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DISCUSSION
HYDROCARBONS
Hydrocarbons and many related compounds are often used as fuels in our highly industrialized
society, but we have not looked closely at their structures and differences. At this point, it is
useful to take a closer look at the many types or classes of hydrocarbons and some related
compounds, as theses have many uses beyond those as fuels. There are four classes of
hydrocarbons: the alkanes, which contain carbon-carbon single bonds; the alkenes, which
contain one or more carbon-carbon double bonds; the alkynes, which contain carbon-carbon
triple bonds; and the aromatics, which consists of benzene, benzene derivatives and fused
benzene rings.
CLASSIFICATION OF ORGANIC
COMPOUNDS
1. Classification of Hydrocarbons:
Hydrocarbons are compounds containing only carbon and hydrogen. Hydrocarbons are
classified into two main types (according structure):
I. Aliphatic hydrocarbons or open chain compounds (carbon atoms in chains).
Aliphatic hydrocarbons are subdivided into:
A. Saturated hydrocarbons or the Alkanes – Saturated hydrocarbons are
compounds in which the four valence heads of carbon are fully satisfied by atoms
for hydrogen or carbon and hydrogen. They are characterized by single heads
between carbon atoms. Ex. Methane, CH4; ethane, CH3 – CH3.
B. Unsaturated hydrocarbons are characterized by double or triple heads
between carbon atoms. The two series of unsaturated hydrocarbons are:
1. Alkanes are characterized by a double bond between carbon atoms.
Ex. Ethene. CH2 = CH2.
2. Alkynes are characterized by a triple bond between carbon atoms.
Ex. Acetylene or Ethyne, CH – CH.
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II. Cyclo hydrocarbons (carbon atoms in rings or closed chains).
1. Aromatic hydrocarbon or benzene series. These compounds are
characterized by a closed chain of carbon atoms possessing a special type
unsaturation since the carbon atoms are linked by alternate single and double
bonds.
Ex. Benzene, whose molecule formula is CH. Its structural is
CH
HC CH
|| |
HC CH
CH
2. Alicyclic hydrocarbons. These are the cycloalkanes or the cycleolefins.
Ex. Cyclobutane
CH 2 – CH2
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CH 2 – CH2
3. Heterocyclic compounds are mentioned under closed chain or ring
compounds. These compounds are not composed only of carbon and hydrogen,
but are cyclic compounds in which at least one atom of the ring is that of some
element other than carbon. Ex. Thiopene, C4H4S or
S
HC CH
|| ||
HC CH
SOURCES OF HYDROCARBONS
The most common sources of the hydrocarbons are coal, natural gas, and petroleum.
Coal:
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Coal is an indirect source for aromatic hydrocarbons. It is a complex mixture of high molecular
weight hydrocarbons that are about 85 % carbon by mass. It usually contains a relatively small
but variable amount of sulfur. The small amount of sulfur can be a significant factor when one
considers its potential as a contributor to air pollution and acid precipitation. About 88 % of our
annual coal production is burned to produce electricity. Only 1 % is used for residential and
commercial heating. Although the use of coal is on the rise, its use as a heating fuel has
declined because it is a relatively dirty fuel, bulky to handle, and a major cause of air pollution
(because of its sulfur content). The dangers of deep coal mining and the environmental
disruption caused by strip mining contributed to the decline in the use of coal.
Coal represents about 91 % of the world’s known fossil fuel reserves with approximately equal
percentages of natural gas and oil making up the remaining 9 %. Only a small percentage of the
world’s coal has been mined to date. It is estimated that the world’s proven coal reserves will
last at least 200 years at the current rate of usage.
On destructive distillation of coal to produce coke, some of the coal is converted into a black,
viscous liquid called coal tar. This tar-like liquid is separated into pure compounds by fractional
distillation, together with crystallization processes, centrifuging, and solvent extraction. One ton
of coal yields about 140 lbs. of tar, along with about 1500 lbs. of coke. 10,000 cu. Ft. of coal gas
(mostly hydrogen and methane) and about 25 lbs. of ammonium salts. The 140 lbs. of coal tar in
turn produces naphthalene, benzene, toluene, xylenes, and varying amounts of other aromatic
hydrocarbons, and the residue left is pitch.
