
(1) (2) (3) (4) (5)

(3) (4) (5) (6) (7)

2. CH3-CH-CH2-CH2-CH2-CH3

CH2-CH3
(2) (1)

CH3CH2 CH3
3.) CH3-CH2-CH-CH2-CH-CH3
(6) (5) (4) (3) (2) (1)

Rule Number 3:
Name the parent chain by adding the suffix –ane. Name all the
substituent groups that are attached to the parent chain. The
substituents are named by their respective prefix (example: meth-
methane, eth-ethane, prop-propane, but-butane, etc.) and end with –yl
(if alkyl groups are attached). Names must be arranged alphabetically.
Examples:
1.) CH3-CH2-CH2-CH2-CH3 - Pentane
(1) (2) (3) (4) (5)

(3) (4) (5) (6)

2.) CH3-CH2-CH-CH2-CH2-CH3 - 3-ethylhexane

CH2-CH3
(2) (1)

CH3 CH2-CH3
3.) CH3-CH2-CH-CH2-CH-CH3 - 2-ethyl-4-methylhexane
(6) (5) (4) (3) (2) (1)
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4.) CH3-CH-CH2-CH-CH3 - 2-bromo-4-ethylpentane

Br CH2-CH3

Cl CH3
5.) CH3-CH-CH2-C-CH2-CH-CH2-CH3 -2-chloro-6-ethyl-4,4-dimethyldecane
CH3 CH2-CH2-CH2-CH3
V. CYCLOALKANES

Rule Number 1:
For a mono substituted cycloalkane, the ring supplies the root
name and the substituent group is named as usual. A location number is
unnecessary.
Examples:
1.) Cyclopropane 4.) Cyclopentane

2.) Cyclobutane 5.) Ethylcyclooctane

CH2CH3

3.) Methylyclohexane

CH3

Rule Number 2:
If alkyl substituent is large or complex, the ring may be named
as a substituent group of an alkane.
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Examples:
1.) Cyclopropylcyclobutane

2.) Cyclobutylpentane
CH2-CH2-CH2-CH2-CH3

Rule Number 3:
If several substituents are present on the ring, they are listed
in alphabetical order. Numbering starts at the first cited substituent
of higher alphabetical priority.
Examples:
1.) 1-chloro-3-methylcyclopentane

Cl

CH3

2.) 1,2-dibromo-5-propylcycloheptane

Br CH2-CH2-CH3
Br

Br

3.) 1-bromo-2-chloro-3-methylcyclohexane

Br Cl

CH3
 PS18/9

VI. PHYSICAL PROPERTIES

1. Physical State. The physical state of alkanes depends upon the

intermolecular forces of attraction present between molecules which
turn, depend upon the surface area or the molecules. As the
molecular mass of the alkanes increases, their surface area also
increases, which in turn, increases the intermolecular forces of
attraction and accordingly, the physical state of alkanes changes
from gaseous to liquid and then to solid.
2. Density. The density of alkanes increases with the increase in
molecular mass which increase with the increase in the number of
carbon atoms. All alkanes are less dense than water.
3. Boiling Point. The boiling point of alkanes also increases with
the increase in the molecular mass. In straight chain alkanes, the
increase in boiling points due to the increase in surface area of
the molecules.
4. Melting point. Similar to the boiling points, the melting points
of alkanes also increase in their molecular mass, but there is no
regular variation in melting point. The melting points of alkanes
depend not only upon the size and shape of the molecules but also
on the arrangement of the molecules in the crystal lattice.

VII. CHEMICAL PROPERTIES

With the exception of cyclopropane, alkanes and cycloalkanes are

probably the least reactive class of organic compounds. They are
generally inert towards acids, bases oxidizing and reducing agents. The
low reactivity of alkanes with many reagents can be explained by the
high bond enthalpies or bond energy, the energy that is needed to break
a particular bond in a gaseous compound, of the C-C and C-H bonds and
the very low polarity of the 𝛼- bonds present. Despite their relative
inertness, alkanes undergo several important reactions that are
discussed in the following section.
1. Combustion. Combustion is effectively a technical word for burning.
It usually occurs when a hydrocarbon reacts with oxygen to produce
carbon dioxide and water. Alkanes readily burn in the presence of
oxygen. This combustion of alkanes is highly exothermic, explaining
their use as fuels. In equation it can be represented as:

𝑅 + 𝑂2 → 𝐶𝑂2 + 𝐻2 𝑂

where 𝑅 represents alkane or cycloalkane. Let us take the

combustion of methane for an example.
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𝐶𝐻4 + 𝑂2 → 𝐶𝑂2 + 𝐻2 𝑂
Then we balanced the equation,

𝐶𝐻4 + 2𝑂2 → 𝐶𝑂2 + 2𝐻2O

2. Halogenation. Halogenation is the reaction of halogen with another
substance in which a halogen atom ends up as part of that substance.
The reaction of 𝑅(alkane/cycloalkane) and 𝑋2 (halogens) results to
the incorporation of 𝐼𝑅 and 𝐼𝐻 to alkane and cycloalkane. Halogens
are also known as the heavenly seven in group VIIa of the Periodic
Table of Elements. They are Fluorine, Chlorine, Bromine, Iodine,
Astatine and Ununseptium. In Equation halogenation can be
represented as:

𝑅 + 𝑋2 → 𝑅 − 𝑋 + 𝐻 − 𝑋

where 𝑅 represents alkane or cycloalkane and 𝑋2 represents

halogens. The chlorination of methane shown below provides a simple
example of this reaction.

𝐶𝐻4 + 𝐶𝑙2 → 𝐶𝐻3 𝐶𝑙 + 𝐻𝐶𝑙

3. Substitution. Substitution is the reaction in which a part of small
reacting molecule replaces an atom on a hydrocarbon. It is a non-
stop process aided by sunlight (the process is called photo
activation). Furthermore, it is the complete removal of hydrogen +
an acid. As an example, chlorination of methane is given below.

𝐶𝐻4 + 𝐶𝑙2 → 𝐶𝐻3 𝐶𝑙 + 𝐻𝐶𝑙

𝐶𝐻3 𝐶𝑙 + 𝐶𝑙2 → 𝐶𝐻2 𝐶𝑙2 + 𝐻𝐶𝑙
𝐶𝐻2 𝐶𝑙2 + 𝐶𝑙2 → 𝐶𝐻 𝐶𝑙3 + 𝐻𝐶𝑙
𝐶𝐻𝐶𝑙3 + 𝐶𝑙2 → 𝐶𝐶𝑙4 + 𝐻𝐶𝑙

The first product formed, chloromethane, 𝐶𝐻3 𝐶𝑙, results from

replacement of one H on 𝐶𝐻4 by a 𝐶𝑙. The second product formed,
dichloromethane, 𝐶𝐻2 𝐶𝑙2 , results from replacement of one H on 𝐶𝐻3 𝐶𝑙 by a
𝐶𝑙. The third product formed, trichloromethane, 𝐶𝐻𝐶𝑙3, results from
replacement of one H on 𝐶𝐻2 𝐶𝑙2 by 𝐶𝑙. The fourth product formed,
tetrachloromethane, 𝐶𝐶𝑙4 , results from replacement of one H on 𝐶𝐻𝐶𝑙3, by
𝐶𝑙.
VIII. COMMON ALKANES AND THEIR USES

Alkanes are both important raw materials of the chemical industry

and the most important vehicle fuels. The two primary sources of alkanes
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are natural gas and crude oil. Crude oil is a mixture of liquid alkanes
and other hydrocarbons. Natural gas contains primarily methane with some
ethane, propane and butane; some gas sources deliver up to 8% CO2. Some
of the common alkanes are:

Methane 𝐶𝐻4
Ethane 𝐶𝐻3 − 𝐶𝐻3
Propane 𝐶𝐻3 − 𝐶𝐻2 − 𝐶𝐻3
Butane 𝐶𝐻3 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻3
Pentane 𝐶𝐻3 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻3
Hexane 𝐶𝐻3 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻3
Heptane 𝐶𝐻3 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻3
Octane 𝐶𝐻3 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻3
Nonane 𝐶𝐻3 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻3
Decane 𝐶𝐻3 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻3
The uses of alkanes can be determined according to the number of
carbon atoms present in it. Some of the common uses of alkanes are:

 Heating
 Electricity generation
 Cooking production of polymers
 Serve as intermediate in the synthesis of drugs, pesticides
and other chemicals
 Components of gasoline
 Paraffin wax

The first four alkanes are used for heating, cooking and
electricity generation. The main components of natural gas are methane
and ethane.
Propane and butane are used as LPG (Liquefied Petroleum Gas).
Propane is also used in the propane gas burner, butane in disposable
cigarette lighters. They are also used as propellants in aerosol sprays.
The alkanes from pentane to octane are highly volatile liquids and
good solvents for non-polar substances. They are used as fuels for
internal combustion engines.
Alkanes from nonane to hexadecane are liquids of higher viscosity,
being used in diesel and aviation fuel. The higher the melting point of
these alkanes can cause problems at low temperatures and in Polar
Regions, where the fuel becomes viscous.
Alkanes with 17 to 35 carbon atoms form the major component of
lubricating oil. They also act as anti-corrosive agents, as their
hydrophobic nature protects the metal surface from contact with water.
Solid alkanes also find use as paraffin wax in candles.
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Alkanes with a chain length above 35 carbon atoms are found in

bitumen (as it is used in road surfacing). These higher alkanes have
little chemical and commercial value and are usually split into lower
alkanes by cracking.
IX. SUMMARY

Alkanes are saturated hydrocarbons with the general chemical

formula of CnH2n+2. Continuously branched alkanes are referred to as
cycloalkanes or cyclic alkanes. The general chemical formula for
cycloalkanes is CnH2n. In naming alkanes we follow a set of logical rules
devised and used by organic chemists to circumvent problems caused by
arbitrary nomenclature known as IUPAC Nomenclature System.
Physical properties are the same to both alkanes and cycloalkanes.
Generally, alkanes and cycloalkanes are insoluble in water but are
soluble in organic solvents. They have lower density than water and
exhibits high boiling point. Alkanes are generally inert towards acids,
bases oxidizing and reducing agents but despite of this relative
inertness, they still undergo several important reactions. They react
with oxygen to produce carbon dioxide and water through combustion. They
react with halogens through halogenation which results to the
incorporation of IR and IH to alkane and cycloalkane. In substitution
reaction, they react with halogens for the complete removal of hydrogen
+ an acid.
The uses of alkanes can be determined according to the number of
carbon atoms present in it. Some of the common uses of alkanes are for
heating, electricity generation and cooking production of polymers which
serve as components of gasoline, paraffin wax and as intermediate in the
synthesis of drugs, pesticides and other chemicals.
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X. EXERCISES

I. Direction. Write the word TRUE if the statement is correct and FALSE
if it is incorrect. Place your answers on the space provided before each
number.
________1.)Alkanes are either acyclic or cyclic and are unsaturated in
nature.
________2.)The IUPAC nomenclature system is a set of rules used to
eliminate problems in arbitrary nomenclatures.
________3.)In naming branched cycloalkanes, the alphabetical order of
substituents is not necessary.
________4.)The longest carbon chain is considered as the parent chain
or the backbone of the molecule.
________5.)Cycloalkanes are often termed as cyclic alkanes because they
exhibit a ring-like structure.
II. Show what is asked for the following alkanes.
1. Butane
a) combustion
b) halogenation
c) substitution

2. Pentane
a) combustion
b) halogenation

III. Give the condensed formula of the following alkane.

1. 2,3-dimethylpentane
2. 4-butylheptane
3. 1,2-dibromopentane
4. 1,2-dimethylcyclohexane
5. 1-cyclobutane-3-cyclopropanecyclohexane

IV. Give the name of the following Alkanes and Cycloalkanes.

CH3
1.) CH3-CH2-CH-CH-CH3
CH2-CH3
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Br
2.) CH3-CH-CH-CH2-CH2-CH-CH2-CH3
Cl CH2-CH2-CH3

3.) Br
F

CH3

4.)
Cl

CH2-CH3

CH2-CH3
5.) CH-CH2-CH-CH2-CH2-CH3
CH2-CH-CH-CH3
Cl F
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Chapter II: Alkenes

This chapter introduces the general structure, kinds and common

forms of Alkenes. The physical and chemical properties and preparations
are also discussed. Emphasis is given on the rules of naming different
kinds of Alkenes.
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Learning Objectives

At the end of this chapter, the learners should be able to:

 To know and identify the parent chain in Alkenes.

