Organic Chemistry

Science

Math

Humanities

... and beyond

Socratic Meta
Featured Answers

Topics

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

1 Answer

Aug 8, 2015

The most striking example is the acidity of alkynes.

Explanation:

(from www.chem.ucalgary.ca)

An alkane $C-H$ $"C-H"$ bond is $s p^{3}$ $sp^3$ hybridized and has 25 % $s$ $s$ character.
An alkene $C-H$ $"C-H"$ bond is $s p^{2}$ $sp^2$ hybridized and has 33 % $s$ $s$ character.
An alkyne $C-H$ $"C-H"$ bond is $s p$ $sp$ hybridized and has 50 % $s$ $s$ character.

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

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

Related questions

See all questions in Factors Determining Strength

Impact of this question

3637 views around the world

You can reuse this answer
Creative Commons License