INTRODUCTION TO ORGANIC CHEMISTRY

Objectives:
At the end of this module, the students are expected to:
• Understand the basic principle of organic chemistry.
• Differentiate organic from inorganic compounds through chemical bonding, melting points, boiling points, and the
likes.
• Understand the tetrahedral structure of carbon.
• Identify alkanes: names, properties, structures, and reactions.
• Distinguish the different functional groups.

Organic Chemistry
An organic chemistry is a branch of chemistry dealing with carbon containing compounds. Organic compound is
any member of a large class of chemical compounds whose molecules contain carbon and hydrogen, therefore, carbides,
carbonates, carbon oxides, and elementary carbon are classified inorganic. Examples are carbon monoxide (CO),
carbon dioxide (CO2), silicon carbide (SiC), and the likes.

Organic compounds tend to dissolve in organic solvents which are either pure substances like ether or ethyl
alcohol, or mixtures such as paraffinic solvents–petroleum ethers and white spirits, and pure or mixed aromatic solvents
from petroleum or tar fractions by physical separation or by chemical reaction.

Friedrich Wohler, a German chemist, successfully synthesized Urea (NH3CONH3)–a principal component of urine
and produced in the kidney.

Organic compounds
• A compound made from carbon (C) atoms
• Has one or more carbon atoms or carbon–carbon bond
• Many hydrogen (H) atoms
• Also contains oxygen (O), sulfur (S), nitrogen (N), and halogens (chlorine (Cl), iodine (I), bromine (Br), and fluorine
(F) atoms)

Properties of Organic compounds as compared to Inorganic compounds

Examples
Organic compound: propane (C3H8)
Inorganic compound: sodium chloride (NaCl)
Properties Organic Example: C3H8 Inorganic Example: NaCl
Chemical bonding Mostly covalent Covalent Many have ionic Ionic
bonds, only few are
covalent
Bond polarity Non-polar Non-polar Mostly are ionic Ionic
and/or polar covalent
Melting point Usually low –1880C Usually high 8010C
Boiling point Usually low –42 C
0 Usually high 141.30C
Flammability High Burns in the air Low Does not burn
Solubility in water Not soluble unless a Insoluble Most are soluble Soluble
polar group is present
Note: In organic chemistry, like dissolves like, which means organic compounds are soluble only to organic solvents. Most organic
compounds are insoluble in water (inorganic solvent) especially those which contains higher carbon-carbon bonds.

Formula of Carbon compounds

Carbon atom has four valence electrons, which means there are four electrons found on the outermost energy
level. These electrons make a carbon atom capable of forming tetrahedral bond. In organic chemistry, carbon is special
due to its property that it can bond to four different atoms and even to itself.
• H
•C• To achieve an octet, carbon atom forms four bonds H–C–H
• H methane (CH4)

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 VSEPR theory predicts that a carbon atom with four single
covalent bonds has a tetrahedral shape.

In organic molecules containing more carbon atoms:

• Valence electrons are shared
• Covalent bonds form between carbon and carbon atoms
• Covalent bonds form between carbon and hydrogen atoms.

H H H H
•• ••

H C  C H H C C H
•• ••
H H H H ethane (CH3–CH3)

In molecules with two or more carbon atoms, each carbon atom with four single bonds has a tetrahedral shape.

Carbon atom
• It is the sixth element in the periodic table with the symbol C.
• Electronic configuration is 1s2 2s2 2p2
• August Kekule von Stradonitz (1829–1896), a German chemist and Archibald Scott Couper (1831–1892), a
Scottish chemist, were the first to recognize that carbon is tetravalent – it can form four covalent bonds with other
elements.
• It is commonly found in carbonates, coal, other fossil fuels, and in living organisms.
• Carbon is a non-metal, it is found in three different forms (crystalline): graphite, diamond, fullerenes.

