An organic compound with molecular formula C7H7NO2 exists in three isomeric forms, the isomer ‘A’ has the highest melting point of the three. ‘A’ on reduction gives compound ‘B’ with molecular formula C7H9N. ‘B’ on treatment with NaNO2/HCl at 0-5 0C to form compound ‘C’. On treating C with H3PO2 ,it gets converted to D with formula C7H8 , which on further reaction with CrO2Cl2 followed by hydrolysis forms ‘E’ C7H6O . Write the structure of compounds A to E . Write the chemical equations involved. (a) Account for the following: (i) N-ethylbenzenesulphonyl amide is soluble in alkali . (ii) Reduction of nitrobenzene using Fe and HCl is preferred over Sn and HCl. (b) Arrange the following in: (i) decreasing order of pKb values C6H5NH2, C6H5NHCH3, C6H5CH2NH2, CH3NH2, NH3 (ii) increasing order of solubility in water C2H5Cl, C2H5NH2, C2H5OH (iii) decreasing boiling point CH3COOH, C2H5OH, CH3NH2, CH3OCH3
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