Natural Gas:
Natural gas is a mixture of gases trapped with petroleum in Earth’s crust and is recoverable
from oil wells or gas wells where the gases have migrated through the rock. Natural gas is also
being used as a vehicle fuel, and worldwide there are more than 2.5 million vehicles powered by
natural gas. Vehicles powered by natural gas emit minimal amounts of carbon monoxide,
hydrocarbons, and particulates, and the price of natural gas is about one-third that of gasoline.
The main disadvantages of natural gas vehicles include the need for a cylindrical pressurized
gas tank and the lack of service stations that sell compressed natural gas.
Natural gas is often encountered in drilling wells for petroleum. Natural gas is found to contain
from 50 to 94% methane. Some ethane, propane and other paraffin hydrocarbons of low
molecular weight are also present. Natural gas is thought to have originated as petroleum did,
that is from plant and animal materials.
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Petroleum:
Petroleum is a complex liquid solution of gaseous, liquid, and solid hydrocarbons. Also present
are small amounts of nitrogen and sulfur compounds. Crude petroleum is a complex mixture of
thousands of hydrocarbon compounds, and the actual composition of petroleum varies with the
location in which it is found. For example, Pennsylvania crude oils are primarily straightchain
hydrocarbons, whereas California crude oil is composed of a larger portion of aromatic
hydrocarbons.
How long will petroleum be viable as a source of energy and starting materials for consumer
products? This is difficult to estimate because of continued revisions of recoverable crude oil
resources. For example, estimates of global petroleum reserves increased 43 % between 1984
and 1994, primarily because of re-evaluation of oil reserves in the Middle East, where more than
65 % world’s oil resources are located. Oil production would continue for several decades after
thus; however, the increasing cost and lower availability will favor increased use of natural gas,
coal, and alternative sources such as wind energy and solar energy, particularly electricity
obtained through the use of photovoltaic cells.
Methanol and Ethanol:
Methanol and ethanol are being considered as replacements for gasoline, especially in urban
areas that have extremely high levels of air pollution caused by motor vehicles. What are the
advantages and disadvantages of switching to methanol- and ethanol-powered vehicles? Both
methanol and ethanol burn more clearly than gasoline, and levels of troublesome pollutants
such as carbon monoxide, unreacted hydrocarbons, nitrogen oxides, and ozone are reduced.
However, there is concern about the higher exhaust emissions of carcinogenic formaldehyde
from alcohol-powered vehicles. Since the number of these vehicles is relatively limited, it is
difficult to assess the extent to which these formaldehyde emissions will contribute to the total
aldehyde levels from other sources.
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Different types of Formula:
The general formula, it is a type of empirical formula that represents the composition of any
member of an entire class of compounds. Every member of the class of paraffin hydrocarbons
is, for example, composed of hydrogen and carbon, the number of hydrogen atoms always
being two or more than twice the number of carbon atoms. Given that n stands for “any
number,” the general formula of this class is therefore CnH2n + 2.
The molecular formula, which expresses the actual number of each kind of atom present, can
be derived from the empirical formula. The molecular formula may be the same as the empirical
formula or some multiple of it. In order to derive the molecular formula from the empirical
formula, the molecular weight (molecular mass) of the compound being analyzed should be
determined.
The empirical formula, which expresses the relative numbers of the different atoms present in
a molecule, can easily be calculated from the data on elemental analysis.
The structural formula, a formula which shows the arrangement of atoms in the molecule of a
compound. It is identify the location of chemical bonds between the atoms of a molecule. A
structural formula consists of symbols for the atoms connected by short lines that represent
chemical bonds—one, two, or three lines standing for single, double, or triple bonds,
respectively.
For example, the structural formula of ethane is signifying that the compound consists of two
carbon atoms each linked to the other and to three hydrogen atoms by single bonds. Structural
formulas are particularly useful for showing how compounds with the identical kind and number
of atoms differ.
EXAMPLES:
Table 1.1
Hydrocarbons General Formula
Alkane CnH2n + 2
Alkene CnH2n
Alkyne CnH2n - 2
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Note: C stands for carbon
H stands for Hydrogen
n stands for the no. of atoms
if n is equal to 2 substitute to the general formula of each hydrocarbon.