Graphite
• Commonly found in lead pencils
• It can conduct electricity. It is soft, black, and slippery in nature
• Its carbon atoms are connected into sheets of hexagons
• Density: 2.25 g/cm3
• Carbon also exists in amorphous forms of graphite such as:

Carbon black
Produced when methane is heated with a very small amount of oxygen. It is used in the purification of water,
pigment in the black ink, and production of black tires.

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 Charcoal
Formed when wood is heated to the most without the presence of air. It is used in diminishing odors in the air and
as well as source of heat.

Coke
Produced when coal is heated in the absence of air. An impure form carbon and is used as a reducing agent in
metallurgical industry.

Diamond
• Came from a Greek word “adamas” meaning invincible
• It is clear, luster, and hard solid in which four atoms form covalent bonds
• It is the crystalline form of carbon, wherein gem and industrial diamonds are expressed in metric carats
• It is produced because of the following uses: drills, glass cutters, surface film (for computer chips), and in grinding
wheels and sharpening tungsten.

Fullerenes
• It is an allotrope of carbon which is a soccer-ball in shape and it is as well molecular forms of carbon.
• Also known as Buckminster fullerene or the buckyball
• It has a potential use in superconduction when combined with rubidium and thallium.

Hydrocarbons
Compounds that contain only carbon and hydrogen. Hydrocarbons are also used as raw materials for synthesis
of plastics, lubricants, fibers, solvents, explosives, and as well as industrial chemicals.

HYDROCARBONS

ALIPHATIC ALICYCLIC AROMATIC

(linear C-C chain) (cyclic C-C chain) (contains benzene ring)

Unsaturated
Saturated (contains double and
triple C-C bonds)

Alkanes Alkenes
(single bond C-C) (double bond C=C)

Alkynes
(triple bond C=C)

SATURATED HYDROCARBON
Alkanes
• These are aliphatic hydrocarbons with the general formula CnH2(n) + 2 where n represents the number of carbon
atoms
• Non-polar molecules and much denser than water.
• Melting points increases as the molecular weight increase.
• Low boiling points
• Sometimes called the “paraffin series” due to their lack of affinity or reactivity.
• The simplest alkane is methane CH4
• In naming alkane, Greek prefix + -ane ending is used

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The first ten Alkanes
Number
of Molecular Boiling point
Name Structural formula
carbon formula (0C)
atoms
1 Methane CH4 C H4 -161.0
2 Ethane C2H6 C H3 C H3 -88.5
3 Propane C3H8 C H 3 C H2 C H3 -42.0
4 Butane C4H10 C H 3 C H2 C H2 C H3 0.5
5 Pentane C5H12 C H 3 C H2 C H2 C H2 C H3 36.0
6 Hexane C6H14 C H 3 C H2 C H2 C H2 C H2 C H3 68.7
7 Heptane C7H16 C H 3 C H2 C H2 C H2 C H2 C H2 C H3 98.5
8 Octane C8H18 C H 3 C H2 C H2 C H2 C H2 C H2 C H2 C H3 125.6
9 Nonane C9H20 C H 3 C H2 C H2 C H2 C H2 C H2 C H2 C H2 C H3 150.7
10 Decane C10H22 C H 3 C H2 C H2 C H2 C H2 C H2 C H2 C H2 C H2 C H3 174.1

Stems used in different Hydrocarbon Backbones

Number of C atoms Greek prefixes
1 Meth-
2 Eth-
3 Prop-
4 But-
5 Pent-
Number of C atoms Greek prefixes
6 Hex-
7 Hept-
8 Oct-
9 Non-
10 Dec-

In naming alkanes, Greek prefixes are used to indicate the number of carbon atoms present in a chain. Alkanes are
written with structural formulas that are:
• Expanded to show each bond
• Condensed to show each carbon atom and its attached hydrogen atoms

Condensed: CH4 Expanded: H

H C H

H
Carbon atoms in Alkane maintain a tetrahedral shape, connected in a zigzag pattern, drawn as 2-dimensional, and can
be written in several conformations.

Because each C atom has a tetrahedral arrangement, the order of atoms is not a straight line but a zigzag pattern. A
line-bond formula abbreviates the carbon atoms and shows only the zigzag pattern of bonds from carbon atom to
carbon atom.

