ALKENES (CnH2n-2)

In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at

least one carbon-carbon triple bond.

 the triple bond is known as the

‘acetylenic bond’

 Ethyne (C2H2) or trivial name

acetylene is the first member of
the alkyne family, with two
carbon atoms connected by a
triple bond.
This the simplest of the alkynes, consisting of two carbon atoms connected by
a triple bond, leaving each carbon able to bond to one hydrogen atom.

Formula common name Formula common name

CH≡CH acetylene CH≡CH acetylene

CH3C≡CH allylene CH3C≡CH allylene

CH3C≡CCH3 crotonylene CH3C≡CCH3 crotonylene

FORMULA COMMON NAME (Acetylene derive system) In this

system, acetylene is considered
HC≡CH acetylene
to be the parent members of
CH3C≡CH methyl acetylene the alkyne series and all other
CH3C≡CCH3 dimethyl acetylene alkyls are named alkyl or aryl
derivatives ofacetylene
CH3C≡CC2H5 ethylmethyl acetylene
(IUPAC) The common name of
the alkynes do not bear any
relationship and are based on
the names of related
compounds.
ISOMERISM in Alkynes

Alkynes show three types of isomerism

1. Chain isomerism --It is due to the different arrangement of carbon

atoms in the chain that is straight-chain or branched.

Example: 4-methylpent-2-yne and hex-2-yne

2. Position isomerism --It is due to the difference in the location of the

triple bond

Example: Pent-1-yne and pent-2-yne

3. Functional isomerism --Alkynes are isomeric with alkadienes both

being represented by the general formula CnH2n-2.

Example: But-1-yne and buta-1,3-diene

Physical properties of alkyne

The first three numbers are gases, next eight members are liquids,
and the higher alkynes are solids. they all are colorless and odourless
except acetylene which has garlic odour.

They are slightly soluble in water but highly insoluble in organic

solvent such as benzene, acetone, chloroform etc.

The boiling point, melting point and specific gravity show a regular
increase with the increase in molecular weights. The branched chain
alkyne have relatively lower boiling point.

Dipole moment of some alkynes, through small, are grater than those
of the corresponding alkenes. The reason for the difference is that
the elctron density in a sp-orbital lies closer to the nucleus than it
does sp2 and sp3. The sp hybridized carbon in alkyne is some what
more electronegative than sp2 carbon which in turn is more
elctronegative than sp3 carbon. Hence, the dipole moment of alkyne
is slightly greater than alkene and alkane.

Physical Properties of Alkynes

Property Description Reason

State The first three The increasing molecular

alkynes (acetylene weight leads to stronger
propyne and London dispersion forces
butyne) are gases between molecules increasing
at room boiling point.
temperature. The
next eight are
liquids.
Odor Odorless (except Alkynes are nonpolar
for acetylene, hydrocarbons, and their
which has a slight molecules do not have specific
odor). functional groups that
contribute to a strong odor.
Color Colorless Alkynes are nonpolar
hydrocarbons, and their
molecules do not absorb
visible light.
Solubility Slightly soluble in Alkynes are nonpolar
polar solvents (like molecules and have limited
water) but soluble interaction with polar
in organic solvents solvents. However, they can
(like benzene). dissolve in nonpolar organic
solvents due to similar
intermolecular forces.
Boiling point Higher than The presence of the triple
corresponding bond increases the molecular
alkanes and surface area, leading to
alkenes. stronger London dispersion
forces between molecules.
Density Lower than water Alkynes are composed of
carbon and hydrogen atoms,
which are less dense than
oxygen and hydrogen atoms in
water.
Chemical Properties of Alkynes
Property Description Reason

Acidity Slightly acidic, The sp-hybridized

especially terminal carbon atoms in
alkynes. alkynes are more
electronegative
than sp3-hybridized
carbon atoms in
alkanes. This makes
the C-H bond in
terminal alkynes
more polar, allowing
for deprotonation
by strong bases.
Addition reactions Alkynes can undergo The triple bond
various addition contains two pi
reactions, such as bonds, which are
hydrogenation, electron-rich and
halogenation, susceptible to attack
hydration, and by electrophiles.
hydrohalogenation.
Combustion Alkynes burn in air to The carbon-
produce carbon dioxide hydrogen bonds in
and water. alkynes are oxidized
during combustion,
releasing energy.
Polymerization Alkynes can polymerize The triple bond can
to form polyalkynes, participate in
which are materials polymerization
with unique properties. reactions, forming
long chains of
repeating units.
Reactivity Alkynes are generally The additional pi
more reactive than bond in alkynes
alkenes due to the provides more sites
presence of two pi for chemical
bonds. reactions to occur.
Rules in Naming ALKYNES

1) The longest chain must include the triple bond.

2) Change the suffix in the parent chain from “ane” to “yne”.

