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Acid-Base Chemistry and Proton Transfer

Manual: General · Subject: Molecular Science

Analyze proton donors, proton acceptors, and molecular structure effects on acidity and basicity.

Brønsted-Lowry and Lewis Concepts

Two Complementary Views

A Brønsted-Lowry acid donates a proton, and a base accepts a proton. In Lewis terms, acids accept an electron pair and bases donate an electron pair. These definitions are especially useful in molecular mechanisms.

Which species is the Brønsted-Lowry base in the reaction NH3+H2O⇌NH4++OH−\mathrm{NH_3 + H_2O \rightleftharpoons NH_4^+ + OH^-}?

What is the conjugate acid of OH−\mathrm{OH^-}?

Acidity, pKa, and Stability of Conjugate Bases

Why Some Acids Are Stronger

Acidity increases when the conjugate base is stabilized by electronegativity, resonance, inductive effects, or greater atom size. Lower pKa\mathrm{p}K_a corresponds to stronger acid.

Major Stabilizing Factors

Resonance
Delocalizes negative charge
Inductive effect
Electron-withdrawing groups stabilize nearby charge
Electronegativity
More electronegative atoms stabilize negative charge better across a row
Atom size
Larger atoms disperse charge better down a group

Which acid is usually stronger?

What does a lower pKa indicate?