Solutions_Manual_for_Organic_Chemistry_6th_Ed 480

Solutions_Manual_for_Organic_Chemistry_6th_Ed 480 - 20-12(a...

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20-12 (a) first intennediate :O-H i + II RC-�H :O-H .. :O-H 1 + RC - OH .. } :O-H 1 + RC==�H second intennediat RC ( i ·· :O-H / RC \ \ i Y -H } RC \ :OR :OR +OR . . .. (b) The mechanism of acid-catalyzed nucleophilic acyl substitution may seem daunting, but it is simpl)' a succession of steps that are already very familiar to you. Typically, these mechanisms have six steps: four proton transfers (two on, two off), a nucleophilic attack, and a leaving group leaving, with a little resonance stabilization thrown in that makes the whole thing work. The six steps are
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