Hybridization and Reactivity

$sp, sp^{2}, sp^{3}, dsp^{3}, d^{2}sp^{3}$

Isabel Nakoud 4D
Posts: 101
Joined: Fri Sep 28, 2018 12:27 am

Hybridization and Reactivity

Homework Problem 4.91 asks us to evaluate why Benzyne would be highly reactive based off what we know about its hybridization in its structure. What is the relationship between hybridization and reactivity? Can someone walk me through the process of using knowing about Hybridization to predict reactivity character?

Kyleigh Follis 2H
Posts: 64
Joined: Fri Sep 28, 2018 12:28 am
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Re: Hybridization and Reactivity

This is no ordinary triple bond as the second π interaction results from a weak interaction of sp2 hybrid orbitals lying in the plane of the ring.
The triple bond is non-linear due to the constraints of the 6-membered ring. Benzyne is strained and highly reactive.

Kate_Santoso_4F
Posts: 72
Joined: Fri Sep 28, 2018 12:29 am

Re: Hybridization and Reactivity

Benzyne would be highly reactive because the two carbon atoms that are sp hybridized are constrained to have a very strained structure compared to what their hybridization would like to adopt (linear arrangment) with 180 degree angles at these C atoms. The formation of a diradical would allow the C angles to adopt more reasonable angles.