UNIT-6

Hydrocarbons and their Natural Sources

6.1 Introduction
Organic compounds
 are carbon compounds
 they refers compounds that contain carbon element except:
 oxides of carbon (CO, CO2)
 Carbonates & hydrogen carbonates
 Carbides (compounds containing C& other element; eg SiC).
 Primarily organic compounds found in and derived
from plants and animals.
i.e: The primary source of organic compounds are plants
and animals
 They also synthesized in laboratories.
 Most of the foods; like fruits, vegetables, sugar,
fats, starch, and vinegar are organic compounds.
 Pesticides, herbicides, fuels, dry cleaning
chemicals, soaps and detergents, pharmaceuticals,
alcoholic beverages, are also organic compounds.
 Every living organism is made of organic
compounds.
 The organic compounds that are synthesized by
living organisms are called natural products.
 Plants have principally been used as a source of
useful organic compounds like traditional
medicine.
 Plants also provide some organic compounds that are drugs
of abuse and psychotropic chemicals which lead to
addiction and have negative socio-economic effects.
Examples
 Nicotine from tobacco plant,
 Cathinone from Chat (khat); from Catha edulis;
 Opium (morphine) from poppy plant and
 Cocaine from coca leaf are some.
 Some of these drugs are also used in doping.
 Doping is the misuse of certain substances to enhance
sporting performance and stamina.
 Although these compounds are perceived as useful to boost
zealous, increase energy, and decrease fatigue, they have
serious side effects such as personality disorder, low
productivity, increased accidents, reduction of
competitiveness, inability to cope with tasks that require
higher-level judgment and fine motor skills.
6.1.1 History of Organic Chemistry
 The science of organic chemistry began to flourish
with the demise of a nineteenth century theory
called Vitalism theory.
 According to Vitalism theory:
 organic compounds were only those that
came from living organisms.
 only living things could synthesize organic
compounds through the intervention of a
vital force.
 Inorganic compounds were considered those
compounds that came from non-living sources.
However, the German chemist Friedrich Wöhler,
discovered that organic compound (called Urea)
could be synthesized in the laboratory in 1828.
 So, Urea was the first organic compound
synthesized in the laboratory.
 It is synthesized by evaporating an aqueous
solution of the inorganic compound ammonium
cyanate.

Ammonium cyanate Urea

 After this discovery, chemists have developed
ability to design and synthesize new organic
compounds in the laboratory; like medicines,
dyes, polymers, and a host of other substances
that are helpful to society.
 Including both those isolated from natural
sources and those synthesized in the
laboratories, over 50 million organic
compounds are known.
 All of the organic compounds, whether of
synthetic or natural origin, contain the element
carbon.
 The branch of chemistry that studies carbon
compounds is called Organic chemistry.
 Why is carbon special, among other elements?
 The reason is that duet o the unique property of
carbon called catenation.
 Catenation is the ability of atoms of the same
element to join together to form short or long chains
and rings molecule.
 This is the main reason for the presence of millions of
carbon compounds.
 Carbon atoms can form strong covalent bonds to one
another to form rings and chains of carbon atoms.
 Carbon atoms can also form strong bonds with
hydrogen, nitrogen, oxygen, and sulfur.
 A few other elements like sulphur, silicon and boron
show this behavior, but to a much lesser extent.
6.1.2. Structural Representations of Organic
Molecules
 Carbon has four valence electrons and it forms
four covalent bonds with other atoms.
 Lewis structure /Lewis Formula/ Electron-dot notation
 Is a representation of bonds using valence
electrons.
 The shared electron pairs, that formed bonds, are
shown as pairs of dots or lines between the two
atoms.
 The lone pair electron (nonbonding electrons) are
shown as pairs of dots on individual atoms.
Ex: CH3OH:

