HYDROCARBONS (5 hrs. LEC/10 hrs.

LAB)

A hydrocarbon is an organic chemical compound composed exclusively of hydrogen and carbon

atoms. Hydrocarbons are naturally-occurring compounds and form the basis of crude
oil, natural gas, coal, and other important energy sources.
Hydrocarbons are highly combustible and produce carbon dioxide, water, and heat when they
are burned. Therefore, hydrocarbons are highly effective as a source of fuel.

CLASSIFICATION OF HYDROCARBONS

The term HYDROCARBONS mean organic compounds which contain only carbon and hydrogen.
By using this definition, four classes of hydrocarbons are included: alkanes, alkenes, alkynes
and aromatic.
The simplest compounds containing 2 carbons shown on the LEFT are as follows:

 Alkanes Alkenes Alkynes

 SATURATED means that each

carbon is bonded to four other
atoms through single covalent  UNSATURATED hydrocarbons contain either double or triple
bonds. Hydrogen atoms bonds. Since the compound is unsaturated with respect to
usually occupy all available hydrogen atoms, the extra electrons are shared between 2
bonding positions after the carbon atoms forming double or triple bonds.
carbons have bonded to each
other.

 PARAFFINS which is derived
 Alkenes are also  Alkynes are also generally
from a Latin word meaning
called OLEFINS because they known as ACETYLENES from
"little activity", and means that
form oily liquids on reaction the first compound in the
the compounds are very
with chlorine gas. series.
unreactive.

AROMATIC COMPOUNDS

Aromatic compounds derive their names from the fact that many of these compounds in the
early days of discovery were grouped because they were oils with fragrant odors, hence the
name aromatic.
The current definition of aromatic compounds includes only those with a benzene ring, which
is a special six carbon ring compound with three alternating double bonds. This structure
imparts unique properties to benzene which are different from other ring compounds.

Sources of Hydrocarbons

The main source of hydrocarbons is fossil fuels—coal, petroleum, and natural gas. Fossil fuels
formed over hundreds of millions of years, as dead organisms were covered with sediments
 and put under great pressure. Giant ferns in ancient swamps turned into coal deposits.
The Figure below shows one way that coal deposits are mined. Dead organisms in ancient
seas gradually formed deposits of petroleum and natural gas.

Properties of Hydrocarbons

The size of hydrocarbon molecules influences their properties, including

their melting and boiling points. As a result, some hydrocarbons are gases at
room temperature, while others are liquids or solids. Hydrocarbons are generally nonpolar,
which means that their molecules do not have oppositely charged sides. Therefore, they do not
dissolve in water, which is a polar compound. In fact, hydrocarbons tend to repel water. That’s
why they are used in floor wax and similar products

TEACHER’S INSIGHT

Hydrocarbons are compounds that contain only carbon and hydrogen. Hydrocarbons are
the simplest type of carbon-based compounds. Hydrocarbons vary greatly in size, which
influences properties such as melting and boiling points. At room temperature,
hydrocarbons may be gases, liquids, or solids. They are generally nonpolar and do not
dissolve in water. Hydrocarbons are placed in two basic classes—saturated and
unsaturated hydrocarbons—based on the number of bonds between their carbon atoms.
Hydrocarbons have a wide variety of important uses, but their most important use is as
fuels. The main source of hydrocarbons is fossil fuels—coal, petroleum, and natural gas.
Self-Reflection:
Based from your readings of the above notes, and the videos you watched on hydrocarbons,
answer the following questions as best as you can. Please write your answers in your notebook
and your output will be graded using a rubric.

1. What is a hydrocarbon?
2. Compare and contrast saturated and unsaturated hydrocarbons.
3. List some uses of hydrocarbons.
4. Where do hydrocarbons come from? 

Activity 4:

Title: Concept Mapping

Direction:
 Draw a concept map of then topic Hydrocarbons. Your output will be graded with a
rubric.
 Write your answers in a sheet of a short bond paper. Write the date of your activity at
the top right portion of your paper and your name at the left top portion.
 Compile your output in your learning portfolio.

Activity 5:

Title: Am I Saturated or Unsaturated?

