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Model 3: The synthesis of 3-ethylaniline from benzene The synthesis of 3-ethylaniline from benzene represents a common complex synthesis problem in organic chemistry. The target molecule has two new substituent groups with particular regiochemistry. Furthermore, there are limitations to the direct synthesis of the molecule due to peculiarities groups attached to the molecule Amino groups cannot be directly added to the ring · Amino groups react strongly with Lewis acids forming a highly deactivated ring Friedel-Crafts reactions will not work on deactivated rings. 11) Why does the regiochemistry of 3-ethylaniline present a synthetic challenge to making this molecule? 12) Explain why each step in the following retrosynthetic strategy is appropriate for 3-ethylaniline H2N O2N 0 13) Write in appropriate reactants for each arrow of the synthesis below based on the retrosynthetic analysi in question 12. NO2 NH2


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