Solutions_Manual_for_Organic_Chemistry_6th_Ed 368

Solutions_Manual_for_Organic_Chemistry_6th_Ed 368 - 16-48...

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Unformatted text preview: 16-48 The key concept in parts (a)-(c) is that an aromatic product is created. (a) + U A 5.:\ I h. B + H+ � The protonated carbonyl generateresonance-stabilized cation. Protonation of the singly bonded oxygen does not gives a a resonance-stabilized product. + o· ----- 0 :O-H :O-H 0 I :O-H .. .. + -. · · .. .. a c I The the resonance form shows that ion. In this second is aromatic products are more favored than lastthe first reactionnonaromaticthe cationasproduced reaction, theand therefore more stable than in corresponding which is interpreted the reactant being more basic than (b) +0 AROMATIC 6� 6· :O-H + H+ ---- :O-H .. .. o c I :O-H · .. .. er (r •• C CI ".....-A CI- + Ih•• D CI ".....-A O o + H B .. .. CI- + The product from ionization of alsostabilized andresonance.more stable. rproduct that is not i aromatic by ionization eaction of only resonance-stabilized but is wills usually happentherefore Themilder conditions because the produces more stable product faster under transition astate leading to that product will be stabilized, leading to a lower activation energy. AROMATIC C O o + H .. .. O Ih- H 0 c I A. O +0 H A D 3 62 ...
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