 To appreciate that Alkenes are not only used as fuels but also as
building blocks to produce other chemicals.
 To apply the knowledge about Alkenes in identifying chemicals in
everyday life.

I. ALKENES

Alkenes contain carbon-carbon double bonds and are unsaturated

hydrocarbons.
Molecular formula: CnH2n.
Prefix + ‘ene’
Simplest: Ethene (CH2 = CH2)

II. IUPAC NAMING

1. Locate the longest Carbon chain.

CH2 = CH-CH2-CH2-CH3

2. Number the chain nearest to the double bond.

1 2 3 4 5
CH2 = CH-CH2-CH2-CH3
1 2 3 4 5
CH2 = CH-CH2-CH2-CH3

CH2CH3

3. Alkenes are named as if they were alkanes, but the "-ane" suffix is
changed to "-ene". If the alkene contains only one double bond and that
double bond is terminal (the double bond is at one end of the molecule
or another) then it is not necessary to place any number in front of the
name.

butane: C4H10 (CH3CH2CH2CH3)

butene: C4H8 (CH2=CHCH2CH3)

Pentene CH2 = CH-CH2-CH2-CH3

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1 2 3 4 5
4-ethylpentene CH2 = CH-CH2-CH-CH3

CH2CH3

4. If the double bond is not terminal, then the carbons should be numbered
in such a way as to give the first of the two double-bonded carbons the
lowest possible number, and that number should precede the "ene" suffix
with a dash, as shown below.
1 2 3 4 5
2-pentene CH3CH=CHCH2CH3

2-ethyl-5-methyl-2-hexene CH3C=CHCH2CHCH3

CH2CH3 CH3

1-methylcyclobutene

cyclopentene

5. If there is more than one double bond in an alkene, all of the bonds
should be numbered in the name of the molecule - even terminal double
bonds. The numbers should go from lowest to highest, and be separated
from one another by a comma. The IUPAC numerical prefixes are used to
indicate the number of double bonds. If more than one double bond is
present the compound is named as a diene, triene or equivalent prefix
indicating the number of double bonds and each double bond is assigned
a locator number.

2,4- octadiene: CH3CH=CHCH=CHCH2CH2CH3

1,5- decadiene: CH2=CHCH2CH2CH=CHCH2CH2CH2CH3

5 Br 6

4 CH3 1

3 Cl 2
6-bromo-2-chloro-1-methyl-1, 3-cyclohexadiene
 PS18/18

III. PHYSICAL PROPERTIES

Physical state

At room temperatue, alkenes exist in all three phases, solid,

liquids, and gases. Ethene, Propene, and Butene exists as colorless
gases. Members of the 5 or more carbons such as Pentene, Hexene, and
Heptene are liquid, and members of the 15 carbons or more are solids.

Density

Alkenes are lighter than water and are insoluble in water due to
their non-polar characteristics. Alkenes are only soluble in nonpolar
solvents.

Solubility

Alkenes are virtually insoluble in water, but dissolve in organic

solvents. The reasons for this are exactly the same as for the alkanes.

Boiling Points

Boiling points of alkenes depends on more molecular mass (chain

length). The more intermolecular mass is added, the higher the boiling
point. Intermolecular forces of alkenes get stronger with increase in
the size of the molecules.

Melting Points

Melting points of alkenes depends on the packaging of the

molecules. Alkenes have similar melting points to that of alkanes;
however, in cis isomers molecules are package in a U-bending shape,
therefore, will display a lower melting point to that of the trans
isomers.

Polarity

Alkenes display weak dipole-dipole interactions due to the

electron-attracting sp2carbon. The sp2 carbon is much more electron-
withdrawing than the sp3 hybridize orbitals, therefore, creates a weak
dipole along the substituent weak alkene carbon bond. The two individual
dipoles together form a net molecular dipole. In trans-subsituted
alkenes, the dipole cancels each other out. In cis-subsituted alkenes,
there is a net dipole, therefore contributing to higher boiling in cis-
isomers than trans-isomers.
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IV. CHEMICAL PROPERTIES

1. Combustion
Alkenes, like alkanes, are highly combustible. Alkenes burn with a
luminous flame to give carbon dioxide and water. The flame becomes
luminous because of the higher carbon content of alkenes than alkanes.
Their combustion reactions are exothermic.

CnH2n + O2 H2O + CO2

Ex.
Butene (C4H8)
C4H8 + 6O2 4H2O + 4O2
2. Halogenation
Alkenes react with halogens to break the double bond.
Halogens are the six elements in Group VIIA, the next-to-last column of
the periodic table. These elements all form diatomic molecules (H2, F2,
Cl2, Br2, I2, and At2), and they all form negatively charged ions.

Ex.

Butene (C4H8) with Cl2

CH3CH=CHCH3 + Cl2 CH3CH-CHCH3

Cl Cl

V. PREPARATIONS

1. Dehydrohalogenation of alkyl halides

The dehydrohalogenation of alkyl halides, involves the loss of a

hydrogen and a halide from an alkyl halide (RX). Dehydrohalogenation is
normally accomplished by reacting the alkyl halide with a strong base,
such as sodium ethoxide.
 PS18/20

In the reaction of 2‐chlorobutane with sodium ethoxide, the major product

is 2‐butene.

Dehydrohalogenation reactions proceed via the following mechanism.

1. A strong base removes a slightly acidic hydrogen proton from the

alkyl halide via an acid‐base reaction.

2. The electrons from the broken hydrogen‐carbon bond are attracted

toward the slightly positive carbon atom attached to the chlorine
atom. As these electrons approach the second carbon, the halogen atom
breaks free, leading to the formation of the double bond. The
diagram below summarizes this mechanism.

2. Dehalogenation.

Vicinal dihalides, which are alkane molecules that contain two

halogen atoms on adjacent carbon atoms, can form alkenes upon reaction
with Zinc.
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3. Dehydration of alcohols.

A molecule of water is eliminated from an alcohol molecule by

heating the alcohol in the presence of a strong mineral acid. A double
bond forms between the adjacent carbon atoms that lost the hydrogen ion
and hydroxide group.

The mechanism of this dehydration reaction consists of the following

steps.

1. Protonation of the alcohol.

This step is a simple acid‐base reaction, which results in the

formation of an oxonium ion, a positively charged oxygen atom.

2. Dissociation of the oxonium ion.

Dissociation of the oxonium ion produces a carbocation, which

are positively charged carbon atom and an unstable intermediate.

3. Deprotonation of the carbocation.

The positively charged end carbon of the carbocation attracts

the electrons in the overlap region that bond it to the adjacent a
carbon. This electron movement makes the α carbon slightly positive,
which in turn attracts the electrons in the overlap regions of all other
 PS18/22

atoms bonded to it. This results in the hydrogen on the α carbon becoming
very slightly acidic and capable of being removed as a proton in an acid‐
base reaction.

VI. COMMON ALKENES AND THEIR USES

Alkenes are produced from the alkanes in crude oil by a process

called cracking. Cracking uses heat and a catalyst to decompose alkanes.
The cracking process is important because it turns less useful alkanes
into more useful smaller ones and produces very useful alkenes like
ethene, the starting material for many plastics.

Ethene (C2H4) is an important raw material for the petrochemical

industry. More commercial chemicals are produced from Ethene than from
any other hydrocarbon intermediate. This unique position of ethene is
due to favorable inherent properties as summarized below :

a. Simple but reactive structure

b. Inexpensive
c. Easily available through cracking of hydrocarbons

Alkenes are extremely important in the manufacture of plastics.

All plastics are in some way related to alkenes. The names of some
plastics (Polythene or Poly Ethene, Polypropene), relate to their alkene
partners.

Lower alkenes are used as fuel and illuminant. These may be obtained
by the cracking of kerosene or petrol.

Alkenes are also use for the manufacture of a wide variety of

polymers, (e.g., polyethene, polyvinylchloride (PVC) and teflon etc) and
also as raw materials for the manufacture of industrial Chemicals such
as alcohols, aldehydes, and etc.

Alkenes are also used for artificial ripening of fruits, as a

general anesthetic, for making poisonous mustard gas (War gas) and
ethylene-oxygen flame.

VII. SUMMARY

Alkenes are family of unsaturated hydrocarbons containing Carbon-

Carbon double bond. It can be express using the general formula: CnH2n
with Ethene (CH2=CH2) being the simplest. The physical properties of
Alkanes and alkenes are almost the same. Alkenes are named with the
prefix + ‘ene’. They also undergo chemical reactions such as Combustion
and Halogenation. Alkenes are usually produced from Alkanes in crude oil
 PS18/23

by cracking and are important material for petrochemical industry,

manufacture of plastics and for ripening of fruits.

VIII. EXERCISES

A. Give the correct name for the following:

1. CH3-CH2-CH=CH-CH3

2. CH3-CH2-C=CH-CH3

CH3

3. CH3-CH2-C=CH2

CH2-CH2-CH2-CH2-CH3

4.

CH3

Cl
5.
CH3

CH3CH2CH2 CH3

6. CH3-CH-CH-CH-CH=CH2

CH3

7. CH2=CH-C=CH2

CH2-CH2-CH3

8.
 PS18/24

9. Br

10. CH2=CH-CH2-CH3

B. Draw the structural formula for the following:

1) 1,2-dichlorobutene
2) 1,3-dichlorocyclobutene
3) 1,4-cyclohexadiene
4) 2-ethyl-1,4-octadiene
5) 4-propyl-2-heptene
6) 2,3-cyclohexadiene
7) 3-ethyl-1-propene
8) 1,7-octadiene
9) 2,2,3-trimethylheptene
10) cyclooctene
 PS18/25

Chapter III: Alkynes

This Chapter talks about the Unsaturated Hydrocarbon (alkyne,) the

nomenclature of alkynes, its physical and chemical properties,
preparations, Common alkynes and their practical uses.
 PS18/26

Learning Objectives

At the end of the lesson, the student will be able to:

 Understand what are alkynes and its importance.

 Appreciate the uses of alkynes in everyday living.
 Perform activities on the reactions of Alkynes.

I. ALKYNES

Alkynes are unsaturated hydrocarbons which are organic chemical

compounds containing Carbon (C) and Hydrogen (H) atoms, and the feature
that makes them recognized as alkynes is the presence of triple bonds.
GENERAL FORMULA- CnH2n- 2

STRUCTURAL FORMULA: HC≡CH

Ethyne is the simplest alkyne.

II. IUPAC NAMING

1. Find the longest carbon chain that includes both carbon of the triple
bond.
3 2 1
CH3- CH2- CH2- C≡ CH3
|
4 CH2
|
5 CH2
|
6 CH3

1 2 3 4 5 6 7
CH3- C≡ C- CH2- CH2- CH2- CH3
|
CH2
|
CH3

2. After finding the longest chain, change the -ane ending of the parent
alkane to -yne.
 PS18/27

1. CH≡CH – Ethyne

2. CH3- C≡CH - Propyne

3. CH3- C≡ C- CH3 - Butyne

3. If there is substituent, label each of the substituent at its

corresponding carbon. While writing out the name of the molecule, arrange
the substituents in alphabetical order. If there is more than one of the
same substituents, use the prefix di, tri, tetra, etc. This prefixes are
not taken into account in the alphabetical order.

Cl Cl CH3
| | |
1. CH3- CH2- CH2- CH2- CH2- C≡ CH
|
CH3

4,5- dichloro- 3,3- dimethyl heptyne

*If the substituent is Alcohol (OH). The suffix should be -ynol, because
the alcohol group takes priority over the triple bond.
Cl Cl CH3
| | |
CH3- CH2- CH2- CH2- CH2- C≡ CH
| |
OH CH3

3,4- Dichloro- 5,5- dimethyl- 6-heptyne- 3-ol

4. When there are 2 triple bonds in the molecule, number the longest
chain starting at the end closest to the triple bond that appears first.
The suffix should be used to name this molecule should be
-diyne.

Ex. CH3- C≡C- C≡CH

1,3- pentadiyne

5. If there is alkene (double bonded Carbon to Carbon atom), alkene takes

place over the triple bond.
1 2 3 4 5
Ex. CH2=CH- CH2- C≡CH
 PS18/28

1-penten-4-yne

*But other books: A molecule that contains both double bonds and triple
bonds is called alkenyne. The Chain can be numbered starting with the
end closest to the functional group that appears first.

