Alkynes

Alkynes are hydrocarbons that contain carbon–carbon triple bonds. Alkynes are also called
acetylenes because they are derivatives of acetylene, the simplest alkyne. The chemistry of the
carbon–carbon triple bond is similar to that of the double bond.

A triple bond gives an alkyne four fewer hydrogens than the corresponding alkane. Its molecular
formula is like that of a molecule with two double bonds: CnH2n-2. Therefore, the triple bond
contributes two elements of unsaturation.

Nomenclature of Alkynes
IUPAC Names the IUPAC nomenclature for alkynes is similar to that for alkenes. We find the
longest continuous chain of carbon atoms that includes the triple bond and change the -ane ending
of the parent alkane to –yne. The chain is numbered from the end closest to the triple bond, and
the position of the triple bond is designated by its lower- numbered carbon atom. Substituents are
given numbers to indicate their locations.

When additional functional groups are present, the suffixes are combined to produce the compound
names of the alkenynes (a double bond and a triple bond), alkynols (a triple bond and an alcohol),
and so on. The new IUPAC system (placing the number right before the group) helps to clarify
these names. The IUPAC rules give alcohols higher priority than alkenes or alkynes (which are
given equal priority), so the numbering begins at the end closer to an alcohol. If the double bond
and the triple bond are equidistant from the ends of the chain, number the chain so that the double
bond receives a lower number than the triple bond (because “ene” comes before “yne” in the
alphabet).

Physical Properties of Alkynes

The physical properties of alkynes are similar to those of alkanes and alkenes of similar molecular
weights. Alkynes are relatively nonpolar and nearly insoluble in water. They are quite soluble in
most organic solvents, including acetone, ether, methylene chloride, chloroform, and alcohols.
Many alkynes have characteristic, mildly offensive odors. Ethyne, propyne, and the butynes are
gases at room temperature, just like the corresponding alkanes and alkenes. In fact, the boiling
points of alkynes are nearly the same as those of alkanes and alkenes with similar carbon skeletons.

Uses of Alkynes
1-Welding Torch
One of industry that uses alkynes the most is in welding industry. The triple bonds in alkynes are
really helpful to weld hard material such as steel and wire.
2- Organic Solvent
Alkynes as pure compound is an organic solvent for organic chemicals. Some of the most useful
compounds for industry are derivates of alkynes. Some of the derivations of alkynes are ethanal,
acrylic acid, acetylene, and ethanoic acid.
3- Starting Material
Alkynes is very important in the preparation of starting material such as the highly used polymers.
Some derivation of alkylenes work for starting materials in various compound. For instance, vinyl
chloride that is alkynes derivation is starting material for PVC.
Manufacture of Acetylene
Acetylene, one of the cheapest organic chemicals, is made from coal or from natural gas. The
synthesis from coal involves heating lime and coke (roasted coal) in an electric furnace to produce
calcium carbide. Addition of water to calcium carbide produces acetylene and hydrated lime.

The synthesis of acetylene from natural gas is a simple process. Natural gas consists mostly of
methane, which forms acetylene when it is heated for a very short period of time.
The Structure of Alkynes
Each carbon is sp hybridized, so each has two sp orbitals and two p orbitals. One sp orbital
overlaps the s orbital of a hydrogen, and the other overlaps an sp orbital of the other carbon.
Because the sp orbitals are oriented as far from each other as possible to minimize electron
repulsion, ethyne is a linear molecule with bond angles of 180°.

The two remaining p orbitals on each carbon are oriented at right angles to one another and to the
sp orbitals. Each of the two p orbitals on one carbon overlaps the parallel p orbital on the other
carbon to form two p bonds. One pair of overlapping p orbitals results in a cloud of electrons
above and below the σ bond, and the other pair results in a cloud of electrons in front of and
behind the σ bond. The electrostatic potential map of ethyne shows that the end result can be
thought of as a cylinder of electrons wrapped around the σ bond.

The carbon–carbon bond length in acetylene is 1.20 Å, and each carbon–hydrogen bond is 1.06 Å.
Both bonds are shorter than the corresponding bonds in ethane and in ethene.

The triple bond is relatively short because of the attractive overlap of three bonding pairs of
electrons and the high s character of the sp hybrid orbitals. The sp hybrid orbitals are about
one-half s character (as opposed to one-third s character of sp2 hybrids and one-fourth of sp3
hybrids), using more of the closer, tightly held s orbital. The sp hybrid orbitals also account for the
slightly shorter C¬H bonds in acetylene compared with ethylene.