Solutions_Manual_for_Organic_Chemistry_6th_Ed 483

Solutions_Manual_for_Organic_Chemistry_6th_Ed 483 - 20-14...

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20-14 (a) ° { : 0 : :0± - } II Ii . . I . R-C-OH R±C²OH R±C±Oh ±± H+ + I + + i ' H h BAD±two adjacent positi ve charges (b) Protonation on The OH gives only two resonance forms, one of wHIch Is bad because oF ²³J´CENt µOSitiv¶ charges. Protonat·on on the C=O is good because of three resonance ¸orMs distRbutIng the ¹ositive cºarGe over three atoms» wIth no additional cha¼ge se¹aration. i + ² t : 0 : : O²H : O³H : O´H ±I H+ . . ± + i + RC-Oµ ± rC-¶H RC-¶H rC·9 . H (c) ½he carbonYl oxygen is More "basic" because» bY definiTion» it reacts witº a ¾ro¿on More readiLYÀ Át does
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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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