An organic compound (A) havig molecular formula, C_(2)H_(4)O reduces tollens' reagent. Two moles of (A) react with Al(OC_(2)H_(5))_(3) to yield C_(4)H_(8)O_(2)(B) which reacts with NH_(3) to give C_(2)H_(6)O(C) and C_(2)H_(5)NO(D). Identify A,B,C and D.

An organic compound (A) havig molecular formula, C_(2)H_(4)O reduces t

1.	An organic compound (A) havig molecular formula, C_(2)H_(4)O reduces tollens' reagent. Two moles of (A) react with Al(OC_(2)H_(5))_(3) to yield C_(4)H_(8)O_(2)(B) which reacts with NH_(3) to give C_(2)H_(6)O(C) and C_(2)H_(5)NO(D). Identify A,B,C and D.
Answer» Solution :(i) Since compound (A) with M.F. `C_(2)H_(4)O` reduces tollens' reagent, it must be an ALDEHYDE, i.e., acetaldehyde `(CH_(3)CHO)`. `underset("Acetaldehyde")(CH_(3)CHO) +underset("Tollens' reagent")(2[Ag(NH_(3))_(2)]^(+))+3OH^(-)to CH_(3)COO^(-)+2Ag darr+4NH_(3)+2H_(2)O` (ii) In presence of `Al(OC_(2)H_(5))_(3)`, aldehydes undergo Tischenko reaction to give esters. thus, when two moles of acetaldehyde `(CH_(3)CHO)` react in presence of `Al(OC_(2)H_(5))_(3)`, ethyl acetate (B) with M.F. `C_(4)H_(8)O_(2)` is PRODUCED. `underset("Acetaldehyde (A) (two moles)")(CH_(3)CHO+OHC CH_(3)) underset(("Tischenko reaction"))OVERSET(Al(OC_(2)H_(5))_(3))to underset("Ethyl acetate (B) "M.F.C_(4)H_(8)O_(2))(CH_(3)COOCH_(2)CH_(3))` (ii) The structure of ethyl acetate (B) is confirmed by the observation that on treatment with `NH_(3)`, it gives one molecule of an alcohol, i.e., ethyl alcohol, `CH_(3)CH_(2)OH(C)` and one molecule of an amide, i.e., acetamide, `CH_(3)CONH_(2)(D)` `underset("Ethyl acetate (B)")(CH_(3)COOCH_(2)CH_(3))overset(NH_(3))to underset("Ethyl alcohol (C) "M.F.C_(2)H_(6)O)(CH_(3)CH_(2)OH)(CH_(3)CONH_(2))`.