Direction:
 Identify the following if it is a saturated or an unsaturated hydrocarbon and write what
materials or chemical compounds it can be found.
 Write your answers in a sheet of a short bond paper. Write the date of your activity at
the top right portion of your paper and your name at the left top portion.
 Compile your output in your learning portfolio.

Ethylene Isobutane
Methane Ethane
Propylene Hexyne
Acetylene butadiene

Chapter End Evaluation:

Direction: Read and analyze the questions below. Write your answers on your notebook and
each item is equivalent to 10 points.

1. a. What are the origins of most hydrocarbons and other organic compounds?
b. List three sources of hydrocarbons.
c. What is the main source of hydrocarbons used for fuels?

2. What are isomers? Give one example of a set of isomers for a molecular formula?

3. Describe how the boiling point changes as the chain length of an aliphatic compound
increases. Explain why this happens.

4. Briefly compare alkanes, alkenes, and alkynes. (Give both similarities and differences.)

5. Describe the difference between structural isomers and cis-trans isomers.

Key Terms:

 Hydrocarbons
 Alkane
 Alkene
 Alkynes
 Aromatic hydrocarbons
 Cyclohexane
 Cyclohexene
 Saturated hydrocarbons
 Unsaturated hydrocarbons
SATURATED HYDROCARBONS (5 hrs. LEC/10 hrs. LAB)

Saturated hydrocarbons are hydrocarbons that contain only single bonds between carbon
atoms. They are the simplest class of hydrocarbons. They are called saturated because each
carbon atom is bonded to as many hydrogen atoms as possible. In other words, the carbon
atoms are saturated with hydrogen. You can see an example of a saturated hydrocarbon in
the Figure below. In this compound, named ethane, each carbon atom is bonded to three
hydrogen atoms. In the structural formula, each dash (-) represents a single covalent bond, in
which two atoms share one pair of valence electrons.

Saturated hydrocarbons are given the general name of alkanes. The name of specific alkanes
always ends in –ane. The first part of the name indicates how many carbon atoms each
molecule of the alkane has. The smallest alkane is methane. It has just one carbon atom. The
next largest is ethane with two carbon atoms. The chemical formulas and properties of
methane, ethane, and other small alkanes are listed in the Table below.
The boiling and melting points of alkanes are determined mainly by the number of carbon
atoms they have. Alkanes with more carbon atoms generally boil and melt at higher
temperatures.
Alkane Chemical Formula Boiling Point(°C) Melting Point(°C) State (at 20 °C)

Methane CH4 -162 -183 gas

Ethane C2H6 -89 -172 gas

Propane C3H8 -42 -188 gas

Butane C4H10 0 -138 gas

Pentane C5H12 36 -130 liquid

Hexane C6H14 69 -95 liquid

Heptane C7H16 98 -91 liquid

Octane C8H18 126 -57 liquid

Structural formulas are often used to represent hydrocarbon compounds because the molecules
can have different shapes and a structural formula shows how the atoms are arranged.
Hydrocarbons may form straight chains, branched chains, or rings (see Figure below). You can
read about each type below.

Structural Isomers are molecules which have the same molecular formula but have different
connectivity (The Order They Are Put Together). Alkanes can be very simple examples of this.
With the structural formula C4H10 there are two different isomers possible.

As the number of Carbons in an alkane increases, the number of structural isomers also
increases. This happens quite dramatically, as is shown by the following table.
Another simple example of Structural Isomerism is that between Alcohols and Ethers.
The molecular formula of both Ethanol (An Alcohol) and Methoxymethane (An Ether) is C 2H6O

NOMENCLATURE OF HYDROCARBONS AND ALKYL HALIDES

THE BASICS OF ORGANIC NOMENCLATURE:

Organic chemistry nomenclature is very specific following the general format shown in Figure 1.
The International Union of Pure and Applied Chemistry (IUPAC) has devised a system of
nomenclature that begins with the names of the alkanes and can be adjusted from there to
account for more complicated structures.

Figure 1.

