State aqueous hcl and heat to give a clear aqueous solution

Reference no: EM13253890

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 aqueous Ag2O and heat, gives a compound C, C9H19N, plus styrene, C6H5-CH=CH2. Compound C, when treated with excess CH3I, then aqueous Ag2O and heat, gives a single alkene D that is identical to the compound obtained when cyclohexanone is treated with the ylid -:CH2- PPh3. Give the structure of A.

Reference no: EM13253890

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