C≡ CH2- CH- CH= CH- CH2-CH3

|
CH3

3- Methyl- 1,4- nonenyne

III. 2 TYPES OF ALKYNES

1. Terminal Alkynes
- At the beginning or at the end of the Carbon chain.

CH≡ C- CH2 –C≡CH

2. Internal Alkynes
- At the middle of the chain.

CH3- CH2- C≡ C- CH2- CH3

* Internal alkynes have the highest boiling point than terminal alkynes
because we have to break first the triple bonds on the terminal until
to the internal part of the chain.

IV. PHYSICAL PROPERTIES

 Insoluble in water but soluble in organic solvents (ether,

alcohol, etc.)
 Colorless and odorless.
 Less dense than water (float).
 The longer the carbon chain, the longer the required boiling
point.
 Alkynes have the highest boiling point than alkenes and
alkanes.
 Mostly in gaseous form (acetylene, propylene, and butyne) at
room temperature.
 PS18/29

V. CHEMICAL PROPERTIES

1. Combustion
- Burn in air with a luminous alkyne, smoky flame forming CO2 and H2O.
Formula: CnH2n-2 + (3n- 1/2)O2→ (n)CO2 +(n+1)H20
Ex. 1. 2C2H2+ O2 →4CO2+ 2H2O
11
2. C4H6 + /2O2 →4CO2+ 3H2O

2. Oxidation
- Alkyne is oxidized by a dilute aqueous solution of Potassium
Permanganate (KMnO4) to form oxalic acid (O=COH). Thus, if alkyne is
bubbled through a solution of KMnO4, the solution will be decolorized.
This is Baeyer's test for unsaturated organic compound.
KMnO4
Ex. 1. C2H2 + O2 → O=COH

KMnO4
2. C4H6 + O2 → O=COHC3H5

3. Addition Reaction
- Because of the unsaturated nature of alkyne, addition reaction can
occur across the triple bond.

A. Addition of Hydrogen
- When alkyne and H+ are passed over the catalyst (nickel) at 150°C,
alkene is formed first and then, this is further reduced to alkane.
Ni/Pt
C2H2+H2 → C2H4 + H2 → C2H6

B. Addition of Halogen
- Ethyne reacts explosively with chlorine at room temperature forming
Hydrogen chloride and Carbon. To control the reaction, acetylene and
chlorine (or bromine) is added. The product is halogenated alkane.
Ex. 1. C2H2 + Cl → Cl2CH2CL
2. CH≡C- CH2- CH3 + Cl2 → CH2= C- CH2- CH3
| |
Cl Cl
 PS18/30

C. Addition of Hydrogen Halides/ Binary acids.

- Alkyne reacts with halogen acid at 100°C, there is no catalyst in the
reaction.
Ex. 1. C4H6 + HCl → C4H6 –Cl
2. C5H8 + HCl → C5H9 –Cl

D. Addition of Water (Hydration)

- Hydration of ethyne occurs when the gas is passed to a dilute Sulfuric
acid (H2SO4) at 60°C. Mercuric Sulfate (HgSO4) is used as a catalyst for
the reaction.
Naming: Alkyne + H2O → ”nal”
Ex. 1. C2H2 + H2O → CH3CHO (Ethanal)

2. C4H6 + H2O → C3H7CHO (Butanal)

4. Nitrile formation
- 573°C
Alkyne + NH3 → prefix to nitrile + H2

Ex. 1. C2H2 + NH3 → CH3CN+ H2

2. C4H6 + NH3 → C3H7CN + H2

VI. PREPARATION

DECOMPOSITION/DEHYDROHALOGENATION
FORMULA: R-X + Hydroxides/Halides→H2O+ NaX + RX

This reaction is particularly useful since dihalides are readily obtained

from the corresponding alkenes by addition of halogen.

Ex. 1. C2H2Br2+ H2O+ NaBr +BrC2H

2. C5H10Br2+ H2O+KBr+BrC5H7

DEHALOGENATION
-This reaction is severely limited by the fact that these halides are
themselves generally prepared from the alkynes. The triple bond maybe
 PS18/31

protected by conversion into a tertrahalide with subsequent regeneration

of the triple bond by treatment with zinc (Zn).

Br Br
| |
Ex. 1. CH-CH + 2Zn→ 2ZnBr2 + CH≡CH
| |
Br Br

2. CH3-CH-C-CH3 + 2Zn → 2ZnBr2 + CH3 –C≡C-CH3

VII. COMMON ALKYNES AND THEIR USES

ACETYLENE
- for welding/cutting metals
- fuel for welding
- act as refrigerant
- ingredients for contraceptives, rubbers and fiber glass
- for ripening of fruits
- generally they are poisonous (indirect ingestion)

PROPYNE
- also known as methylacetylene
- commonly used as a substitute for acetylene as fuel for welding
torches.
- it is also being investigated as possible fuel for rockets in space
crafts.

VIII. SUMMARY

Many of the reactions of alkynes are similar to the corresponding

reactions of alkynes because both involve π bonds between 2 carbon atoms.
Like the π bond of an alkene, the π bonds of an alkyne are also electron
rich and readily undergo addition reactions. Alkynes are also used in
many industries (for welding purposes, production of plastics,
ingredients for contraceptives, etc.)
 PS18/32

IX. EXERCISE

A. Name the following Alkynes:

CH3
|
1. CH3- C≡ C-C- CH- CH2-CH3
| |
CH3 CH3

OH Cl CH3
| | |
2. CH3- CH2-CH2- CH2- CH2- C≡CH
| | |
OH Cl CH3

Cl
|
3. CH2 =CH2-C -CH2-C≡C- CH3
|
Cl

Cl Br
| |
4. CH3- CH2- CH2- CH2- C≡ CH3
| | |
OH OH OH

5. CH2 =CH2- CH2- CH2- C≡ CH

6. CH3- CH2- C≡ C- CH- CH2

| | |
Br Br CH3

7. CH3- CH2- C≡ C- CH2- CH3

B. give the structural formula of the following:

1. 4- methyl- 2-pentyne
2. 3-hepten- 5-yne
3. 3-chloro-2-methyl-4-pentyne-1-ol
 PS18/33

4. 2,4-dihexyne
5. 5,6-dimethyl- 1-heptyne
6. ethyne
7. 2,3-dibromo-4-chloro-7-octyne-5,6-diol

C. Perform the following chemical reactions of Alkynes:

1. Oxidation of Hexyne
2. Combustion of Pentyne
3. Nitrile formation of octyne
4. Halogenation of Butyne
5. Hydration of Propyne
6. Decomposition of Octyne
 PS18/34

Chapter IV: Alcohols,

Ether and Thiols

This chapter discusses what is alcohol, its classifications,

physical and chemical properties. It explains how alcohols were prepared
and named. Functions of common alcohols and phenols, and tests for
alcohol and phenol identification are also given.
This chapter will bring you into the world of alcohols, ethers and
thiols. How they are different from each other will be explained and
discussed in detail.
 PS18/35

Learning Objectives

By the end of the chapter, the students will be able:

 to differentiate alcohols, ethers and thiols from other functional

groups
 to draw the structural formula of alcohols, ethers and thiols
 to appreciate the uses and functions of different alcohols, ethers
and thiols

ALCOHOLS

I. DEFINITION OF ALCOHOLS
Alcohols are organic compounds containing a hydroxyl (-OH)
functional group that is connected to a saturated carbon atom. Alcohols
include a part consisting of an oxygen atom (attached to one of the
carbon atoms in the molecule), to which a single hydrogen atom is also
attached. Its general formula is R-OH.

II. CLASSIFICATION OF ALCOHOLS

The classification of compounds makes their study systematic and
hence simpler. Therefore, let us first learn how alcohols were
classified.
Alcohols are classified according to how many carbon atoms are
attached to carbon bearing the OH group:
1. A primary alcohol (1ᵒ) is an alcohol in which
the hydroxyl group is bonded to ONE carbon atom.

2. A secondary alcohol (2ᵒ) is an alcohol in which

the hydroxyl group is bonded to TWO carbon atoms.

4. A tertiary alcohol (3ᵒ) is an alcohol in

which the hydroxyl group is bonded to THREE
carbon atoms.
 PS18/36

III. PROPERTIES of ALCOHOLS

Alcohols exhibit unique set of physical and chemical properties.

These properties are mainly due to the presence of hydroxyl group (-OH).
Some prominent physical and chemical properties of alcohols are given
below:
PHYSICAL PROPERTIES
Many of the physical properties of alcohols are directly related
to the hydrogen bonding exhibited by the hydroxyl group. Some of its
physical properties are stated below:
1. Physical state. Most of alcohols up to 12 carbon atoms appear to be
liquid at room temperature while alcohols with more than 12 carbon atoms
appear to be solid at room temperature.
2. Boiling point. Alcohols have higher boiling points in comparison to
other hydrocarbons. This is due to the intermolecular hydrogen bonding
between hydroxyl groups of alcohols. It’s boiling point increases with
increase in number of carbon atoms. On the other hand, it decreases with
increase of branching in carbon chain (because of decrease in van der
Waals forces with decrease in surface area).
3. Solubility. Hydrogen bonds between water and alcohol makes alcohol
soluble in water. This decreases as the length of chain increases because
of high energy requirement to break the hydrogen bonds.
4. Miscibility. Alcohol’s lower molecular mass caused it to be miscible
with water.
5. Odor. The unpleasant odor is produced in alcohols with more than 4
carbon atoms while pleasant odor is produced in alcohols with 1-3 carbon
atoms.
6.Flammability. Alcohols are also flammable compounds. It’s flammability
decreases as its size and mass increases this is due to high energy
requirement to break energy bonds.
7. Viscosity. Alcohols also have the ability to resist flow. This ability
is called as viscosity.
8. Acidity. Alcohols react with active metals such as sodium, potassium
etc., these reactions of alcohols indicate their acidic nature. The
acidic nature of alcohols is due to the polarity of –OH bond.
CHEMICAL PROPERTIES

Alcohols are versatile compounds. They exhibit wide range of

chemical properties. Some of them are the following:
 PS18/37

1. Combustibility
It is the ability of alcohols to break covalent bonds in order to
increase its mass and size of molecules.
R-OH + (1.5n)O2 (n+1)H2O + nCO2
Example:
CH3CH2OH + 3O2 4H2O + 3CO2

2. Reaction with Sodium

Alcohols react with active metal like sodium yield corresponding
alkoxides and hydrogen.
2R-OH + 2Na 2R-O-Na + H2
Example:
2CH3CH2CH2OH + 2Na 2CH3CH2CH2-O-Na + H2
3. Esterification
Alcohols react with carboxylic acids, acid chlorides and acid
anhydrides to form esters.
a. Esters from carboxylic acid and alcohols
O O
R-OH + R-C-OH R-CO-R + H2O
Example:
O O
CH3CH2OH + CH3COH CH3COCH2CH3 + H2O
b. Esters from acid chlorides and alcohols
Example:
CH3COCl + CH3CH2OH CH3COOCH2CH3 + HCl
c. Esters from acid anhydrides and alcohols
Example:
(CH3CO)2O + CH3CH2OH CH3COOCH2CH3 + CH3COOH
4. Alcohol Dehydration
a. Intramolecular alcohol dehydration is a dehydration reaction
in which the components of water (-H and -OH) are removed from the
alcohol at 180ᵒC with the aid of sulphuric acid as catalyst to form
 PS18/38

alkenes. Intramolecular hydrogen bond is formed within the same

molecule.
Example: CH3-CH2-CH2-OH CH3-CH=CH2 + H2O
b. Intramolecular alcohol dehydration is a dehydration of two
alcohol molecules combine to form an ether at 140ᵒC. Only true to primary
alcohols. Intermolecular hydrogen bond is formed between non-identical
molecule.
Example: Two methanol dimethyl ether + water
IV. PREPARATIONS OF ALCOHOLS

1. Reduction of Carbonyl Compounds

a. Catalytic hydrogenation of aldehydes and ketones
b. Use of hydride reagents
b.1 Reduction of aldehyde leads to primary alcohol
RCOH + H2 R-CH-R
OH
Example: CH3COH + H2 CH3CH2
OH
b.2 Reduction of ketone leads to secondary alcohol
RCO + H2 R-CH-R
OH

Example: CH3CH3CO + H2 CH3CHCH3

OH

c. Hydration of Alkenes
The addition of an alkene and a water will be producing an
alcohol.
V. TESTS FOR ALCOHOLS

Alcohols undergo tests in order to determine its identity,

structure and particular kind of alcohol. Some known tests used for
alcohols are stated below:
 PS18/39

1. Iodoform Test is a specific test for alcohols which have a free methyl
group (- CH3 )and a hydrogen attached to the carbon bearing the hydroxyl
group such as ethanol and sec-butanol. The alcohol is oxidized to the
corresponding aldehyde or ketone by the action of the produced oxidizing
agent such as sodium hypoiodite, which also causes the aldehyde or ketone
to be tri-iodinated on the terminal methyl group producing iodoform as
a yellow precipitate.
2. Lucas Test is performed to distinguish between the different types
of alcohols (primary, secondary, or tertiary)
3. Salicyclic Acid Test is used to form methyl salicylate (oil of
wintergreen) with the involvement of the reaction between methanol and
salicylic acid.
4. Resorchinol Test is a test with different steps. First is the
oxidation of formaldehyde with resorcinol and concentrated sulphuric
acid to form a pink or purple junction between acid and resorcinol layer.
5. Arcolein Test is done specifically for glycerol, it involves
dehydration by the aid of Potassium hydrogen sulphate to form an
unsaturated aldehyde.

