What is an example to how hybridization affects the equilibrium the strength of an acid?

1 Answer
Ernest Z.
Aug 8, 2015

The most striking example is the acidity of alkynes.

Explanation:

www.chem.ucalgary.ca
(from www.chem.ucalgary.ca)

  • An alkane "C-H" bond is sp^3 hybridized and has 25 % s character.

  • An alkene "C-H" bond is sp^2 hybridized and has 33 % s character.

  • An alkyne "C-H" bond is sp hybridized and has 50 % s character.

The "p"K_"a" of an alkane is 62, and the "p"K_"a" of an alkyne is 26.

The change in hybridization from sp^3 to sp increases the acidity by a factor of 10^36!.

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