NAMING ALKANES AND ALKYL HALIDES

The IUPAC nomenclature for alkanes and alkyl halides is based on two rules:
Rule 1. Identify the longest chain of carbon atoms (PREFIX+ANE). The longest chain of carbons
in the structure is referred to as the parent chain.   A two-carbon parent chain is called ethane;
a three-carbon parent chain, propane; and a four-carbon parent chain, butane. Longer parent
chains are named as follows: pentane (five-carbon chain), hexane (6), heptane (7), octane (8),
nonane (9), and decane (10). These prefixes can be seen in the names of the alkanes described
in Table 1.

Alkane Molecular Formula Condensed Structural Formula

methane CH4 CH4
ethane C2H6 CH3CH3
propane C3H8 CH3CH2CH3
butane C4H10 CH3CH2CH2CH3
pentane C5H12 CH3CH2CH2CH2CH3
 hexane C6H14 CH3(CH2)4CH3
heptane C7H16 CH3(CH2)5CH3
octane C8H18 CH3(CH2)6CH3
nonane C9H20 CH3(CH2)7CH3
decane C10H22 CH3(CH2)8CH3
tetradecane C14H30 CH3(CH2)12CH3
octadecane C18H38 CH3(CH2)16CH3
Table 1. Some n-alkanes, meaning normal alkanes, indicating that they are straight chains of
carbon units, no branching.  The prefixes indicating the number of carbons in the longest chain
is underlined.

Rule 2. Names and position of the substituents:  Substituents are branches or functional groups
that replace hydrogen atoms on a chain.  If there are substituents on the parent chain, their
names and position on the chain must be included at the front of the name. The position of a
substituent or branch is identified by the number of the carbon atom it is bonded to in the
chain. We number the carbon atoms in the chain by counting from the end of the chain nearest
the substituents. Multiple substituents are named individually and placed in alphabetical order
at the front of the name.

When more than one substituent is present, either on the same carbon atom or on different
carbon atoms, the substituents are listed alphabetically. Because the carbon atom numbering
begins at the end closest to a substituent, the longest chain of carbon atoms is numbered in
such a way as to produce the lowest number for the substituents. The ending -o replaces -
ine at the end of the name of a halide substituent.  For example, an iodine substituent would be
called iodo. The number of substituents of the same type is indicated by the
prefixes di- (two), tri- (three), tetra- (four), penta- (five) and so on (for
example, difluoro- indicates two fluoride substituents).
Example 1
Name the molecule whose structure is shown here:

 
Solution:

The four-carbon chain is numbered from the end with the chlorine atom. This puts the
substituents on positions 1 and 2 (numbering from the other end would put the substituents on
positions 3 and 4). Four carbon atoms mean that the base name of this compound will be
butane. The bromine at position 2 will be described by adding 2-bromo-; this will come at the
beginning of the name, since bromo- comes before chloro- alphabetically. The chlorine at
position 1 will be described by adding 1-chloro-, resulting in the name of the molecule being 2-
bromo-1-chlorobutane.

CYCLOALKANES

Cycloalkanes are cyclic hydrocarbons, meaning that the carbons of the molecule are arranged in
the form of a ring. Cycloalkanes are also saturated, meaning that all of the carbons atoms that
make up the ring are single bonded to other atoms (no double or triple bonds). There are also
polycyclic alkanes, which are molecules that contain two or more cycloalkanes that are joined,
forming multiple rings.

Many organic compounds found in nature or created in a laboratory contain rings of carbon
atoms with distinguishing chemical properties; these compounds are known as cycloalkanes.
Cycloalkanes only contain carbon-hydrogen bonds and carbon-carbon single bonds, but in
cycloalkanes, the carbon atoms are joined in a ring. The smallest cycloalkane is cyclopropane.