VI. PHENOLS

Phenols are organic compounds in which an —OH group is attached to

a carbon atom that is part of an aromatic carbon ring system or an
arylgroup (aromatic carbon ring system from which one hydrogen atom has
been removed). Its general formula is Ar-OH.
VI.1. PHYSICAL PROPERTIES OF PHENOLS: Simple phenols are liquids
or low- melting solids, frequently with a very characteristic odor,
moderately soluble in water and very soluble in most organic solvents.
They are generally very toxic.
Examples:

VI.2. CHEMICAL PROPERTIES OF PHENOLS: Unlike alcohols, phenols are

weak acids in solutions. Phenols have antioxidant and antiseptic
properties.
 PS18/40

VI.3. TESTS FOR PHENOLS: Phenols are identified through Ferric

chloride Test and Millon’s Test. Ferric chloride test are specifically
used to phenolic compounds having a free ortho position and those which
do not contain electron-attracting groups. It produces violet color
indicating that it is a phenol. Another, Millon’s test is used to
determine amino acid tyrosine. It produces red to pink color of solution
indicating a positive result for phenols.

VII. NOMENCLATURE FOR ALCOHOLS and PHENOLS

A. Common Naming
Rule 1: Name all of the carbon atoms of the molecule as a single alkyl
group.
Example: Methyl (C1), Ethyl (C2), propyl (C3) butyl (C4) − Rule 2:
Add the word alcohol, separating the worlds with a space.
Example: CH3OH-methyl alcohol, CH3CH2OH-ethyl alcohol
B. IUPAC System
Rule 1: Name the longest chain from the end nearest the –OH group. For
the chain name, the -e in alkane name is replaced with -ol.
Example: CH3CH2CH2OH - 1-propanol
Rule 2: Use the appropriate number to indicate the position of –OH group.
Remember that hydroxyl group has the priority over double bonds, triple
bonds, alkyl, cycloalkyl and halogen substituents. Name and locate
substituents alphabetically.
Example:CH3 OH
CH3CHCH2CH2CHCH3 5-methyl-2-hexanol
OH
Cyclohexanol
Rule 3: Alcohols containing more than one hydroxyl group are referred to
as polyalcohols. Use the suffix –diol or –triol.
Example: HO-CH2-CH2-OH 1,2-ethanediol
OH
HO-CH2-CH-CH2OH 1,2,3-propanetriol
 PS18/41

Rule 4: The hydroxyl group can also be attached to an aromatic

hydrocarbon. If the benzene ring has multiple hydroxyl groups benzene
is used as the root word. CH3
Example: OH OH
OH 2-methylbenzene-
1,3-diol
Phenol
Rule 5: If the hydroxyl group is attached to a cyclic hydrocarbon,
remember to number the ring so that the hydroxyl group has the lowest
number possible, and use the prefix cyclo-.
Example: CH3
OH 2-methylcyclopentanol

IX. FUNCTIONS OF COMMON ALCOHOLS and PHENOLS

X.

1. Methyl Alcohol (Methanol) is a good fuel and used as a solvent in

paints. It is commonly called as wood alcohol because of its original
method of preparation was by heating wood at high temperature in the
absence of air.
2. Ethyl Alcohol (Ethanol) is also called as grain alcohol since it was
obtained by fermentation of grains like corn, rice and barley. It is an
excellent solvent and a fuel. It is also used in cleaning solutions,
explosives and intoxicating beverages.
3. Glycerol (1,2,3-Propanetriol) is a triol with three -OH groups
attached on three adjacent carbon atoms. It is a clear thick liquid and
a byproduct of fat metabolism. It is used in skin lotions, soaps, shaving
creams due to its lubricating properties. It is often referred as
biological antifreeze.
4. Isopropyl Alcohol (2-Propanol) is a three-carbon monohydroxy alcohol.
A 70% isopropyl alcohol in water is marketed as rubbing alcohol (used
to combat high body temperature by rubbing on the skin). Isopropyl
alcohol has a bitter taste. In the body it is oxidized to acetone.
5. Ethylene glycol (antifreeze) is a pure ethylene glycol freezes at
11°F, but a 50:50 mixture of ethylene glycol and water freezes at -37°F.
It is used as airplane de-icer, humectant (keeps other substances moist)
and ball point pen inks.
 PS18/42

6. Cinnamic alcohol is used in perfumes, particularly in lilac and other

floral scents. It can be also used as flavoring agents, soaps and
cosmetics.
ETHER

I. DEFINITION
An ether is an organic compound containing an oxygen atom between
two carbon atoms in a chain. Alcohols (ROH) can be thought of as
derivatives of water in which one of the hydrogen atoms has been replaced
by an alkyl group. If both of the hydrogen atoms are replaced by alkyl
groups, we get an ether (ROR).
The general structure for ether are the following: R-O-R, Ar-O-R
or Ar-O-Ar. Ethers are known for their common name rather than their
IUPAC names.
II. NOMENCLATURE FOR ETHERS
A. Common Naming
B.

Rule 1: Name the two hydrocarbon groups attached to oxygen atom of the
ether.
Rule 2: Add the word ether.
Rule 3: When both hydrocarbon(R) groups are same, used the prefix di-
before the name of R group.
Rule 4: The hydrocarbon groups are listed separately and in alphabetical
order.
Rule 5: Cyclic ethers (contain the ether functional groups as part of
a ring system) are named by their common names
Examples:
CH3-O-CH2CH3 ethylmethyl ether
CH3-O-CH2-CH2-CH2-CH2-CH2-CH2-CH3 methylheptyl ether

Tetrahydrofuran (THF) 1,4-Dioxane

 PS18/43

B. IUPAC Naming

Rule 1: Select the alkyl group to which oxygen is connected and use its
name as the base name.
Rule 2: Number the carbon starting from the left terminal point.
Rule 3: Change the ―yl ending of the remaining group to ―oxy to obtain
the alkoxy group name.
Examples: methyl becomes methoxy, ethyl becomes ethoxy
Rule 4: Place the alkoxy name, with a locator number, in front of the
base chain name.
Rule 5: If both groups are complex then the ether can be named using –
oxa
Example: CH3OCH2CH2CH3 2-oxapentane
III. PHYSICAL PROPERTIES

The boiling points of ethers are similar to those of alkanes of

comparable molecular mass and are much lower than those of alcohols of
comparable molecular mass. Ethers more soluble in water than alkanes.
Ether molecules are miscible in water, this is attributed to the fact
that like alcohols, the oxygen atom of ether can also form hydrogen bonds
with a water molecule. They are flammable and slightly polar. Ethers are
moderately inert. They do not react with reducing agents or bases under
normal conditions. However, they extremely volatile and highly flammable
(easily oxidized in air).
IV. CHEMICAL PROPERTIES

Ethers exhibit the following chemical properties:

1. Ethers resist hydrolysis.
2. Cleavage of C-O bond: Ethers are generally very unreactive in nature.
When an excess of hydrogen halide is added to ether, cleavage of C-O
bond takes place leading to the formation of alkyl halides. The order
of reactivity is given as HI>HBr>HCl.
R-O-R + HX RX + R-OH
Example: CH3-O-CH3 + HBr CH3Br + CH3OH
3. Reaction with hydrogen halides: It only happens in avery high
temperature with concentrated acids like HCl, HBr and HI.
 PS18/44

R-O-R + HX R-O-H +RX

Ar-O-R + HX Ar-O-H + RX
Example: C2H5 -O-C2H5 + HI C2H5 - I + C2H5OH
4. Friedel Craft’s reaction of ethers: Aromatic ethers undergo Friedel
Craft’s reaction for example addition of alkyl or acyl group upon the
reaction with alkyl or acyl halide in the presence of a Lewis acid as
catalyst.
Example:

5. Reaction of ethers with sulphuric acid: On heating with dilute

sulfuric acid under pressure, ethers are hydrolysed to alcohols.
Example: C2H5OC2H5 + H2O 2C2H5OH
6. Peroxide Formation: Ethers form peroxides by the action of
atmospheric oxygen or ozonised oxygen due to co-ordination of one lone
pair of the ethereal oxygen with another oxygen atom
Example:
C2H5O2H5 + O (C2H5)2O (diethyl ether Peroxide) O
V. COMMON ETHERS AND THEIR USES

1. Methyl t-butyl ether (MTBE) is a common gasoline additive used as

an octane booster to oxygenate the gas, and make it burn with less
"knocking." It has been used since 1979 as a replacement for
tetraethyl lead (leaded gasoline). This additive is the subject of
intense debate because of potential health hazards of drinking water
contaminated with MTBE.
2. Diethyl ether is one of the best known ethers. It is often referred
to simply as “ether.” The formula for diethyl ether is (C2H5)2O).
Originally, diethyl ether was used as an anesthetic. Now it has a variety
of uses ranging from cocaine production to diesel engine fluid.
3. 18-crown-6 A "crown ether" (Charles J. Pedersen, Donald J. Cram, and
Jean-Marie Lehn, Nobel Prize, 1987), which is capable of binding metal
ions.
4.Dimethyl ether as a fuel source, unlike diesel, it does not release
sulfur and aromatic compounds.
5. Anisoles, also known as methoxybenzenes. It is used in perfumes,
cosmetics. and pharmaceuticals.
 PS18/45

6. Polyethylene glycol (PEG) is a long-chained, organic compound. Its

uses vary in its length. Low molecule PEG chains can be used as laxatives,
skin creams, lubricants, dispersants in toothpastes, thickening agents,
and binding agents in tablets and molds, among others. Larger molecule
PEG chains are used as packing materials for foods, binding agents and
thickeners for paints, and polar stationary phases for gas
chromatography.

THIOLS AND DISULFIDES

I. DEFINITION
Thiols (R-SH) are sulfur analog of alcohols (R-OH). Thiols (R-SH)
react with mild oxidizing agents to yield disulfides (R-S-S-R). they
are originally known as mercaptans.
II. PROPERTIES
Thiols are more volatile than are the corresponding alcohols and
have a very disagreeable odor. Various thiols are found in nature, e.g.
1propanethiol is released when an onion is peeled and thiols are
responsible for the odor of garlic. Thiols are more reactive than alcohol
and ether counterparts. A carbon–sulfur covalent bond is weaker than a
carbon–oxygen bond.
III.NOMENCLATURE
In IUPAC System, thiols are named in the same way as alcohols
except that the suffix –ol becomes –thiol.
Examples:
CH3CH2CH2SH propanethiol

SH cyclopentanethiol

IV. COMMON THIOLS AND ITS USES

1. Propanethiol lachrymator produced when onions are cut.
2. Allyl thiol or Allyl sulfide are partially responsible for the odor
and flavor of garlic.
3. Cysteine is an amino acid that contains a sulfhydryl group. Cysteine
is found in many proteins and plays an important role in the conformation
of the protein by forming disulfide bonds with other cysteine molecules
within the protein.
 PS18/46

SUMMARY

Alcohols, ethers and thiols are example of functional groups

Alcohols are organic compounds containing a hydroxyl (-OH)
functional group bonded to a saturated carbon atom. It is classified
according to the number of carbon bonded to carbon attached to –OH group:
primary alcohols –OH bonded to one carbon; secondary alcohols –OH bonded
to two carbons; and tertiary alcohols –OH bonded to three carbons.
Alcohols exhibit physical and chemical properties. For physical
properties, alcohols may be in a solid and liquid state depending on the
number of carbon atom; it has high boiling points; soluble and miscible
in water; had pleasant and unpleasant odor; flammable, viscous and acidic
in nature. For chemical properties, alcohols are combustible; highly
reactive to Sodium; form esters; can be dehydrated. Alcohols are prepared
through reduction of carbonyl compounds. Phenols are organic compounds
in which an —OH group is attached to a carbon atom that is part of an
aromatic carbon ring system. Phenols’ physical properties are almost the
same with alcohols. However, phenols have low acidic level and it has
antiseptic and antioxidant properties. Alcohols and phenols can be named
by its common name or in IUPAC system. Tests were done to identify
alcohols and phenols. Some alcohols and phenols are methanol, ethanol,
glycerol, isoprophyl alcohol, ethylene alcohol an cinnamic alcohol. On
the other hand, ether contains an oxygen atom between two carbon atoms
in a chain. It is often named by its common name. Ethers also exhibits
physical and chemical properties. Some known ethers are Methyl t-butyl
ether (MTBE), Diethyl ether, 18-crown-6 A "crown ether", Dimethyl ether,
Anisoles, etc. Thiols are sulfur analog of alcohols. They are named
almost the same with alcohols except for changing the suffix –ol into –
thiol. Some important thiols are propanethiol, allyl thiol (allyl
sulfide) and cysteine.
EXERCISES

I. Name the structural formula of the following alcohol. Write your

answer in the box.

