A compound A (C 22 H 27 NO) is insoluble in acid and base but reacts with

Question:

A compound A (C₂₂H₂₇NO) is insoluble in acid and base but reacts with concentrated aqueous HCl and heat to give a clear aqueous solution from which, on cooling, benzoic acid precipitates. When the supernatant solution is made basic, a liquid B separates. Compound B is achiral. Treatment of B with benzoyl chloride in pyridine gives back A. Evolution of gas is not observed when B is treated with an aqueous solution of NaNO₂ and HCl. Treatment of B with excess CH₃I, then Ag₂O and heat, gives a compound C, C₉H₁₉N, plus styrene, Ph—CH = CH₂. Compound C, when treated with excess CH₃I, then Ag₂O and heat, gives a single alkene D that is identical to the compound obtained when cyclohexanone is treated with the ylidGive the structure of A and explain your reasoning.