1-l7 In SoLved ProbLem 1±4, the stRuctures of etHanoL and methyLamine a²e shown to be siMiLa² to ³ethanoL and ammon´aµ respect´veLy. We must infer that thei² acid¶base prope²ties a²e aLso simiLa²· (a) THis proBLe³ can be v¸ewed in two ¹ays. 1º QuantitativeLy, the pKA va»Ues dete¼ne t½e o²der of acidity. 2) QuaL¸tativeLyµ the stabi»it¸es of the conjugate bases dete²¾ine the o²de² of acidity (see ¿oLved ProB»e³ 1À4 For stRÁctures): the conjUgate base of acetic acid, acetate ionµ is ²esonanceÂstabiLized, so acetic acid is the most acidic; the conjUgate base oF ethanoL has a negative cha²ge on a very eLectronegative oxygen atomÃ the conjUgate base of ³ethyLa³ine has a negat¸ve cha²ge on a mÄ»d»y eLectronegative nitrogen ato³ and is the²eFore tHe Least stabiLizedµ so met½y»amÄne ¸s the »east ac¸d¸c· acet´c acid > ethanoL > ³ethyLaÅne pKÆ 4.74 pkÆ" Ç5È5 pkÆ " 33 strongest acid ¹eaÉest ac¸d
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