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Conformations of Alkanes

The groups attached to a C-C single bond:

• Rotate around the bond
• Give different relative arrangements
called conformations

Example: Conformation of butane (C4H10)

• Rotation of the end CH3 in butane provides for its different conformations

Some structures of Butane

Cycloalkanes
• Are cyclic alkanes
• Have 2 hydrogen atoms fewer than the open chain.
• Named by using the prefix cyclo- before the name of the alkane chain with the same number of carbon atoms.
• Formula: CnH2(n) where n represents the number of carbon atoms

Examples: Represented using line-bond formula

Cyclopropane Cyclobutane

Cyclopentane Cyclohexane

Nomenclature of Hydrocarbons
The increasingly large number of organic compounds identified with each passing day, together with the fact
that many of these compounds are isomers of other compounds, requires that a systematic nomenclature be developed.

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 Isomers
• Have the same molecular formula
• Have different atomic arrangements
• In other words, isomers are compounds having the same molecular
formula but different structure.
Example: Butane (top) and its isomer, 2-methylpropane (bottom)

Rules in Naming Alkanes

Names of alkanes are determined by the International Union of Pure and Applied
Chemistry (IUPAC) system.
1. Find and name the longest continuous carbon chain.
Example: Six carbon atoms are present in the chain, thus,
this alkane is named “hexane”.

2. In case of a substituents (an atom or a group of atoms other

than carbon and hydrogen), identify and name the group/s
attached to the longest continuous chain.

Alkyl group – alkanes that are missing one H. It is named with a –yl
ending.

Halo group – halogen atoms attached to the chain.

3. Number the chain consecutively, starting at the end nearest to

a substituent group.

4. Designate the location of each substituent group by an appropriate number and name.
5. Assemble the name, listing groups in alphabetical order.
6. The prefixes di, tri, tetra, penta, etc. are used to designate several groups of the same kind. Prefixes are
not considered when sorting in alphabetical.

As to the example in item 3, the longest continuous carbon chain consists of 4 carbons (but-), single bonded (-ane
ending) and with methyl groups in carbons 2 & 3, therefore, the name of the compound is 2,3-dimethylbutane.

Examples:

Give the IUPAC name for each of the following:

A. CH3 CH3
| |
CH3─CH─CH2 ─CH─CH2─CH3 2,4–dimethylhexane
1 2 3 4 5 6
In the second example (B), the
B. Cl CH3 designation of numbers are
| | reversed (from right to left)
CH3─CH2─CH─CH2─C─CH2─CH3 3,5-dichloro-3-methylheptane since there are more substituents
| (2 groups) located on the right
side compared to the other side
Cl
(which has 1 group). The
7 6 5 4 3 2 1
designation of numbers on the
continuous chain is dependent on
the amount of substituents
attached nearer to each side.

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 For cycloalkanes with one
Naming Cycloalkanes with Substituents substituent, the carbon to where
the substituent is attached always
The name of a substituent is placed in front of the cycloalkane name.
designated as the first carbon,
Examples: while for cycloalkanes containing
two or more substituents, the
carbon with the lowest group (in
methylcyclobutane alphabetical order) always
1-bromo-2-chlorocyclopentane designated the first carbon as
shown in the
1-bromo-2-chlorocyclopentane
compound.
Drawing Alkane and Cycloalkane structures

1. Draw the main chain of carbon atoms (the main chain is always found at the last part of the name).
2. Number the chain and place the substituents on the carbons indicated by the numbers.
3. Add the correct number of hydrogen atoms to give four bonds to each carbon atom.