1. 2.
 PS18/47

3. 4.

5. 6.

7. 8.

9. 10.

II. Draw the structural formula of the following alcohol.

Note: (If you think there is NO answer write not possible.)

1. 1-propanol

2. 3-hexanol

3. cyclohexanol

4. 4,5,6-triiodo-3-hexanol

5. 1-ethyl-3-heptanol
 PS18/48

6. 2-methyl-3-hexanol

7. 2-methyl-1-propanol

8. 2-methyl-2-pentanol

9. 1,1-dimethylpentanol

10. 4-pentanol

Name the following structural formula of the following thiols.

1.CH3SH

2. CH3CH2CH2CH2SH

3. CH3CHCH2SH
CH3

4. SHCH3CHCH2CH3

5.
SH

6. SH

7. CH3CH2SH
8. CH3CHCH2CHCH2SH
CH3 CH3
CH3
9. CHCH2CH2CH3SH
CH3
 PS18/49

10. CH3CH2CH2CH2CH2CH2SH
Name the following the structural formula of the following ethers.

1. CH3-O-

2. CH3-O-CH2CH3
3. O-CH3

4. CH3-O-CH2CH2CH2CH3

5. OCH3
OCH3
OCH3
6. SH

7. CH3CH2CH2-O-CH2CH2CH3

8. CH3CH2-O-CH2CH2CH3

9. CH3CH2CH2-O-CH2CH2CH3

10. CH3CHCH2CH3
O-CH3
 PS18/50

Chapter V: Amines

This chapter discusses about the functional group amines. From

IUPAC Naming into common naming, Physical Properties and Chemical
Properties, preparation and practical application.
 PS18/51

Learning Objectives

At the end of the lesson, the students will be able to;

 define what is an amine,

 draw and illustrate the structural formula of amines,and
 to apply the knowledge about amines in everyday life.

I. AMINES

Amines are organic derivatives of ammonia (NH3) in which the ammonia

hydrogens are replaced by alkyl or aryl groups. Amines with one
substituent are called a primary amine and if it has two or three
substituent it is then called as secondary or tertiary amines.
•CH3CH2NH2 (Primary amine)
•CH3CH2NHCH2CH3 (Secondary amine)
•CH3CH2NCH2CH3 (Tertiary amine)
CH2CH3
II. NOMENCLATURE OF AMINES

COMMON NAME
Amines are named as alkylamines, in common name the suffix amine is
given after the names of the alkyl groups that is bonded to the nitrogen.
Write the names of the alkyl groups bonded to N atom in an alphabetical
order in front of amines. The prefixes –di, -tri, -tetra are used to
describe two or three or four identical substituent.
Examples:
•CH3CH2CH2CH2NH2 (butylamine)
4 3 2 1
•CH3NHCH2CH3 (ethyl methyl amine)
IUPAC NAMING

Amines are named as alkanamines. Find the longest continuous chain

of carbon atoms. Number the longest continuous chain of carbon atoms to
show the position of amino group. Then name the chain by dropping the
finale –e from the alkane and adding the suffix –amine.
 PS18/52

Example:
3 2 1
•CH3CHCH2CH2NH2 (3-methylpentanamine)
CH2CH3
4 5
In diamines, the finale –e of the hydrogen chain is retained.
Example:
•H2NCH2CH2CH2CH2CH2NH2 (1,5-pentanediamine)
1 2 3 4 5
In secondary and tertiary amines, the longest alkane chain is numbered
and each alkyl group bonded to the N atom is named as a N-alkyl group.
Examples:
•CH3CH2CH2NHCH3 (N-methyl-1-propanamine)
3 2 1
• NHCH3 (N-methylcyclopentanamine)

• NHCH2CH3 (N-ethyl-2-pentanamine)
CH2CHCH2CH2CH3
1 2 3 4 5
The simplest aromatic amine, a benzene ring bearing an amino group
is called aniline. Other simple aromatic amines are named as derivatives
of aniline. Alkyl group on the N atom use the prefix N and the alkyl
name.
Examples:
• NH2 (aniline) • NHCH3 (N-methylaniline)

III. PHYSICAL PROPERTIES

The boiling points of amines are higher than alkanes and lower than
alcohols of similar mass. Tertiary amines have lower boiling points than
primary and secondary amines of similar molecular weight. Primary and
secondary amines do form hydrogen bonding but tertiary amines do not
 PS18/53

because they have no NH bonds while comparing alcohol amines from weaker
hydrogen bond as nitrogen is less electronegative than oxygen. Amines
including tertiary amines form hydrogen bonds with hydroxylic solvent
such as water and alcohols and therefore amines are soluble in water if
they have 1-5 carbon atoms because the N atom in smaller amines form
hydrogen bonds with the polar OH bond in water.

IV. CHEMICAL PROPERTIES

Basicity of Amines
Amines are bases due to the lone pair of electrons on the nitrogen
atoms of amines. These react with water to form hydroxyl ions. Bases
are those that donate OH ions (hydroxyl ions).
NH3+HOH NH4+OH (ammonium hydroxide)
Substituted ammonium ion is an ammonium ion in which one or more
alkyl groups have been replaced for hydrogen atoms. It may happen in
primary and secondary amine but not in tertiary.
Example:
H20
•CH3CH2CH2NH2 CH3CH2CH2NH3+OH

Amine Salt
An amine salt forms when an amine is neutralized by acid. It is
named by replacing the amine part of the name with ammonium followed
by the name of negative ion.
Example:
•CH3NH2+HCl CH3NH3+HCl
Amines are base, their reactions with an acid produces a salt.
Properties of Amine Salt
Amine salts are solid at room temperature. They are soluble in
water and they are also used for drugs. Example of this is cocaine (a
solid illegally as an amine salt). It is reacted with NAOH to produce
the free amine from known as “crack”.
 PS18/54

V. REACTIONS OF AMINES

Alkylation
In the alkylation of amines with alkyl halides it will form to
alkyl ammonium halides. If this alkyl ammonium halides has N-H bonds,
further alkylation takes place which means that the reaction do not
usually stop at one alkylation.
NH3+R-X R-NH3X
Example:
•NH3+CH3Cl CH3-NH3Cl
Amines can be converted into quaternary ammonium salt. This process is
called quarternization.

VI. HETEROCYCLIC AMINES

In heterocyclic amines, the N atoms of amine groups are either part

of aromatic or non-aromatic ring system. These heterocyclic amines
have often strong odor and some are agreeable and others are not.
Example:
N
•CH3CH2 (2-ethyl-5-ethylpyrazine)
OCH2CH3
N

Caffeine is a derivative of heterocyclic amine, a bitter alkaloid

C8H10N402 found especially in coffee, tea, cacao and kola nuts and
used medicinally as a stimulant diuretic.
Nicotine is a poisonous alkaloid C10H14N2 that is the chief active
principle of tobacco and is used as an insecticide.
VII. SUMMARY

Amines are organic derivatives of ammonia (NH3) in which the

ammonia hydrogens are replaced by alkyl or aryl groups. Amines can be
classified as primary (RNH), secondary (RNH2) and tertiary (RNH3). In
 PS18/55

naming amines, it is the same as naming an alcohol. The only

difference is, instead of adding the suffix –ol use the suffix –amine.
VIII. EXERCISES

A. Determine the following amines if it is primary, secondary or

tertiary amines.
1. CH3CH2CH2CH2NH2
2. CH3CH2NHCH2CH2CH3
3. NHCH2CH3

4. CH3CH2NCH3
CH3
5. NH2

B. Give the common and IUPAC name of the following amines.

1. CH3CH2CH2NH2
2. CH3CH2NCH3
CH3
3. CH3CH2CH2CH2NH2
4. CH3NCH3
CH3
5. CH2CH3NHCH2CH2CH3
C. Write the structural formula of the following:
1. 2-pentanamine
2. N-methyl-1-butanamnie
3. 2,4-dibromobenzanamine
4. 1,3-propanediamine
5. Hexanamine
D. Write the structures of the products that form when each of the
following reactions involving amines or amine salt takes place.
1. CH3CH2NHCH3+HCl
 PS18/56

2. CH3CH2NHCH2CH3+HCl
3. CH3CH2CH2CH2CH2NH2+H2SO4
4. CH3NHCH2CH3Cl+NaOH
5. NHCH2CH3+H2SO4
 PS18/57

Chapter VI: Aldehyde and Ketone

This chapter introduces the general structure, general formula,

kinds and common forms of Aldehydes and Ketones. It also shows the
physical and chemical properties of both aldehyde and ketone. This
chapter emphasizes the IUPAC and common naming for both functional
groups.
 PS18/58

Learning Objective

At the end of the lesson, the students are expected to:

 Learn the general structure of Aldehyde and Ketone

 Understand the different physical and chemical properties
 Explain the different rules in IUPAC and common naming of
both Aldehyde and Ketone
 Identify the difference between Aldehyde and Ketone

I. ALDEHYDES

Aldehydes are derived in the removal of hydrogen or the

dehydrogenation in alcohol (from which the word aldehyde came from). It
is an organic compound that has a carbon atom that shares a double bond
with an oxygen(C=O), a single bond hydrogen, and a single bond alkyl or
aryl group. The general formula of aldehydes is RCHO and the general
structure is:

NOTE: Aldehyde is always at the terminal(end) of the chain thus it

cannot form a cyclic structure.
II. IUPAC NAMING

1.Select the longest carbon chain containing the carbonyl group.

Note: The squared part is the parent chain.

2.Name the parent chain as you name the alkane. Drop the –e ending and
replaced it with the suffix –al.
 PS18/59

pentane(alkane) pentan-al

3.In numbering, the carbonyl group must always be numbered “1”(note:

it is not necessary to include the number in the name).

1 2 3 4 5

4.Name the substituents attached to the chain in the usual

way(alphabetically).

3,4-dimethylpentanal

III. COMMON NAMING

For common naming, use the format: form(for 1 carbon),

acet(for 2 carbon), propion(for 3 carbon),butyr(for 4 carbon),valer(for
4 carbon),capro(for 6 carbon) plus the word aldehyde and it should be
in one word.
 PS18/60

Formaldehyde Acetaldehyde propionaldehyde butyraldehyde

IV. AROMATIC ALDEHYDES

It contains an aldehyde group that is directly attached to

a benzene ring.

NAMING
The parent compound is the benzaldehyde and the carbon to
which the aldehyde group is attached will be numbered as carbon number
1.

4-bromobenzaldehyde

V. PHYSICAL PROPERTIES

Aldehydes with fewer than about 5 Carbon atoms are soluble in

water but as the hydrocarbon portion increases, the water solubility
decreases. It has higher boiling points than alkanes but have lower
boiling points than alcohol. Aldehyde tends to have lower melting point
due to the presence of alkyl groups and unsaturated chain. Carbon 1 and
Carbon 2 is gases at room temperature. Carbons 3 to Carbon 11 are liquids
and higher aldehydes are solid. Lower molecular mass have unpleasant
odor and higher molecular mass have fragrant odor especially
benzaldehydes derivative.
 PS18/61

VI. KETONE

Ketone is a carbonyl group that has a carbon atom bonded to two

hydrocarbon group (alkyl,cycloalkyl or aromatic). Its general formula
is RCOR. The general structure is:

Note: Ketones are always in between the hydrocarbon

chain and can also form a cyclic structure.
VII. IUPAC NAMING

1.Select the longest carbon chain that contains the carbonyl atom as
parent chain, then name the parent chain as you name the alkane but
the –e ending should be replace by the suffix –one.

