ORGANIC CHEMISTRY 1 (ONE)

TOPIC: HYDROCARBONS
CONTENT:
1. STRUCTURE AND VALENCY OF CARBON, HYDROCARBON – MEANING AND
EXAMPLES,
2. HOMOLOGOUS SERIES- CHARACTERISTICS, AND FUNCTIONAL GROUP
3. SATURATED HYDROCARBON -ALKANES

PERIOD 1:
DEFINITION OF ORGANIC CHEMISTRY
Organic chemistry is the study of the structure, properties, composition, reactions, and preparation of
carbon-containing compounds. Most organic compounds contain carbon and hydrogen, but they may
also include any number of other elements (e.g., nitrogen, oxygen, halogens, phosphorus, silicon, sulfur).
Carbon dioxide (CO2), water (H2O), and calcium carbonate (CaCO 3) are not organic compounds because
they do not contain carbon-hydrogen (C-H) bonds.

H2CO3
UNIQUE NATURE OF CARBON
Carbon atom belongs to group IV of the periodic table of element.
1. The excited state electronic configuration of carbon is 1s 2 2s1 2px1 2p1y 2pz1. A carbon has four electrons
in its outer shell and uses by sharing electrons to form covalent bonds (tetravalency).
2. It has no d-orbital available for bonding, therefore it can only form four bonds, and these gives rise to
a variety of neutral compounds having single, double and triple bonds.
3. There are three (3) types of orbital hybridization available to carbon namely Sp 3, Sp2 and Sp.
Hybridization is a process in which two or more atomic orbitals of comparable energy in the valence-
shell of an atom (central atom of a molecule or ion) mix together and give rise to the formation of new
degenerate (having the same energy level) orbitals known as hybrid orbitals. The size of the hybrid
orbital decreases as the percentage of s-character increases. As a result, the size of the hybrid orbital is:
sp3 > sp2 > sp.
4. Catenation: Carbon atoms have a unique property called catenation, which allows them to bond with
one another in a long and continuous chain, leading to the creation of carbon-based backbones in
organic molecules.
5. The bond between carbon and hydrogen is almost non-polar. Thus, hydrogen atoms attached to
carbon do not weaken the C-C bonds. The electronegativity value of carbon and hydrogen are 2.5 and
2.1 respectively.

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HYDROCARBONS MEANING AND EXAMPLES

Acyclic or Open Chain Compounds

The carbon atoms are present in the form of an open chain.This chain may either be a straight chain or a
branched chain. These were initially known as Aliphatic compounds because the compounds of this class
were derived from either animal or vegetable fats
Straight Chain Compounds: The carbon skeleton is in the form of a straight chain. Examples: n-
Propane CH3-CH2-CH3 Propene CH2=CH-CH3
Branched Chain Compounds: The carbon skeleton is in the form of a branched chain. Examples:
Isobutylene

Cyclic or Closed Chain Compounds

They are marked by the presence of one or more closed chains or ring of atoms in their structure.
Depending on whether there is a presence of any other atom apart from carbon in the constitution of the
ring, they are further classified as:
1. Homocyclic or Carbocyclic Compounds: The rings in these compounds are entirely made up of carbon
atoms. No other atom is present in the ring skeleton.These can be further divided into two sub-classes:
Alicyclic Compounds and Aromatic Compounds
Alicyclic Compounds
Their name is attributed to their resemblance to Aliphatic compounds in their properties. The examples
of this category include cyclopropane, cyclobutane, cyclopentane, cyclohexane, etc.
Aromatic Compounds
These are cyclic unsaturated compounds. They derive their name from the Greek word Aroma which
means “fragrant smell” since most of these compounds bear a pleasant smell. Aromatic compounds are a

