Acid-base chemistry controls proton transfers, leaving-group quality, nucleophile strength, and equilibrium direction, so it quietly governs most mechanisms in both semesters.
Use pKa values to predict equilibrium direction and compare acids over wide ranges of strength.
Apply the four common acidity factors: atom, resonance, induction, and orbital hybridization.
Distinguish basicity from nucleophilicity and choose suitable bases for substitution, elimination, or enolate formation.
Predict the major protonation state of common functional groups under acidic, neutral, and basic conditions.
Checkpoint Questions
Q: Why is a terminal alkyne more acidic than an alkene?
A: The acetylide conjugate base puts negative charge in an sp orbital, which has greater s character and holds electrons closer to the nucleus.
Q: Would methoxide deprotonate acetic acid completely?
A: Yes. Acetic acid (pKa ~4.8) is much stronger than methanol (pKa ~15.5), so the equilibrium strongly favors acetate plus methanol.