CH 3-3: Mechanism of Acid/Base Reactions

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Presentation transcript:

CH 3-3: Mechanism of Acid/Base Reactions conj. base conj. acid In organic chemistry the products of any reaction can usually be predicted if we understand the mechanism for that reaction. The mechanism for a reaction consists of one, or a series of balanced equations (i.e., steps) where the movement of pairs of electrons are represented by curved arrows.

The Mechanism of Acid-Base Reactions For the partial reaction below: -label the acid and base reactants; -use curved arrows to show electron pair movement; -draw the products; -label the conjugate acid and conjugate base; -indicate if products or reactants are favored. ? Base Acid CA CB

Predicting the Equilibrium Direction of Acid-Base Reactions Estimate the pKa of the acid reactant and CA product; Equilibrium will favor the weaker acid…….WHY? pKa ~ 16 Base Acid (more stable acid) CA CB pKa ~ 9 (more reactive acid)

The Mechanism of Acid-Base Reactions For the partial reaction on the next slide: -label the acid and base reactants; -use curved arrows to show electron pair movement; -draw the products; -label the conjugate acid and conjugate base; -label each acid species with its approx. pka -indicate if products or reactants are favored.

Example Base ~5 Acid CA CB ~9