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, not by resonance with the N'slone pair. Only theorthoandpara-substitutedintermediatesbenefitfromthisadditionalresonancestabilizationwiththeN'slonepair(see structure above)1meta-substituted111
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Midterm Answers 6 of 118.Propose a synthesis of the following compound from benzene. Show all required reagents and intermediates. An analysis and retrosynthesis are not required. (11 points)Note:your synthesis must give the compound shown as the major product of the sequence. OMeNH2HNO3H2SO4NO2SO3H2SO4NO2SO3Hthese steps can be reversedNaOHΔNO2OHNaOH (strong base)CH3INO2OCH3Sn, HClOMeNH2111111111Order of reactions:1 point - Both electrophilic aromatic substitutionsbefore other reactions1 point - Generate the phenol and methylate itBEFORE reducing the nitro group