Can anyone help me with this? Even in orgo I am having trouble withacids and bas

Question

Can anyone help me with this? Even in orgo I am having trouble withacids and bases : (
My text doesn't give me a very good explanation and I'm justwondering if anyone can give me some general rules on how to figurethis out.

Rank the acidity of these compounds.
(CF3)2CHOH    CH3C|||C-H  (CH3)3COH     CH3CH2OH
         a                       b                      c                        d

I can't make a triple bond (why can't we drawmolecules on here?) so ||| is a triple bond : )

THANK YOU
I really want to understand this!

Explanation / Answer

I am going to list from most acidic to least A, D, C, B The definition of how acidic a compound is based upon how willingis that compound to give up its Hydrogen this is based upon howstable the conjugate base is. For example HF(hydroflouric acid) isa very strong acid because the F-(flouride ion) producedis very stable. The first one is the most acidic because those three carbonhave flourine on them which is a highly electronegative atom,electron withdrawing group. This causes those carbons to be somewhat lacking in electron density which in turn make the centralcarbon lacking in electrons and ready to receive some more if itcan.This is called inductive effect. The effect will allow thathydrogen to come off very easily because the conjugate base producehas a very stable resonance structure. Its like feeding someone whois hungry because their friends took their lunch. C has a less stable conjugate than D because each one of theCH3 is an electron donating group making the centralcarbon more and more electron rich. So for that hydrogen to comeoff it would cause for an unstable conjugate base. Its like addingwater to and already full bath tub. And as for B that hydrogen probably will never going to come offnaturally because that carbon is electron rich and there isdifference in electronegativity between carbon and hydrogen.

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