Pentane(alkane) pentan-one

2.Number the chain starting to the end closest to the carbonyl group,
note that the carbonyl group should have the lowest possible number.

1 2 3 4 5
 PS18/62

3.Name the substituents that are attached the usual way

(alphabetically).

3-ethyl-2-pentanone
4.In cyclic ketones, the carbonyl group is always number as 1. Name as
you name the usual way.

2-methylcyclohexanone

VIII. COMMON NAMING

The alkyl or aryl groups that are attached to the carbonyl

functional group are named in alphabetical order then add the word
ketone. Note that it should be in separate words.

Isobutyl methyl ketone ethyl propyl ketone

 PS18/63

IX. PHYSICAL PROPERTIES

Ketones are polar because of C=0 bond. They have stronger

intermolecular forces than hydrocarbon that’s why they have higher
boiling point. Small ketones are soluble in water but its solubility
decreases as the chain increases, simple ketones have distinctive odors
that are unpleasant. Ketones are more volatile than alcohols and
carboxylic acids of similar molecular weight.
Lower members of the series are liquids and higher members are
either solid or liquid. Note that both are colorless.
X. CHEMICAL PROPERTIES OF ALDEHYDES AND KETONES

1. Oxidation
Aldehydes are oxidized easily to form carboxylic acid while
ketones do not undergo oxidation.

2. Reduction
Both aldehydes and ketones can easily reduce to alcohols
with hydrogen with the presence of Nickel, Platinum or
Copper as a catalyst.
 PS18/64

3. Reaction with Alcohol

Aldehydes or ketones that react with alcohol in the
presence of an acid as a catalyst will result to a
hemiacetal or hemiketal.

 Hemiacetal is an organic compound that came from the

reaction of aldehyde with alcohol and possesses a carbon
atom that is attached to an hydroxyl(OH) and an alkoxy(OR)
group.

 Hemiketal is a compound that derives from a ketones with

its reaction to alcohol and like hemiacetal, it possesses a
hydroxyl and an alkoxy group.

4. Nucleophilic addition
This reaction uses weak acids as a catalyst. It involves
the addition of ammonia and its derivatives.

XI. PREPARATION

1. Oxidation of primary alcohol

Depending on the condition of the reaction, primary alcohol
can be oxidized to aldehydes. Aldehydes are formed if the excess
amount of an alcohol is used and when the aldehyde will distill
off as soon as it forms.
 PS18/65

Primary Alcohol Aldehyde

2. Oxidation of secondary alcohol
When secondary alcohol is oxidize, it will form a ketone.

3.Friedel-Craft’s reaction
It is an overall transformation of Ar-H to Ar-COR (ketone).
The reagent is usually an acid halides with AlCl3.

XII. COMMON ALDEHYDES AND KETONES

 PS18/66

XIII. SUMMARY

Carbonyl groups composes a C=O structure. There are two types of

carbonyl group-aldehydes and ketones. Aldehyde is in the end of the chain
while ketones are in between the two-hydrocarbon group. In naming
aldehydes and ketones, it uses some rules (IUPAC Naming and common
naming). The physical properties of aldehyde is according to their
 PS18/67

physical state (liquid,solid,gas), melting point(lower), boiling

point(higher than alkanes and lower than alcohol), odor(high molecular
mass has pleasant odor and low molecular mass has unpleasant odor),
solubility(as the chain increases, the solubility decreases. Ketones
have the same solubility with aldehydes and they also has an unpleasant
odor and have high volatility. Carbonyl groups have the same chemical
properties: oxidation, reduction, reactions with alcohol and
nucleophilic addition. It also have the same preparation: oxidation of
primary and secondary alcohol and the Friedel Craft’s Reaction.

XIV. EXERCISES

A. Name the following Aldehydes and Ketones :

1. Br O
CH3 CH CH2-C-H

2. CH3 CH3 O
CH3 CH2 CH2CH-C-H

O
3. H-C-CH2 CH2-Cl

O CH3
4. H-C-CH CH CH2 CH3
CH2CH3

5.
 PS18/68

6. O CH3
CH3 C-CH CH CH2 CH3
CH3

7. O
CH3CH2-C-CH CH2 CH2 CH3
CH2 CH3

8. O
CH3 -C-CH2 CH3

B. Draw the structure of the following:

1.3-ethyl-2-pentanone
2.2,4,6-trimethylheptanal
3.3-ethylcyclopentanone
4.4-chloropropanal
5.2-pentanone
6.4-hexen-2-one
7.3-ethyl-2-butanal

C. Predict the product:

1.reduction of pentanal
2.reaction of 2-propanone and ethanol
3.oxidation of 2-propanone
4.reduction of butanol
5.oxidation of 2-pentanal
 PS18/69

Chapter VII: Carboxylic Acid

This chapter introduces about carboxylic acid. It contains

definition, general formula and the two types of carboxylic acid namely
monocarboxylic acid and dicarboxylic acid. It includes their physical
properties, chemical properties and the naming of carboxylic acid both
IUPAC and Common names. It also includes methods of preparation of
carboxylic acid and the introduction in aromatic carboxylic acid.
 PS18/70

Learning Objectives

After the lesson the students should be able to:

 Define what a carboxylic acid is and identify the types of

carboxylic acid.
 Explain what are the physical properties, chemical properties
and method of preparation.
 Know the following steps and guidelines in naming carboxylic
acids.

I. CARBOXYLIC ACID

It is an organic compound that contains a carboxyl group (COOH).

The general formula of a carboxylic acid is R–COOH. Carboxylic acids
occur widely and include the amino acids which make up proteins and
acetic acid which is part of vinegar and occurs in metabolism.

II. CHARACTERISTICS OF CARBOXYL GROUP

It is bonded with hydroxyl group. The carboxyl group can be found

on the terminal position of the carbon chain. It can be a cyclic as long
as it is attached to the carboxyl group.

III. 2 Types of Carboxylic Acid

1. Monocarboxylic Acid - is an organic compound containing one carboxyl

functional group.

IV. IUPAC NAMING

As with aldehydes, the carboxyl group must be located at the end

of a carbon chain. In the IUPAC system of nomenclature, the carboxyl
carbon is designated #1 and the other substituents are located and named
accordingly. The characteristic IUPAC suffix for a carboxyl group is
drop the “-e” and change to "oic acid", and care must be taken not to
confuse this systematic nomenclature with the similar common system.
 PS18/71

Carbon Chemical IUPAC Name Prefix Common Name

Atom Formula
1 HCOOH Methanoic acid Form Formic acid
2 CH3COOH Ethanoic acid Acet Acetic acid
3 CH3CH2COOH Propanoic acid Propion Propionic
acid
4 CH3(CH2)2COOH Butanoic acid Butyr Butyric acid
5 CH3(CH2)3COOH Pentanoic acid Valer Valeric acid
6 CH3(CH2)4COOH Hexanoic acid Capro Caproic acid
7 CH3(CH2)5COOH Heptanoic acid Enanth Enanthic acid
8 CH3(CH2)6COOH Octanoic acid Capryl Caprylic acid
9 CH3(CH2)7COOH Nonanoic acid Pelargon Pelargonic
acid
10 CH3(CH2)8COOH Decanoic acid Capr Capric acid
11 CH3(CH2)9COOH Undecanoic Undecyl Undecylic
acid acid
12 CH3(CH2)10COOH Dodecanoic Laur Lauric acid
acid
13 CH3(CH2)11COOH Tridecanoic Tridecyl Tridecylic
acid acid
14 CH3(CH2)12COOH Tetradecanoic Myrist Myristic acid
acid
15 CH3(CH2)13COOH Pentadecanoic Pentadecyl Pentadecylic
acid acid
16 CH3(CH2)14COOH Hexadecanoic Palmit Palmitic acid
acid
17 CH3(CH2)15COOH Heptadecanoic Margar Margaric acid
acid
18 CH3(CH2)16COOH Octadecanoic Stear Stearic acid
acid
19 CH3(CH2)17COOH Nonadecanoic Nonadecyl Nonadecylic
acid acid
20 CH3(CH2)18COOH Icosonoic acid Arachid Arachidic
acid
 PS18/72

Examples:

CH3-CH-CH-COOH CH3-CH-CH2-COOH CH3-CH2-CH2-CH-COOH

| | | |
Br CH2CH3 CH3CH2CH3 CH3
Answer: Answer: Answer:
3-bromo-2-ethylbutanoic 3-methylhexanoic 2-methylpentanoic
acid acid acid
V. COMMON NAME OF CARBOXYLIC ACID

a. LACTIC ACID –produced during Kreb cycle. Too much of lactic acid
will cause cramps.
b. GLYCERIC ACID –produced during glycolysis
c. PYRUVIC ACID –produced during Kreb cycle
d. FUMERIC ACID – citric acid gel
e. OXALOACETIC ACID – oxaloacetate
f. MALIC ACID – produced during Kreb cycle
g. CITRIC ACID – found in fruits

VI. PHYSICAL PROPERTIES

Carboxylic acids are polar because they are both hydrogen-bond

acceptors (carbonyl –C=O) and hydrogen-bond donors (hydroxyl –OH) and
they exhibit strong hydrogen bonding between molecules. They tend to
have higher boiling points than water, not only because of their
increased surface area but because of their tendency to form stabilized
dimers. They have also low boiling point because of the hydroxyl group
that attracts electron where the lower the density, the lower the boiling
point. They are typically weak acids. It means that they only partially
dissociate into H+ cations and RCOO− anions in neutral aqueous solution.
They often have strong odors which are unpleasant especially the volatile
derivatives. Most common are acetic acid (vinegar) and butyric acid
(human vomit). They are colorless. Smaller carboxylic acids (1 to 5
carbons) are soluble in water whereas higher carboxylic acids are less
soluble due to the increasing hydrophobic nature of the alkyl group.
VII. CHEMICAL PROPERTIES

a. Esterification
- reaction of carboxylic acid to alcohol producing ester and water.
 PS18/73

RCOOH +ROH RCOOR +HOH

CH3COOH + CH3OH CH3COOCH3 + HOH

b. Acidity
- reaction of carboxylic acid to water producing hydronium ion and
carboxylate ion

RCOOH + HOH H3O+ + RCOO–

CH3COOH + HOH H3O+ + CH3COO–

c. Basicity or Salt of Carboxylic Acid

- reaction of carboxylic acid to strong base like sodium hydroxide
producing water and salt of carboxylic acid.

RCOOH +NaOH HOH + RCOONa

CH3CH2CH2COOH + NaOH HOH + CH3CH2CH2COONa
VIII. PREPARATION OF CARBOXYLIC ACID

Oxidation
Catalyst: Potassium Permanganate
CARBOXYL ACID ALDEHYDE PRIMARY ALCOHOL
PRIMARY ALCOHOL ALDEHYDE CARBOXYL ACID
OH RCOH RCOOH

IX. DICARBOXYLIC ACID

2. Dicarboxylic Acid - is an organic compound containing two carboxyl

functional group. The general formula for dicarboxylic acid is HOOC-R-
COOH.
X. IUPAC NOMENCLATURE

In naming dicarboxylic acids, it is the same with monocarboxylic

acids except that the suffix is -dioic acid.
 PS18/74

Examples:

HOOC-CH2-CH2-COOH HOOC-CH2-CH2-CH2-COOH HOOC-CH-CH2-CH2-COOH

|
Answer: Answer: CH3
1,4-butandioic acid 1,5-pentandioic acid Answer:
2-methyl-1,4-
Common name Nomenclature of dicarboxylic acids is pentandioic
aided by theacid
acronym
OMSGAP.
Chemical Formula IUPAC NAME Common Name
HOOCCOOH Ethanedioic acid Oxalic acid
HOOCCH2COOH Propanedioic acid Malonic acid

Succinic
HOOCCH2CH2COOH Butanedioic acid
acid
Glutaric
HOOCCH2CH2CH2COOH Pentanedioic acid
acid
HOOCCH2CH2CH2CH2COOH Hexanedioic acid Adipic acid
HOOCCH2CH2CH2CH2CH2COOH Heptanedioic acid Pimelic acid

XI. PHYSICAL PROPERTIES

A dicarboxylic acid has physical properties that are almost

the same as monocarboxylic acid. Dicarboxylic acid has fragrant or
pleasant odor. The boiling point is higher than monocarboxylic acid. In
terms of its solubility in water: as the carbon increases, the solubility
decreases. Higher than 4 carbons they have less soluble in water but
soluble in other organic solvents.

