An organic compound (A) of molecular formula C_5H_8 when treated with sodium in liquid ammonia followed by reaction with n-propyl bromide yields (B), C_8H_14. (A) gives a ketone ©, C_5H_10O when treated with dilute H_2SO_4 and HgSO_4. (B) on oxidation with alkaline KMnO_4 gives two isomeric acids (D) and (E) C_4H_8O_2. Give structures of compound (A) to (E) with proper reasoning.

An organic compound (A) of molecular formula C_5H_8 when treated with

1.	An organic compound (A) of molecular formula C_5H_8 when treated with sodium in liquid ammonia followed by reaction with n-propyl bromide yields (B), C_8H_14. (A) gives a ketone ©, C_5H_10O when treated with dilute H_2SO_4 and HgSO_4. (B) on oxidation with alkaline KMnO_4 gives two isomeric acids (D) and (E) C_4H_8O_2. Give structures of compound (A) to (E) with proper reasoning.
Answer» Solution :(i) (A) reacts with SODIUM in liquid ammonia and thus it is TERMINAL ALKYNE i.e. `C_3H_7C-=C-H` `C_3H_7C-=CHoverset(Na)rarrC_3H_7C-Naoverset(CH_3=CH_2-CH_2-Br)rarrC_3H_7C-=C-underset((B))(CH_2)-CH_2-CH_2-CH_3` (iii) `C_3H_7C-=CHoverset(HgSO_4)underset(H_2SO_4)rarrC_3H_7CO-CH_3` (iv) `C_3H_7C-=C-CH_2-CH_2-CH_3overset([O])underset(KMnO_4)rarrCH_3-CH_2underset((D))-CH_2-COOH+underset((E))(C_3H_7COOH)` SINCE (D) and (E) are isomers, thus the STRUCTURE of (E) is