Examples:

2,4–dimethylhexane where:
2,4 – the location of branches on the main chain
dimethyl – means two methyl (CH3–) groups attached (tri for 3, tetra
for 4, etc.)
hexane – 6 carbon atoms present on the main chain with single C–C
bonds

1,3 –dibromo–2–chloro–2–ethylcyclohexane
where:
1,3 & 2 & 2 – the location of the branches on the main chain namely (bromine, chlorine, and ethyl, respectively)
dibromo – two bromine atoms were attached on the first and third carbon atoms
chloro – chlorine atom is attached on the second carbon
ethyl – C2H5– group is attached on the second carbon
cyclohexane – 6 carbon atoms are present on the main cycloalkane chain with single C–C bonds

5 4

6 3 Br
6
1 2
Cl
Br
C2H5

Properties and Reactions of Alkanes

Alkanes are non-polar, insoluble in water, less dense compared to water, and flammable in the air.

Alkanes with one to four carbon atoms:
• Methane, ethane, propane, and butane
• In gaseous state at room temperature
• Used as heating fuels (such as LPG and butane)
Alkanes with nine to seventeen carbon atoms:
• Liquid at room temperature
• Have higher boiling points
• Found in kerosene, diesel, and jet fuels.
Alkanes with five to eight carbon atoms:
• Liquid at room temperature
• These are pentane, hexane, heptane, and octane
• Very volatile and it is used to make gasoline
Alkanes with eighteen or more carbon atoms:
• Have high molar masses
• Waxy solids at room temperature
• Used for waxy coatings of fruits and vegetables

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Boiling Points of Alkanes
• Are lowest of organic compounds
• Increasing as the number of carbon
atoms increase due to elevated
dispersion forces.
• Decrease for branched alkanes
• Increase for cycloalkanes

Classification of Carbon atoms

The classification of carbon atoms
indicates the number of carbon atoms attached.
• Primary carbon (10) bonds to one
carbon atom
• Secondary carbon (20) bonds to two
carbon atoms
• Tertiary carbon (30) bonds to three
carbon atoms

CH3 —CH2—CH—CH3

CH3
Combustion of Alkanes
Alkanes undergo combustion by reacting with oxygen to produce carbon dioxide, water, and energy. The
reaction of alkanes are typically not very reactive due to strong C–C single bonds

Example:
Propane is used to provide heat for cooking or warming a room. Write a balanced equation for the complete
combustion of propane. In the example given, we need to
calculate how many molecules of
C3H8 + O2 CO2 + H2O O2 are needed to complete the
combustion reaction of propane.
To give the exact number of
Complete combustion: molecule, we should balance the
C3H8 + 5O2 3CO2 + 4H2O equation – the number of each
atom in the reactant’s side is equal
to the number of atoms present on
the product’s side.
Halogenation of Alkanes (Substitution Reaction)
When alkanes react with halogens:
• The reaction is called substitution, one or more H atoms are replaced with a halogen usually Cl or Br
• Light or heat is required
• A mixture of halogenated products result, but we write the equation with the monosubstituted product.
Example:
The halogenation of ethane with chlorine to produce chloroethane compound.
light
CH3—CH3 + Cl2 CH3—CH2 —Cl + HCl
ethane Chloroethane
or
Ethyl chloride
Functional Groups
Functional groups are:
• specific groups of atoms within the molecules that are responsible for the characteristic chemical reactions of
those molecules.
• These are attached to the carbon backbone of organic molecules.
• The word moiety is often used synonymously to functional group but according to IUPAC definition, moiety is a
half of a molecule including its substructures of the functional groups.

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List of Functional Groups

Functional groups in everyday items

Methyl amine (fish)

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 UNSATURATED HYDROCARBONS
Objectives:
This module aims to:
• Name and draw the structures of alkenes, alkynes, and
aromatic hydrocarbons.
• Predict the products of a reaction and the reactants needed
in preparing another compound
• Draw the 3D shapes of organic molecules using different
molecular representations.