If you count the carbons and hydrogens, you will see that they no longer fit the general
formula CnH2n+2CnH2n+2. By joining the carbon atoms in a ring, two hydrogen atoms have
been lost. The general formula for a cycloalkane is CnH2nCnH2n. Cyclic compounds are not all
flat molecules. All of the cycloalkanes, from cyclopentane upwards, exist as "puckered rings".
Cyclohexane, for example, has a ring structure that looks like this:

Figure 4.1.2: This is known as the "chair" form of cyclohexane from its shape, which vaguely
resembles a chair. Note: The cyclohexane molecule is constantly changing, with the atom on
the left, which is currently pointing down, flipping up, and the atom on the right flipping down.
During this process, another (slightly less stable) form of cyclohexane is formed known as the
"boat" form. In this arrangement, both of these atoms are either pointing up or down at the
same time

In addition to being saturated cyclic hydrocarbons, cycloalkanes may have multiple substituents
or functional groups that further determine their unique chemical properties. The most common
and useful cycloalkanes in organic chemistry are cyclopentane and cyclohexane, although other
cycloalkanes varying in the number of carbons can be synthesized. Understanding cycloalkanes
and their properties are crucial in that many of the biological processes that occur in most living
things have cycloalkane-like structures.

Glucose (6 carbon sugar)

Ribose (5 carbon sugar)

 Cholesterol (polycyclic)

Although polycyclic compounds are important, they are highly complex and typically have
common names accepted by IUPAC. However, the common names do not generally follow the
basic IUPAC nomenclature rules. The general formula of the cycloalkanes
is CnH2nCnH2n where ‘n’ is the number of carbons. The naming of cycloalkanes follows a
simple set of rules that are built upon the same basic steps in naming alkanes. Cyclic
hydrocarbons have the prefix "cyclo-".

For simplicity, cycloalkane molecules can be drawn in the form of skeletal structures in which
each intersection between two lines is assumed to have a carbon atom with its corresponding
number of hydrogens.

 same as   same as 

Cycloalkane Molecular Formula Basic Structure

Cyclopropane C3H6

Cyclobutane C4H8

Cyclopentane C5H10
 Cyclohexane C6H12

Cycloheptane C7H14

Cyclooctane C8H16

Cyclononane C9H18

Cyclodecane C10H20

NAMING CYCLOALKANES

1) The ring will be the parent chain (even if there is a longer linear chain attached to the ring). 
The ring is named by the number of carbons (as before) but with the prefix cyclo-.

            i.e.    cyclohexane (six-carbon ring) or cyclooctane (eight-carbon ring)

2) Number the ring starting from the carbon that will give the lowest substituent numbers.  In
the case of a tie, start with the carbon with the substituent name that is earliest in the
alphabet.  Number in the direction that give the lower overall substituent numbers.  (In more
complex situations go in the direction that is alphabetical).          

3) Name any groups (substituents) attached to the parent ring.

            -carbon substituents are named methyl, ethyl, propyl etc.
            -halogen substituents are named fluoro, chloro, bromo etc.

4) Groups repeated substituents together using prefixes: di-, tri-, tetra- etc.

5) List the substituents in alphabetical order ignoring the prefixes.

            i.e.    ethyl before methyl

                     ethyl before dimethyl
         
6) Write out the name in the format:
            #, #-prefix + substituent-#-prefix + substituent + parent chain
Examples 1:

Parent Chain = cyclohexane (six-carbon ring) 

Numbers start from the carbon with the Br substituent and go clockwise.  This gives the lowest
substituent numbers (1,1,3).

Substituents = 1-bromo 1-methyl   3-chloro

Order of substituents with prefixes:

        1-bromo before 3-chloro   before 1-methyl

Put all together:

        1-bromo-3-chloro-1-methylcyclohexane
Parent Chain = cyclobutane (four-carbon ring)

Examples 2:

Numbers start from the carbon with the butyl substituent and go counter-clockwise.  Starting
from the butyl(counter-clockwise) or chloro (clockwise) would give the same numbering
(1,2,3).  So, butyl is chosen over chloro as carbon 1 because it is first alphabetically.

