Compound 1 can serve as a precursor in the synthesis of flutamide (2), a drug used in
Chapter 16, Problem 16.75(choose chapter or problem)
Compound 1 can serve as a precursor in the synthesis of flutamide (2), a drug used in the treatment of prostate cancer (J. Chem. Ed. 2003, 80, 14391443): O2N CF3 NH2 O2N CF3 N H O Cl O Pyridine 1 2 (Flutamide) Ha Hc Hb Ha Hb Hc (a) Compound 1 has three distinct aromatic protons, labeled Ha, Hb, and Hc. Identify which aromatic proton gives rise to the signal most downfield. Justify your choice with an analysis of resonance effects and inductive effects. (b) Consider the same three aromatic protons in compound 2. Do you expect these three signals to be shifted upfield or downfield relative to the same three signals for compound 1? Explain your reasoning and predict which of the protons are most affected by the transformation of 1 to 2.
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