The Alkyne’s Terminal Hydrogen Is Acidic

CH3 C C CH3 CH3 C C H

the triple bond ends
an internal alkyne a terminal alkyne in a hydrogen atom

Compared to other C-H bonds,

the terminal hydrogen of a
terminal alkyne is acidic. Yes, compared to other C–H
bonds this one is acidic
it is a weak acid, but
comparatively speaking, it is
acidic. Deprotonation results
in a carbon-centered anion that
CH3 C C H H + CH3 C C
an acetylide anion
is sp hybridized. This anion is
called an acetylide anion. As pKa = 25
stated earlier, sp hybrid orbitals
are more effective at
stabilizing negative charge
than sp2 or sp3 orbitals. It is H
H
the stability of the anion that CH2 C H +
makes the C-H of a terminal
CH2
alkyne more acidic than other
H
a vinylic anion
C-H bonds.
pKa = 44