AAMC Section Bank B/B #13

[AWolfman]

Won't chlorinating the methyl group add electron withdrawing groups, therefore decreasing the amount which acetic acid ionizes?

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[popopopop]

You're making it a better Lewis Acid in the process, and making the acidic hydrogen more ionizable.

 

[Wolfpack93]

Think of this like common ion effect. HCl fully dissociates to H+ and Cl- so if you have extra H+, less of your weak acid would dissolve

 

[Wolfpack93]

electron withdrawing groups would stabilize the anion, so that would increase the ionization

 

[AWolfman]

That makes a whole lot more sense. I keep making silly mistakes which seem to be the bane of my MCAT existence.