HYDROCARBON

Mr. Muhammad M. Shukur

Organic Chemistry– DENT 193
First Semester
1

Second Week
02/01/2024

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➢Outlines:
1. Hydrocarbons.
2. Chemical structures of compounds.
3. IUPAC naming of Alkane.
4. Cycloalkane.

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➢Objectives:
1. Draw structures of compounds.
2. Naming alkanes.
3. Distinguish between open chain and cyclic alkanes.
4. Compare between alkanes according to physical properties.

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➢ Organic compounds:
Organic chemistry is the study of carbon compounds. Organic compounds typically contain
carbon (C) and hydrogen (H), and sometimes oxygen (O), sulfur (S), nitrogen (N), phosphorus
(P), or a halogen (F, Cl, Br, and I). The formulas of organic compounds are written with carbon
first, followed by hydrogen, and then any other elements.
Many organic compounds are nonpolar molecules, are not soluble in water, and are less
dense than water.
➢ Hydrocarbons:
They are compounds that contain only carbon and hydrogen atoms.

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 Generally, compounds such as the alkanes, whose molecules contain only single
bonds, are referred to as saturated compounds because these compounds contain
the maximum number of hydrogen atoms that the carbon compound can possess.

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 Compounds with multiple bonds, such as alkenes, alkynes, and aromatic
hydrocarbons, are called unsaturated compounds because they possess fewer
hydrogen atoms, and they are capable of reacting with hydrogen under the proper
conditions.

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❖ Structural formulas for hydrocarbons:
➢ Expanded structural formula:
We can draw an expanded structural formula of a compound by showing all
the bonds between atoms.

Methane ethane propane

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➢ Condensed structural formulas:
In a condensed structural formula, each carbon atom and its attached hydrogen
atoms are written as a group. A subscript indicates the number of hydrogen atoms
bonded to each carbon atom.

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➢ Skeletal formula:
When an organic molecule consists of a chain of three or more carbon atoms, the
carbon atoms do not lie in a straight line. Carbon bonds arrange in a zigzag pattern.
The structure called the line-bond or skeletal formula represents only the carbon
skeleton, in which carbon atoms are represented as the ends of each line or as
corners in a zigzag line. The hydrogen atoms are not shown, but each carbon is
understood to have the proper number of atoms including hydrogen atoms to give
four bonds.

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 By contrast, the molecular formula gives the total number of each kind of atom
but does not indicate their arrangement in the molecule.
Condensed Structural Formulas

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 IUPAC nomenclature of alkanes

Today, chemists use a systematic nomenclature developed and updated by the

International Union of Pure and Applied Chemistry (IUPAC).
The names for several of the unbranched alkanes are listed below. The ending
for all of the names of alkanes is (-ane). The stems of the names of most of the
alkanes are of Greek and Latin origin. For example (one, two, three, four, and five)
become (meth-, eth-, prop-, but-, and pent-).

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➢ Nomenclature of alkyl groups:
In the IUPAC names for alkanes, a carbon branch is named as an alkyl group, which is an
alkane that is missing one hydrogen atom. The alkyl group is named by replacing the (-ane)
ending of the corresponding alkane name with (-yl).

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➢ Nomenclature of branched-chain alkanes:

Branched-chain alkanes are named according to the following rules:

1. Locate the longest continuous chain of carbon atoms; this chain determines the
parent name for the alkane.

2. Number the longest chain beginning with the end of the chain nearer the
substituent.
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3. Use the numbers obtained by application of rule 2 to designate the location of the
substituent group.

4. When two or more substituents are present, give each substituent a number
corresponding to its location on the longest chain.

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5. When two substituents are present on the same carbon atom, use that number
twice:

6. When two or more substituents are identical, indicate this by the use of the
prefixes di-, tri-, tetra-, and so on.
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7. When two chains of equal length compete for selection as the parent chain,
choose the chain with the greater number of substituents:

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Example: Give IUPAC naming for the following compound?

Solution:
Step 1: Write the alkane name of the longest chain of carbon atoms. In this alkane, the longest
chain has five carbon atoms, which is pentane.

Step 2: Number the carbon atoms starting from the end nearer a substituent. Number the chain
from 1 to 5 starting at the end nearer the branch of (CH3). Once you start numbering, continue in
that same direction.
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Step 3: Give the location and name of each substituent (alphabetical order) as a prefix to the name
of the main chain. Place a hyphen between the number and the substituent name.