Table 1.2
Molecular Empirical Structural formula Name
formula formula
H H
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Alkane C2H6 CH3 H–C–C–H ethane
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H H
H–C = C–H
Alkene C2H4 CH2 | | ethene
H H
Alkyne C2H2 CH H–C C–H ethyne
? SAQ 1
A. Using the Table 1.2, determine the molecular, empirical, and structural formula using the
general formula for the three hydrocarbons when n = 3.
2. Isomerism:
Two or more compounds with the same molecular formula but different arrangements of atoms
are called isomers. Isomers differ in one or more physical or chemical properties such as
boiling point, color, solubility, reactivity, and density. Several different types of isomerism are
possible for organic compounds.
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Different types of Isomerism:
Structural isomers: Isomers that differ in the order in which the atoms are bonded
together.
Branched-chain isomers: Structural isomers of hydrocarbons that have carbon-carbon
bonds in side chains.
Straight-chain isomers: Structural isomers of hydrocarbons with no side chains.
EXAMPLE:
Three isomers are possible for the isomeric pentanes (C3H12). Draw condensed formulas for
theses isomers.
CH3CH2CH2CH2CH3
Condensed formula: pentane
CH3
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CH3CHCH2CH3
Condensed formula: 2-methylbutane
CH3
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CH3CCH3
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CH3
Condensed formula: 2, 2,-dimenthylpropane
? SAQ 2
A. Give the isomers of butane (C4H10). Draw the condensed formula for this isomers.
Table 1.3 THE FIRST EIGHT STRAIGHT-CHAIN SATURATED HYDROCARBONS
Name Formula Boiling Point Condensed Use
(ºC)* formula
Principal
Methane CH4 – 162 CH4 component in
natural gas
Ethane C2H6 – 88.5 CH3CH3 Minor component
in natural gas
Propane C3H8 – 42 CH3CH2CH3 Bottled gas for
Butane C4H10 0 CH3CH2CH2CH3 fuel
Pentane C5H12 36 CH3(CH2)3CH3
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Hexane C6H14 69 CH3(CH2)4CH3 Some of the
Heptane C7H16 98 CH3(CH2)5CH3 components of
gasoline
Octane C8H18 126 CH3(CH2)6CH3
Notice the gradual increase in boiling point as the molecular weight increases. Fractional distillation of
petroleum is possible because of these differences.
Summary
Petroleum. Crude petroleum is a complex mixture of thousands of hydrocarbon
compounds, and the actual composition of petroleum varies with the location in which it
is found.
Natural Gas. Natural gas, a mixture of gases trapped with petroleum in Earth’s crust, is
the fastest-growing energy in the United States.
Coal. Coal is a complex mixture of high molecular weight hydrocarbons that are about
85 % carbon by mass.
Isomers. Two or more compounds with the same molecular formula but different
arrangements of atoms.
Structural isomers. Isomer that differ in the order in which the atoms are bonded
together.
Branched-chain isomers. Structural isomers of hydrocarbons that have carbon-carbon
bonds in side chains.
Straight-chain isomers. Structural isomers of hydrocarbons with no side chains.
Alkyne. An organic compound containing a carbon-carbon triple bond.
Cycloalkane. A saturated hydrocarbon with carbon atoms joined in a ring.
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Aromatic compound. A compound with one or more benzene rings or rings with
benzene-like chemical properties.
References
Brown, Le May and Bursten, Burdge, 2004, Chemistry The Central Science (9 th edition),
Pearson Education (Asia) Pte Ltd.
Cengage Learning Asia Ltd., 2019, General Chemistry 2 (Philippine edition),
Rex Book Store Inc.
Malone, Leo J., Dolter, Theodore D., 2010, Basic Concepts of Chemistry (8th edition),
John Wiley and Sons, Inc.
Masterton, William L., Hurley, Cecile H., Peterson, James F., Sack, Dorothy. Gabler,
Robert E., 2018, Chemistry for Engineering Students (Philippine edition),
C & E Publishing, Inc.
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