MCAT Organic Chemistry Review 2018-2019

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Figure 3.7. sp-Hybridized   Orbitals
A molecule with these orbitals has linear geometry, and the two unhybridized p-oribtals can be used
to form π bonds.

RESONANCE


Resonance delocalization of electrons occurs in molecules that have conjugated bonds.
Conjugation requires alternating single and multiple bonds because this pattern aligns a number of
unhybridized p-orbitals down the backbone of the molecule. π electrons can then delocalize
through this p-orbital system, adding stability to the molecule. Resonance structures are drawn as
the various transient forms the molecule takes, as shown in Figure 3.8.


Figure 3.8. Resonance   Forms   of  Carbonate
These forms have equal stability and therefore contribute equally to the true electron density of the
molecule.

However, these forms aren’t in any sort of equilibrium—the electron density is distributed
throughout, making the true form a hybrid of the resonance structures, as shown with ozone in
Figure 3.9.

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