Chapter 4.6: Molecular Structure and Acidity
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How does stability of the anion and equilibrium relate?
• Equilibrium favors the side with the more stable anion
What is the polarization of the electron density of a covalent bond caused by the electronegativity of a nearby atom?
inductive effect
Describe the relationship between stability of the anion and the strength of the acid
• The more stable the anion the greater the acidity of the acid, HA
Describe the ways to stabilize the anion in order of decreasing stability
o Having the negative charge on a more electronegative atom o Having the negative charge on a larger atom o Delocalizing the negative charge as described by resonance contributing structures o Spreading the negative charge onto electron-withdrawing groups by the inductive effect (polarization of sigma bonds) o Having the negative charge in an orbital with more s character
What is a zwitterion?
• When the same molecule has a positive and negative charge, it is called a zwitterion
Define inductive effect
the polarization of the electron density of a covalent bond caused by the electronegativity of a nearby atom