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1. (10 points). Using resonance and inductive effect arguments explain why the pKa values of the five different phenols listed below clearly). (hint: draw out the full structure of the -NO2. are so different? (Draw all the resonance structures and explain OH OH OH OH OH NO2 NO2 CI NO2 NO2 pKa 10 9.38 7.15 8.4 0.4 2. (5 points). Show all the steps necessary for the following transformations. Pay attention to directing effects when you plan your synthesis. Note in some cases it may be impossible to avoid getting mixtures of isomeric if this is the case indicate it. products; CH3 NO2 O OH H2N 3. (5 points). Why is product A observed for the Birch reduction of nitrobenzene, not Product B? Use mechanism and resonance to answer this question. NO2 NO2 A B

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