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NOTES-The Acidity of Terminal Alkynes PDF

The terminal hydrogen of a terminal alkyne is more acidic than other C-H bonds due to the stability of its deprotonated form, an acetylide anion. Upon deprotonation, the terminal alkyne forms a carbon-centered acetylide anion that is sp hybridized, which is better at stabilizing negative charge than sp2 or sp3 hybridized carbons. This makes the pKa of a terminal alkyne hydrogen around 25, lower than the pKa of 44 for a vinylic hydrogen.

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Shashikant Thakre
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417 views1 page

NOTES-The Acidity of Terminal Alkynes PDF

The terminal hydrogen of a terminal alkyne is more acidic than other C-H bonds due to the stability of its deprotonated form, an acetylide anion. Upon deprotonation, the terminal alkyne forms a carbon-centered acetylide anion that is sp hybridized, which is better at stabilizing negative charge than sp2 or sp3 hybridized carbons. This makes the pKa of a terminal alkyne hydrogen around 25, lower than the pKa of 44 for a vinylic hydrogen.

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Shashikant Thakre
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© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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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

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