Solutions_Manual_for_Organic_Chemistry_6th_Ed 489

Solutions_Manual_for_Organic_Chemistry_6th_Ed 489 - acidic...

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20-33 Acetic acid derivatives aRe often used as a test of electronic effects of a se±es of substituents: they are fai²ly easiLy synthesized (oR aRe comMe²cially aVailable), and pK³ values aRe easi´y MeasuRed by tit²ation. Substituents on ca²bonµ2 of acetic acid can express only an inductive effect; no ²esonance eFect is Possible because the CH¶ is sp · hyb¸dized and no Pi ove²lap is possible¹ Two conclusions can be dRawn froº the given Pk» values¼ ½irst, all fouR substituents are electron¾ withdrawing because all four substituted acids a²e stronger t¿an acetIc acid¹ Second, the ºagnitude Of t¿e electronÀwit¿drawing efÁect incReases in t¿e o²de²Â ÃÄ < CL < ÅN < Nƶ¹ (Çt is alwaYs a saÁe assuºPtion t¿at nit²o is the st²ongest elect²onÈwiÉhd²awing grouP of aLL t¿e coÊon substËtuents¹) 20-34
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Unformatted text preview: acidic because of the adjacent carbonyL gouP See pa (c) (b) Ascorbc acid, p 4.71, is alMost identical to te aciditY of acetic acid pK 474 H &quot; CH _ ene , ' diol I (c) The Moe acidic wilL be the one tat, wen reoVed, giVes te Moe stable conjugate base star heRe -l _ } { 1 } H H . . . . t . . . . t TE Moe only two esonnce f ! (d) n the sLightly basic PH of Pysiological fluid, ascorbic acid :-e resoance f acidic '. Is pResent as te conjugate base, ascorbate, whose structure can R be epresented by any of te tree resonance f on the Left 20-35 (a) Q r CHH \ C (e) o i) C CH of Part (c) CHC (b) (f i CHCH CHCH 8 (C) o (d) C (h) C CH (G) C (k) o C...
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