Nomenclature of Alkynes
Alkynes are organic molecules made of the functional group carbon-carbon triple bond and are
written in the empirical formula of CnH2n−2. Simple alkynes are named by the same rules that
are used for alkenes, except that the ending is -yne instead of -ene. Alkynes cannot exhibit E, Z
(cis-trans) isomerism; hence, in this sense, their nomenclature is simpler than that of alkenes.
They are unsaturated hydrocarbons. Like alkenes have the suffix - ene, alkynes use the ending -
yne; this suffix is used when there is only one alkyne in the molecule. The more commonly used
name for ethyne is acetylene, which is used industrially.
Acetylene
The fabrication industry uses acetylene for many major applications. It is the only fuel gas that
can be used for welding. It is also ideal for brazing, cutting, flame gouging, spot heating,
hardening, texturing, cleaning, and thermal spraying many materials.
Introduction
Here are the molecular formulas and names of the first ten carbon straight chain alkynes.
Name Molecular Formula
Ethyne C2H2
Propyne C3H4
1-Butyne C4H6
1-Pentyne C5H8
1-Hexyne C6H10
1-Heptyne C7H12
1-Octyne C8H14
1-Nonyne C9H16
1-Decyne C10H18
Naming Alkynes
Like previously mentioned, the IUPAC rules are used for the naming of alkynes.
Rule 1
Find the longest carbon chain that includes both carbons of the triple bond.
1|Page
Rule 2
Number the longest chain starting at the end closest to the triple bond. A 1-alkyne is
referred to as a terminal alkyne and alkynes at any other position are called internal alkynes.
For example:
4-chloro-6,6-diiodo-7-methylnon-2-yne
Rule 3
After numbering the longest chain with the lowest number assigned to the alkyne, label each of
the substituents at its corresponding carbon. While writing out the name of the molecule,
arrange the substituents in alphabetical order. If there are more than one of the same
substituent use the prefixes di, tri, and tetra for two, three, and four substituents
respectively. These prefixes are not taken into account in the alphabetical order.
For example:
If there is an alcohol present in the molecule, number the longest chain starting at the end closest
to it, and follow the same rules. However, the suffix would be –ynol, because the alcohol group
takes priority over the triple bond.
5-methyl-6-octyn-3-ol
2|Page
When there are two triple bonds in the molecule, find the longest carbon chain including
both the triple bonds. Number the longest chain starting at the end closest to the triple bond
that appears first. The suffix that would be used to name this molecule would be -diyne.
For example:
4-methyl-1,5-octadiyne
Rule 4
Substituents containing a triple bond are called alkynyl.
For example:
4-bromo-1-chloro-1-ethynylcyclohexane
Here is a table with a few of the alkynyl substituents:
Name Molecule
Ethynyl -C≡CH
2-Propynyl -CH2C≡CH
2-Butynyl -CH3C≡CH2CH3
Rule 5
A molecule that contains both double and triple bonds is called an alkenyne. The chain can be
numbered starting with the end closest to the functional group that appears first. For
example:
(E)-6-ethyl-3-methyl-non-4-en-1-yne
3|Page
If both functional groups are the exact same distance from the ending of the parent chain, the
alkene takes precedence in the numbering.
hex-1-en-5-yne
6-ethyl-3-methylnon-4-en-1-yne
Synthesis of Alkynes
The more general way to synthesize an alkyne is via the elimination reaction of vicinal
dihalides. Recall that vicinal dihalides (the two halides are attached to the adjacent carbons, as
opposed to the geminal dihalides where the two halides are attached to the same carbon) are
the halogenation products of alkenes. The vicinal dihalide can then be subjected to a double
dehydrohalogenation reaction with a strong base to produce an alkyne.
Synthesis of internal alkyne by dehydrohalogenation
Exercise
1) Name the following compounds:
4|Page
2) Draw the following compounds:
a) 4,4-dimethyl-2-pentyne
b) 3-octyne
c) 3-methyl-1-hexyne
d) trans 3-hepten-1-yne
3) Do alkynes show cis-trans isomerism? Explain.
Solutions
1)
A -3,6-diethyl-4-octyne
B - 3-methylbutyne
C - 4-ethyl-2-heptyne
D - cyclodecyne
2)
3)
No. A triply bonded atom can form only one other bond and has a linear electron
geometry so there are no “sides”. Alkynes have two groups attached to each inyl
carbon with a trigonal planar electron geometry that creates the possibility of cis-
trans isomerism.
5|Page
