ALKYNES

Alkynes are hydrocarbons that have

a triple bond between
two carbon atoms, with the formula
CnH2n-2.
 Alkynes are traditionally known as
acetylenes, although the
name acetylene also refers specifically
to C2H2, known formally as ethyne
using IUPAC nomenclature. Like other
hydrocarbons, alkynes are generally
hydrophobic but tend to be more
reactive.
 Alkynes

Carbon-carbon triple bonds

Names end in -yne

HCCH ethyne(acetylene)

HCC-CH3 propyne

LecturePLUS Timberlake 4
 Naming Alkenes and Alkynes
When the carbon chain has 4 or more C atoms,
number the chain to give the lowest number to the
double or triple bond.

1 2 3 4
CH2=CHCH2CH3 1-butene
CH3CH=CHCH3 2-butene
CH3CHCHCH3 2-butyne
CHEMICAL PROPERTIES

Alkynes are characteristically more

unsaturated than alkenes. Thus they
add two equivalents of bromine
whereas an alkene adds only one
equivalent. Alkynes are usually more
reactive than ALKENES.
 They show greater tendency to
polymerize or oligomerize than alkenes
do. The resulting polymers,
called POLYACETYLENES (which do not
contain alkyne units)
are CONJUGATED and can exhibit
semiconducting properties.
Addition Reactions of Alkynes

A carbon-carbon triple bond may be located at any

unbranched site within a carbon chain or at the end
of a chain, in which case it is called TERMINAL.
Because of its linear configuration ( the bond angle
of a sp-hybridized carbon is 180º ), a ten-membered
carbon ring is the smallest that can accommodate
this function without excessive strain. Since the
most common chemical transformation of a carbon-
carbon double bond is an addition reaction.
Reactions of Alkynes
 1. Catalytic Hydrogenation
The catalytic addition of
hydrogen to 2-butyne not
only serves as an
example of such an
addition reaction, but
also provides heat of
reaction data that reflect
the relative
thermodynamic
stabilities of these
hydrocarbons, as shown
in the diagram to the
right.
From the heats of
hydrogenation, shown in blue
in units of kcal/mole, it would
appear that alkynes are
thermodynamically less stable
than alkenes to a greater
degree than alkenes are less
stable than alkanes.
The standard bond
energies for carbon-carbon
bonds confirm this conclusion.
Thus, a double bond is
stronger than a single bond,
but not twice as strong.
The difference ( 63 kcal/mole )
may be regarded as the strength
of the π-bond component.
Similarly, a triple bond is stronger
than a double bond, but not 50%
stronger. Here the difference ( 54
kcal/mole ) may be taken as the
strength of the second π-bond.
The 9 kcal/mole weakening of this
second π-bond is reflected in the
heat of hydrogenation numbers (
36.7 - 28.3 = 8.4 ).