Solutions_Manual_for_Organic_Chemistry_6th_Ed 498

Solutions_Manual_for_Organic_Chemistry_6th_Ed 498 - 20-44...

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

View Full Document Right Arrow Icon
This is the end of the preview. Sign up to access the rest of the document.

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...
View Full Document

{[ snackBarMessage ]}

Ask a homework question - tutors are online