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Example:

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 Classification of hydrogen atoms

The hydrogen atoms of an alkane are classified on the basis of the carbon atom to
which they are attached. A hydrogen atom attached to a primary carbon atom is a
primary (1°) hydrogen atom, and so forth. The following compound, 2-
methylbutane, has primary, secondary (2°), and tertiary (3°) hydrogen atoms:

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 On the other hand, 2,2-dimethylpropane, a compound has only primary hydrogen
atoms:

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➢ Physical properties of alkanes:
If we examine the unbranched alkanes, we notice that each alkane differs from
the preceding alkane by one — CH2 — group. Butane, for example, is
CH3(CH2)2CH3 and pentane is CH3(CH2)3CH3.
A series of compounds like this, where each member differs from the next
member by a constant unit, is called a homologous series.
Members of a homologous series are called homologues.

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➢ At room temperature (25°C) and 1.0 atm pressure the first four members of the
homologous series of unbranched alkanes (1 to 4) carbon atoms (methane,
ethane, propane, and butane) are gases.

➢ The C5—C17 unbranched alkanes (pentane to heptadecane) are liquids; alkanes

having (5 to 8) carbon atoms (pentane, hexane, heptane, and octane) are highly
volatile liquids.

➢ The unbranched alkanes with 18 and more carbon atoms are solids.

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1. Boiling points: The boiling points of the unbranched alkanes show a regular
increase with increasing molecular weight in the homologous series of straight-
chain alkanes. Branching of the alkane chain, lowers the boiling point.

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 The boiling points of branched alkanes are generally lower than the straight-chain isomers.
The branched-chain alkanes tend to be more compact, which reduces the points of contact
between the molecules.

Cycloalkanes have higher boiling points than the straight-chain alkanes with the same number
of carbon atoms. Because rotation of carbon bonds is restricted, cycloalkanes maintain a rigid
structure.
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2. Melting point: melting points of unbranched alkanes show a regular increase
with increasing molecular weight in the homologous series of straight-chain
alkanes. branched alkanes have fewer attractions, they have lower melting and
boiling points.

3. Density: Alkanes are the least dense of all groups of organic compounds;
having densities considerably less than 1.00 g mL-1. As a result, petroleum (a
mixture of hydrocarbons rich in alkanes) floats on water.

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4. Solubility: Alkanes are almost totally insoluble in water because of their very
low polarity and their inability to form hydrogen bonds. Liquid alkanes are soluble
in one another, and they generally dissolve in solvents of low polarity. Good
solvents for them are benzene, carbon tetrachloride, chloroform, and other
hydrocarbons.

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 Cycloalkanes
Cycloalkanes are alkanes in which all or some of the carbon atoms are arranged in a ring.
Alkanes have the general formula (CnH2n+2); cycloalkanes containing a single ring have two
fewer hydrogen atoms and thus have the general formula (CnH2n).

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 The simplest cycloalkane, cyclopropane, C3H6, has a ring of three carbon atoms bonded to six
hydrogen atoms. Most often, a cycloalkane is drawn using its skeletal formula, which appears as a
simple geometric figure. As seen for alkanes, each corner of the skeletal formula for a cycloalkane
represents a carbon atom. A cycloalkane is named by adding the prefix cyclo to the name of the
alkane with the same number of carbon atoms.

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 Alkanes and cycloalkanes are so similar that many of their properties can be
considered side by side. Some differences remain. However, certain structural
features arise from the rings of cycloalkanes.

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 Monocyclic alkane compounds (substituted)
➢ Naming substituted cycloalkanes is as follow:
We name them as alkyl-cycloalkanes and halo-cycloalkanes, and so on. If only one
substituent is present, it is not necessary to designate its position. When two substituents are
present, we number the ring beginning with the substituent first in the alphabet and number in the
direction that gives the next substituent the lower number possible.

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 When three or more substituents are present, we begin at the substituent that leads
to the lowest set of locants:

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 When a single ring system is attached to a single chain with a greater number of
carbon atoms, or when more than one ring system is attached to a single chain, then
it is appropriate to name the compounds as cycloalkylalkanes. For example,

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Q: Give names for the following substituted alkanes:

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 Bicycloalkanes
An alkane that contains two rings that share two carbon atoms is classified as a
bicycloalkane. The shared carbon atoms are called bridgehead carbons, and the
carbon chain connecting them is called a bridge.

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Homework:
1- Draw the expanded structural formula and give the name for the following
skeletal formula:

2- Determine primary, secondary and tertiary carbon and hydrogen atoms for the
following structures?
CH3CH2CH2CH2CH3 CH3CH2CH2CH3

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3- Give IUPAC naming for the following compound?

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References:
1. Organic chemistry by morrison and boyd.
2. Organic chemistry by solomon and fryhl, 10th Edition, 2011.

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