The Minimized Structure Of Phenacetin Is Planar And The Chemical Shifts Of The A

The minimized structure of phenacetin is planar, and the chemical shifts of the aromatic protons in the NMR spectrum can be rationalized by electron delocalization. When drawn in the planar conformation, are any of the aromatic protons related by a valid symmetry operation? Explain why the resonances in the aromatic region produce two doublets instead of more complex splitting patterns. HINT: Think about bond rotation.

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