UNSATURATED HYDROCARBONS
• Are those wherein at least a carbon–carbon double or
triple bond is present as that of the alkenes and alkynes.
• Have fewer hydrogen atoms attached to the carbon chain than alkanes

Alkenes
According to VSEPR theory, three groups in a double bond are bonded at 1200 angles.
Alkenes are flat because the atoms in a double bond lie in the same plane.
The simplest alkene is ethene. The general formula is CnH2(n)

The names of alkenes use the corresponding alkane name only the ending will be changed to –ene

Alkene IUPAC name Common name

H2C=CH2 ethene ethylene

H2C=CH–CH3 propene propylene

cyclohexene

Alkynes
The groups attached to triple bond are at 1800 angles.
Contains carbon to carbon triple bond.
The general formula is CnH2(n)–2. The simplest alkyne is ethyne.

The names of alkynes use the corresponding alkane name only the ending will be changed to –yne.

Alkyne IUPAC name Common name

HC=CH ethyne acetylene

HC=C–CH3 propyne

Guide to Naming Alkenes and Alkynes

1. Name of the longest carbon chain with a double or triple bond.
2. Number the carbon chain starting from the end nearest a double or triple bond.
3. Give the location and name of each substituent (in alphabetical order) as a prefix to the name.

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 Examples:
CH2=CH─CH2─CH3 1–butene
1 2 3 4

CH3─CH=CH─CH3 2–butene
1 2 3 4

CH3–CH2–CH2 –C=C–CH3 2–hexyne

6 5 4 3 2 1

Naming Alkenes and Alkynes with Substituents

Alkenes
1. Name the longest carbon chain.
2. Number the chain from the double bond.
CH3

CH3–CH–CH=CH–CH3
5 4 3 2 1

3. Give the location of each substituent.

4–methyl–2–pentene
Alkynes
1. Name the longest carbon chain
2. Number the chain from the triple bond.
CH3

HC=C–CH–CH3
1 2 3 4

3. Give the location of each substituent.

3–methyl–1–butyne

Stereochemistry of Unsaturated Hydrocarbons

Stereochemistry is the study of the three-dimensional structure of molecules. The cis and trans isomers are forms
of stereoisomers, differing structurally only in the location of the atoms of the molecule in three‐dimensional space. Such
stereoisomers can have different physical and chemical properties.
In an alkene, cis and trans isomers are possible because the double bond
• Is rigid
• Cannot rotate
• Has groups attached to the carbons of the double bond that are fixed relative to each other.

Cis–trans isomerism
It can be modeled by making a double bond with your
fingers with both thumbs on the same side or opposite from
each other. It is occur when different groups are attached to
the double bond.

Cis isomer, groups are attached on the same side of the double
bond.

Trans isomer, the groups are attached on opposite sides.

Cis-trans isomers do not occur if a carbon atom in the double

bond is attached to identical groups.

Neither cis nor trans since identical groups (bromine atoms) are attached to the same
carbon atom.
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Reaction of Unsaturated Hydrocarbons

Addition Reactions
In addition reactions, reactants add to the carbon atoms in double
or triple bond to produce a saturated hydrocarbon. A double or triple bond
is easily broken, which makes it very reactive.
In addition reaction, there are four different types depending on
the reactants added, namely: hydrogenation, halogenation,
hydrohalogenation, and hydration.

Hydrogenation
• Hydrogen atoms added to the carbon atoms of a double or triple
bond.
• Catalysts such Pt or Ni are used to speed up the reaction

H H
Pt
H2C CH2 + H2 H2C CH2

H H
Ni
HC CH + 2H2 HC CH
H H
Halogenation
• In halogenation, halogen atoms add to the carbon atoms of a double or triple bond.
Br Br
H2C CH2 + Br2 H2C CH2

Cl Cl

HC C CH3 + 2Cl2 HC C CH3

Cl Cl
Hydrohalogenation
• In hydrohalogenation, atoms of a hydrogen halide add to the carbon atoms of a double bond or triple bond.
H Cl
CH3 CH CH CH3 + HCl CH3 CH CH CH3

H
+ HBr

Br
Markovnikov’s Rule
• When an unsymmetrical alkene undergoes hydrohalogenation, the H in HX adds to the carbon in the
double bond that has the greater number of H atoms.
H Cl
CH3 CH CH2 Does not form

CH3 CH CH2 + HCl

C with the most H
Cl H
CH3 CH CH2 Product that forms
Hydration
• In hydration, water (H2O) molecule is added to a double bond forming an alcohol compound.
• An H atom bonds to the carbon in the double bond with the most hydrogen atoms while the OH (hydroxyl) bonds
to carbon atom with fewer H atoms.