XII. CHEMICAL PROPERTIES

Dicarboxylic acids have the same chemical properties to

monocarboxylic acid.
 PS18/75

a. Esterification

HOOC-R-COOH + R-OH RCOOR + HOH

HOOC-CH2-COOH + CH3-OH HOOC-CH2-COOCH3 + HOH

b. Acidity

RCOOH + HOH H3O+ + RCOO –

HOOC-CH3-COOH + HOH H3O+ + HOOC-CH3-COO–

c. Basicity

RCOOH + NaOH HOH + RCOONa

HOOC-CH2-CH2-COOH + NaOH HOH + HOOC-CH2-CH2-COONa
XIII. METHODS OF PREPARATION

Dicarboxylic acids are suitable substrates for preparation of

organic acids for the pharmaceutical and food industries. Furthermore,
they are useful materials for the preparation of fragrances, polyamides,
adhesives, lubricants, and polyesters.
XIV. Aromatic Carboxylic Acid

It oxidizes a carbon side chain on a benzene derivative. The

simplest aromatic carboxylic acid is the benzoic acid.

_____COOH
Examples:
_______CH2CH3
CH3___ _____COOH
CH3___ _____COOH

Answer: 4-methylbenzoic acid Answer: 2-ethyl-4-methylbenzoic acid

XV. SUMMARY

Carboxylic Acid is an organic compound that contains a carboxyl

group (COOH). The general formula of a carboxylic acid is R–COOH. There
are two types namely, monocarboxylic acid and dicarboxylic acid.
Carboxylic acids are polar and they exhibit strong hydrogen bonding
 PS18/76

between molecules. They tend to have higher boiling points than water.
They are typically weak acids. They often have strong odors which are
unpleasant. They are colorless. Smaller carboxylic acids (1 to 5 carbons)
are soluble in water. The chemical properties are esterification, acidity
and basicity. The characteristic IUPAC suffix for a carboxyl group is
drop the “-e” and change to "oic acid". In naming dicarboxylic acids,
it is the same with monocarboxylic acids except that the suffix is -
dioic acid.

XVI. EXERCISE

A. Direction: Draw the structural formula.

1. 2-ethyl-3-methylheptanoic acid
2. 3,5-dibromobenzoic acid
3. 2-ethylpentanoic acid
4. Octandioic acid
5. Hexadioic acid
6. Pentadioc acid
7. 4-methylbenzoic acid
8. 2-ethylpentanoic acid
9. 2-methylbutandioic acid
10. Butandioic acid

B. Direction: Name the following.

1. CH3-COO-CH2-CH2-COO-CH3
2. HOOC-(CH2)3-COOH
3. CH3-CH-CH-COOH
| |
Br CH3
4. CH3-CH2-CH-COOH
|
CH2CH2CH3

5. ____COOH

__BR

CH3____ ____CH3
 PS18/77

6. CH3-CH-CH-COOH
| |
Cl Cl
7. HOOC-CH2-CH2-CH2-COOH
8. CH3-(CH2)4-COOH
9. CH3-CH2-CH-COOH
|
CH2CH2CH2CH3
10. ___COOH

I___
 PS18/78

Chapter VIII: Esters

This chapter’s main purpose to introduce and discuss esters (a

carboxylic acid derivative). It contains the definition and general
structure and formula of esters. Its physical and chemical properties.
It will also help us know on how to prepare/ produce esters using
different reactions. This chapter also includes the naming of esters
both IUPAC naming and COMMON naming. Since esters are common in our
society, this also includes the common esters found on our surroundings.
 PS18/79

Learning Objectives

At the end of this lesson, the student should be able:

 To identify and differentiate esters from the other

functional groups through their definition, physical
properties and chemical properties.
 To name and draw the structures of different esters.
 To appreciate the existence of common esters.

I. ESTERS

Definition and General Structure

Ester is a carboxylic acid derivative that consist of an
acid part and an alcohol part. An ester is formed when an alcohol
reacts with a carboxylic acid. It has a general structure of
RCOOR.

II. IUPAC NAMING

1. Identify the oxygen that is part of the continuous chain

and bonded to carbon on both sides.

2. Begin numbering the carbon chains on either side of the oxygen

identified in step 1.
 PS18/80

3. Next, use this format: [alkyl on side further from the

carbonyl] (space) [alkane on the side with the carbonyl].

4. Finally, change the ending of the alkane on the same side as

the carbonyl from -e to -oate.

5. When an ester group is attached to a ring, the ester is named

as a substituent on the ring.

Benzenecarboxylic acid (Benzoic acid)

Examples:
1.

2.CH3COOCH2CH3 methyl propanoate

3.CH3COOCH2CH2CH2CH2CH2CH2CH2CH3 octyl ethanoate

4.CH3CH2CH2COONa sodium propanoate

5.CH3COOCH2CH2COOCH3 dimethyl butanoate

 Common names of esters are derived from the organic acid and the
alcohol from which they are derived. For example, when acetic
acid reacts with ethyl alcohol, the ester formed is called ethyl
acetate.
 PS18/81

III. PHYSICAL PROPERTIES

Esters do not form hydrogen bonds. Their boiling point is

lower than alcohols and carboxylic acids. Esters are soluble in
water yet the more carbon chain there is, the less soluble the
ester becomes. They are also colorless and they have pleasant
odors. They are also chemically unreactive at room temperature.
Esters are also mildly polar due to the presence of carbonyl
(=C=O) group and act as hydrogen bond acceptors not as donors.
Esters are volatile in nature and have low boiling and melting
points. Many esters are found in natural foodstuffs.
IV. CHEMICAL PROPERTIES

1. Hydrolysis. Esters may be broken apart under acidic

conditions by water (a hydrolysis reaction) to form a
carboxylic acid and an alcohol. This is the reverse of
esterification.

Example:
a. CH3COOCH3 + HOH CH3COOH + CH3OH
b. CH3CH2COOCH2CH3 + HOH CH3CH2COOH + CH3CH2OH

2. Saponification. It is the hydrolysis of a carboxylic acid

ester under basic conditions. The direct products are a
carboxylic acid salt and an alcohol.

RCOOR + NaOH RCOONa + ROH

Example:
a. C3H7COOC2H5 + NaOH C3H7COONa + C2H5OH
b. C4H9COOC3H7 + NaOH C4H9COONa + C3H7OH

V. PREPARATION OF ESTERS

1. Making esters using carboxylic acids

 PS18/82

Example:

2. Making esters using acyl chlorides (acid chlorides)

3. Making esters using acid anhydrides

VI. COMMON ESTERS

Ethyl Methanoate H-CO2-CH2-CH Rum

Methyl Phenyl C6H5-CH2-CO2-CH3 Honey

Ethanoate
Benzyl Ethanoate C6H5-CH2-CO2CH3 Jasmine

Pentyl Ethanoate CH3-CO2-CH2-CH2-CH2-CH2-CH3 Pear

3-Methylbutyl CH3-CO2-CH2-CH2-CH(CH3)-CH3 banana

Ethanoate
 PS18/83

Octyl Ethanoate CH3-CO2-CH2(CH2)6-CH3 orange

Methyl Butanoate CH3-CH2-CH2-CO2-CH3 pineapple

Ethyl Butanoate CH3-CH2-CH2-CO2CH2CH peach

3-Methylbutyl-3- CH3CH(CH3)CH2CO2CH2CH2CH(CH3)CH3 apple

Methylbutanoate

Methyl Anthranilate C6H4(NH2)-CO2-CH3 grapes

 There are also esters that acts as hormones in animals:

1. Methyl hydroxybenzoate (in dogs)
2. Isoamyl acetate (in bees)
 Esters are also used in medication such as benzocaine use as
local anesthetic.

VII. THIOESTERS

--SR replacing the OR group.

Examples:

a. CH3COOH + CH3CH2SH HOH + CH3COSCH2CH3

b. CH3CH2COOH + CH3CH2SH HOH + CH3CH2COSCH2CH3
c. C3H7COOH + C3H7SH HOH + C3H7COSC3H7

VIII. SUMMARY

Esters are carboxylic acid derivatives that has a general

structure of RCOOR. It has an acid and alcohol part. Esters are
mildly polar and have pleasant aromas mostly found in natural
foodstuffs. They are soluble in water yet the more carbon it has
the less soluble it is in water. They do not also form hydrogen
bonds and their boiling point is lower than alcohol and carboxylic
acids. Esters are also known as volatile in nature. Esters undergo
reactions such as hydrolysis and saponification. Hydrolysis is
breaking apart of esters by acidic conditions of water to form
carboxylic acid and alcohol. Saponification is the breaking apart
of esters by sodium hydroxide and potassium hydroxide to form
carboxylate salts and alcohols. Esters are made through the process
esterification the reverse of hydrolysis. Esters are named by
 PS18/84

naming the alcohol which appears first then change the suffix to –
oate by the IUPAC naming. Common names are derived by the organic
acid and the alcohol that reacted. There are also common esters
which are used as an aroma for our flavored drinks.

IX. EXERCISE

Draw structural formulas for the following esters:

1. methyl butanoate

2. ethyl propanoate

3. sodium butanoate

4. propyl benzoate

Name the following:

1.

2.

3.

4.
 PS18/85

Key Answers
Alkanes
I.
1. FALSE
2. TRUE
3. FALSE
4. TRUE
5. TRUE

II.
1. Butane
13
a) 𝐶4 𝐻10 + 2 2
𝑂 → 4𝐶𝑂2 + 5𝐻2 𝑂
b) 𝐶4 𝐻10 + 𝐶𝑙2 → 𝐶4 𝐻9 𝐶𝑙 + 𝐻𝐶𝑙
c) 𝐶4 𝐻10 + 𝐶𝑙2 → 𝐶4 𝐻9 𝐶𝑙 + 𝐻𝐶𝑙
𝐶4 𝐻9 𝐶𝑙 + 𝐶𝑙2 → 𝐶4 𝐻8 𝐶𝑙2 + 𝐻𝐶𝑙
𝐶4 𝐻8 𝐶𝑙2 + 𝐶𝑙2 → 𝐶4 𝐻7 𝐶𝑙3 + 𝐻𝐶𝑙
𝐶4 𝐻7 𝐶𝑙3 + 𝐶𝑙2 → 𝐶4 𝐻6 𝐶𝑙4 + 𝐻𝐶𝑙
𝐶4 𝐻6 𝐶𝑙4 + 𝐶𝑙2 → 𝐶4 𝐻5 𝐶𝑙5 + 𝐻𝐶𝑙
𝐶4 𝐻5 𝐶𝑙5 + 𝐶𝑙2 → 𝐶4 𝐻4 𝐶𝑙6 + 𝐻𝐶𝑙
𝐶4 𝐻4 𝐶𝑙6 + 𝐶𝑙2 → 𝐶4 𝐻3 𝐶𝑙7 + 𝐻𝐶𝑙
𝐶4 𝐻3 𝐶𝑙7 + 𝐶𝑙2 → 𝐶4 𝐻2 𝐶𝑙8 + 𝐻𝐶𝑙
𝐶4 𝐻2 𝐶𝑙8 + 𝐶𝑙2 → 𝐶4 𝐻𝐶𝑙9 + 𝐻𝐶𝑙
𝐶4 𝐻𝐶𝑙9 + 𝐶𝑙2 → 𝐶4 𝐶𝑙10 + 𝐻𝐶𝑙
2. Pentane

a) 𝐶5 𝐻12 + 8𝑂2 → 5𝐶𝑂2 + 6𝐻2 𝑂

b) 𝐶5 𝐻12 + 𝐶𝑙2 → 𝐶5 𝐻11 𝐶𝑙 + 𝐻𝐶𝑙

III.

1. CH3 – CH - CH2 - CH3

CH2 CH3

CH3

2. CH3 – CH2 – CH2 – CH – CH2 – CH2 – CH3

CH3 – C – CH3

CH3
 PS18/86

3. CH2 – CH - CH2 – CH2 - CH3

Br Br

4.

CH3

CH3

5.

IV.
1. 3,4-dimethylhexane
2. 3-bromo-2-chloro-6-ethylnonane
3. 1-bromo-3-floro-5-methylcyclohexane
4. 1-chloro-3-ethylcyclopentane
5. 3-chloro-2-floro-5-propylnonane

Alkenes

1) 2-pentene
2) 3-methyl-2-pentene
3) 2-ethyl-1-heptene
4) 3-methylcyclopropene
5) 2-chloro-3,4-dimethyl-5-propylcyclopentene
6) 4-methyl-1-hexene
7) 2-ethyl-1,4-pentadiene
8) Cyclobutene
9) 3-bromocyclohexene
10) butene

B.