 However, as the size of the compound increases, it

becomes difficult to portray/show the structure of
molecules with the use of Lewis structure.
 This is why scientists have developed the following
other structural representation.
 Complete structural formula,
 condensed structural formula,
 bond-line representation, and
 polygon formula.
A. Complete (Detailed) Structural Formula
 is the structure obtained by representing the shared two-
electron of covalent bond by a single dash.
Ex1: Methane (CH4):
 Contains one carbon atom and four hydrogen atoms.
 The carbon atom contributes its 4 valence electrons and
each H atom contributes one electron.
 Therefore, the Lewis structures of methane, which has
4 + 4 = 8 electrons is drawn as flows:

Lewis Formula Complete Structural Formula

Ex2: Complete tructure of Pentane (C5H12)

 A single dash represents a single bond:

Ex: CH3CH3: CH3 ─ CH3
 a double dash represents a double bond and
Ex: CH2CH2: CH2 ═ CH2
a triple dash represents a triple bond.
Ex: Ethyne (C2H2): H ─ C ≡ C ─ H
NB: Lone pairs of electrons on atoms may or may not be shown.
ex:

a. Lone pair e─ are shown b. Lone pair e─ are not shown

B. Condensed Structural Formula
 It is obtained by omitting some or all the dashes that
represent covalent bonds.
 It is the structure abbreviated from structural formula.
Ex: Structure of Pentane (C5H12)

CH3CH2CH2CH2CH3
Structural Formula Condensed Structural Formula
 The condensed structural formula can further be
condensed by indicating the repetitive unit using
subscripts.
Ex: CH3CH2CH2CH2CH3 can be condensed to
CH3(CH2)3CH3
C. Bond-Line Structural Representation
 It is the structure in which lines represent carbon-carbon bonds
in zig-zag fashion.
 Carbon and hydrogen atoms are not shown.
 The turning of zig-zag represents carbons.
 Number of hydrogen understood from which each carbon
forms 4 covalent bonds.

Hexane, C6H14 Hexyl bromide C6H13Br

 Only heteroatoms need to be indicated in bond line
representation.
 If there is no heteroatoms at terminal, the terminals denote
methyl (CH3)
d. Polygon Formula
 Is the structure that represents compound, which
its carbon atoms are joined in a ring/ cyclic using
bond-lines.
 The carbon and hydrogen atoms are not shown.
 The corners of a polygon represent a carbon atom.
 The sides of a polygon denote a carbon - carbon
bond.
 If atoms or group of atoms other than hydrogen is
attached to carbon, they must manifested/shown in
this structure.
Examples

Cyclopentane (C5H10) Cyclopentanol (C5H10O)

Cyclohexane (C6H12), Bromocyclohexane (C6H11Br)

6.1.3. Classes of Organic Compounds
 Organic compounds are generally classified based
on their functional group.
 The functional group is the part of a molecule
that determines the chemical properties of that
molecule.
 It is structural feature which is responsible for the
properties of that members of a given family/class
of Organic Compound.
 Organic compounds in the same family/class often
have similar chemical behavior.
 Based on their functional groups, organic compounds
classified as:
 Alkanes,
 Alkenes,
 Alkynes,
 Aromatics,
 Alcohols,
 Aldehydes,
 Ketones,
 Carboxylic acids and
 Esters.
 In this grade level, only alkanes, alkenes, alkynes, and
aromatics will be discussed.
Table 6.1: Some classes of organic compounds
Organic Functional group Name Example
compound ending
Alkane They have C– C and C– H – ane CH3─ CH3
single bonds. Ethane
But these bonds also present in
other organic compounds.
So, Alkanes do not have a
functional group.
Alkene – ene CH2═CH2
Ethene
Alkyne – yne H–C ≡ C–H
ethyne
Aromatic – none

