Chemistry 1027A/B Lecture : Organic Chemistry Acids and Bases
16 Sep 2013
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A small ka value produces a large pka value. Base which will win the tug of war for the proton. Negative charges are constrained, larger atoms have less charge density d. e. f. The anions are larger and therefor less stable, creating stronger acids. P orbitals are not as good at stabilizing a charge, there is a node with 0 electron density and they are further away from the nucleus. Cl will polarize the molecules next to it. Does not need to sp2 hybrid to be constrained. Negative charge is not directly attached to the. Lone pair of e- next to a pi system. In both instances the negative charge is on the carboxylic acid. The chlorine acts as an inductive effect stabilizing the charge better. N e- is more available for protonation due to electronegativity. Delocalization due to resonance makes acetamide more stable and less available for protonation.
