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Chemistry 1027A/B
Mel Usselman

Organic Chemistry Key Concepts: Acids & Bases (Usselman Version) -An acid is a proton donor: HA (acid) H (proton) + A (conjugate acid) -A base is a proton receptor: B: (base) + H (proton) BH (conjugate acid) -Acid and base reactions occur simultaneously. Every acid-base reaction must have both an acid (to supply a proton) and a base (to accept the proton). Organic compounds act as weak acids and bases. -For a general weak acid HA: HA + H O H O (aq) + A (aq) *The long arrow shows the 2 3 equilibrium position. *Neutrality = more stability than ionization. + - K a [H O3][A] / [HA] pK a -log K a -Recognize that as organic acids (weak) get stronger, their K gets laraer, and their pK gets smallea. Concentrate on recognizing the structural features that affect acid (and base) strength. -It is the pulling of an electron pair by an atom in a covalent bond that introduces reactivity. The stability - - of A is a good indicator of acid strength. Any feature that weakens the HA bond and/or stabilizes the A anion will shift the equilibrium to the right and increase acid strength. -Electron motion is responsible for every molecular reaction. -The more electronegative the atom bearing a hydrogen, the more acidic that hydrogen. Note that every organic molecule that bears an H atom can act as an acid. -Within a column of the periodic table, the larger the atom bearing a hydrogen, the more acidic that hydrogen (the larger the atom, the more it can hold a negative charge). Note that size effect is more important than electronegativity effects for elements in the same column. 3 -Electrons with more‘s’ character in their hybrid orbital are more electronegative. The sp hybrid orbital makes hydrogen less prone to escape as the electrons are further away from A in the covalent bond. -The stabilization (or destabilization) of charges by through-bond effects of neighbouring atoms is termed an inductive effect. -In general terms,
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