1) CH=CH-CH2-CH3

Cl Cl
 PS18/87

2) Cl

Cl

3)

4) CH2=C-CH2-CH=CH-CH2-CH2-CH3

CH3CH2

5) CH3-CH=CH-CH-CH2-CH2-CH3

CH3CH2CH2

6)

7) Not possible

8) CH2=CH2-CH2-CH2-CH2-CH2-CH=CH2

9) CH3

CH2=CH2-CH-CH2-CH2-CH2-CH3

CH3 CH3

10)

Alkynes
A.
1. 4,4,5-trimethyl- 2-heptyne
2. 4,4- dichloro-5,5-dimethyl-6-heptyne- 3-diol
 PS18/88

3. 3,3- dichloro-1- hepten-5-yne

4. 3-bromo-2-chloro-5-hexyne-2,3,4-triol
5. 1-penten-5-yne
6. 4,5-dibromo-3-heptyne
7. 3-hexyne
B.

1. CH3- C C- CH -CH3
|
CH3

2. CH3- CH2-CH= CH- C C- CH3

3. CH3- CH- CH2- C CH

| | |
OH CH3 Cl

4. CH3-C C-C C- CH3

CH3 CH3
| |
5. CH3- CH2-CH= CH2- CH2- C CH

6. CH CH

7. CH3- CH- CH- CH- CH- C-C CH

| | | | |
Br Br Cl OH OH

C.

1. C6H10 + O2 → O=COHC5H9

2 C5H8 + (3(5)- 1/2)O2→ (5)CO2 +(5+1)H20

C5H8+ 7O2 →5CO2+ 4H2O

3. C8H14 + NH3 → C7H15CN+ H2

 PS18/89

4. C4H6 + Cl2 → ClCH2Cl

5. C3H4+ H2O → C2H5CHO
6. C8H14Br2+ NaOH → H2O+ NaBr+ BrC2H11
Alcohol, Ethers and Thiols
Alcohols
I.
1. 3,5-dimethylhexanol
2. 2-methyl-2-butanol
3. 6-methyl-3-heptanol
4. 2-bromo-5-chlorocyclopentanol
5. ethandiol
6. propantriol
7. 6,8-dimethyl-3-decanol
8. 1,2-propandiol
9. 1-methylcyclopentanol
10. 2-hexanol
II.
1. CH3CH2CH2OH
2. CH3CH2CHCH2CH2CH3
OH

3. OH

4. CH3CH2CHCHCHCH3
OH
5. NOT POSSIBLE
6. CH2CHCHCH2CH2CH3
OH OH
7. OHCH2CHCH3
 PS18/90

OH
OH
8. CH3CCH2CH2CH3
CH3
9. NOT POSSIBLE
10. CH3CH2CH2CHCH3
CH3
Thiols
1.Methanethiol
2. Butanethiol
3. 2-methylpropanethiol
4. Butanethiol
5. Cyclopentanethiol
6. Cyclobutanethiol
7. Ethanethiol
8. 2,4-dimethyloentanethiol
9. 2-methylpentanethiol
10. Hexanethiol
Ethers
1.methoxybenzene
2.methoxyethane
3. methoxycyclohexane
4. methoxybutane
5. 1,2,4- trimethoxybenzene
6. methoxy-2-butanol
7. propoxybutane
8. ethoxypropane
9. propoxypropane
10. 2-methoxybutane
Amines
 PS18/91

A.
1. Primary amine
2. Secondary amine
3. Secondary amine
4. Tertiary amine
5. Primary amine
B.
1. Common: 1-propylamine
IUPAC: 1-propanamine
2. Common: ethyldimethylamine
IUPAC: N,N-dimethylethanamine
3. Common: 1-butylamine
IUPAC: 1-butanamine
4. Common: trimethylamine
IUPAC: N,N,N-trimethanamine
5. Common: ethylpropylamine
IUPAC: N-ethyl-N-propanamine
C.
1. CH3CHCH2CH2CH3
NH2
2. CH3CH2CH2CH2NHCH3
3. NH2
Br

Br
4.NH2CH2CH2NH2
5. CH3CH2CH2CH2CH2CH2NH2
D.
1. CH3CH2NHCH3 + HCl CH3CH2NH2CH3 + Cl
2. CH3CH2NHCH2CH2 + HCl CH3CH2NH2CH2CH3 + Cl
 PS18/92

3. CH3CH2CH2CH2CH2NH2 + H2SO4 CH3CH2CH2CH2CH2NH3 + HSO4

4. CH3NH2CH2CH3Cl + NAOH CH3NHCH2CH3 + NaCl + HOH
5. NHCH2CH3 NH2CH2CH3
+ H2SO4 + HSO4

Carboxylic Acid
A. Draw the structural formula.
1. CH3-CH2-CH-CH-COOH
| |
CH3 CH2CH3

2. Br__ ___COOH

___Br

3. CH3-CH2-CH2-CH2-CH2-CH-COOH
|
CH2CH3
4. HOOC-CH2-CH2-CH2-CH2-CH2-CH2-COOH
5. HOOC-CH2-CH2-CH2-CH2-COOH
6. HOOC-(CH2)3-COOH

7. ____COOH

CH3___

8. HOOC-CH-CH2-CH2-CH3
|
CH2CH3
9. CH3-CH2-CH-COOH
|
CH3
10. COOH-CH2-CH2-COOH

B. Name the following.

 PS18/93

1. 2,5-hexadioic acid
2. pentadioic acid
3. 3-bromo-2-methylbutanoic acid
4. 2-ethylpentanoic acid
5. 2-bromo-3,4-dimethylbenzoic acid
6. 2,3-dichlorobutanoic acid
7. pentadioic acid
8. hexanoic acid
9. 2-ethylhexanoic acid
10. 4-iodobenzoic acid

Esters

Draw the structure of the following esters: (answers)

1. CH3COOCH2CH2CH3
2. CH3CH2COOCH2CH3
3. CH3CH2CH2COONa
4. CH3COOCH2CH2COOCH3
Name the following esters. (answers)
1. propyl ethanoate
2. 3-bromopentyl 2-chlorobutanoate
3. ethyl hexanoate
4. ethyl 3-bromopentanoate

References
 PS18/94

Alkanes
https://socratic.org/questions/what-is-halogenation
http://www.vias.org/genchem/orgcomp_alkanes_occurrence_use.html
http://alevelchem.com/aqa_a_level_chemistry/unit3.1/sub316/03.htm
https://www2.chemistry.msu.edu/faculty/reusch/virttxtjml/funcrx1.htm
https://hzorganicchemistry.wordpress.com/uses-of-alkene
http://authors.library.caltech.edu/25034/5/BPOCchapter4.pdf
http://www.oneonta.edu/faculty/knauerbr/221lects/alkrxns.pdf
Alkenes

http://www.google.com.ph/url?q=https://chem.libretexts.org/Core/Organi
c_Chemistry/Alkenes/Naming_the_Alkenes&sa=U&ved=OahUKEwil6IC8tq3TAhUW1
2MKHZPQAu8QFggYMAQ&usg=AFQjCNHi-UrKf9oYym9dB3Ug-U_HXROw

http://www.google.com.ph/url?q=https://chem.libretexts.org/Core/Organi
c_Chemistry/Alkenes/Properties_of_Alkenes/Physical_Properties_of_Alken
es&sa=U&ved=OahUKEwiYn7eet63TAhVGy2MKHSPhAggQFggWMAM&usg=AFQjCNGbDbBt_
GFUolo15SvMsPDMbidxFA

http://www.google.com.ph/url?q=https://www.ucc.ie/academic/chem/dolche
m/html/dict/alkenes.html&sa=U&ved=OahUKEwj-
qtLat63TAhUOzWMKHb1rAskQFggZMAQ&usg=AFQjCNGp2IL36pAcZTINJONBylDMuja-CA

http://www.google.com.ph/url?q=https://chem-
guide.blogspot.com/2010/04/chemicql-properties-of-
alkene.html%3Fm%3D1&sa=U&ved=OahUKEwj-
qtLat63TAhUOzWMKHb1rAskQFggeMAY&usg=AFQjCNGuO-sEh4uRQgYrvc3W-NwWAxrZ6Q

http://www.google.com.ph/url?q=https://chem.libretexts.org/Core/Organi
c_Chemistry/Alkenes/Naming_the_Alkenes&sa=U&vedOahUKEwjU6MTBuK3TAhvM12
MKHcG5DVEQFggVMAI&usg=AFQjCNHi-UrKf9o6tYym9dB3Ug-UNaXXNow

http://www.google.com.ph/url?q=https://www.askiitians.com/iit-jee-
alkenes-and-alkynes/general-methods-of-preparation-of-
alkenes/&sa=U&ved=OahUKEwiJt5DEua3TAhUHHGMKHc2aCEcQFggSMAI&usg=AFQjCNE
WhvS8yIeFKiIR3djxan9NaXXNow

http://www.google.com.ph/url?q=https://alkenes.wordpress.com/2010/01/3
1/uses-of-
alkenes/&sa=U&ved=OahUKEwjmuuzAuq3TAhUEyGMKHS9XCGsQFggSMAI&usg=AFQjCNG
H5BBZ6W_900JThn6WBajt1wYkeO

http://www.google.com.ph/url?q=https://legacy.jefferson.kctcs.edu/user
s/kaya.muller/che120/supplements/orgnomenclature/worksheets/alkene/wor
 PS18/95

ksheet.html&sa=U&ved=OahUKEwj8-
N6qu63TAhVV62MKHXU_AW8QFggLMAA&usg=AFQjCNHza_GOOSm1jUoDrecXW1GSwuNKBA

Alkynes
https://wwww.ucc.ie/academic/chem/dolchem/html/dict/alkynes.html
nptel.ac.in/courses/104103071/pdf/mod4.pdf
Alcohols, Ethers and Thiols
https://www.khanacademy.org/science/biology/properties-of-
carbon/hydrocarbon-structures-and-functional-groups/a/functional-
groups
module 5: Organic Chemistry: Functional Groups pp.11-16
https://chem.libretexts.org/Core/Organic_Chemistry/Ethers
https://chem.libretexts.org/Core/Organic_Chemistry/Thiols_and_Sulfides
http://saylordotorg.github.io/text_the-basics-of-general-organic-and-
biological-chemistry/s18-06-esters-structures-and-names.html
Amines
https://www.google.com.ph/search?ei=pVf4WKrxlcGyO=amines
• file:///data/data/com.android.browser/files/basicity-of-amines.mht
• http://www.chem.purdue.edu/gchelp/molecules/nicotinb.html
• http://www.emcdda.europa.eu/publications/drug-profile/cocaine
• Merriam-Webster
Aldehydes and Ketones
https://www.britanica.com/science/aldehyde
https://www.slideshare.net/mobile/VictorOribe/aldehyde-15294067
https:// www.slideshare.net/mobile/mizakamaruzzaman/chapter-3ketone
https:// www.slideshare.net/mobile/mizakamaruzzaman/chapter-2-aldehyde
http://www.newwordencylopedia.org/entry/ketone
http://legacy.chemgym.net/as_a2/topics/caebonyl_compounds/quiz_2.html
htpp://crab.rutgers.edu/-alroche/ch18.pdf
Carboxylic Acid
https://chem.libretexts.org/Core/Organic_Chemistry/Carboxylic_Acids/No
mentaclature_of_Carboxylic_Acids
http://colapret.cm.utexas.edu/courses/Nomenclature_files/carboxylic_ac
ids.htm
 PS18/96

https://www2.chemistry.msu.edu/faculty/reusch/virttxtjml/crbacid1.htm
Ester
Leigh, G. J., H. Favre, and Val Metanomski. Principles of Chemical
Nomenclature A Guide to Iupac Recommendations (IUPAC Chemical Data
Series). Malden: Blackwell Science, 1998.
McNaught, A. D., and A. Wilkinson. Compendium of Chemical Terminology.
2nd ed. Blackwell Science, 1997.
Vollhardt, K. Peter C., and Neil E. Schore. Organic Chemistry Structure
and Function. New York: W. H. Freeman, 2007.
http://en.wikipedia.org/wiki/Esters
http://en.wikipedia.org/wiki/IUPAC_n...emistry#Esters