CHAPTER 2 - HYDROCARBONS
MODULE 3
CHAPTER OUTLINE:
1. Structure of Organic Molecules
2. Classification of hydrocarbons
3. Alkanes (Structure, nomenclature, physical properties)
4. Alkenes (Structure, nomenclature, cis-trans and E-Z isomers,
physical properties)
5. Alkynes (Structure, nomenclature, physical properties)
Lesson 2.5
ALKYNES
Alkynes are the second type of unsaturated hydrocarbon. An alkyne is an
unsaturated acyclic hydrocarbon with one or more carbon–carbon triple
bonds. As a result, the alkyne functional group is a C≡C group. The characteristic
ending associated with a triple bond is -yne, as the family name alkyne suggests.
The general formula for an alkyne with one triple bond is CnH2n-2. Thus, the
simplest member of this type of alkyne has the formula C2H2, and the next member,
with n = 3, has the formula C3H4.
A carbon–carbon triple bond in a molecule always results in a linear
arrangement for the two atoms attached to the triple bond's carbons. As a result,
ethyne is a linear molecule.
The simplest alkyne, ethyne (C2H2), is the most important alkyne from an
industrial standpoint. A colorless gas, it goes by the common name acetylene and
is used in oxyacetylene torches, high-temperature torches used for cutting and
welding materials.
IUPAC NOMENCLATURE FOR ALKYNES
The rules for naming alkynes are identical to those used to name alkenes,
except the ending -yne is used instead of -ene.
Consider the following structures and their IUPAC names.
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Common names for simple alkynes are based on the name acetylene, as
shown in the following examples.
EXAMPLE 1
Assign an IUPAC name to each of the following unsaturated hydrocarbons.
1.
2.
3.
4.
ALKENES AND ALKYNES
Alkenes and alkynes are considered to have equal priority.
For the purposes of the name, “-ene” comes before “-yne” alphabetically.
So, when an alkene and an alkyne are present in the same molecule, the ending
will always be “yne”.
For the purposes of numbering, whichever is closer to the end of the chain
determines the direction of numbering. In the case where each would have the
same position number, the double bond takes the lower number.
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PHYSICAL PROPERTIES OF ALKYNES
The physical properties of alkynes are
similar to those of alkenes and alkanes. Alkynes
with lower Carbon atoms in the range of C2-C4,
are all gases, mid-range Carbon atoms like C5-
C12 are all liquids, and the higher ones exist in
solid forms at room temperature.
In general, alkynes are insoluble in water but soluble in organic solvents,
have densities less than that of water.
Compared to alkanes and alkenes, alkynes have slightly higher boiling
points. Similarly, the melting point of alkynes increases with increase in molecular
mass. The carbon atom in an alkyne is sp hybridized, as a result, the structure is
linear. This allows the molecules to get closer, and therefore a higher
intermolecular force of attraction. So, the high intermolecular forces of attraction in
alkynes (owing to its linear structure) results in a higher boiling point.
Alkynes, like alkenes and alkanes, are flammable, that is, they readily
undergo combustion reactions.
PRACTICE EXERCISE
Answer the following problems.
1. Assign an IUPAC name to each of the following unsaturated
hydrocarbons.
a.
b.
c.
d.
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