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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