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class of organic compounds characterized by a unique ring structure called an aromatic ring or benzene
ring. These compounds are best known for their distinctive stability, reactivity, and aromaticity, which
refers to the presence of delocalized π (pi) electrons within the ring.
2.Heterocyclic Compounds: contains carbon, hydrogen and other elements.
HOMOLOGOUS SERIES AND FUNCTIONAL GROUP
HOMOLOGOUS SERIES
Definition: A homologous series is a family of organic compounds which follows a regular structural
pattern, in which each successive member differs in its molecular formula by a – CH 2 group.
CHARACTERISTICS OF HOMOLOGOUS SERIES
1. All members of a series share a general molecular formula.
2. Each successive member of a series differs in its molecular formula by the addition of a----- CH 2
group and in its relative molecular mass by an increase of 14.
3. The physical properties of the members in a series change gradually as the number of carbon
atoms per molecule increase.
4. All members of a series can usually be prepared by using the same general method.
5. The members of a series show similar chemical properties.
6. All members of the same family have the same functional group.
Functional group
Functional group is an atom, bonds or group of atoms that identifies an organic compound and
determines its chemical properties. They influence the physical and chemical properties of organic
compounds, including boiling points, melting points, solubility, acidity, basicity, and chemical reactivity.
Alkanols, for instance, have a -OH group that promotes solubility while having an alkyl group that
opposes this action/effect. Alkyl groups larger than C 4H9, this opposing effect is sufficient to greatly limit
the solubility of the compound in water.
THE ALKYL GROUPS: The general term alkyl group includes all groups derived from the alkanes by the loss of hydrogen atom.
They are given the general symbol, R. Example of the alkyl groups.

FORMULA NAME
CH3- Methyl
C2H5- Ethyl
C3H7 Propyl
C4H9 Butyl

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 Homologous series General molecular General Functional group
formula structural
formula
1. alkanes CnH2n+2 R-H
2. Alkene CnH2n
C=C

Alkyne CnH2n-2 - C≣C-

Haloalkanes CnH2n-1x K-X -X

Alkanol CnH2n+1OH R-O-H -OH

Alkanoic acid CnH2n+1COOH R-COOH -COOH

Alkanoate CnH2n+1COOCnH2n+1 R-COOR1 -COOR
Alkanal CnH2n+1CHO RCHO -CHO
Alkanone CnH2n+1COCnH2n+1 RCOR -COR
Amide CnH2n+1CONH2 RCONH2 -CONH2
Amine CnH2n+1NH2 RNH2 -NH2
Nitrile CnH2n+1CN RCN -CN

SATURATED AND UNSATURATED COMPOUNDS

Saturated compounds are compounds containing atoms joined together by single covalent bond.
Alkanes are saturated compounds, e.g ethane, C2H6

Unsaturated compounds are compounds containing atoms joined together by double or triple bonds.
Alkenes and alkynes are unsaturated compounds an alkene is an unsaturated hydrocarbon with two
carbon atoms connected together by a double bond. An alkyne is an unsaturated hydrocarbon with two
carbon atoms connected together by a triple bond. e.g Ethene, C 2H4 and C2H2

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FORMULAE OF ORGANIC COMPOUNDS
Organic compounds are characterized by the following formulae
1. Empirical formula
2. Molecular formula
3. Structural formula

-Empirical Formula An empirical formula represents the simplest whole-number ratio of various atoms
present in a compound. The empirical formula of a compound gives the simplest ratio of the number of
different atoms present in compound
- Molecular Formula The molecular formula shows the exact number of different types of atoms
present in a molecule of a compound. Molecular formula gives the actual number of each different atom
present in a molecule.
Example: For Acetylene the empirical formula is CH, while the molecular formula for Acetylene is C 2H2
The empirical formula of Boron Hydride is BH3. Calculate the molecular formula when the measured mass
of the compound is 27.66.
Solution
The atomic mass is given by = B + 3(H) = 10.81 + 3(1) = 13.81u

But, the measured molecular mass for Boron atom is given as 27.66u

By using the expression, Molecular formula = n × empirical formula

n = molecular formula/empirical formula

27.66
=2
13.81

Putting the value of n = 2 in the empirical formula we get molecular formula as

Molecular formula = 2(BH3) = B2H6.

-Structural Formula. A structural formula is a representation of a molecule that includes the
arrangement of atoms and chemical bonds within the molecule.
Structural formula can be
1. Open structural formula/skeletal formulas
2. Condensed structural formula
Condensed structural formulas, which are put in a single line to save space and make them easier and
faster to write out, it shows the order of atoms similarly to a structural formula.
THE IUPAC NOMENCLATURE FOR ALIPHATIC COMPOUNDS
In IUPAC nomenclature, every name of organic compound consists of a ROOT, SUFFIX and PREFIX names.
Root name: Name of the parent aliphatic hydrocarbon of the longest carbon chain in a molecule.
Suffix name: Name of the principal functional group on the longest carbon chain in a molecule.
Prefix name: Name of the other substituents on the longest carbon chain which are not functional groups.
For example, 1- chloroethane- 1- ol; has 1-chloro as prefix, ethane as root and -1-ol as suffix.

