Solutions_Manual_for_Organic_Chemistry_6th_Ed 20

Solutions_Manual_for_Organic_Chemistry_6th_Ed 20 - 1 -l7 In...

Info iconThis preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
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 atomà 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 pK Æ 4.74 pk Æ " Ç5È5 pk Æ " 33 strongest acid ¹eaÉest ac¸d
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.
Ask a homework question - tutors are online