Question

(i). An organic compound having the formula C₃H₈O on treatment with cooper at 573 K gives B. B does not reduce Fehling's solution but gives a yellow precipitate of the compound C with I₂/NaOH. Deduce the structure of A, B and C. 

(ii). Give the structure of A and B in the following sequence of the reaction 

C₆H₅NO₂ + Fe/HCl ⟶  A+ NaNO₂ + HCl/273-278 K ⟶  B

Answer 1

(i) Compound B gives positive iodoform test, it means it contains —COCH₃ (methyl ketone) group i.e., it is a ketone. Moreover, B is obtained by the oxidation of A, thus A must be a 20 alcohol (As only 20 alcohol give ketones on oxidation with Cu at 573 K.

(ii) A= C₆H₅NH₂ , B= C₆H₅N₂ + Cl^-