Benzene
6.2 Saturated Hydrocarbons:
 Hydrocarbons are organic compounds that contain only
carbon and hydrogen atoms.
 They may be classified as aliphatic ("fat-like") or
aromatic on the basis of their sources and properties .
 Aliphatic hydrocarbons
 Refers to hydrocarbons derived by chemical degradation of
fats or oils
 They exhibit a “fat-like” behavior.
 This includes alkane, alkene, alkyne, or their derivatives.
 Aromatic hydrocarbons
 Refers to hydrocarbons obtained by chemical degradation of
pleasant smelling plant extracts.
 This includes hydrocarbons that contain a low hydrogen-to-
carbon ratio (benzene, C6H6).
 Hydrocarbons may also be classified as saturated and
unsaturated, based on the number of hydrogen they contain.
Saturated hydrocarbons
 are hydrocarbons containing only single bonds
 This includes alkane Ex: methane, CH4.
 They are called Saturated, because they contain the maximum
number of hydrogen atoms per carbon atoms that the carbon
compound can possess.
Saturated hydrocarbons
 are hydrocarbons containing multiple bonds (double or triple
bond).
 They are called Unsaturated, because they possess hydrogen
fewer than the maximum number of hydrogen atoms per carbon,
and they are capable of reacting with hydrogen.
 This includes:
 alkenes, which contain double bond
 alkynes which contain triple bond and
 Aromatic, which contain benzene.
Alkanes (Paraffins), CnH2n+2
 Alkanes are saturated hydrocarbons.
 They are occasionally called aliphatic compounds, a
name derived from the Greek aleiphas, meaning “fat.”
 The structures of alkanes can be unbranched (normal)
or branched.
 They contain chains of carbon atoms linked by
carbon-carbon and carbon-hydrogen single bonds only
 Every carbon atom in the molecule forms four single
covalent bonds with other atoms.
 Alkanes have the general formula of CnH2n+2, where,
n = 1, 2, 3 . . . is number of carbon atom.
Table 6.2: Some members of unbranched alkanes.
No. of Name Molecular No. of Name Molecular
Carbon formula Carbon formula
1 Methane CH4 11 Undecane C11H24
2 Ethane C2H6 12 Dodecane C12H26
3 Propane C3H8 13 Tridecane C13H28
4 Butane C4H10 14 Tetradecane C14H30
5 Pentane C5H12 15 Pentadecane C15H32
6 Hexane C6H14 16 Hexadecane C16H34
7 Heptane C7H16 17 Heptadecane C17H36
8 Octane C8H18 18 Octadecane C18H38
9 Nonane C9H20 19 Nonadecane C19H40
10 Decane C10H22 20 Eicosane C20H42

A group of compounds in which each member of the group

differs from the next member by a –CH2 is called a
homologous series.
The individual members of the group are called homologues.
Example:
For unbranched alkane having six carbon, write:
a. Molecular formula
b. Complete structural formula and
c. Condensed structural formula
Answer:
a. Molecular formula: C6H14
b. Complete structural formula

c. Condensed structural formula

CH3CH2CH2CH2CH3
Further condensed to: CH3(CH2)4CH3
6.2.2 Physical Properties of Alkanes
 At room temperature (25℃ and 1 atm
pressure), the first four members of the
homologous series of unbranched alkanes are
gases.
 The C5-C17 unbranched alkanes are liquids.
 Unbranched alkanes with 18 and more carbon
atoms are solids.
 Alkanes are the least dense of all groups of
organic compounds.
 All alkanes have densities considerably less
than 1.00 g mL−1(the density of water at 4 °C).
 As a result, petroleum (a mixture of
hydrocarbons rich in alkanes) floats on water.
6.2.3 Nomenclature of Alkanes
 Alkanes can be named in two ways:
 common names and
 IUPAC names.
Common Names of Alkanes
 Lower members of the alkane homologous series
have common names (can be named by common
names).
 The prefixes used in the common names are:
 n- (normal),
 „iso-‟ and
 „neo-‟.
 n- (normal) -is used when all the carbon atoms
form a continuous chain (linked in straight chain).

Ex:

 Iso- is used when all of the carbon atoms form a

continuous chain, except the carbon next to the last
carbon.

Ex:
Neo -is used when the central carbon is
bonded to four other carbon atoms.

Ex: