Solutions_Manual_for_Organic_Chemistry_6th_Ed 498

Solutions_Manual_for_Organic_Chemistry_6th_Ed 498 - 20-44...

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Unformatted text preview: 20-44 continued Steric inhibition of ResonanCe! In benzoiC acid, the phenyl ¡¢Ng and the carboxyl gRoup ARe alL iN the £ame plane, and Benzene is able to donate eleCtRons by ResonaNce overlap thRough paRallel p oRbitals. This stabilizes the sta¡ting acid (and destabilizes the carboxylate aNioN) aNd Makes the acid weaKer thaN it would be withoUt resonaNce. :0: < C¤¥H . . 0:9: .. + ¦§O¨H .. plUs other resoNance fo©s PuttiNg sUbstitUents at the 2ª and 6«posit¬oNs prevents the carboxYL or carboxylate Fro­ CoplaNa®itY wi¯° the ±ng. ²esoNance is inte¡³pted, and Now the cArboxyL groUp sees a phenyl substituent which caNNot ´tµ¶D·Z¸ the acid throUgh resonance; the stabiLizat¬oN of the a¹¬d is lostº »t the saMe ti­e, the electrn-withdRWINg inDucTive efect of the benzene r¼ng stabilizes ½he carboxylate aNioN¾ ¿hese two eÀfects work together to ­aKe this acid unUsUally strongÁ (ÂppareNtly, the sLight electroNÃdoNatiNg inductive effect of the methÄÅs Æs...
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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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