A compound A (C22H27NO) is insoluble in acid and base but reacts with concentrated
Chapter 23, Problem 23.63(choose chapter or problem)
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, PhCHCH2. 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 ylid CH2 P
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