The triple bond should receive the lowest possible locant in the
parent chain despite the presence of alkyl substituents. The latest
IUPAC recommendation is to place the locant before the suffix “yne.”
However, both options are acceptable.
Notice that the parent chain changes from nonane to octane because it is
only possible to include the triple bond in a eight-carbon continuous chain.

And the second change is the numbering – the triple bond should receive the
lowest number possible, despite the presence of alkyl substituents.

For example, in this molecule, even though starting from left would place the
methyl group on position two, triple bond in that case would have been on
position 7 which is incorrect:

How to Name an Alkyne Containing Other Functional Groups

In the example above,

the molecule had one
functional group – the
alkyne. So, what if
there are halogens or a
double bond?

Well, for
halogens it is
easy as they do
not take any
advantage over
the triple and
double bonds
and not even
simple alkyl
substituents.

For example,
the parent
chain below is selected to include the triple bond and it still should
get the lowest possible number despite the bromo group getting
number one when numbering otherwise:
How to Name an Alkyne Containing a Double Bond

If the other functional group is a double bond, there are two possible
scenarios.

1) Numbering the parent chain gives different number to the alkene

and the alkyne.
 2) Numbering the parent chain gives the same number to the
alkene and the alkyne.

If there is a difference depending on the direction you number the

parent chain, simply number it in the direction producing a name
with the lower number for either the double bond or the triple bond;
whichever comes first – no preference for a double or a triple bond.

For example, the alkyne suffix (yne) gets the lower number in the
compound on the left and to the alkene suffix (en) in the compound
on the right.

The alkene suffix

changes from “ene”
to “en”. The “e” is
dropped to avoid
two adjacent
vowels.

Scenario 2:

If both directions for

numbering the
parent chain
give the same
number, the alkene
gets a priority, so
you need to number
the chain in the
direction that
gives the double
bond the lower suffix number.
For example, both directions below give either the double or triple bond
locant one. However, the parent chain is numbered such that the alkene gets
a lower locant than the alkyne does even though the other substituents get
higher numbers:

Notice that the second possibility

shown on the right, would have
put the Br and Cl substituents with
lower number (3,5 beats 4,6).
However, the alkene has a priority
over the triple bond and the
parent chain is numbered based
on this principle.

Uses of Alkyne

 Since ethyne has a very hot flame, it is commonly used in

oxyacetylene gas welding and oxyacetylene gas cutting. As ethyne is
burned with oxygen, the resulting flame is known to have a
temperature of about 3600 Kelvin.

 The overriding alkyne in acetylene is used as a fuel, with millions of

kilograms created annually by fractional oxidation of natural gases.
Chemical compounds such as ethanoic acid, acrylic acid, and ethanol
are made from some of these alkynes.

 Ethyne is most commonly used to make organic compounds such as

ethanol, ethanoic acid, and acrylic acid. It’s also used to make
polymers and the raw materials for them.
  Acetylene is broken down into its two components, carbon and
hydrogen. This reaction creates a lot of heat, which can cause the gas
to ignite even if there is no air or oxygen present.

 Alkynes are generally used as the starting materials for the

manufacture of a large number of organic compounds of industrial
importance such as chloroprene, vinyl chloride etc.

 Acetylene is commonly used to make organic compounds such as

ethanoic acid, ethanol, and acrylic acid.
 Alkyne is also used in the production of polymers and polymer raw
materials.
 Acetylene is used as a fuel, with many kilograms produced each year
through fractional oxidation of natural gases.
 Alkynes are commonly used in the chemical ripening of fruits and
vegetables.

Frequently Asked Questions – FAQs

1. What is the structural formula of Ethyne?

The formula for ethyne condensed structure is HC≡CH. C2H2 is the

molecular formula for ethyne. That means ethyne has two carbon
atoms and two hydrogen atoms, with the two carbon atoms bound
together by triple bonds.

2. How are alkynes named?

Higher alkenes and alkynes are called by adding a -ene (alkene) or -

yne (alkyne) suffix to the stem name of the unbranched alkane with
that number of carbons and counting the number of carbons in the
longest continuous chain that includes the double or triple bond.
 3. What is an alkyne group?

Alkynes have the empirical formula CnH2n-2 and are organic molecules
with the functional group carbon-carbon triple bonds. They are
hydrocarbons that are unsaturated. Alkynes have the suffix –yne,
which is used when there is just one alkyne in the molecule, similar to
how alkenes have the suffix –ene.

4. How are alkynes prepared?

To make a vicinal dihalide from an alkene, chlorine or bromine is

combined with an inert halogenated solvent like chloromethane. The
formed vicinal dihalide is then heated and reacted with a strong base
to create an alkyne.

5. How can we reduce alkyne to alkene?

With sodium dissolved in an ammonia solution, alkynes can be

converted to trans-alkenes. In a carbon-carbon triple bond, a Na
radical donates an electron to one of the pi bonds. In an ammonia
solution, this creates an anion, which can be protonated by hydrogen.