Substituents = 1-butyl   2-bromo   3-chloro

Order of substituents with prefixes:

        2-bromo before 1-butyl   before 3-chloro

Put all together:

        2-bromo-1-butyl-3-chlorocyclobutane
REACTIONS OF ALKANES

In the absence of a spark or a high-intensity light source, alkanes are generally inert to
chemical reactions. However, anyone who has used a match to light a gas burner, or dropped a
match onto charcoal coated with lighter fluid, should recognize that alkanes burst into flame in
the presence of a spark. It doesn't matter whether the starting material is the methane found in
natural gas,

CH4(g) + 2 O2(g)  CO2(g) + 2 H2O(g)

the mixture of butane and isobutane used in disposable cigarette lighters,

2 C4H10(g) + 13 O2(g)  8 CO2(g) + 10 H2O(g)

the mixture of C5 to C6 hydrocarbons in charcoal lighter fluid,

C5H12(g) + 8 O2(g)  5 CO2(g) + 6 H2O(g)

or the complex mixture of C6 to C8 hydrocarbons in gasoline.

2 C8H18(l) + 25 O2(g)   16 CO2(g) + 18 H2O(g)

Once the reaction is ignited by a spark, these hydrocarbons burn to form CO 2 and H2O and give
off between 45 and 50 kJ of energy per gram of fuel consumed.
In the presence of light, or at high temperatures, alkanes react with halogens to form alkyl
halides. Reaction with chlorine gives an alkyl chloride.

light
CH4(g) + Cl2(g) CH3Cl(g) + HCl(g)
Reaction with bromine gives an alkyl bromide.

light
CH4(g) + Br2(l) CH3Br(g) + HBr(g)

TEACHER’S INSIGHT

 Saturated hydrocarbons are hydrocarbons that contain only single bonds between carbon
atoms. As a result, each carbon atom is bonded to as many hydrogen atoms as possible.
 Saturated hydrocarbons are given the general name of alkanes. The name of specific
alkanes always ends in –ane and has a prefix to indicate how many carbon atoms it has.
 Hydrocarbons may form straight chains, branched chains, or rings. Ring-shaped
hydrocarbons are called cyclic hydrocarbons.
Self-Reflection:

Based from your readings of the above notes, and the videos you watched on hydrocarbons,
answer the following questions as best as you can. Please write your answers in your notebook.
1. What is a saturated hydrocarbon?
2. How are saturated hydrocarbon compounds named?
3. What are the name and chemical formula of the saturated hydrocarbon that has the
following structural formula seen below?

4. Compare and contrast straight-chain, branched-chain, and cyclic alkanes.

Activity 6:

Title: Concept Mapping

Direction:
• Draw a concept map of then topic Saturated Hydrocarbons. Your output will be graded
with a rubric.
• Write your answers in a sheet of a short bond paper. Write the date of your activity at
the top right portion of your paper and your name at the left top portion.
• Compile your output in your learning portfolio.

Activity 7:

Title: Naming Alkanes/Cycloalkanes and Drawing their Structural Formulas

General Rule: Write your answers in a sheet of a short bond paper. Write the date of your
activity at the top right portion of your paper and your name at the left top portion. Compile
your output in your learning portfolio.

A. Write the correct IUPAC name for each alkane/cycloalkane.

1. ____________________________
 2. ____________________________

3. ____________________________

4. ____________________________

5. ____________________________

6. ____________________________

7. ____________________________

B. Draw a structural formula/diagram (line, condensed or skeletal) for each

alkane/cycloalkane.

1. 2-methlypentane
2. 2,3,4-trimethylheptane
3. 4-butyl-6-ethyl-2,5-dimethylnonane
4. cyclooctane
5. 1,3-dimethylcyclobutane
6. 3,3-dimethylhexane
7. 3-ethyl-3-methylhexane
8. 5,5-diethyl-2,2,4,4-tetramethyloctane

Chapter End Evaluation:

Direction: Answer the following questions below and write your answers in your notebook.

1. Crude oil is a mixture of mainly alkanes. Alkanes are a group of chemicals which contain
carbon and hydrogen atoms, the smallest of which is methane. Describe how a mixture of
alkanes can be separated using fractional distillation. (10 points)

2. The alkane methane has the following structural formula.

Draw the structural formula of propane in the box above. (10 points)

3. Alkane are described as consisting of saturated hydrocarbon molecules. What is the meaning
of saturated hydrocarbon molecules? (10 points)

Key Terms:

 Saturated Hydrocarbons
 Alkanes
 Cycloalkanes
 Alkyl halides
 Parent chain
 Substituent
 Nomenclature