Solutions_Manual_for_Organic_Chemistry_6th_Ed 368

Solutions_Manual_for_Organic_Chemistry_6th_Ed 368 - 16-48...

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16-48 The key concept in parts (a)- ( c) is that an aromatic product is created. ( a ) + ( b ) 5.:\ U + H + A :O-H -- -- - .. .. :O-H I + - . 0 · · 0 :O-H I c a .. .. The protonated carbonyl gives a resonance-stabilized cation. Protonation of the singly bonded oxygen does not generate a resonance-stabilized product. + 6� :O-H :O-H :O-H I I c c o · 0 I . + H + -- -- .. .. .. .. h- B AROMATIC The last resonance form shows that the cation produced is aromatic and therefore more stable than the corresponding nonaromatic ion. In this second reaction, the products are more favored than in the first reaction which
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