Solutions_Manual_for_Organic_Chemistry_6th_Ed 497

Solutions_Manual_for_Organic_Chemistry_6th_Ed 497 - 20-44...

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20-44 continued (c) The sImpler case fIrst±INdUctIoN O²ly: o Ii o II CH30-CH2 ±C²O³h Is a stro²ger aciD tHa² h²CH´ ±CµO³h ³here is no rEsonAnCe overlap betweE² the methoxy GRouP and the CArboxyl Group, so this is A Pure inductiVE eFFect. The methoxy subst´tue²t i²creases the acIditY, so methoxy mUst be electronµwIthdrAwInG bY ´nduction. ³his shouLd Come as no surprise as oxYGen is the second most eleCtroneGative element. ³he anomAly comes ´n the decreAsed acidity of 4µmethoxybe²zoic acid¶ o 0 C¶30 - > C ²0 · ¶ Is a weaker acid thAn ± ² c - 0 · H ³hrouGh rEsonA²CE· a PAir oF elect¸o²s from the MethoxY oxYGen can be do²ated th¸ouGh thE bE²zE²e rI²G to the carboxyl Group±a stab´lizI²G efFect. ¹owever· this eLectron donatio² destabilIzes the carboxylatE aniº» as there is alr¼adY a nEgatIve charGe o² the carboxYL GrouP; thE resonance do²atio² I²te²siFies the neGAt½v¾
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This note was uploaded on 02/27/2010 for the course CHEM 140 taught by Professor Wade during the Spring '10 term at Whitman.

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