Advices For Studying Organic Chemistry

(Wang) #1

  1. Carboxylic acids are much more acidic than the corresponding alcohols:

    1. pKas for R–COOH are in the range of 3-5;.pKas for R–OH are in the range of
      15-18.




COH


O
H 3 C H 3 C CH 2 OH

Acetic acid Ethanol
pKa = 4.75 pKa = 16
'G° = 27 kJ mol−^1 'G° = 90.8 kJ mol−^1


Figure 3.7 A diagram comparing the free-energy changes that accompany
ionization of acetic acid and ethanol. Ethanol has a larger positive
free-energy change and is a weaker acid because its ionization is more
unfavorable.

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