An organic compound `(A)` on treatment with ethyl alcohol gives a carboxylic acid `(B)` and compound `( C)`. The hydrolysis of `( C)` under acidic conditions gives `(B)` and `(D)`. Oxidation of `(D)` with `KMnO_4` also gives `(B)`. `(B)` on heating with `Ca(OH)_2` gives `(E)` (molecular formula, `C_3 H_6 O`). `(E)` does not give Tollens test and does not reduce Fehling's solution but forms a `2,4-`dinitrophenyl hydrazone. Identify `(A),(B), ( C), (D)`, and `(E)`.

Explanation

(E ) is acetone `(CH_(3)COCH_(3))`. The (B) is, therefore, acetic acid `(CH_(3COOH)` and (D) ethyl alcohol `(C_(2)H_(5)OH)`. Thus, (C ) is ethyl acetate `(CH_(3COOC_(2)H_(5))`. Since the compound (B) (acetic acid) and (C) (ethyl acetate) are obtained by treating (A) with ethyl alcohol, so the compound (A) is acetic anhydride `(CH_(3)CO)_(2)O`.