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RULES FOR THE IUPAC NOMENCLATURE
1. Select the longest continuous carbon chain as parent hydrocarbon.
2. Number the longest carbon chain starting from the end that gives lowest possible number to the
suffix (functional group).
3. Indicate the other substituents by prefixes preceded by numbers to show their position on the
carbon chain.

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4. If the same alkyl or other substituents group occurs more than once as side chain, show how
many are present by using prefix di, tri, tetra etc and indicate by various numbers the position of each
group on the longest carbon chain.
5. If there are several different alkyl groups attached to the parent chain, name them in alphabetical
order.
ISOMERS
Isomers are chemical compounds that share the same chemical formula but exhibit variations in both
their properties and the arrangement of atoms within their molecules. Consequently, the compounds
that display isomerism are referred to as isomers. Isomers are molecules that have the same molecular
formula, but have a different arrangement of the atoms in space.
Isomerism is the existence of two or more organic compounds (known as isomers) with the same
molecular formula but different molecular structures.
TYPES OF ISOMERISM
There a
re two major types of Structural Isomerism and Stereoisomerism. The classification of different types of
isomers is illustrated below.

STRUCTURAL ISOMERISM
Structural isomerism is commonly referred to as constitutional isomerism. The functional groups and the
atoms in the molecules of these isomers are linked in different ways.
CHAIN ISOMERISM
These isomers arise because of the possibility of branching in carbon chains. For example, there are two
isomers of butane, C4H10. In one of them, the carbon atoms lie in a "straight chain" whereas in the other
the chain is branched. It is also known as skeletal isomerism.

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POSITION ISOMERISM
Typically, this isomerism involves the attachment of the functional groups to different carbon atoms in
the carbon chain. An example of this type of isomerism can be observed in the compounds having the
formula C3H7Cl.
In position isomerism, the basic carbon skeleton remains unchanged, but important groups are moved
around on that skeleton.

For example, there are two structural isomers with the molecular formula C 3H7Br. In one of them the
bromine atom is on the end of the chain, whereas in the other it's attached in the middle.

FUNCTIONAL ISOMERISM
It is also known as functional group isomerism. it refers to the compounds that have the same chemical
formula but different functional groups attached to them.

Another common example is illustrated by the molecular formula C 3H6O2. Amongst the several structural
isomers of this are propanoic acid (a carboxylic acid) and methyl ethanoate (an ester).

METAMERISM
This type of isomerism arises due to the presence of different alkyl chains on each side of the functional
group.
It is a rare type of isomerism and is generally limited to molecules that contain a divalent atom (such as
sulphur or oxygen), surrounded by alkyl groups.
Example: C4H10O can be represented as ethoxyethane (C2H5OC2H5) and methoxy-propane (CH3OC3H7).
TAUTOMERISM
A tautomer of a compound refers to the isomer of the compound which only differs in the position of
protons and electrons.
Typically, the tautomers of a compound exist together in equilibrium and easily interchange.
It occurs via an intramolecular proton transfer.
An important example of this phenomenon is Keto-enol tautomerism.
RING-CHAIN ISOMERISM

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In ring-chain isomerism, one of the isomers has an open-chain structure whereas the other has a ring
structure.
They generally contain a different number of pi bonds.
A great example of this type of isomerism can be observed in C3H6. Propene and cyclopropane are the
resulting isomers, as illustrated below.
STEREOISOMERISM
Stereoisomerism is a type of isomerism in chemistry where two or more compounds have the same
molecular formula and the same connectivity of atoms but differ in their three-dimensional spatial
arrangement.
GEOMETRIC ISOMERISM
These isomers have different spatial arrangements of atoms in three-dimensional space. Geometric
isomers, also known as cis-trans isomers, occur when there is restricted rotation around a bond, typically
a double bond or within a ring. This restriction leads to different spatial arrangements of substituent
groups around that bond.
Cis-Isomer: In a cis-isomer, similar groups or atoms are on the same side of the molecule with respect
to the restricted bond.

Trans-Isomer: In a trans-isomer, similar groups or atoms are on opposite sides of the molecule with
respect to the restricted bond.

Example: The classic example is in the case of a double bond in organic molecules. In cis-2-butene, two
methyl groups are on the same side of the double bond, while in trans-2-butene, they are on opposite
sides.

OPTICAL ISOMERISM
Optical isomerism, also known as enantiomerism, is a specific type of stereoisomerism in chemistry. It
occurs when two or more compounds have the same molecular formula and the same connectivity of
atoms but differ in their three-dimensional spatial arrangement in a way that they are non-
superimposable mirror images of each other. These non-identical mirror-image compounds are called
enantiomers.