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Polymers
• Large, long chain molecules
• Found in nature, including cellulose in plants, starches in food, proteins and DNA in the body.
• Also synthetic such as polyethylene and polystyrene, Teflon, an nylon.
• Made up of monomers–a small repeating units
• Made by reaction of small alkenes.

In polymerization, a small repeating units called monomers join to form a long chain polymer.
H H H H H H
C C + C C + C C
H H H H H H
Ethylene monomers
H H H H H H
chain continues C C C C C C chain continues
H H H H H H

Polyethylene
List of Polymers

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Examples of Polymers

Recycling Plastics
Recycling is simplified by using codes found on plastic items.

1 PETE – Polyethyleneterephtalate
2 HDPE – High-density polyethylene
3 PV – Polyvinyl chloride
4 LDPE – Low-density polyethylene
5 PP – Polypropylene
6 PS – Polystyrene

Aromatic Compounds
Any compound that contains this benzene ring. It is referred to us by the aroma of these compounds.
The different structural formulas of benzene and its chemical formula.

Benzene
• Has six electrons shared equally among the six carbon atoms.
• It has alternating carbon to carbon double bond.
• It is also represented as a hexagon with a circle drawn inside. The circle inside represent the alternating
double bond.

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 Examples of Aromatic compounds found in nature and health

O
CH O
Vanillin Aspirin
COH O
C O CH3
OCH3
OH

Ibuprofen NH C CH3

CH3 CH3 O
Acetaminophen
H3C CH CH2 CH COH
OH

Aromatic compounds are named:

• With benzene as the parent chain
• With one side group named in front of benzene.

CH3 Cl

Methylbenzene Chlorobenzene

Benzene ring with substituents

Some substituted benzene rings:
• Have common names used for many years
• With a single substituent use a common name or are named as a benzene derivative
CH3 NH2 OH

toluene aniline phenol

(methylbenzene) (benzenamine) (hydroxybenzene)

Aromatic compounds with two groups

Two naming systems are used when two groups are attached to a benzene ring.
• Number the ring to give the lowest numbers to the side groups
• Use prefixes to show the arrangement:
• Ortho (o) for 1 & 2
• Meta (m) for 1 & 3
• Para (p) for 1 & 4
CH3 Cl OH
Cl

Cl
1,4-dichlorobenzene 2-chlorophenol
3-chlorotoluene
Cl (p–dichlorobenzene) (o–chlorophenol)
(m–chlorotoluene)

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Properties and reactions of Aromatic Compound
Aromatic compounds:
• Have a stable aromatic bonding system
• Are resistant to many reactions
• Undergo substitution reactions, which retain the ability of the aromatic bonding system.

Substitution reactions
In a substitution reaction, a hydrogen atom on a benzene ring is replaced by an atom or a group of atoms.

Type of substitution Hydrogen on benzene replaced by

• Halogenation chlorine or bromine atom
• Nitration nitro group (–NO2)
• Sulfonation –SO3H group

Halogenation
• An H atom of benzene is replaced by a chlorine or bromine atom
• A catalyst FeCl3 is needed in chlorination while FeBr3 catalyst for bromination
H Cl
FeCl3
+ Cl2 + HCl

Benzene Chlorobenzene

Nitration
• An H atom of benzene is replaced by a nitro (–NO2) group from HNO3
• An acid catalyst such as H2SO4 is needed
H NO2
H2SO4
+ HNO3 + HOH

Benzene Nitrobenzene

Sulfonation
• An H atom on benzene is replaced by –SO3H group from SO3
• An aci catalyst such as H2SO4 is needed
H SO3H
H2SO4
+ SO3

Benzene Benzenesulfonic acid

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