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An organic compound (A) of molecular for...

An organic compound (A) of molecular formula `C_(5)H_(8)` when treated with Na in liquid ammonia followed by reaction with -Propyl iodide yeidls (B) `C_(8)H_(12)` (A) gives a ketone `C_(5)H_(10)O` (e) when treated with dil `H_(2)SO_(4)` and `HgSO_(4)` (B) on oxidation with alkaline `KMnO_(4)` gives two isomeric acids (D) and (E) `C_(4)H_(8)O_(2)`. Give structures of compounds (A) to (E) with proper reasoning .

Text Solution

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(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
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